The Baton Handoff in the Rio Olympics and Winning Gold in Sales

Allyson Felix passing the baton to English Gardner at the 2016 Rio Olympics

Baton handoffs make, or break, Olympic history. At the 2008 Beijing Olympics, the United States men’s and women’s 4×100-meter relay teams dropped batons in a disastrous performance that cost the United States crucial medal counts. Four years earlier, at the 2004 Athens Olympics, imprecise baton passing by the American men’s team had allowed a British relay team to win in an upset, while the United States women’s team were disqualified after a botched exchange.

In the 2016 Rio de Janeiro Olympics, a scandal erupted over the baton handoff between the United States sprinters in the women’s 4×100 race. In the final leg of the relay race, Allyson Felix, a veteran US sprinter, was in the lead and about to pass the baton to English Gardner. In the crucial hundredths of a second where a near instantaneous baton handoff can mean the difference between a gold medal and failure, disaster struck. Felix appeared to stumble and flipped the baton into the air, the baton landing with the sound no one wants to hear in a race they have prepared for over four arduous years.

Ping. Ping. Ping.

As CEO, I pay a lot of attention to baton handoffs. They happen every day — between sales and marketing, product and sales, and sales and customer service. Revenue growth requires these baton handoffs to be flawless — so we don’t hear that sound of dropped deals, leading to missed quarterly numbers and slow growth.

Are You in Sales, or Are You On a Sales Team?

Let’s say you are a salesperson at a large retail electronics store like Best Buy. You are in sales, and you are in a sales team, but you are not on a sales team. Your success in selling printers or calculators or ream of copy paper doesn’t rely on the rest of the sales team — it is proportional to your individual skills. There’s not much that the rest of the sales team can do to help you make that sale of a calculator. The product is easily understood by both the buyer (the consumer standing in the aisles) and the seller (you). You see a prospect looking around the store, you say hello and ask if you can help him, and then direct him to the calculators. There, your individual sales skills come into play — you can ask them if they need a calculator for business, and if so, suggest they purchase the model that has the sales tax function.

Now let’s say you’re not selling calculators at a store, but you’re in a competitive industry like tire sales, or you’re selling specialized equipment like industrial robots. This is where you can’t rely on just your individual sales skills to sell more. If you’re selling tires, then you better have a savvy marketing team that delivers leads by building and attracting prospects to sites like Tire Rack. Or if you’re selling industrial robots, you’re going to need the assistance of sales engineers and product managers to help you sell. In either competitive industries, or complex sales, great sales is all about the smooth functioning of a great sales engine, not the individual salesperson.

This is where the Chief Revenue Officer (CRO), or for a smaller company, the CEO, CMO and SVP Sales comes in. More often than not, however, decisions are taken that emphasize the individual, or department, over the company. Nowhere is this more apparent than in the selection of sales enablement tools. When we sell our Dossier lead generation platform to enterprises, we ask if the CMO or the CRO has reviewed the requirements. If the answer is no, and that the decision will be taken by a departmental leader, then the risk is that the decision will be weighted towards the needs of that department.

For example, first-generation website chat products were designed for either customer service departments, or for appointment-setting sales teams. When the head of customer service or inside sales evaluates these products, his qualification criteria will end with their own team’s goal — i.e. reducing time to resolution for customer service, or increasing appointments for inside sales. These leaders are trainers for individual athletes, and all they care about is how fast that athlete runs to win the 100m sprint. But like a national team coach, the CMO, CRO or CEO, doesn’t care just about the appointment — they care about the handoff to the account executive who will turn that win into an enterprise sale. These are national coaches that care about the country bringing in 50 gold medals — and winning on the international circuit.

And to the best sales and marketing leaders, creating a relay team isn’t about taking the four fastest runners and putting them together. They must work amazingly well as a team. They must learn to pass the baton to the next person on the team — from marketing to inside sales; from inside sales to an account executive; from the account executive to the sales engineer; and to the customer success manager; and finally to the customer service manager.

Winning gold is all about the baton handoff.

Lead Handoff from Website to Email

Let’s review the first handoff of a lead, or prospect, who visits your website — when the baton is passed from marketing to sales. Like baton handoffs in a race, precision and timing matters if you want to win gold. Our goal is to efficiently convert site visitors to qualified prospects, then a sales opportunity, and then close that deal. Since website visitors are anonymous when they come directly to your site, getting to know them by name and email is essential for the personal service we aim to offer.

We used our customer communications app Dossier to track the stages of a lead from discovery to close. First, we connected Dossier to the apps we use: G Suite, Google Drive, Slack, Asana and Salesforce — so that we could organize all customer conversations that happened on email, website chat or SMS.

G Suite is where we start all conversations, but we sync it with these apps

Let’s Start the Chit Chat

To capture the lead, we decided to do away with forms and use chat on our website. However, the first generation of chat software works if you have a transactional sale, because the goal of the chat is to answer the questions of someone who’s on your site, about to buy, but for some reason cannot take that step — ex. she wants to know more about the warranty. This first generation chat was designed for service teams to resolve customer requests, but they were not designed for sales and marketing teams. Chatbots are also inadequate when dealing with an enterprise, consultative or higher value sale, which often requires follow up with other internal teams, such as sales consultants, professional services, customer service or contract and finance teams.

First-generation chat was designed for customer service, not for sales and marketing. Customer service agents are motivated by reducing or eliminating the question in the first place. Sales and marketing teams, unlike customer service, seek to create an experience that encourages the website visitor to return and ask more questions. Questions are good for sales, because it allows for a dialogue. Dialogues lead to an understanding of the prospect and a personal relationship to be built with a salesperson.

Let’s illustrate this by an enterprise sales example. Many of you at are familiar with getting a call like this:

Salesperson: “Hi, this is ____ from _____. We’re calling because we can do ____ for you. How’s tomorrow at 10 or 11 am for us to talk?

You: “I’d like to learn more about your solution and how it compares to others. Is this like ___ or _____?”

Salesperson: “Sure, I’d be happy to schedule a meeting with our account executive. Are you available tomorrow at 10 or 11 am?”

You: Not really. I’d really like to know more before scheduling this call.

and then you politely disengage.

In that cold call, the appointment-setting sales rep should have been able to patch in a more knowledgeable salesperson immediately — except, it’s a bit awkward to do that on the phone. However, in a second-generation conversational sales platform, the chat can handle increasing complexity of conversations. Sales Development Reps (SDRs) can include other sales experts on the chat. Sales engineers (SEs) supporting the sale to a large, named account can feed the salesperson with private messages to use in her chat with the prospect. It’s also very natural for an SDR to include the Account Executive (AE) in that first chat.

We therefore designed a process — to help sales and marketing teams communicate with leads and customers, with zero disruption to the ways our internal teams already communicate. Here were our first principles.

#1: Humanize First Contact on Your Site

Many website chat apps look and feel exactly the same — leading to the perception that they are commoditized and your site visitors become immune to these similar-looking chat widgets greeting them. Our first goal in deploying Dossier chat on our site was to fit into the site’s color scheme and be very human. Putting pictures to the faces who are available to chat with the visitor

and a customizable color palette are important . We designed Dossier chat to humanize the experience with salespeople, and be customizable to the site’s design.

Website chat works well when it fits in with your brand guidelines

#2: Forms are Just Bad Form

Our next diktat of user experience was — don’t make visitors fill out a form. Forms, even beautifully designed ones, are impersonal! Imagine you walked into a clothing store, and then needed some help finding your size. You look around, but instead of helpful salespeople on the floor that you could quickly talk to, you see a kiosk tucked away in the corner.

You walk over and the kiosk says “Hi! What’s your name, email address, enter it again just because I don’t trust you to fill out your email address right the first time, and oh yes, your phone, and ah, your company name… also, we need a title to know if you’re worth letting into our fitting room, and finally, don’t forget to click that BIG BUTTON right there… and, Thanks! Someone will be with you as soon as possible, usually between 1 and 24 hours, if you’d like to wait with bated breath.” That’s what a form feels like to your visitors. Um, no forms.

We decided, instead, to create a lead experience using a conversational platform that would capture all the information needed by the marketing and sales teams. While we’re gearing up to respond, our chatbot, DossierBot, greets the visitor and collects the visitor’s name, email and organization, then passes on the lead to a human being, with an automatic reply sent to the user. Suddenly things felt a lot more human, on both ends of the chat!

Chat on a retail website asks the visitor for their contact info

#3: Zero Disruption to the Ways You Already Communicate

In the modern sales enterprise, your sales reps staffing the website chat are not sitting at their desk all day. Even when they’re working, they’re mobile — when a chat comes in. Slack is the best mobile app for responding to website chats — it is portable, conversations are visible to your entire team, and you can easily manage multiple chats with Slack channels. If one rep isn’t available on Slack, the chat can be handled by someone else on also on Slack. The baton handoff is built into Slack teams.

Dossier chat was designed to make your apps work better. Since our salespeople use Slack, we wanted to reply to our site visitors right from it, as this causes zero disruption to the ways we already communicate. No new apps to learn.

Now, with every familiar knock-brush Slack sound, we instantly know we have a visitor on that wants to chat with us. Website chats appear instantly in a Slack channel.

Responding to a website chat from the Slack mobile app

#4: Visibility Speeds up Sales Handoffs

A month into our deployment of Dossier chat, website visitors were responding well to chats, conversations were had with them — with our team responding via Slack — and leads were being qualified was happening at a pretty fast clip! Once the chat is completed, the lead needs to be sent to a salesperson who can address the next stage in the customer lifecycle.

As we handed off Marketing Qualified Leads, or MQLs, to the sales team, we didn’t want the conversion of this lead be dependent solely on the availability of one specific salesperson handling it. Enterprise salespeople are often busy in meetings with clients, yet there are supporting staff who can assist, such as account managers, sales engineers, and product specialists. We wanted a more robust sales process, but with the speed of a startup.

In all business, and especially in sales, knowledge is power. Dossier handles the transition that leads make from being online visitors to going offline on email, texts or messaging.

What if you could not only hand off MQLs to the sales team, but also help sales managers, support staff and executive stakeholders watch the progress of this prospect and assist the salesperson? We have that visibility in the lead conversation. Not only are chats visible to sales managers, but all followups that are offline, on email, or text messages, or Whatsapp, could also be analyzed. No sales manager ever had to ask “What’s going on with that prospect?” They would already know.

Curating the handoff to sales meant that we should streamline our process so that we were not simply handing a set of leads over to sales. We assign salespersons to the chat conversation from the very beginning. As Dossier chat collects the visitor’s name, email and company, we look up the named account in Salesforce, our CRM, and pick the appropriate team of sales development reps (SDRs) to join the chat. Since the sales crew is usually online on Slack, Dossier automatically adds them to a chat channel with the website visitor without any human intervention.

Responding to a website chat from the Slack mobile app

#5: Speeding up Contract Management

Once an opportunity has been created in Salesforce, the deal is in play. In an enterprise sale, delays happen in contract process because the G&A contracts team is often oversubscribed with contracts that may or may not be related to closing sales that quarter. Managing this process is essential. With Dossier, the account manager converts the chat with the client into a task, usually in a task management tool like Asana. The account manager assigns it to the legal counsel for review of the contract. Our contracts team now has every request from sales in their Asana task management tool. The account manager gets a response from Dossier: “Revcyclery contract review created in Asana”. When the contracts person logs in to Asana, she will see tasks in her inbox related to deals in the pipeline.

Creating an Asana task from an email
…and the tasks, in Asana

#6: Speeding up Post-Sales Onboarding

After the sale has closed (yay, sales team! Ring the bell), a different team, either Customer Success, Professional Services, or Onboarding, gets involved. They usually start by getting a briefing from the salesperson involved in the deal. We’ve eliminated this hand-off entirely by converting client emails into a list of open tasks in Asana, that are then delivered to the CSMs. Without any delay, the CSM has what he or she needs to take the reins on the account. All onboarding actions are communicated to the clients, no matter where they are. If they are on our website, they see a task list like the one below. Note that the first item in the website feed is an Asana task — the client knows that it’s an open task.

When your client visits your website, they see a dossier with all their open requests

When the client visits the website some days later, Dossier chat intelligently recognizes she’s back and shows her the Asana task and the assignee. She also has a dossier of white papers, left by the CSM ready for her to review.

The lead-to-close lifecycle — a visitor turning into a prospect and then a customer — is now complete. During this process we’ve made our existing apps, such as Gmail/Outlook, Slack, Asana, Box/Dropbox/GDrive/OneDrive, Salesforce and our website work better — all powered by the one app that organizes all customer conversations — Dossier.

Winning the Gold Medal

At the 2016 Rio Olympics, the US women’s team appealed the circumstances of the infamous Rio baton fumble. Replays of the race showed Brazil’s third runner, Kauiza Venancio, pumping her arms as she gets ready to receive the baton from Franciela Krasucki. Venacio’s left arm makes contact with Felix’s right one and throws her off balance as she was attempting to pass the baton to Gardner. Felix let out a yelp as her handoff missed its mark and the baton tumbled to the ground. Ping. Ping. Ping. She picked up the baton and urgently yelled to Gardner to finish the race — a crucial action that allowed them to qualify for an appeal. The 2016 Rio Olympics worked out for the US women’s team. In a sudden-death 4×100 race, USA’s Allyson Felix, English Gardner, Tianna Bartoletta and Tori Bowie celebrated after they won the Women’s 4x100m Relay Final on Aug. 19, 2016. Their baton handoff was flawless and they came home with gold.

The victorious US women’s 4×100 relay race winners at the 2016 Rio Olympics (Ian Walton/Getty Images)


About Vik Chaudhary

Vik Chaudhary is the CEO of Dossier ( in San Francisco. To business professionals and teams, Dossier is an app for organizing communications with customers. In his spare time, Vik observes how CMOs and CROs lead their teams to gold or fumble the baton handoff.

Dossier is an app for organizing customer conversations, no matter where it happens, with zero disruption to the ways you already communicate. Based in San Francisco, Dossier is helping business owners, business professionals and teams around the globe intelligently sync their customer communication channels and organize documents, tasks and more. Welcome to a new way to build better customer relationships and a better business. Sign up for a free account today at

Pick Up the Slack, or Why Speed Matters for Customers

Slack. The word conjures up relaxation, or even lethargy, slowness, torpor, lassitude. Far from it. Slack, the messaging product used daily by over 5 million people, is anything but slow. Spend three months with Slack, like our team at Dossier did, and if you’re a fast-moving team at any knowledge-based business, you just know that Slack isn’t about lethargy or relaxation. It’s about harnessing the speed of collaboration, about learning the ways speed can make you, your team, and your company listen faster, say faster, build faster, feedback faster, and earn faster. How do you use Slack to respond faster to customers? Read on.

Fast. Faster. Fastest.

The success of Slack has been written about, and the numbers I repeat aren’t new. 5 million daily active users, 1.5 million paying customers, and $150 million in annual recurring revenue as of Jan. 31. As of just yesterday, there is talk of Amazon offering $9 billion for the messaging company. Slack has delivered a product that has been hugely successful, and as a Silicon Valley company using Slack for internal team messaging, we see why both the speed of messaging as well as the plethora of application integrations make it a must-have product.

In the years since Slack rocket-shipped into our lives, many products have come (and some, gone), aiming to spurn Slack, denounce the very lightness that gives the product its edge, harangue its philosophy of quick chats, and even supplant it. Slow down, they say. The problem with Slack, they say, are the unending streams without a beginning, a start and an end, the dozens of channels that require you to pick and choose your way through communications. Organize. Even, turn it off.

How wrong they are.


Speed is the secret DNA of Slack’s success—and the killer application for customer acquisition, engagement and success.


Moving at the Speed of Business

The team at our company, Dossier, knows a thing or two about speed. 100% of us are engineers who came from a software infrastructure company Dynatrace, which acquired a company we had previously built. Our software was used to speed up websites, and it was used by Microsoft, Yahoo, FedEx, Citibank, Sony, and many others. A SaaS application, we collected almost 1 billion records in our Oracle database every day, each one of these a signal that would tell us if a website, a mobile app, or a server was slowing down, compared to, say 60 seconds ago. We analyzed months of this voluminous data in seconds. Analysts give it fancy names – Big Data, Predictive Intelligence, Application Performance Management. We analyzed these large data sets in seconds because speed was essential to our customers. If Amazon’s website or mobile app were slow, or even down, every second would be crucial to revenue for Amazon. So we became speed junkies—driven by the need to alert quickly, move faster, fix quickly, and make the world all right, again.

What we learnt is this – if you have a team that is fundamentally driven by the need for speed, it changes how you operate. In industries such as finance, retail, e-commerce, or media—speed was essential to survival, revenue, and brand. Safeway moved like a lumbering giant all these years, while Whole Food Market moved quickly. You could tell in the litheness and speed of the Whole Foods staff, compared to the stolid slowness of Safeway employees. Amazon purchased Whole Foods for over $13 billion. Grocery stocks plummeted: Kroger fell 13.4%. SuperValu was down 16%. Costco sank 7.5%. What made these stocks fall was the concern of investors that Amazon valued speed, and that speed—of merchandising, logistics and customer service—is what will shake up the grocery industry.

One area that we felt was overlooked was the speed at which companies communicated with and on the behalf of customers.  CRMs like Salesforce, Microsoft Dynamics and HubSpot were designed around the work of a salesperson, to help them organize and shape how they communicated internally on how sales deals were going. A new notion began to make the roundsthat organizations needed not just a system of record, but also a system of engagement, with some debate over whether they were one or separate products. The fact is that systems of engagementthose tools that make it possible to connect with customers, and, on behalf of these customers, with internal teams—have to be designed from the ground up to focus on communications, not organization. That’s why systems of record like Salesforce, Dynamics and HubSpot are designed around companies, contacts and deals.  

Products like Slack and our product, Dossier, are designed around the concept of messaging and underscored by speedy technologies. In Slack, send a message, and it appears, for tens or hundreds of people in your team, on all the desktop computers and smartphones they are on, instantly. Slack, though, is designed around making internal communications faster, and it’s just starting to use Slack to connect two organizationsthis configuration is called the Slack Enterprise Grid. We wanted to extend the use of Slack to communicate naturally with customers—gaining the speed of Slack, but without the complexity of forcing customers to choose our communication channels.

So we built Dossier, an app for organizing customer conversations, no matter where it happens, with zero disruption to the ways you already communicate.  And it gives us great pleasure to announce our FREE Slack app that allows you to reply to website chats and customer emails without leaving Slack. This video shows you how you can use Slack to talk to website visitors. Check out for more information. Dossier is FREE for up to 5,000 messages, and if we can be useful to you, we’d of course, love it if you signed up.


Productivity is not just a goal designed for internal teams to collaborate. It is essential to extend productivity to all customer interactions with clients and prospects. Leads visit your website, ask questions, and you answer them instantly—in Slack. Sometimes these leads are new contacts within companies that you already work with, or they are existing clients that need to be routed to their account manager. Handing the baton to different teams is where impedance begins. Customers can email, text, tweet, or facebook you or someone in your organization. Your company has at least 5 different communication channels, and anywhere from 5 to tens of thousands of customer facing employees. Speeding up customer communications becomes harder as teams diverge around time zones, geographies, and divisional structures. An organization naturally fills with torpor, and there is slack in the system. By using Slack on the front lines of your customer channels, you can speed up customer issue resolution, lead routing, or account management. Our mantra is:



About Vik Chaudhary

Vik Chaudhary is the CEO of Dossier ( in San Francisco. To business professionals and teams, Dossier is an app for organizing communications with customers. In his spare time, Vik observes how companies communicate with customers.

Dossier is an app for organizing customer conversations, no matter where it happens, with zero disruption to the ways you already communicate. Based in San Francisco, Dossier is helping business owners, business professionals and teams around the globe intelligently sync their customer communication channels and organize documents, tasks and more. Welcome to a new way to build better customer relationships and a better business. Sign up for a free account today at

Atlassian’s Trello Acquisition and the Three Principles for SaaS Market Expansion

SaaS companies that expand from selling to IT to selling to business teams (or, vice versa) rely on 3 principles, which I call The Three Principles of SaaS Market Expansion. It requires these companies to take a resolute approach that is similar to the crossing of the Rubicon. “The phrase Crossing the Rubicon means to pass a point of no return, and refers to Julius Caeser’s army’s crossing of the Rubicon River in the north of Italy in 49 BC, which was considered an act of insurrection and treason. Julius Caesar uttered the famous phrase alea iacta est—the die is cast—as his army marched through the shallow river.”—Wikipedia.


Atlassian Buys Trello for $425 Million

This week, Atlassian broke the news that it was acquiring Trello, a simple list-making software company, for $425 million. It’s an amazing price for Trello, 15 times TTM (trailing twelve months revenue). Forbes wrote about why Atlassian bought Trello, and the primary reason was, as CEOs know, an adjacent market move. Adjacency thinking leads CEOs to consider how to expand to a different buying group within the kinds of companies they already sell to. Atlassian has now expanded from selling to IT to selling to business teams. As Forbes wrote:

“Atlassian’s existing products, including Jira, sell mostly to software developers and IT departments. Trello, on the other hand, is popular not just with coders, but with marketers, HR departments, sales teams, media companies, and other non-technical groups.”


As the CEO of Dossier, and having made 17 acquisitions previously, we know a thing or two about making acquisitions work. Every day we have thousands of teams using Dossier, an app for organizing customer conversations. Our team, like that of any startup, is small—and made powerful by the way we use software to automate how we can communicate with our customers. We use many self-service products to run our business—we wrote 20 Affordable Tools to Run Your Sales, Marketing and Service Stack for a total $1,000/mo. Also, many teams that use Dossier have also attached CRM tools like HubSpot and Salesforce, and task management tools like Asana and Trello, so we’ve learned much from our common customers. Atlassian’s purchase of Trello is a textbook example of market expansion—a playbook that large companies employ to grow their market share. How do you make such an acquisition work?

You’ve got to hand it to the Atlassian management team—they weren’t content doing what they always do, but have taken a bold move to enter an adjacent market. As I wrote in my previous article, Your Corporate Strategy is a Prisoner of History (or, Why CEOs Should Listen to Their Inner Revolutionary), at our previous company, which we sold for $395 million, “The thinking behind our corporate (expansion) strategy was that our sales teams were selling products to IT teams only, and that we needed to expand our brand to business teams at Internet and e-commerce companies like Facebook, Amazon, eBay, and brand managers at Chase and FedEx—all customers”. How do you make such a strategy work?

Selling to IT and Selling to Business

How easy is it to expand from selling to IT to selling to Business, or vice versa? On paper, the thesis sounds great. Start by selling a niche, but highly differentiated, product to your first audience. Start with a departmental sale, rather than to the enterprise. Expand capabilities so that federation occurs—i.e. you land in one team (say, to an IT buyer), and then expand to another team (still, another IT buyer). And then when you’ve established a strong brand with a specific buyer persona, then make an acquisition of a company that knows how to sell to the other side (this time, a business buyer), and then rinse and repeat. It’s been done in the technology industry.

Adobe started with multimedia and creativity products, then acquired Omniture to sell to marketing teams. Since then, it has added several more acquisitions to deepen its footprint for marketing automation. Oracle started with the database business, selling only to IT, then acquired Siebel Systems to enter the CRM market, changing its persona from IT to business rapidly. Autodesk, on the other hand, has stuck to its knitting—once glance at Autodesk’s list of acquisitions tells you that these apples don’t fall far from the tree (of CAD automation). Salesforce has tried to expand from selling to business teams (it’s core CRM business) to selling to IT (by the acquisition of Heroku)—but it is not yet working to dislodge entrenched competitors like Amazon Web Services.

So what is the secret to adjacent market expansion? The Harvard Business Review provides insights in its seminal article, Growth Outside the Core. It identified six ways to expand outside a business’ core, and provides nuggets such as this: “One was that most sustained, profitable growth comes when a company pushes out the boundaries of its core business into an adjacent space. We identified six types of adjacencies, ranging from adjacent links in the value chain to adjacent customers to adjacent geographies“.

Market expansion for SaaS businesses may follow these six strategies, and any MBA worth her $200,000 degree, will tell you—business expansion is a time-honored tradition. Yet, like any industry, the technology industry, and, in particular, software-as-a-service companies (I’ve worked for no other type since I left Oracle), have a different set of rules. To make such a market expansion work, consider these characteristics of the companies acquiring, and being acquired:

1. Transactional Sales

When two SaaS companies both have transactional sales, rather than expertise-driven consultative sales, market expansion is much easier. Atlassian sells ticketing software like JIRA, and it’s a transactional sale—i.e. it does not require a high degree of domain expertise for the sales team that is selling it. Prospective buyers sign up for or download the software, learn how to use it or get some general assistance in getting the software to work, and then they buy it for a per user price. Trello also has a transactional sale, marketing and HR teams that purchase its software also follow the same pattern as the JIRA sale. The synergies between the two businesses are all about operational effectiveness—making the sales process more efficient. Expect a lot of consolidation of IT infrastructure costs between the companies as they merge their teams. On the other hand, consider why Salesforce, which sells to business teams, isn’t able to effectively compete in the AWS market. Selling an enterprise-level CRM is a consultative sale, but selling cloud infrastructure services is a very transactional sale—hence, there are no sales synergies.

2. Inbound Marketing

SaaS companies thrive when marketing teams generate a large number of inbound leads. Companies like HubSpot have perfected this approach, practically writing the playbook for inbound lead generation that is then fulfilled by inside sales teams. As long as the combined marketing teams are able to use their expertise to generate relevant content, the success of market expansion is increased. On the other hand, if the acquired company’s marketing team is decimated under the false assumption that the acquiring company’s marketing team will be able to handle the marketing, then the acquisition has a high chance of failing. Inbound lead generation is an expertise-driven business—your marketers have to understand the content that generates interest, the experts to be interviewed, the guest blog authors to be invited, etc. If a marketing team understand how to sell to the business buyer, they are not likely to know how to sell to to the IT buyer, and vice versa. So, Atlassian, I imagine you’ll be sweetening the deal for the Trello CMO.

3. Internationalization

Traditional companies can expand in other markets if they expand the geographies in which they sell. The same happens for SaaS companies, virtually overnight, if they can internationalize their software. Think, for example, about the signup workflow of any transactional SaaS application. If it can be translated into a dozen languages, that’s another 30 countries it could sell in. Online advertising makes it a cinch to enter these markets. A caution, though—the product must not require telephone calls to sell or support the product. It must be done online, via email and chat, because then it can be done in countries which specialize in customer service—such as the Philippines, or Ireland.

When SaaS Market Expansion Fails

SaaS companies that require expertise-driven sales, rather than transactional sales, are not likely to be able to successfully expand markets when they cross the Rubicon with the buyer persona. We once acquired a company that sold primarily to business audiences, and the sale was highly consultative. When the COO of the acquired company decided to not come along with the acquisition, that caused a ripple effect in the sales organization and many of the expertise-holding salespeople left. And with it, went their customer relationships, and the acquisition we made failed to yield any market expansion results. Note that this is different from non-consultative salespeople leaving the company. It’s because the salespeople had expertise that the clients relied upon, such as presenting findings from quarterly reports to their management team, that the customers were happy. Take away these salespeople, and the customers walked as well.

However, if the above 3 characteristics match between companies as they acquire their way to market expansion, the acquisition has a high rate of success. We’re going to be watching Atlassian and Trello work this one during the integration—the signals look great because the 3 fundamental factors for successful SaaS mergers are present in both companies.


About Vik Chaudhary

Vik Chaudhary is the CEO of Dossier ( in San Francisco. To business professionals and teams, Dossier is an app for organizing communications with customers. In his copious spare time, Vik—well—asks CEOs to not screw up large acquisitions.

Dossier is an app for organizing customer conversations, no matter where it happens, with zero disruption to the ways you already communicate. Based in San Francisco, Dossier is helping business owners, business professionals and teams around the globe intelligently sync their customer communication channels and organize documents, tasks and more. Welcome to a new way to build better customer relationships and a better business. Sign up for a free account today at

The New ABC of Sales: Always Be Chatting

Arabella Moretti (Arby to her friends) is finally on her flight home to San Francisco after being stuck in Munich Airport for hours due to a raging storm.  A full week of negotiations with a global brand based in Munich, and her proposal still needs approval from their SVP.  And he’s concerned about Arby’s digital agency being too small to handle their service needs. “How many people do you have in account management, and what percentage work European hours?” was the last question that Phil van Troppe, the SVP, asked Arby. Arby’s agency was small, no doubt, yet their ability to work long and hard for their clients was high. “We need to demonstrate this, decisively,” mused Arby. 

Always Be Chatting

As the plane climbs over the storm to 35,000 feet and the clink of champagne flutes fills the first class cabin, Arby settles into her seat and connects to the in-flight Wi-Fi. There is a “water drop” sound on her smartphone, indicating a chat on her agency website, and the person chatting has a question: “If I had an escalation right now, at 3 a.m. your time—how quickly would your agency handle it?”

Arby gets notified on chats from prospects because she has elected to be on the chat list. The old sales adage “ABC: Always Be Closing” should now be “ABC: Always Be Chatting”, as more leads come to a site and use chat as a way to begin the prospect conversation. Arby, having spent her teen years with the latest smartphones her parents could buy, is used to texting, but more importantly, more and more of their clients are, as well.


Arby looks at the chat and thinks “Nobody is online at 3 a.m. in San Francisco; maybe I should respond.” In a split second, an automated response pings out from her agency’s web site—it’s the DossierBot saying “Hi, we’re finding someone to respond! What’s your name?” Whew, at least the visitor wasn’t kept waiting—if responses aren’t delivered in the blink of an eye, web site visitors leave the site, never to return.

The Intelligent DossierBot Syncs with Salesforce

The DossierBot intelligently asks the chatter for his name and email (“in case we get disconnected!” says the DossierBot).  A few seconds later, the person chatting has entered his email: The DossierBot instantly connects to the company’s Salesforce CRM, looks up Phil’s email, finds the company he works for, looks for all account managers, checks who’s online to chat, and immediately identifies the chatter. It’s Phil van Troppe, the SVP from Global Brands, and whose approval Arby needs! As Arby is online and is one of the account managers for Global Brands, DossierBot makes her automatically visible to Phil in the chat. She quickly taps out a reply: “Good morning, Phil, this is Arby Moretti, the agency’s account manager for Global Brands. Thank you for contacting us, and I assure you that we’re always available to help our customers.”

In the background, the engines cut back to a smooth purr as the jet steadies at 35,000 ft. Phil taps his response, “I’m impressed. I expected to speak to a chat agent, if I could at all, since it is 3 a.m. your time. Where are you?”

Arby laughs to herself, and taps out “Actually, I’m on the flight to San Francisco. It was great to meet you and the team. I did want to say that there are other people who can help you right now. This chat window shows you who your account team is, and who’s online. And if we’re not, your request immediately gets sent to the relevant person via email and also logged in our task management system as an open task.”

Phil writes back: “This is great service, and I like the responsiveness already.  Can you send me the contract right now, so I can review the terms again?”

DossierBot Syncs with Box, Dropbox, Google Drive, and OneDrive

“Of course , Phil, here you go!” And with a click of a button on her phone, Arby connects to her Google Drive storage, attaches the Global Brands contract to the chat, and sends it to Phil.  Phil takes a screen shot of the clause he wants to have edited, marks it up, sends it back to Arby in the chat, and ends with “Let’s get this signed.”

While the chat has been happening, every message in the conversation and the file attachments has been getting transferred to an intelligent workspace in the Dossier dashboard named after the account, “Global Brands.” All files sent or received on this chat are also saved in Arby’s Google Drive folder of the same name.


DossierBot Converts Chats to Asana Tasks

Arby converts the chat message to a task and assigns it to their Legal Counsel for review of the contract.  The Legal Counsel, she knows, is dealing with many email requests, and so he has instructed her team to put every request from sales into Asana, a popular task management tool. Arby gets a response from Dossier: “Request transferred to project “Deal Desk at Legal” in Asana”.  When the Legal Counsel connects to his Asana app, he will see this task in his Asana inbox.

James McCaulay, the Legal Counsel, happens to be traveling himself, and he is in his hotel in London, checking messages in Asana. He sees the Asana task for Global Brands with the contract file attachment.  He opens it, accepts the change, and Docusigns it, sending a copy to Global Brands and Arby.


Back in Munich, Phil also Docusigns the contract and sends it back online. Arby taps out a new message to Phil and marks it to be delivered when he’s next online on their web site. Phil goes to Arby’s agency’s web site to learn more about their services.  As he scans a page, a friendly message from Arby pings out from the web site as a chat message. “Welcome, Global Brands. We’re so happy to work with you.  Arby.”

Phil is pleased.  He thinks “I’m going to enjoy working with this agency. They may be small, but they think smart and act fast. Getting work done is what they’re about.”

At 35,000 ft., the Deal Is Closed

As the flight attendant reaches her seat with the champagne bottle, Arby smiles and says “I’m ready for the champagne. I just closed our biggest deal in-flight.”

The flight attendant smiles. The well-dressed man seated next to her says, “Sorry, I couldn’t help overhear…on your phone? How did you do that? Not on email?” Arby pulls out her iPhone and shows him the chat with Phil and points out:

“Dossier—conversations with customers, no matter where I am or my customers are,” Arby laughs. “And that’s my secret weapon.”

The gentleman next to her remarks, “Hey, I’d like to take a look at that app!’  Arby smiles, “Try it for free if you like—that’s what I did,” goes to, and shows him the web site. Arby pops her phone back into her purse, and leans back into her seat.  She takes a sip of champagne and settles into the long flight home.

Then she hears the water drop sound again. And she smiles.

How Dossier Chat Works

Customers converse with a business on your web site, on email, or using messaging apps. Adding chat to your web site makes it easy to for them to ask you a question. You can add chat to your site effortlessly in minutes!

Your business is very likely to be one that doesn’t have employees tethered to desks. Employees work at coffee shops while on their phones, or they are in conference rooms away from their desks. Or they are on the go, overseeing warehouse orders, or traveling from Munich on a plane…and a chat comes in and a potential customer wants to talk.

With Dossier, your team can respond to web site chats on your smartphone. Because it has two-way integration with Gmail for Work and Outlook 365, replying to a chat is as simple as replying in email. There’s no need to have a dedicated customer service staff to respond to web site chats. Any employee can respond to incoming chats simply by using their email app—Gmail for Work or Outlook 365.

Dossier also:

  • Identifies the visitor by name and company.
  • Pages the visitor’s salesperson if it’s an important account.
  • Adds the salesperson to the chat instantly so the best person can respond.
  • Lets the salesperson know the customer has returned to the site, where he is on the website, and what he is doing.

Add Dossier Chat to Your Web Site

About Su Piercy

Su joined Dossier to stay ahead on the exciting technology speedway that is the world of SaaS apps. Working out of her home office in Colorado Springs, CO, Su uses Dossier to get new customers up to speed with Dossier.  She’s amazed at the recursiveness of it all.

Dossier is an app for organizing customer conversations, no matter where it happens, with zero disruption to the ways you already communicate. Based in San Francisco, Dossier is helping business owners, business professionals and teams around the globe intelligently sync their customer communication channels and organize documents, tasks and more. Welcome to a new way to build better customer relationships and a better business. Sign up for a free account today at

It’s a Bird, it’s a Plane, it’s Super CRM Heroine!

Remember reading Supergirl, Wonder Woman or Batgirl comics and marveling at the amazing ability of superheroes to see through walls, or hear a whisper a continent away? Today’s customer-centric leaders can look to modern CRM and Big Data technology to give them superhuman skills. Imagine that you, a business owner or manager, could, with the click of a button, listen in on or even participate in any customer conversation that your employees were engaged in?

The team at Dossier, previously from companies like Oracle and Keynote, wished we had this amazing ability, without having to check in with far-flung employees to find out what was the latest with a deal, or stalk them on Slack, Gmail or Hipchat. Most CEOs have a list of top 10 deals and top 10 customers on their mind at all times. Yet, they often ask their head of sales: “what’s happening with ______?” The best that the sales head can do is to quickly tap out a message to his or her regional directors or account managers, and ask what’s going on with ______. Information then filters up in unpredictable ways, sometimes on email, sometimes being paraphrased, but the source of truth is too far away. Often that leads to an inaccurate picture of what’s happening at a client, and critical sales information is hidden, inadvertently or deliberately.

A team of CRM and Big Data experts got together to figure out how to make lead and customer conversations transparent, fast, and make our teams super responsive. That’s why we built the new Join feature in Dossier by Dossier, an app which transforms email, chat and messaging into a customer response app. Here are some examples of how business owners and managers use this feature:

meg-circle-profile Laura Macintosh is CEO of a marketing and design agency. She has been worrying over timely customer communications, because email conversations her team and contractors have with customers are sometimes invisible to her. So she’s asked to be cc’d on every email, and now her inbox is overflowing. None of them can keep up with emails to see which customers need followup, and what actions are assigned to their contract designers and copywriters.
ken-circle-profile Marcus Price, VP of Customer Success at a B2B software company, EasyBillings, is finding it more and more difficult to obtain continuous visibility into top clients’ interactions. Fortune 500 customers have recently started using EasyBillings, and Marcus is not always cc’d in those emails; yet he wants to know immediately when requests come in from those clients. Sometimes the request is very time-sensitive and he is not made aware of it until it’s late.
lamar-circle-profile Jonathan  Abrams, the new Chief Revenue Officer at Global Technologies, is raring to go. For 30 days since he was brought on, the board of directors asked for more accuracy on this quarter’s forecast. He has been waiting to get deeper insights into the sales pipeline with his account team. Instead of calling each of the sales directors every Monday, he signs up for Dossier, an app for organizing customer communications that can help him gain that precious insight into any conversation between his reps and top leads or clients.

Have you ever found yourself in any of the situations above? Wouldn’t it be nice and highly productive for you and your team to immediately jump in to timely conversations with customers, vendors, or contractors? Without being cc’d or emailed ad nauseam? 

Enter Dossier.

Dossier is a state-of-the-art app that speeds up conversations with customers, leads, and team members, giving you and your team members the ability to join current email, chat and messaging conversations with one click. No more rifling through your overflowing inbox looking for the latest emails from team members to your customers and vice versa. No more leaving voicemails and waiting for responses from your client facing team. You can respond immediately, and Dossier shows you which customers are online so that you can Skype or message them instantly. And now this feature is available to all customers.

How to Join Any Customer Conversation in Dossier

  1. Sign in to Dossier at
  2. Dossier magically identifies customers and finds all conversations.
  3. Invite any number of your team members to Dossier for free.
  4. When your team members sign in to Dossier, they immediately see all the conversations in which they can participate simply by clicking Join.
  5. As your team begins conversations with customers you previously didn’t have access to, you are able to view and join these conversations.

Join conversations with customers

JOIN Gives You Immediate Visibility into Customer Conversations

Millions of Customer Records Collected Daily

At your company, whether you are small or large, hundreds to tens of thousands of customer conversations happen every day. These conversations are, increasingly, tracked in your CRM, such as Salesforce or Hubspot, since these are your systems of record. However, saving conversations that are happening in real-time in the CRM is like looking in the rear-view mirror as you pass your customer stranded on the highway – it’s impossible to turn back time and address the situation immediately. What we need is a system of real-time customer engagement – with an application that needs to intimately aware of the collective intelligence in lead and customer conversations. Transforming all channels of communications – thousands of email inboxes, web site chats, in-app chats, helpdesk tickets, and assigned tasks – into a customer response system calls for real-time CRM and Big Data expertise. The Dossier team’s engineers worked at Oracle (the biggest system of record in the world), Keynote (an analytics company whose systems collected close to 1 billion rows in an Oracle database every single day), and other team members from Salesforce and Pegasystems (an enterprise CRM company). The intelligent routing technology designed by the Dossier team analyzes these conversations and enables us to analyze millions of customer records every day.

About Su Piercy

Su joined Dossier to stay ahead on the exciting technology speedway that is the world of SaaS apps. Working out of her home office in Colorado Springs, CO, Su uses Dossier to get new customers up to speed with Dossier. She’s amazed at the recursiveness of it all.

Dossier is an app for organizing customer conversations, no matter where it happens, with zero disruption to the ways you already communicate. Based in San Francisco, Dossier is helping business owners, business professionals and teams around the globe intelligently sync their customer communication channels and organize documents, tasks and more. Welcome to a new way to build better customer relationships and a better business. Sign up for a free account today at

20 Affordable Tools to Run Your Sales, Marketing and Service Stack for a total $1,000/mo

Recently, VCs have been regularly opining with punditry on how your startup–never, their startup–needs to cut back. As a technology startup CEO, I want to share how we run our company’s sales, service, and marketing stack for about $1,000 a month. Here’s our stack.

“Cash is king,” “Tighten the belts,” “The party is over,” “Valuations need to come back to earth,” and other similar VC insights abound.  It feels like the same set of articles that were written in 2008, and they all sound like variations of this one. It’s true that many well-funded startups offer outrageous employee perks, such as nap pods, in-house gyms, yoga classes, etc. as reported by The Economist.  A CFO at a 40-person startup in San Francisco told me that the company spends money like there’s no tomorrow.  It’s part of the aura the CEO wants to create to attract employees and, likely, potential acquirers. M&A executives from stodgy firms and big bank balances like to visit the startup’s exposed-pipes-and-brick-walls office and crave some of that positively not-trying-to-be-cool cool that comes off its team with their Dre Beats headphones, daily Zesty lunches, and apparent lack of awareness that when the next Big One hits in San Francisco, offices with brick walls are literally going to come crashing down.  So, with advice that’s at 50,000 feet coming from board-wallahs, how does a startup actually keep costs low?

Don’t rent offices with brick walls in San Francisco.

As a startup CEO, it is obvious to you where your money is going. It may be the insane rent that you’re paying to have a super-cool office in SOMA, San Francisco or Castro Street, Mountain View, CA. So, save yourself $10,000/mo (or $125,000/mo as the hot startup CFO told me their rent was for a 40-person office), and cut the office lease loose.  Move the core team into a co-working space, and let the rest WFH until the VC winter blows over. Review your headcount and only keep people who are building your product or selling to customers. You don’t need on your payroll that “R” data analyst who can give the CEO the answer to the question about churn that bothers him while he is sipping his morning $5 latte made with beans that have been crushed under the feet of vestigial virgins from Amazonian forest tribes. Buy Excel instead and watch the 11 lectures on Udemy on how pivot tables work

I mean, dude(tte), you don’t need me to tell you this stuff. You could move to Brussels or Bangalore, where there are some great engineers, but that’s not realistic. I wish I could move to a tropical island and run our business (like our co-founder just did, living in Thailand for a month – he actually worked harder). I can’t, if for no reason other than this–my wife runs a food company with a 10,000 square foot commercial kitchen in San Francisco and she can’t just move to Brussels–not unless she wants to take Indian Bento global. So what’s a tech CEO to do to keep costs low?

Save money with the right tools for your Sales, Marketing, and Service tech stack.

You could save money on your tech infrastructure stack, but that’s an article for another time. 100% of our team comes from Keynote, a 700-person company that made websites faster (an early employee, I was the CMO & EVP Corpdev, managing marketing, products and corporate development, and our 18th M&A deal was to sell it for $395 million). Our engineering team knows how to build highly performant software that uses less server resources, reduces bandwidth usage, and still delivers the Dossier product at the right speed and latency, so we have pared down our costs as much as we possibly could there.

What I do know is how we can run our marketing, sales, and customer service on an affordable budget, and I know you can do the same. Today, I had lunch with the CMO of a 400-person analytics startup in Silicon Valley. Their marketing automation SaaS software costs them $50,000/yr, but the complexity of running that software and making it work with their CRM requires them to hire a Marketing Operations staff member whose cost is $175,000/yr. So their marketing automation software actually costs $225,000/yr. And they need more business analysts for the next 3 months to correctly sync their leads between their marketing platform and Salesforce and have the right leads delivered to their sales BDR team. We used the same platform at our previous company and the real cost is in the complexity required to operate it.

At Dossier, we do not have anyone on our staff except engineers building our product and sales and marketing teams selling our product. Of course, that is because our product, Dossier, does all the heavy lifting in helping us communicate with leads from Salesforce, recognize visitors on our website, and support customers in real-time in our application portal. To do this, we integrate Dossier–if that’s the word for the 30 seconds it takes to do this–with tools like Salesforce, Outlook, Dropbox, Asana, and many others. Dossier works out of the box, and our customers do not need to hire staff to learn how to use our product. Here’s our stack and our actual costs on the tools:

OnBoardify Marketing Stack


Awareness: Web Site Stack ($369/mo)

Your web site should be fast and measurable, that’s the place where engagement starts.

  • Facebook Ads ($100/mo) – Display Ads. We buy ads that Facebook users get to see.
  • Google Adwords ($100/mo) – Search ads. Ads displayed to users when they search.
  • Linode ($35/mo) – Hosting provider. Linode has a ton of docs, ’nuff said.
  • Vimeo ($17/mo) – Video hosting. Its analytics are awesome.
  • Dossier ($95/mo) – Chat. Site visitors ask questions and we capture emails.
  • Google Analytics ($0) – Analytics. Measures our audience metrics.
  • Warfare Plugins ($2/mo) – Social Share. Adds social sharing buttons to the site.
  • CrossBrowserTesting ($20/mo) – Browser Testing. Test the site on many browsers.


Outreach: Sales Stack ($310/mo)

Salespeople are directly in charge of their outreach to leads with these tools.

  • Dossier (included) – Outreach. Automate sending emails and update Salesforce.
  • Salesforce ($125/mo). CRM. Update automatically using Dossier.
  • GoToMeeting ($29/mo) – Conferencing. For meetings with prospects.
  • Outlook 365 ($78/mo) – Email.  A necessary evil because it’s the easiest way for customers to reach us.
  • LinkedIn ($48/mo) – Prospecting. Look up prospects for outbound prospecting.


Customers: Service Stack ($80/mo)

Responding to customers and prospects in seconds is our secret sauce.

  • Dossier (included) – Trials. Dossier kicks in to onboard and support customers.
  • Asana ($42/mo) – Support. Convert customers emails to Asana tasks and discuss internally.
  • Dropbox ($17/mo) – Content. All docs and screenshots are stored in the cloud.
  • DocuSign ($21/mo) – Contracts. We speed deal closings by sending Docusign docs.
  • Skype ($0/mo) – Support. We use Dossier to click-to-call via Skype.


Leadgen: Marketing Stack ($349/mo)

Our marketing strategy combines writing insightful articles and targeted email offers.

  • WordPress ($0/mo) – Blog. We installed WordPress on our servers, it’s faster.
  • Lead411 ($209/mo) – Contacts. Lead411 is an inexpensive, though small contact database.
  • SendGrid ($100/mo) – Email. Sendgrid is a newer player in email marketing.
  • Adobe ($40/mo) – Docs. We use Robohelp and Photoshop to create our documentation.


You can pare down your Sales, Service, and Marketing tech costs.

Specific ways to cut your costs, no matter how small or large your business is:

  • Tiny Business ($47/mo) – If you are a tiny business or freelancer, here are the essentials that you need:
  • Small Business ($750/mo) – If you are a small business, you can use most of the tools in the stack above, but drop Facebook Ads, Google Ads, Salesforce, Lead411, and SendGrid and a few more to bring your cost down to $750/mo.
  • Medium Businesses ($1,108/mo) – If you are a larger business, there are many ways you can cut costs. For example, instead of $200/mo on commercial blog software, you can use WordPress for free, instead of using expensive marketing automation software for $4,000/mo you can use Dossier ($95/mo) and SendGrid ($80/mo), and instead of using ticketing software for $400/mo you can use Dossier ($95/mo for your entire team) and Asana ($42/mo for 10 people).

Rather than writing yet another How Your Startup Can Survive the Downturn blog post, we wanted to share our strategy for reducing technology costs for sales, marketing and service teams.


About Vik Chaudhary

Vik Chaudhary is the CEO of Dossier ( in San Francisco. When you sign up for Dossier, he’d love it if you would say hello, and he will respond immediately whether he’s online, on email, or (always) tapping away on his phone. In his copious spare time, Vik–well–blogs.

Dossier is an app for organizing customer conversations, no matter where it happens, with zero disruption to the ways you already communicate. Based in San Francisco, Dossier is helping business owners, business professionals and teams around the globe intelligently sync their customer communication channels and organize documents, tasks and more. Welcome to a new way to build better customer relationships and a better business. Sign up for a free account today at

It’s an App, App, App, App World

In the 1963 movie classic It’s a Mad, Mad, Mad, Mad World, a story sparks a madcap cross-country rush to find some treasure. In today’s business world, where all employees, customers, and partners use a variety of software applications, sales teams could very well go on a dizzying ride to find the right tools to sell, support and market to their SaaS application users. Or, you can read this article.
If I asked a SaaS salesperson whether an application were different from an organization, you’d look quizzically at me. “Apples and oranges,” you would say, “they aren’t the same things at all!”. That’s right, say applications and you think of Salesforce, Oracle, Netsuite, SAP, New Relic, SAP or one of the 1,000 SaaS players in the marketing technology Lumascape. And organizations are entities, such as a business, institution or an group, that has a collective goal and is usually linked to an external environment. So if these are so vastly different, then why do SaaS sales teams use the same tools when selling to people who use applications as they do when selling to people who belong to an organization?

Phone, Email and LinkedIn are Sales Tools for Organizations

If you are selling aircraft parts to a manufacturer, it makes sense to use tools that most effectively allow you to reach your target market. You’re dealing with an organization that has a structure – divisions, titles, and gatekeepers. By all means, using the phone to effectively walk the phone tree, discover the the way to the right people, and leave messages. Guess their email addresses and send them emails, or subscribe to LinkedIn and use an InMail. And if they don’t call you back right away, reach out appropriately, get in touch with an influencer, and leverage your way to a meeting. This approach to sales has great adherents, and are appropriate when working with organizations. Inc. Magazine’s 10 Greatest Salespeople of All Time lists methodical and persevering sales leaders, including Larry Ellison, at whose arms length I learnt how Oracle marketed and sold its products during its growth years when it went from a 1,000-size to a 50,000-strong company. My favorite story there is about Joe Girard, the car salesperson, who felt that “Sales operated according to a law of averages all its own. The more doorbells he rang, the more money he made.” A fascinating read is Harvard Business School’s John H. Patterson and the Sales Strategy of the National Cash Register Company, 1884 to 1922., where the salesperson has a 4-stage process: the Approach, the Proposition, the Demonstration, the Close.

But when your buyers are evaluating or using applications, many of the rules have changed. And the phone, email and LinkedIn are not as relevant as other tools. Here are the new rules of sales in the world of applications:

#1. The Test Drive is Always Happening

When you sell a car, as a salesperson you control the test drive. You offer it when you feel that the prospect is ready for the demonstration. However, when you sell a SaaS application, then more likely than not your company offers a free trial. It’s as if the consumer had walked on to your lot, and Open Sesame! The doors of the cars were unlocked, and off he went, leaving behind a cloud of dust. All you know is that the prospect has anywhere from 14 to 30 days to drive the car as he pleases and then return the keys to the dealership. The evaluation is always happening, and there’s a well-defined system in place that your Marketing and Product departments have honed.

#2. The Drivers are Semi-Professional Racers

Many prospects who sign up for a trial are, if not already expert, extremely educated about their needs and your competition. If you are selling application performance monitoring software, then the chances are that the buyer is somewhat of an expert in translating performance metric to business outcomes, or in internal performance monitoring tools. You know that 7-step tour that your Marketing team spent months perfecting and gets emailed to every contact? Well, great for the newbies, but honestly, there’s no such thing.

#3. Evaluation is a Team Sport

Unless you are selling Turbo Tax or Tax Act Online to the individual taxpayer, most SaaS evaluations are managed by a team. If you’re selling a departmental application, e.g. marketing automation software, then there will be a Director of Demand Generation, a data science analyst, a product marketing manager, and a marketing technologist involved in the evaluation. The thing is, perhaps only one of them signed up for the trial. You can use organizational tools like the phone or email to discover who the other evaluators are, but by the time you do, you might actually have missed the first 3 critical days of the trial. Use social software as part of your trial that encourages users to invite other evaluators to the table. Here’s an example of a social invitation that you can use in a trial – clicking it should simply allow the user to send an invitation to others to come join him in the evaluation of the software (and, preferably, provide them with a login as well).


So What’s a Sales Gal (or Guy) To Do?

First, recognize that you’re living in a world of Application Users – and that it’s a different world from your physical Organization. Use sales tools that are more appropriate to the behavior of the application user, allowing for a selling experience that is tightly integrated with your SaaS application.

icon_analyzeAPPLICATION ANALYTICS – Ask your product managers to evaluate application-centric analytics tools like Mixpanel ($150-$2,000/mo) or Totango ($1,500-3,000/mo). Our organization has years of experience using Totango, as we have over 50% of our customers who use it, so also feel free to ask on this blog or contact us at This tool is primarily used by Customer Success , Product or Data Science teams.

SALEicon_segmentsS SUPPORT & ONBOARDING – Your application users are online, using your application, so should your onboarding tools. Use Dossier ($45-$250/mo) to automate the onboarding process, send timed in-app messages, and provide real-time support that is integrated with 25 SaaS applications including Salesforce CRM, Zendesk and Totango. This tool is primarily used by Pre-Sales, Sales Engineers, and Customer Success teams.


AUTOSEND EMAIL AUTOMATION  – Automate the email messages that you send to your application users. Yes, this flies in the face of our admonition not to use email, so either use an all-in-one tool that does both in-app and email onboarding like Dossier, or at least an email-only tool. There are many tools for sending drip campaign emails, from Autosend ($59-$399/mo), and SendGrid ($79-$399/mo) to Marketo ($1,395-$2,995/mo). These tools are mostly used by Marketing teams.

icon_integrateCRM WITH INTEGRATIONS – If you are a SaaS application company, you will be integrating your account information with other sales and billing tools. The best CRM product for your use is Salesforce ($300-$3,000/yr), particularly because it ties into so many of the other SaaS tools you will be using. Yes, there are a lot of new, modern CRM tools like RelateIQ (also from, but at this point I recommend Salesforce. This tool is used mostly by Sales teams.

If you use application-centric sales tools, then the benefits will roll in. You will accelerate sales because you are able to engage with all evaluators of your application, not just the person who signed up. You will increase retention, because the in-app tools help you foster an ongoing relationship with application users. And you will deliver innovation faster, because you will have a clearer understanding of what drives your application users. So drop your carefully crafted emails and incessant phone calls, and welcome to the world of application-centric selling.

Thor’s Hammer for SaaS Sales

Successful SaaS salespeople have a secret weapon, just like Thor had his hammer. At my previous SaaS company that we sold for $400 million this one principle carried us through the years of exhilaration and turmoil that any company that goes from startup to IPO will go through.

Picture this. You walk into a car dealer looking to buy a new hatchback. You test-drive the car and like the feel of the vehicle. The sales rep tells you everything in exhaustive detail about that car, and answers questions. You walk feeling good about the hatchback, but don’t make the purchase. Something isn’t right.

You walk over to a competitor’s showroom to look at other cars. While test driving one, you develop a great rapport with the sales rep who, through active listening and targeted questions, understood what you were really looking for. The sales rep recommends that you try a smaller SUV model. That evening you drive out of the second dealership in an SUV instead of a hatchback.

What changed your mind? Somewhere during your second experience, you realized that you could trust this sales rep, and hence the company, a lot more than the previous one. Your first impressions immediately tilted your preference.

Building customer trust is fundamental to quicker sales and higher revenue. It is just as important to have a customer believe in who they are buying from, as is the product in itself. When a customer feels personally invested in an organization or vendor, they are less likely to break away during the sales cycle or even after a sale.

Here are some methods that work for sales teams when the “trust” factor comes into play.


Ask any customer what their favorite topic of conversation is. Their secret answer is always – me. While a sales representative spends hours on preparing detailed explanations on every aspect of the product so they can provide the customer with all the information necessary for making a purchase, what a customer sometimes really wants is to see how this particular product will solve their one pressing problem or issue.

Asking the right questions, paying attention to the customer’s today’s burning problem and working with the customer to formulate a solution with the product in hand will really help your customer stop picturing the sales rep as – well, a sales rep.

What your customer needs is someone who will understand their challenge and help them get through it. They will instantly warm up to someone who wants to actually help versus someone with just a sales hat on.

Proactive Engagement

A sales rep probably has dozens (or more) of prospective clients he is selling to at any given point. Being proactive will give him the edge that sets his organization apart. A proactive sales person is organized, knows exactly what all his deal situations are. A proactive sales rep is thorough; he does his homework before and after his client meets to understand everything about the customer’s business and their challenges. A proactive sales rep is a self-critic and has foresight, loves to test his own product’s limits and reports any likely issues that could impact his deals. A proactive sales rep never lets a deal go to sleep. He ensures prospective clients don’t forget him easily, and he does this simply by keeping in touch, so even if a customer doesn’t have a requirement now, he is who the customer will first think of when there is a relevant need.


Nothing turns away a customer faster than watching a sales rep hide something that is obviously a glaring problem. Acknowledging an issue upfront takes away so many unwanted side effects that could surface from trying to pretend it didn’t happen. Whether a problem is in the product itself, or in the contract, or in the solution satisfying the customer’s need, being honest about one’s errors could have a positive impact on a sale, where a customer believes that this is an organization that is transparent and will not take them for a ride.

Most of the times, they just want to know what is going on and aren’t really looking at the issue as a show stopper, unless of course the sales rep blunders by being dishonest. An honest attitude will only reinforce a customer’s trust in the product and organization after a sale, when they see that this company does not tell one story before a deal and another soon afterwards.

Keep it real and keep things transparent for the customer!

Service Quality

It is just as important to retain customer trust as it is to earn it when they make the purchase. The relationships that are built during the sales process are sometimes the ones a customer wishes to fall back on even later. Ensure that the organization has a very forward support team that you can direct the customer to, a team that is not just looking at closing tickets quickly, but one that exhibits ownership and hand holds customers all the way to the solution.

Customers who learn to trust the organization with time not only become sticky and don’t leave easily, but they also become great referrals, thus leading to increased business and hence to the success of a company.

A sales rep who learns the customer’s real need through effective communication, who proactively tries to solve the customer’s problem with innovative ideas and recommendations, who stays transparent about every aspect of the product and the available solutions and who delivers exemplary service by always putting the customer first, can bring in more deals, and more often than not, these deals either turn into top end SUV purchases at the first sale or eventually become one with time.

The Thor Hammer for SaaS sales is the last letter in the word SaaS – “Service”. It’s simultaneously that obviously simple and amazingly hard for us all. I never forget, every day of our life at our company Dossier – which is the #1 onboarding software for application owners –  that we’re in the service industry first, and software company foremost. And that, dear reader, is what it means to be a Software-as-a-Service company.

From Zero to Connect in Sixty Seconds

At Dossier, our mission is that our SaaS client’s sales reps establish continuous, prompt interaction and engagement with their customers through our industry-standard, easy-to-use customer success software that helps application owners connect with application users. We’d be happy if you checked us out at


About Vik Chaudhary

Vik Chaudhary is the CEO of Dossier ( in San Francisco. To business professionals and teams, Dossier is an app for organizing communications with customers, no matter where it happens, with zero disruption to the ways you already communicate. Based in San Francisco, Dossier is helping business owners, business professionals and teams around the globe intelligently sync their customer communication channels and organize documents, tasks and more. Welcome to a new way to build better customer relationships and a better business. Sign up for a free account today at