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