12 Lessons in Early Stage SaaS Sales

It was late 2013. And a close friend of mine, the CEO of a seed-stage startup tapped me on the shoulder and handed me the keys to the customer-facing side of the business. I was  to launch our new SaaS model, and grow MRR from the ground up.

In short, I was thrust into a role I had zero business being in.

I had never done SaaS sales before. Never mind, launch a new freemium offering, and build a scalable sales process for a largely-unproven product. Armed with modest sales knowledge accumulated over years of partnership business development and a few short-term inside sales stints, I felt like a gladiator on the verge of being thrown to the lions.

Alex Deve, a stellar product guy, had founded and built a sophisticated recruiting platform in Whitetruffle. It was already generating “lumpy” revenue through success fees. We had decided to move to a SaaS model to scale through more reliable subscription revenue. Alex was handing me the responsibility of growing the sales engine of his business, his baby, into something sustainable.

Did he see something in me I hadn’t yet, or was this just a situation where he was tapping the next warm body, as is often the case in fledgling startups? Perhaps it was the trust he and I had developed as peers; when he and I were founding CEOs of our respective start-ups a few years prior. Or maybe it was Alex’s willingness to roll the dice; betting he could transform raw energy into tangible execution.

Over the course of the next 18 months, we were able to grow the company to $1.2MM in ARR. We built a scrappy sales and customer success team, and were able to develop an entire SaaS sales playbook from scratch.

We were learning things every single day over that year and a half. I’ve distilled some of the learnings that stood out. Here are the 12 most salient lessons I garnered (much of them through trial and error) in the intensive crash course that followed our switch to SaaS.

1) For modern industries, forget outbound cold calls.

Early on in building out our outbound efforts, I wanted to prove that we could cold call into businesses and book calls for ourselves. It must have been my old school mentality towards sales. Or maybe, it was just the fact that I was exhilarated by the idea of infiltrating an organization via phone. As a small sales team, we tried a lot of things to in order to get our prospects’ attention over the phone. The problem wasn’t our lack of creativity. (I once responded to a prospect asking me why I had called with, “Because I was lonely.” This, in turn, garnered a laugh from my interlocutor and a few minutes of bought time to make my pitch.) Nobody was picking up the phone. Our connect rates were right around 5%. We were stuck in Voicemail Land.

What learning did we draw from bumping our heads against repetitive voicemail greetings? That it was necessary for us to ask for someone’s time on the phone over email. In modern industries like those we were selling into (tech companies, for the most part), folks have become savvy at shielding themselves from undesired outside calls. The key is to grab their attention in their email inbox, and book phone appointments that way. If you’re selling into industries that haven’t adapted yet, or that are used to receiving a lot of inbound calls, like restaurants or car dealerships, you can still cold call and get people on the horn. For more contemporary businesses, you will more than likely find out that unsolicited calls are just a huge waste of time and resources.

2) It’s never too early to start addressing the top of your funnel.

At Whitetruffle, we were converting our free trials to paying customers at a 55-60% clip. We were also getting more than half the folks we spoke to on 14-day free trials. I was thrilled with the middle portion of our funnel, and our account management efforts. Yet, one thing kept me up at night: I couldn’t manage to fill our calendars with calls.

It wasn’t until we figured out the right mix of cold email outreach campaigns, calling on existing customers, upgrading free companies, and obtaining reliable referrals, that we hit our stride from a revenue and revenue growth perspective. As the person responsible for revenue, filling the top of the funnel was an obsession for months until we reached that point. The earlier you address the issue, the sooner your sales machine is humming. And that humming will be the sweetest sound rocking you to sleep every night….

3) Hire a new rep (or a couple of reps, as is usually recommended) only when you have reached capacity yourself. Or at least 80% of it.

When you’re the first sales hire, there is a temptation to want company. Sales feeds on competitive camaraderie. You find yourself hitting the phones and doing well yourself, but you don’t really have any teammates to share your successes with. Or someone to confide in when a call has gone South. It can be feel like a lonely existence when you are the company’s sole point man in sales. But you must resist the temptation to hire until you reach capacity, or close to it.

This will accomplish several things. One, it will allow you to build the beginnings of a sales process, you can then teach to your sales hires.

Second, it will allow you to get a loose approximation on what capacity is for any sales rep. For example, you will know how many calls per day you can handle at most.

Third, you will get a good feel for the productivity odds and ends; like how much time you might need in between calls to properly enter the previous call’s notes into your CRM.

Lastly, and most importantly, it prevents you from hiring someone without having a clear understanding of how to sell the product, or without having an idea about how to generate opportunities.

4) Push for annual contracts early and often.




One of my great regrets at Whitetruffle is not pushing for annual contracts more strongly. Recruiting is a very seasonal business. We knew, for instance, that January and September were very strong months for us, and for the recruiting industry as a whole. Folks hire a lot during those periods and need a sourcing tool like ours to meet with technical talent. November and December tend to be on the quieter side. Activity on the platform would drop in those months. Customers would naturally flock to us in high recruiting periods and hibernate during quiet months.

We had larger enterprise customers who needed to source year-round for a large selection of tech roles. Those companies were happy to pay us a hefty monthly fee, for a steady stream of qualified tech candidates.

Our smaller customers, on the other hand — folks that might only have a couple of tech job reqs open at any one time — the monthly fee we charged was meaningful. It might not make sense to pay it if they were not actively hiring. Those customers had a high risk of churning.

In order to combat the cyclical nature of the business, we used to evangelize the “Always Be Sourcing” motto to internal recruiters. Even if you weren’t currently hiring, there was a strong argument to source nonetheless. The quieter times gave you an opportunity to develop an extensive candidate network by continually sourcing, and getting to know your candidates more intimately. If you know your candidates’ motivations, desires, and ambitions well in advance, you could close them over a phone call, once you are indeed hiring. That thinking only worked part of the time, however. Some internal recruiting organizations saw the value in being proactive. A good chunk regrettably decided to let human nature take over. They stuck to their guns and used us on an as-needed basis. I’m 100% convinced annual contracts could have mitigated churn in those instances.

5) Find ways to control the sale.

One of the big lessons I learned early on was that I needed to control the way the sale was going to unfold. We had decided to structure our SaaS offering with a 14-day free trial that was activated by entering in credit card information. I had been advised that we perhaps didn’t need to demo the product by one of our founders. “This isn’t an enterprise sale”, he had told me. With that in mind, I started chatting with prospects on an introductory call. I qualified the prospect and got them excited about the free trial. Folks generally sounded enthused on the other end of the line when I spoke to them on the intro call. Few companies could refuse the high-value propositions we peddled: access to more software engineers.

When I sensed they were excited about the product, I naively told them to just get started with a free trial, and that I would follow up via email with additional information. Can you guess what ended up happening?

Many of the prospects got lost in the ether and never ended up signing up with us. I was initially dumbfounded. All of these folks had shown a lot of buying signals on our calls. They clearly needed software engineers. And fast. Yet, they didn’t manage to budget the few minutes required to sign up for a free trial.

I needed to find a way to institute a forcing function to get them to do so. I pondered the question for a while. I was going to have to lead the horse to water. But how? After a few days of mulling it over, I instituted a call that was going to act as a forcing function. The call was going to be pitched as an “Account Optimization Call”, in order to “properly get you set up on your new premium account”. In exchange for a full product walk-through, and a detailed explanation of the platform’s bells and whistles, I was making sure the caller would enter their CC info and start their 14-day free trial. Once I instituted this Account Optimization Call, we rarely lost any interested folks. And we didn’t need to spend any money on screen-sharing software. Folks would unlock their free trial of the premium product and I would take them through it with my admin access. Prospects were happy to get a full product tour, so they could leverage the premium side of Whitetruffle to its utmost and hit the ground running on their free trial.

I was thrilled to lock them into a free trial with a credit card to charge after the 14 days were over. Still, about a third of my Account Optimization calls started with folks who hadn’t yet started their free trials. They were apologetic on the phone, “I’m sorry, Paul, I haven’t had the chance to move things along.”  I’d respond, “No worries, whatsoever. We’ve budgeted thirty minutes for this call. We’ve got more than enough time. I can hold, if you need time to enter in your credit card information.”

6) Train your reps in Save Opportunities.      


In SaaS, the value of signing on a new customer is just the same as saving a customer that has been threatening to leave you. Yet, very little training is usually included in the Sales Playbook, that will show you how to save customers. Sales playbooks are usually geared toward customer acquisition. Very few playbooks actually tackle the issue of saving accounts that are on the verge of leaving you. Save opportunities are challenges in their own right. They take a high level of empathy and attentiveness. And although you can have folks that are naturally gifted at saving accounts, it is something you can teach, with the appropriate patience and training. The key is budgeting the time in your training to get your sales reps up to speed in that department.

The term has been getting plenty of press, but it bears repeating here. Empathy is a major component of saving sales opportunities. If the customer feels like you feel her pain, she is more apt to give you another chance. It’s about teaching your reps to be engaged listeners. The first step to instill in any rep faced with a saving opportunity is to find the cause or root for the disappointment. As your reps are getting the elements of the customer’s dissatisfaction, train your reps not to respond immediately with solutions. Doing so will make the customer feel she is not being heard. And it might even sound defensive. Have them pay attention to the customer and make them feel cared for. It is crucial to take copious notes, during this process. This will enable you to respond to each point once you’ve taken in all of the customer’s gripes and perhaps present ways in which you can make the service better for them in the future.

During the save opportunity, the rep’s job is not to convince the customer that they have the best product or solution on the planet. The key is convincing them to stick with you a little while longer so you can turn the corner together. A strong sell at this critical juncture will feel forced and will sound dissonant to your customer. Don’t forget: your customer has the intention to leave the service. The rep’s mission is to paint a picture as to why things will turn around. Obviously, this is a great place to conjure up any best practices, particularly if they haven’t been used during the time when the service didn’t live up to expectations. For example, at Whitetruffle, when companies weren’t getting much love or interest from candidates, we offered to help them beautify their profiles. This was our equivalent of a dating coach giving a client a much-needed makeover. “It looks like you haven’t included funds raised in your company profile. While we understand that some companies are not comfortable publishing this information, companies that do actually get more positive responses from candidates. It gives them the reassurance that you’ll be around for the long haul.”

Before long, you’ll start noticing that it’s easier to save an account than to close a new one. And your churn rate will decrease accordingly.

7) Hire a rep with early-stage experience.

You might see “Salesforce” or “Oracle” on a CV and think it guarantees a candidate has the right chops because she has been through a sales powerhouse. These are mental shortcuts used by recruiters when evaluating resumes. What are brands if anything but mental shortcuts? When you go to a McDonald’s worldwide, you know exactly what you are getting, whether you order your Big Mac in Paris, Tokyo, or DesMoines. The same goes with Starbucks. Or Louis Vuitton. Brands exist to reassure us, that yes, we will be getting what we expect. Brands, in these instances, represent an implicit contract between the consumer and the business; a guarantor of sorts, for the standards set by the business.

With sales rep CVs, “Salesforce” or “Oracle” are branded as well. They tell the recruiter that the salesperson in question has been able to withstand the training at these sales-based organizations, and has more than likely learned some fundamental sales skills. The problem is they don’t address a set of skills that are unique to early-stage SaaS sales. Folks with large organization sales experience are used to being part of large-scale processes. They are used to things being handed to them.

Like getting leads or opportunities handed to them on a daily basis.

Within those large companies, a sales rep’s only worry is about taking those leads or opportunities and moving them forward: from qualification to close.

Working at an early-stage SaaS company means you’ll get a basic process — if you’re lucky — and little-to-no no hand-holding. A lot of times, early-stage existence is about making something happen out of nothing or devising ways that will get you through adversity. It is about taking on a new initiative and running with it. Or picking up a broken process and fixing it.

Nothing about working at large sales organizations will teach you these skills or inner dispositions. That’s why I would rather pick someone who has worked in the early-stage startup world than someone who has worked within proven sales organizations. I want someone who thrives in chaos, who takes initiative, and who has the wherewithal to pick things up that are broken and fixes them without asking for my permission. Or begs for forgiveness later.

For early sales hires in SaaS startups, I will always favor folks who have, for example, done partnership business development work in early-stage startups over someone who has done SaaS sales at a large company.

8) Make sure data is being entered properly into your CRM.

This one seems pretty obvious but it bears repeating in the case of early-stage startups. We have all heard of the rogue sales rep who closes a lot of deals but doesn’t enter information into the company’s CRM. This person ends up holding on to his job only based on his success on the ultimate sales scorecard: substantial revenue generated for the company. That’s because data entry is such an integral part of a sales rep’s job.

You might ask why. Shouldn’t the salesperson worry exclusively about closing deals and bringing in revenue? The answer: a resounding “no”. And here’s why. Data entered into a CRM isn’t just meant to sit there. It is meant to be leveraged in two ways. First, the entire sales organization needs to know how a particular deal is going. A sales manager needs to be able to step in and help out the rep, if he reaches a point of friction. A fellow rep needs to be able to look into an account to make sure she isn’t stepping into any toes when selling to a different department within the same company.

Second, and most importantly, all data entered by individual sales reps is aggregated into analytics leveraged by the Head of Sales and other executives to steer the overall business. If data is not entered, or not entered properly, then the Head of Sales and other executives are left steering the business blindfolded. In high velocity sales models — like the one developed at Whitetruffle — it is critical to get a steady stream of clean data as it is used to make adjustments to the business on a weekly basis.

At a large organization, if one of your 1,000 sales people doesn’t enter data, it might not affect the way you do business very much. At an early stage start-up, if one of your two sales reps isn’t entering data in your CRM, you are losing half of the data you are relying on to make business decisions.

Losing such a data input simply isn’t negotiable. If one of your early stage reps isn’t entering data in properly, it threatens the business, and should call his or her employment into question.

9) Don’t bother with Salesforce until you have a basic sales process in place.


Some people will tell you that Salesforce needs to be implemented once you’re ready to launch your product. That’s inaccurate. At Whitetruffle, we didn’t migrate to Salesforce until we had passed the $1MM ARR plateau. And I don’t think it slowed down our growth one bit.

Let’s face it, Salesforce is the dominant CRM for two main reasons. One, it provides a rich app ecosystem, for add-on bells and whistles to the cloud platform. Two, once set-up properly, the data reporting can be a very powerful function.

At Whitetruffle, getting the rich analytics up-and-running enabled us to nail our outbound cold emailing initiative, for example. What folks rarely talk about is the amount of front-loaded work necessary to set-up Salesforce properly. At Whitetruffle, we called upon a team of consultants that helped us set-up our instance. And I was investing a ton of time as well.

This time investment is significant, and if you aren’t generating revenue already that’s the only thing you should be focused on. Your first customers are your toughest to close. It’s likely that all of your energies and brain power will be needed in getting those first clients over the line.

I would recommend implementing Salesforce once you’ve got a basic sales process in place, and that you’re ready to invest the required time and energy. There are plenty of SMB CRMs (Close.io, RelateIQ, BaseCRM) that will allow you to hit the ground running when you first launch your product.

Additionally, if you haphazardly set up Salesforce early, at some point it will cost you months to fix what you set up as broken in those early days, just like engineering technical debt.

10) Select your signals for churn. And start tracking them very early.

The most beautiful thing about SaaS is that — if you keep churn under control (and that can be a big “if ” for some) — you are constantly building revenue. Sound account management therefore should be about controlling and minimizing churn.

Let’s borrow liberally from early stage product development.

The discipline stipulates that you are should uncover the metrics that drive your product. It’s important to lock into 2-3 metrics that will be the index for the overall health and growth of your product. Those metrics are monitored very closely and your product team will be judged on its ability to deliver against them. In early stage product development, you might not lock into the right metrics right off the bat. It might take a couple of stabs, and some iteration before you get just the right data to monitor on a continual basis. The same pattern applies for account management and churn mitigation.

At Whitetruffle, we started looking at very simple metrics. At first, we would track things like “Logins over last 30 days” or “Matches processed over last 30 days”. To us, these were good early signs of engagement. As we got more sophisticated, we realized that a good indicator for the experience employers were having on the platform was the number of intros they would get to candidates over time. We started looking at monthly intros, and then realized that this time frame was too wide. Customers were likely to drop off if they didn’t get any intros on a weekly basis. So “Intros last 7 days” became a much more relevant metric. Monitoring it allowed us to be more reactive with our customers. A lack of intros over 7 days would send us a red flag. Our account managers would reach out to the customer in question, and ask if everything was going well for them. A lot of times, this opened up a productive dialog with a customer; a conversation that would enable us to better serve them in the long term.

11) Your identified Decision Maker might not be the best way into organizations.

Whitetruffle is a sourcing tool used by internal recruiters to generate tech candidate flow at the top of their recruiting funnel. It doesn’t take much brain power to surmise that you should be selling to the Head of Recruiting. Yet, talking to these Recruiting Czars didn’t end up being our preferred way into organizations. If we had our druthers, we would rather go through the CTO or VP Engineering. Why is that?

There are a few reasons. First, CTOs were seduced intellectually by Whitetruffle. We were solving a very human problem — matching the right companies to the candidates most likely to want to talk to them — with an algorithm that looked at 50+ core signals. That kind of problem solving appealed to the vibrant minds leading tech teams.

Second, CTOs were the most likely affected by a lack of sourcing. When a CTO commits to product deliverables, it is his derriere that is on the line if he can’t deliver on time. Delivery on product milestones is usually a function of technical team size. And Whitetruffle, as a sourcing tool, was (rightly) viewed as a catalyst for technical team growth.

Third, CTOs carry a lot of clout within a tech company. We noticed that once we had buy-in from them on our solution, adoption within internal recruiting was immediate and seamless.

The fact of the matter remains that we talked to both Heads of Recruiting and VPEs/CTOs. And both were effective ways in. But, if we had our choice, the tech leader was the person we would want to get in front of, as it would expedite the sales process.

The overriding lesson is this: before locking into one way into an organization, be as broad and open-minded as possible about how you might infiltrate the fortress. By testing different ways in, and chatting with a varied group of decision-makers, you might stumble on an easier way in to rescue the princess. And you won’t be as spent when you get to her.


12) Set expectations for what represents success (particularly during the free trial period).

In sales, you are taught the importance of setting expectations. Without doing so, you run the risk of having a prospect complain about your service, while you were delivering on the initial promise. Sometimes prospects don’t even know why they aren’t satisfied with you. They will make excuses and might not even be able to articulate why they aren’t continuing to work with you. However, if you make the expectations clear and have them agree to them before getting started, there is no denying them later on.

And guess what? Even if you happen to be a bit shy of them, they might decide to work with you, because you fell short of expectations by a very small amount.

Now, how did we go about doing that at Whitetruffle? In our Account Optimization call, we would tell prospects they could expect 3-4 intros to candidates during the 14-day free trial. It’s a mark we were pretty sure to clear. It therefore positioned our free trial offering favorably in the customer’s eyes. And it contributed to our success in converting our free trials to paying customers at a very high clip: 55-60% of the time.

Eleanor Roosevelt famously said, “Learn from the mistakes of others. You can’t live long enough to make them all yourself.” During my time at Whitetruffle, I felt like I was operating from within a sales lab. I was afforded the freedom to run experiments — large and small, conventional and off-the-wall — in order to grow revenue. We made plenty of mistakes in building out our sales model. And we learned a ton from those errors. Hopefully, you’ve been able learn from some of my blunders. Over time, you’ll make a few of your own. And as the former first lady suggested, until we find the secret to eternal life, we’ll invariably be looking to you for the learnings from those faux pas.