4 Gems learned from leading B2b sales in a software start-up

Key values to build your enterprise sales motion on.

The start-up life is such a grind and truly rewarding. I feel very fortunate to look back and distill a few gems from leading our sales endeavors. For a little context, We are a lean team of four building web and mobile apps. As is with the nature of start-ups, We have needed to wear multiple hats to do what needs to get done in order to build products and get clients. I find that the experience has been rich as it affords the perspective of looking at the entire business from an end-to-end context even as one engages in sales motions.
Having launched a consumer product in 2018 and later on pivoting to an enterprise service in 2019 to date, I have had a front-row seat in contrasting the differences between enterprise and direct-to-consumer sales processes. At the moment, our sales motion is a high touch b2b flow; Focusing on enterprise and small to medium businesses.

Some of these gems are things we have failed at and are ever in the process of refining and making better. Ultimately, I believe that we have had the opportunity to grow through the mistakes because of having a strong team that iterates through our processes ruthlessly, seeking to grow at every motion. Jim Collins, in his book “Built to Last” defines great companies as clock builders and not time-tellers:

The primary output of their efforts is not the tangible implementation of a great idea, the expression of a charismatic personality, the gratification of their ego, or the accumulation of personal wealth. Their greatest creation is the company itself and what it stands for.

While sales tactics and various inbound/outbound strategies vary from business to business depending on your business model; some of these values act as north stars in our strategy implementation.

1. Empathy

The bottom line is:

Every client is different.

An empathy map

It’s super critical to treat every client with great intent and empathy. Enterprise/B2B sales are high-touch processes and offer an amazing opportunity to get to know your clients quite intimately. The punchline with approaching these discovery calls rests in ironically readjusting your primary focus from seeking to close the deal or move the prospect down the funnel but to focus on helping the prospects.
Be a genuine human. In the bulk of conversations I get into with clients and prospects alike, I always receive similar concerns or fears. Most of them are concerned about issues such as pricing, execution timelines while some are even struggling to describe the job to be done. Your work in your discovery phase is to deeply understand their problem, often reiterating their problems back to them and to address each of their concerns thoughtfully and with good context of what/how you will help their situation and bring value to them.
A good tip I have learned through the years is to actually help them by connecting them to other vendors as yourself in case the prospects you meet aren’t a good fit for your business. It is okay to pass up certain prospects and to help them while at it. The law of reciprocation holds in many other ways including referrals as people(prospects) always remember how well they were treated.

2. Punch above your weight

Doing B2B sales for me is much like strength training according to Nassim Taleb

Just as systems learn from extremes, and for preparedness, calibrate themselves to withstand large shocks, so does the human body. Indeed, our body should be seen a risk management system meant to handle our environment, paying more attention to extremes than ordinary events, and disproportionally learning from these.

What appeals to my entrepreneurial nerves every time I engage in sales calls is getting to appreciate our value as a business as we keep doing what we do. I am constantly testing the limits of aspects such as the pricing of our services. The sheer amount of insight and business perspective borne out of this practice is mind-blowing. It has really matured our business outlook and directly impacted the direction and focus of our business. One of the major wins from this is understanding your market segments and how the product assortments for each should look like. It should be codified as a tenet for every founder and entrepreneur involved in sales to ruthlessly run experiments with their pricing.
Additionally, punching above your weight entails looking for the ‘tail’ clients. You won’t lose a thing in cold emailing that CEO of the big company who you think would be a gamechanger in your portfolio. What would it look like to serve a client out of your country or one in a completely unique context than the clients you have served before? Courageously aim for the “tail” clients, the rare ones that would be consequential to your business though of ‘seemingly’ low probability.

3. Communicate

One of the most influential resources I came across when beginning our enterprise sales process was this lecture by Tyler Bolsemy from Clever
It quickly set the ground for the reality of what I needed to do in enterprise sales and it’s amazing how much I still go back to it as the lesson is timeless.
It quickly dawned on me that every sales process involves grinding through plenty of conversations. I find this ironically exhausting yet energizing especially when you begin pushing the needle in your favor.
There are a couple of tips that hold true for me to this day about communication:

  1. Persist: Be respectful and not salesy in your conversations. Emails and messages often get ignored(even from people interested in your product) and that is one thing you need to get over. Assume the best of everyone; that they may be busy or simply have a thousand and one things on their mind. Develop a culture of respectful follow up(don’t be a nagging sales bot). Seek to arrive at a yes or no in your follow up as both of them are great opportunities for insights on your sales process.
  2. Establish open and coherent communication lines: This mainly applies to the customers you are serving. In my experience, I have found people to respect your time as long as you take the lead in establishing how and through what means they can reach out to you in case of any question/updates.

Ultimately, how communication is handled is extremely situational from company to company. Your business model should determine your sales motion and ultimately how high-touch your sales process should be.

4. Watch out for your biases

In our start-up, every sales endeavor is an exercise of getting enough situational context about our prospect’s problem that we can deliver value to their situation with the confidence that we are neither overestimating our service/value nor being doubtful of our capabilities. A certain ‘fit’ sweet spot is desirable.
This has been a painful process of truth and tears for me and my team as it has made me more cognizant of competing biases that I have to keep in mind.

a. The Dunning-Kruger Effect

Illustration credits to Koos Leijesteijn

The Dunning-Kruger effect describes how people with only a little bit of knowledge about a topic vastly overestimate their own abilities. Having engaged in a slew of software projects across different industries, I always feel like my team was ripped out of MCU’s avengers and there’s nothing we can’t build(given enough time). However, two years in the game has made me appreciate the nuance that many situations hold and just how much there is to learn every single time.
One of the practical tips we are applying in our case is to be mindful of our execution timelines for projects, especially to get over mount stupid and figure out and test critical unknowns early on.

b. Information and Confirmation Bias

This bias reigned heavily on us in our early days. Information and confirmation bias speaks to the urge to gain more information about a particular topic and confirming certain hypotheses. In most cases, it doesn’t add any value to the action that needs to be taken.
This is not to clomp over doing good research on problems when you are engaging in a sales process but to keep in mind that most times you may never know the nuances of a particular endeavor/project until you have skin in the game and are in the heart of executing it.
This is where experience is a true differentiator when approaching prospects as one can quite easily overcome this bias and draw from the confidence of positive testimonials and past experiences. However, if you are starting, do whatever you need to do to start getting the experience in and consistently punch above your weight from there:).

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Dominic Mulinda
I think better with a pen in hand. I help world-changers build digital products, fast!