The Power Of Founder Led Sales

It’s an unfair advantage. Do it while you can still sustain it.

Casey Dai

Jan 10, 2024

TL;DR

Founder-led sales, when executed correctly, is when ‘small’ can consistently beat ‘big’.

Level Setting Before Starting

“Sales” is a loaded term — filled with thoughts of a slimy second-hand car salesperson.

I have no idea how this became the default persona for most people, as I’ve yet to meet a slimy second-hand car salesperson IRL.

On a more serious note, in terms of future-proofing your skills, sales is certainly in the conversation for what’s at the peak of Mount Everest.

If we shorten the time horizon used to measure the value of a skill to less than 3 months, sales probably end up as the uncontested winner — dethroning accelerated learning and critical thinking, which I’d easily put in my top 3.

First, let’s reframe “sales” in a more objective lens. I view sales as:

Interactions within a matchmaking process to close a supply-demand gap.

Let’s closely examine the word choices used here.

Interactions: it strips the emotionally charged aspect that comes with words such as pitching and steers it towards having a conversation, which is how it should be.
Matchmaking process: the conversation is built around mutual discovery, meaning it’s curiosity-driven for both parties to get a sense of the overlap between supply and demand.
Supply-demand gap: sales is one of many tools needed to solve this problem. It’s simply how things operate under a capitalist structure. Consider seeing it from a utility perspective rather than a morality one.

Founder-led sales are something my wife and I are living and breathing on a daily basis, as we’re running two bootstrapped owner-operated companies.

Given the circumstances, we encounter well-established companies with better-known brands in almost every single sales interaction. On the surface, it looks like the odds are completely stacked against us, and to some extent, it is.

That doesn’t mean there is no competitive edge to leverage here. The not-so-secret-secret to beating the odds is what Founder-led sales unlocks.

Sure, it doesn’t scale, but that’s not where your head should be to make it out of the early stages of entrepreneurship.

Next, we’ll examine why Founder-led sales give such a big edge over larger competitors.

Eliminate The Principal-Agent Problem

The larger the company, the more agents you’ll need to operate on your behalf — the sales function is no exception. Naval Ravikant gets to the core of this problem in this post.

In essence, you can only share so much upside in equity or rev-share to make everyone a principal with aligned incentives and high degrees of ownership.

The breaking point is around a max of 20 people since anything below 5% equity starts to decrease in effectiveness.

As a solo operator or even with a co-founding team of 2-3, you’re basically all-in on delivering the outcome, without needing any policy or governance mechanisms for dealing with the principal-agent problem.

The sales interaction is where the rubber meets the road. It’s clear who’s a driver vs. who is a passenger.

Nobody Knows It Better Than You

A veteran salesperson may have better technique (for now), but you will always have more heart and soul.

Yes, you can put top salespeople on a rev-share to keep them incentivized, but they’ll never surpass you in terms of communicating your company DNA — if they do, you have way bigger problems than your sales function.

It’s most apparent when you tell your origin story — whereas in a content-led business like mine, it’s tied to the hip with the Founder’s backstory. When describing the evolution of the company’s product, it goes well beyond the benefits and features.

All that is built on an overly optimistic assumption that you have world-class salespeople. Your sales function is likely several notches below world-class, especially in larger enterprises when quality control becomes harder.

Forget “heart and soul”, most agents acting on your behalf will drop the ball at the benefits and features stage.

Tight Feedback Loop, Even Tighter Relationships

If I had to rank the options we have to conduct market research in hopes of finding the magical product-market fit, Founder-led sales would take the pole position.

Early on, you want extremely tight feedback loops and the best way to achieve that is to put yourself in between the product and the customer. Conducting a survey on “user needs” is ok, but it feels like softball compared to trying to actually land a sale.

Real stakes for real feedback — nothing beats introducing money to the equation.

Additionally, you’ll build a deep relationship with your first group of customers. Relationships and referrals are one of the few competitive advantages you can realistically create early on vs. more established players in your industry.

Not to mention, relationships are the most defensible leverage, especially in the early stage, as everything else can be replicated at scale by someone with more resources than you.

Some food for thought before we wrap up.

The sales you make are a lagging indicator of the work you put in previously. Often times it’s that work you put in 3 months ago when you feel like you’re in the gutter.