On this week's episode of How to Unf**k Your Startup, I had the pleasure of sitting down with Alex Kottoor, a seasoned entrepreneur and business leader with over two decades of experience driving profitable growth in startups, SMBs, and Fortune 500 companies. Alex started his career at CDW, where he honed his skills in solving customer problems through technology. He then co-founded his first SaaS company, SceneDoc, which he successfully grew and exited. Now, as the founder and CEO of Dena Growth, Alex is turning his attention towards helping early-stage founders navigate the challenges of scaling, particularly around go-to-market strategy and sales. Having been a founder himself, Alex knows firsthand the challenges they face when transitioning from founder-led sales to a dedicated sales team.
In the early stages of a startup, founders often wear multiple hats, including that of the head salesperson. While this hands-on approach is necessary to understand customers and craft a winning sales formula, there comes a point where founder-led sales can become a bottleneck to growth. Knowing when and how to make the transition to a dedicated sales team is a critical inflection point that can make or break a startup's trajectory. In this episode, Alex shares his framework for navigating this transition strategically, from laying the groundwork with deep customer immersion to codifying a repeatable sales playbook to making the right first sales hires. Founders will come away with a clear roadmap for scaling sales beyond themselves while avoiding common pitfalls that can derail momentum.
Catch the full episode with Alex here for even more founder-led sales wisdom:
But first, here are 5 key takeaways from our conversation:
Alex emphasizes the importance of founders immersing themselves in customer interactions to gain deep insights before bringing on sales hires.
"If you stay in that quintessential trench, and maybe the next trench is not just with prospects, but with paying customers, guess what happens if you spend enough time in that trench? You start to learn about new problems for the same ICP that are just adjacent to the product you've already developed."
This "trench time" allows founders to intimately understand customer needs, challenges, and willingness to pay. These insights are invaluable for iterating on products, refining positioning, and optimizing the sales motion before scaling the sales team.
When making those all-important first sales hires, Alex advises looking for candidates who can handle the unique challenges of an early-stage startup environment.
"I'm talking about the pain of doing sh** on your own. There's no orchestration. There's no support. There's no sales tech stack helping you. There's no team of people helping you write RFPs and build proposals."
The ideal early startup salesperson has a track record of success in similarly scrappy, resource-constrained environments. They can thrive without the support infrastructure of a mature company and aren’t phased by having to wear many hats.
Alex cautions founders not to prematurely abdicate sales responsibilities before they've nailed down a winning formula.
"It's about getting to the point where you, as a founder, can document how you're going to swiftly onboard that first salesperson... You have to do it. Now, do you have to do that alone in a vacuum? No."
Founders must first codify exactly what's consistently working in the sales process before handing off the reins. This involves documenting key elements like the ideal customer profile, sales messaging, objection handling, and closing techniques. Experienced advisors can be a big help in packaging this up into a teachable playbook.
Technical founders who are more passionate about products than sales may be tempted to hand off customer-facing duties as quickly as possible. Alex warns this is a big mistake.
"They can't escape that. They shouldn't escape that. I don't think they should hire to try to circumvent that part of the startup journey. You will be greatly rewarded if you're a technical founder, but you're still able to rally around those fundamentals."
No matter their background, all founders need that first-hand experience engaging with customers to truly understand their world. The insights gleaned are invaluable not just for sales, but for product development and company strategy. Technical founders must fight the urge to hide in the code and shortchange this learning process.
While it's tempting for early-stage founders to want to be everything to everyone, Alex advises a ruthless focus on first nailing a repeatable formula for product-market fit and business model.
"That's how you build companies. Are you the founder that's just building a product, or are you a founder that's building a company?"
Founders need to resist shiny object syndrome and avoid chasing too many products, markets, and use cases in the early days. The priority should be developing strong, demonstrable product-market fit and a profitable business model in a core target market.
Nail it then scale it.
.svg)
