Passion over Pedigree

Building the first sales team

Happy Thursday, 👋

A question we often ask founders is: what is one of the hardest challenges of starting a company? More often than not, the answer is hiring the first salesperson. For many startups, the very concept of “sales” is broader than the word suggests. It’s not just about closing deals. It’s about creating a brand, finding product-market fit, generating excitement around a solution, and guiding customers through the earliest stages of implementation.

In most cases, the founder begins as the first salesperson. They know the product better than anyone and can tell its story with conviction. But that model has a shelf life. Founders can’t scale themselves, and at some point, someone else needs to take over the job full-time. This is where many startups stumble. They often turn to candidates from large companies, individuals with impressive logos on their resumes or those with proven track records of selling big-ticket items. On paper, this seems like a safe bet. In practice, it rarely works.

The reality is that salespeople from established companies are used to working within existing systems. They have marketing support, brand recognition, and a mature sales process. Remove those guardrails, and they may struggle in the chaos of a startup. That does not mean they are not great salespeople. It just means their skillset might not be the right fit for the earliest stages of a company.

Instead, the better hire is someone who is a true evangelist. Someone who sees the potential in the product, understands the customer’s pain points, and cannot wait to share it with others. This might be an initial customer, a domain expert, or simply someone with the right mix of curiosity and grit. The early-stage sales process is less about polished presentations and more about conversations, feedback loops, and persistence. At this stage, passion beats pedigree every time.

Building the Sales Team

For most early-stage companies, the right move is to bring on not one but two early sales hires who report directly to the founder. There are practical reasons for this. First, sales can be lonely. Having a partner allows for idea-sharing, peer support, and shared accountability. Second, two people allow you to measure progress and compare results. If one approach is working better than another, you can double down. And third, multiple perspectives accelerate product refinement and market understanding.

A rough benchmark: when a startup has at least 10-15 customers or over $1 million in ARR, it’s time to think about hiring a head of sales to take over the team. These initial customers often come from founder-led efforts and the scrappiness of the first sale hires who tap into their personal networks to find customers. Once this initial sales push starts to taper off, the company needs a more structured process. At this point, systems and procedures, CRM platforms, pipeline management, and sales KPIs become essential. This is also the point when hiring a more experienced sales leader, possibly someone from a larger organization, makes more sense. It’s at this stage of the company where someone with deep experience in sales can help refine and develop the process instead of building a customer base from scratch.

Embrace the Data

Regardless of stage, data is your friend throughout the sales process. Track every interaction, every meeting, and every email. After a customer conversation, take time to regroup. What worked? What didn’t? These debriefs are key to shaping the sales narrative. Early on, nothing will go exactly as planned. That’s normal. The key is to treat mistakes as learning opportunities, not failures.

Experimentation is part of the process. Test different approaches, but track results so you know what sticks. Remember that early customers are not just evaluating the product, they are also evaluating the company’s ability to survive. Even if your solution perfectly addresses their problem, they still have to decide whether it’s worth the political risk to champion a startup's solution over a more established company. Founders and sales teams need to understand this dynamic and meet customers where they are, with empathy and honesty. Ultimately, the ability to build trust during those early interactions sets the foundation for lasting customer relationships.

Final Thoughts

Early founder frustration often centers on finding the right person to fill an initial sales role. The goal is identifying someone who can carry your story into the market with genuine excitement for the product. In the early stages, it’s less about a sales pedigree and more about who can build momentum with initial customers.

Founders are builders, and most love the product side of the journey. But hiring that first salesperson is where many struggles begin. Storytelling and customer engagement require a different skill set, and filling this gap with the right hire can determine whether a product never leaves the garage or becomes a market success. The roadmap is clear: focus first on people with passion who can create momentum, capture data along the way, then build processes that enable scale. The right early sales hire brings passion for the product, and that passion not only draws customers in but sets the stage for a company that can grow with confidence and purpose.

Wishing everyone a great weekend,

-Eric.