All founders start their companies leading the sale. It's a rite-of-passage for any founder, but the transition away from this, done badly, can steal a huge amount of momentum.
(This advice is specifically for enterprise sales where the ticket size is >£100k ARR.)
The mistake is thinking that moving from a founder-led sale is something that is implemented in one go. When in fact, done right, it is a 3-stage transition with a gradual loosening of the founders hands on the customer engagement.
Stage 1: Founder Led
Between Seed and Series A, this stage is all about finding patterns that are the foundation of repeatability - or in startup lingo, finding your Product Market Fit (PMF).
The goal here is to show that the market is not just nodding along to your value proposition but is actually willing to open its wallet. A solid hint that you've hit PMF is bagging around 5 customers who've all bought essentially the same thing from you.
During these early days, the founder IS the sales process. Because convincing prospects to buy into a brand-spanking-new business is no small feat. Early adopters get on board because they believe in the vision of the founders, and the personal assurances of the founding team, along with the white-glove service are critical to that relationship.
Remove the founder out of this equation too soon, and the confidence they need to make that commitment will evaporate.
If a founder desperately needs additional bandwidth to run the company, getting a personal assistant, or Chief of Staff, is a better investment than a salesperson. They can amplify the founder, enabling them to be fully present in the customer engagement.
The presence of the founder at this point goes far beyond providing prospects the confidence to buy. The signals that buyers send are essential for validating features, and allowing the roadmap of the product to reflect what the market really wants. That unvarnished feedback is critical.
Stage 2: Founder Supported
Once you've clinched those first 5 sales and start seeing patterns emerge, it's a sign that your business might just have legs and you'll heading for a Series A with a well-earned sense of confidence. At this point, the founder is still in the thick of it but might only need to be in half the meetings.
This is your cue to bring on board some sales muscle - but hold your horses before you start looking for a sales manager. Hiring an expensive sales leader is NOT the best course. What you need are individual contributors who can sell with a bit of independence, but are also happy to work hand-in-glove with the founder as the business grows and learns.
Ideally the founder will book end the engagement, meaning they are in the first meeting to show commitment, and appear at the end to make commitments and get the deal signed.
It might be worth the founder getting a sales advisor at this point, to act as a sounding-board and guide them to ensure the foundations of the revenue engine are as strong as possible. In addition, coaching the young salesperson provides redundancy in making sure the deals are on the right track.
You can grow the sales team to 2 or maybe even 3 people in this phase.
Stage 3: Founder Sponsored
Now we're getting to the big leagues. When about 90% of the sales process can progress nicely without the founder having to hover.
The it's time to either bring in a full-time sales leader, or promote one of the early sales into a team lead role. The company is probably a tight-knit crew of around 50-100 by this stage, with a handful of salespeople buzzing about.
Even now, the magic of the founder's touch shouldn't be underestimated. A visible founder, even at this stage, can wield considerable influence.
The sales leader you bring into the fold should still have that hands-on approach, spending the majority of their time with clients and leading by example. You might fancy giving them a flashy title, but remember, what's crucial is their ability to connect with clients and design fantastic prospect experiences that can be repeated and scaled.
Wrapping Up
Navigating the transition from founder-led sales isn't just about timing; it's about understanding the distinct stages of your startup's evolution. Rushing to delegate sales responsibilities before you're ready can be a costly misstep.
If you're looking to scale your sales team and want to ensure you don't drop the ball and damage your momentum feel free to reach out.
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