How Long Should a Founder Sell?
A question that gets tossed around a lot among start-up founders who are selling is, “How long should I be involved in sales?”.
Exactly how founders participate in selling varies depending on the company, of course. Some founders are the first salesperson in their startup and keep personally selling as they grow a team. Others focus on growing the team and remove themselves from actually closing their own deals.
The answer to “how long” these scenarios work is based on a lot of factors. It depends on the founder’s strengths, the team, and the company performance. It also depends on the stage of the company.
I personally sold, and assisted my newly hired AE’s with their deals, for several years as I built the sales team. I never had a self-imposed deadline for when I would stop selling. But I did have a goal (really, a mission) to hire, retain and nurture a high-performing team that would allow me to step back from running my own deals. I stopped selling gradually as I had more reps who became fully self-propelling and were managing deals entirely on their own.
It seemed like one day I had to have a hand in all the deals to some degree and then the next day contracts were coming in that I had nothing to do with. I knew then that it was time for me to step back from selling, and step up to lead.
When that happened I was able to turn my focus towards building my sales department. I created playbooks and scalable processes, I worked on coaching and skill development, I hired not just reps, but sales operations and an SDR team leader. I promoted a sales manager, who became a sales director, who eventually became my defacto sales VP.
My love of sales kept me very close to the team even as we grew. When my sales manager first stepped up, I continued to lead the team. I attended every weekly meeting, I conducted a lot of our training sessions, I led the annual and quarterly kickoffs, and I sat in almost all the opportunity huddles. My newly appointed sales manager was my wingman but I was driving. And, like my personal selling, gradually our roles shifted. I became his wingman over time, with him at the helm. It happened organically, without deadlines.
A founder who, like me, comes from a sales background may always stay very involved in sales leadership. But someone who doesn’t come from a sales background is better served by having strong leadership in place sooner rather than later. I was lucky that I had a natural leader right under my nose and was able to promote from within. That’s rare, and your first sales leadership hire is crucial.
When considering how long a founder should stay involved several factors come into play:
Company performance. Are the sales results strong? If the team is happy and stable and you are hitting your targets, then a leadership change could be counter-productive. In these cases, it’s worth being very thoughtful about how the founder steps out of day-to-day team leadership. An internal promotion, if there is a strong candidate, can be one way to go.
Founder strength. Is sales leadership a strength of the founder? If not, then likely the sales results aren’t strong and this is a moot point. A founder who doesn’t have the skills or aptitude to lead the sales team shouldn’t be in that role.
Founder drive. Is leading the sales team something the founder wants to do? Is it something she is passionate about? Again, an obvious point. It’s not sustainable to lead the sales team if you don’t love doing it.
Other responsibilities. If the founder isn’t exclusively focused on sales leadership then it will be very hard to scale past a certain point with her at the helm. Either other responsibilities will need to be moved off her plate, or strong sales leadership will need to be appointed to help continue to build on the momentum started by the founder. Sales leadership is and should be, a full-time job. If the founder can’t make it their sole focus, it’s not in the best interest of the team or the company to do it part-time.
I think rather than putting a hard and fast deadline or structure around the question of how long a founder should sell, it’s best to let the answer reveal itself. If the founder is killing it and loves it, keep things status quo. If results are suffering or the founder is dispassionate, it’s time to put sales leadership in place to drive things forward.