Your startup is growing. You suspect you have initial product market fit. Time to hire the first head of each department. Sales, marketing, customer success, engineering, product management. Some founders might have experience or exposure into one of these teams. But rarely do they understand every one well enough to hire the right department chief. How should you do it? I've observed three successful strategies.
First, do the job yourself. Great managers manage themselves out of a job. By doing the work yourself first, you'll know exactly what the role entails and what questions to ask. You'll have the experience to judge whether a candidate can outperform you in that role. This is a common strategy for sales. The founders confirm product market fit with the first 10-20 sales and then hire an expert to scale the team and polish the process.
Second, enlist experts from your network and your advisors. Some founders ask advisors to interview candidates directly. Others ask experts to sit through a few interviews to coach, and share observations about candidates. With this strategy, the key is to continue to solicit advice from advisors and experts about how to manage the new leader from those experts after they have been hired.
Third, experiment in a high-velocity, low-cost way. Some founders prefer to hire entry-level teams to staff a new department. They select people who can figure things out, rather than those who might have a track record in the space. The hire and fire quickly until the right person is found and then promote from within.
I've seen each of these approaches work. Tradeoffs exist for each one. Some require more investment of a founder's time. Some skew for more junior teams. Some require substantial coordination. Which one is best for your business is a judgement call.