First-time founders or CEOs typically find it hard to hire the first executives to join the team. As a founder, often without deep work experience, you have pulled off the impossible and created a product or service lots of people want to use or pay for. And you did so without any fancy executive-type people from Google or Facebook, with their expensive paychecks and reliance on process.
At some point, however, you will notice that lots of things start to break down. Communication within the company gets gummed up. Various product teams start to lose coordination. You don’t have time to get every important thing done in the day, and indeed you start to run out of time to think. Your hiring process falls apart, and it takes weeks for you to follow up with candidates. Your sales pipeline is largely dependent on you and a handful of inexperienced individual contributors—and suddenly follow-through crashes to a halt. You may try to promote existing employees (who also have no prior experience) to run various areas, and in most cases this fails or does not really help anything.
Suddenly you realize that you really need someone with more experience on your team.
Hiring executives for the first time can be quite tricky for a founder. However, once you hire your first seasoned exec who works out, you will be grateful for her presence. All sorts of things will magically just get done. People will get hired, deals will get closed, process will tighten up. It can be a wondrous experience. You will kick yourself for not hiring an experienced, high-capacity executive sooner.
“Once you hire your first seasoned exec who works out, you will be grateful for her presence. All sorts of things will magically get done. People will get hired, deals will get closed, process will tighten up. It can be a wondrous experience.”
– Elad Gil
Unfortunately, things could also go badly. The executive is a bad culture fit, or is too senior for the role and spins his wheels. Time is wasted and progress lost on a poor fit—or even worse, some of the best people on your team quit when managed by someone who’s not working out.
Finding a great executive for your company can be challenging, but it’s well worth the effort. And there are some steps you can take to maximize your chances of success:
If you have a 10-person engineering team, and in 12 months it will grow to 30 people, you do not need to hire an SVP from Salesforce whose job is to manage a 1,500-person team. This person will get bored with the small job offered to her and may simply spin her wheels. She is too senior for the role.
When hiring executives, look for people who have the experience and background that would make them a good fit or hire for the next 12–18 months. Anything shorter than that and they will not be able to scale sufficiently far relative to the time it takes to hire them. Anything longer and you will over-hire and end up with someone who is a bad fit for the job.
Whatever the role, there are a few key skills and traits that you want your executives to bring to the table: