One of the best parts about having a strong portfolio filled with smart people is the wise advice that founders share with each other. In this case, one of V1’s portfolio companies has been looking to hire a VP of Sales and I asked Jon Zimmerman (@jpzimmerman), CEO of Front Desk, to share his experiences and insight on the matter.
The resulting dialogue proved so thoughtful and valuable that I wanted to share parts of it with others who might be wondering if it’s time to hire a VP of Sales.
Figure out if you need a VP of Sales or a Director of Sales
A Director of Sales is probably a sales team lead or manager in a sales organization. They can handle a team of up to 15-20 and run the “predictable revenue” playbook. If you have a repeatable sales process and just need someone who can scale transactional sales, this is the level you are hiring. They are easier to find and much cheaper.
There are many candidates out there who can run the playbook. We looked at a lot of candidates like this, including some very strong ones. However, for us, this would have been the wrong hire. We lacked even a single strand of sales DNA and needed someone who had the ability to both execute and add sales DNA to the culture.
The big question is whether you need someone who can “run the play” or someone who can “call the play.”
If you have a repeatable sales process, you can probably pull a manager or director from another SaaS company. However, if you need a VP type, then you are looking for someone very special.
Don’t go it alone
Unless you already have experience hiring a senior sales leader, then you should use a top-shelf recruiter and include a few people who have experience in the section process. I recognized quickly that I was totally ill-equipped to source and assess sales talent. Great sales leaders are as rare as rockstar developers. By definition, they are really good at selling (including themselves) and it is much harder than assessing engineers. We included the VP of Sales of another Version One portfolio company and a few of our board members on loops.
Understand your economics before you hire
If you hire a VP of Sales, I assume it is because you want to ramp up a sales team. This means you are hiring ahead of revenue. It is very easy to see with a simple spreadsheet how things can spin out of control if you get the economics upside down.
Don’t underestimate the cultural fit
I mentioned before that we previously lacked any sales DNA. On the spectrum of product-focus vs. sales-focus, we were 100% product-focus. Until recently it almost seemed like we felt bad when someone actually paid us for our service because we only saw the shortcomings.
Two months post-hire, we have a much healthier balance of sales vs. product. Mike Maples (who sits on the Frontdesk board) made a great comment in reference to moving to a healthier sales versus product focus. He pointed at Sam Osman, another board member and a very successful entrepreneur with a strong sales focus. He said, “You need to inject a single strand of Sam Osman DNA without destroying the host.” We’ve been lucky and made a great cultural fit. That said, I can totally see how the wrong sales leader can do a lot of damage.