Hiring Your First Salesperson

I was recently asked about this topic by a talented first-time founder/CEO and decided to post this excerpt from my response.

So you want to hire your first salesperson?  As founder of your company, you have raised some initial capital, recruited your initial development team and even gotten your product to a beta level.  Now, you’re talking to customers and starting to sell in earnest.  This is a pretty important milestone and decision for you and the company.  Here’s a couple of tips based off my own experience.

  • If your background isn’t in sales, then you should find someone whose background is to help you hire the right person. Salespeople interview well so if you don’t know how to cut through that you’re in for a ride. But the key is to find someone who’s hired 100+ sales people and sales managers in their career and leverage their experience. Put them on your advisory board and interact with them frequently.  You might even retain them as a "buyers agent" to help with recruiting.  Ask them to do actual interviews and help source candidates as well.
  • When in doubt, "hire junior."  Except in rare cases, it is probably premature to hire a VP of Sales that you’ll keep for 2+ years. You want someone who’ll be out in the field selling and bringing back customer feedback (and sales!) probably more of the former in the first year. Terry Gold wrote a good on this some time back.
  • Depending upon how far along the product is, you may also want someone who doesn’t fit the classic sales mold. Ideally, the person who you hire will come back and help translate why the “customer said no/not now” (or "yes" for that matter) into new product features/pricing/packaging. Someone who has product experience or maybe even someone who once worked on a help desk for a product selling into similar firms could work.
  • Read and re-read the “” by Mark Leslie. While it’s not directly relevant to every company, the principals are the best I have seen on how to bring a new product to market and who to recruit to do that.
  • In terms of structuring compensation, be careful not to apply a classic sales compensation package. If you hire someone with a comp package of $70K times two with commission on sales, you’ll end up getting pulled in a direction you may not want to go. In my experience, the right compensation package is a base plus discretionary bonus that gets them to an on-target earnings you both are comfortable with. You’ll want to agree with them to review the metrics every 3-6 months. Put them in writing. To pull this off will require establishing some trust between you and your new hire. Take the time to develop it.
  • I would stay away from hiring through traditional job boards for this position. Assuming you don’t know someone already, I’d place an ad on LinkedIN jobs and also spend a bunch of time doing searches on LinkedIN for people who might be a fit or who may know someone who would. You will want to upgrade your LinkedIN account so you can do searches and send intro notes (costs a couple hundred per year for a biz account, I think).  Network with sales people you admire. Call some of your customers/beta users and ask them who are the sales people or companies whom they admire. I found this to be a great source of candidates early on.