Summary
Jason Boehmig starts the search process for executives far before when the company will actually need them. He met his eventual VP of sales, Damon Miño, when Ironclad had only two or three employees.
Jason knew they'd need a VP of sales at some point and came up with criteria for his dream candidate: someone who had (1) worked at DocuSign or Salesforce, (2) a certain amount of sales experience, (3) a law degree, and (4) worked as in-house counsel (Ironclad's target customer). He found two or three people on LinkedIn that met his criteria and reached out cold to Damon: "I just asked for advice at first. I said, 'We're selling contract software. It's going well but I don't have sales experience and I'm looking for advice from someone who does. Could I get 15 minutes of your time for a call?'"
The call turned into an in-person meeting, where Damon made it clear that he had no interest in joining Ironclad: "Just so you know, I'm happy where I am. What you're doing is interesting and I'm happy to help, but I'm never going to join your company." Jason instead asked him to be an advisor: "I asked if I could pick his brain periodically. We'd meet once a month or quarter for a year. I was half selling him and half asking for advice." After a while, Jason gave him an advisor grant to keep him engaged: "He did really helpful things: giving feedback on our sales deck, helping me think through pricing on a specific deal, helping me come up with the profile for our first sales hire."
As Ironclad gained momentum, Jason was able to get more and more of Damon's attention: "When we first started talking, I was the only salesperson. We hired a great first AE, then more good AEs. Good customers were signing up at a good price point. We had gone from pricing the product at $200 a month to a line of sight into our first six- figure deal."
By the time Jason started a formal VP of sales search—about a year into the relationship—Damon was ready to throw his hat in the ring. But Damon's wife, also a VP of sales, was skeptical, so Jason went over to their apartment and spent an hour pitching and answering questions.
The final step was to put Damon through Ironclad's formal interview process and have him spend time with the team: "Damon and I knew each other well at that point and knew we would work well together, but we wanted to see how the rest of the team would work with him."
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