Who To Hire As The First Salesperson In Your Startup

This is going to sound difficult and run contrary to the industry conventional wisdom, but bear with me. When a B2B SaaS startup is hiring their first salesperson, I think they should look for someone who:

Is a dyed-in-the-wool seller with sales blood coursing through their veins. Their first sales job was in high school and they’ve sold anything from dictionaries to shoes to cars early in their career. When asked, “what’s your favorite part about sales?” they should say “winning.” Not “the process,” or “enabling the team,” or even “money,” but winning. You want to hire the person who will eventually rise to be a CRO managing a large team but who, when they’re approaching retirement, steps down to carry a bag for the last phase of their career — because selling, not managing, was their first love. Such people exist. Go find one.

Has sold to the target buyer before. While many sales skills are generic, you can save six to twelve months of onboarding time by hiring someone who has already sold to your target buyer. CFOs are different from CROs are different from CHROs are different from CCOs are different from CIOs are different from CDOs. Ditto for industries if you’re a vertical SaaS company. Glossing over these differences will do nothing to enhance your sales cycle. As they say in France, vive la difference. Embrace the idiosyncrasies of your buyer because to do so is to truly know and understand them. Certainly, it’s tempting to find “a sales athlete” and assume they can learn about your buyer — and they can — but you’ll lose valuable time teaching them and they’re certain to arrive with precisely zero existing customer and partner relationships for you to leverage. One day, when you’re huge, you may have to hire sales talent unfamiliar with your buyer and build an onboarding program to teach them. But that day is not today.

Has sold deals in your size range before. Size is an excellent proxy for complexity. Simply put, a $20K deal is a lot simpler than a $200K deal which is a lot simpler than a $2M deal. Find someone who has sold deals in your current size range and with some headroom above that. If 30 years in enterprise software taught me one thing, it’s this: deal size is in the eye of the beholder. The candidate must have prior experience selling deals in your current size range, but also be able to “see” how you could do deals that are significantly larger. Never hire someone who’s only done $20K deals before when they’ll be selling your $200K system.. They are going to lose a lot of deals learning the intracies of complex, multi-constituent sales cycles in large organizations. Let someone else pay for that education.

Has the executive presence to work a level above your target buyer. If you’re selling to the VP of FP&A, you want to hire someone with enough polish to meet with the CFO. Or, if you are selling to the VP of Support, you want a seller who can converse with the CCO. This characteristic is hard to quantify, but it goes by words like presence, polish, savvy, and gravitas. Simply put, if you can’t imagine your candidate in a serious conversation with your target buyer’s boss, then don’t hire them. Your seller needs to be looking across at the target buyer’s boss, not up.

Has significant first-line sales management experience. This is my most controversial criteria because with one bullet I wipe out all candidates who are currently individual contributor (IC) sellers. “But the job doesn’t require sales management! For at least a year, all they’ll be doing is selling. Why can’t I just hire an aggressive seller early in their career?” I hear you cry. First, ICs will generally do worse than experienced managers on the polish and presence front. Second, because you are about to put this seller, at a great investment in time and money, through the world’s best onboarding program: 6-12 months of being glued directly to the founder, doing almost every sales call together, doing every customer proposal together, and closing every deal together. There is literally no better sales onboarding program and you don’t want to waste that investment in someone who, at the end of the onboarding, is only equipped to go sell on their own. You want to invest in someone who can say: “Thank you for the amazing training, I am now ready to be unleashed to do what I already know how to do, which is to build, manage, and scale a sales team.” If you get this wrong, you’re stuck with two bad options: (1) promote the IC to a manager and hope they have the aptitude to succeed, or (2) hire them a boss, do a poor job repeating the onboarding you just did, and hope that they succeed and that they don’t drive out the IC you’ve successfully trained.

Is willing to join your company way “too early.” But why would any sane sales manager want to step back into an IC sales job to join your company? Because they see the potential. Because they believe in your vision. Because they believe in you. And because they understand that if they want to be the first sales VP at your company, there’s only one way to do it: join as an IC, get glued to the founder for 6-12 months, and earn it. There is no shortcut. There is no other path. There’s no, “call me back when you’re looking for a sales director in 12 months,” because you won’t be. This also serves as an important test on their commitment to your company’s vision and on their true love of selling. “Carry a bag for 6-12 months, glued to the founder, in order to earn the sales head job? Sure, why not. I love selling.” And, “after that training program, combined with 6-12 months of selling this system myself, I will literally be the best person on earth to build the sales team for this product.”

This is why I say that your first seller should be willing to join the company too early relative to their resume, and be willing to run in a three-legged race with the founder for 6-12 months. That’s the job.

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Now, I’m not arguing that it’s going to be easy to find this person. But I have done it and I know others who have as well. I can’t take solo credit for the idea, either, as it crystallized in my mind many years ago in a conversation with Moveworks founder Bhavin Shah. I had some of the pieces in place, but it all came together in that chat.

The best argument for this approach, as alluded to above, is what happens if you don’t do this. Hard as this approach sounds, I have worked with many, many companies who ended up either riding a IC salesrep into management well beyond their abilities or one day realizing that they’ve spent two years giving the world’s best onboarding person to the wrong person — and now have to start over.

So while my approach may sound difficult and unpleasant, well, consider the alternatives.