How I’ll decide if I want to join your startup
I am a good salesperson. That means I pay for myself in dividends, and I care a lot about what we are building together. Attracting thoughtful and gritty sales talent is not easy. If you’re a leader and want people like me to join your team, here are the four things you should know.
- Our first interaction should be researched and personalized. Recruiters reach out almost daily. You will only cut through the noise if you are personal, specific, and researched. The most recent message I received from a recruiter was: “We are currently expanding our commercial sales team and are looking for a new Commercial Sales Representative. I’ve reviewed your profile and believe you may be a fit for the role. Should you be interested, I would like to discuss the opportunity with you in more detail.” I’m especially uninclined to respond to a message like this. If you have the audacity to claim you reviewed my profile (I hope that’s true!) and really believe I might be a fit, then you have the context to describe why. Is it my industry experience? The types of companies I’ve had success with in the past? Something I posted? Something specific your company is looking for that I have? I get it. These messages are canned and recruiting is a numbers game. But I feel pretty strongly that if you’re trying to hire an epic sales rep, that 10 personalized messages to strategically sourced candidates will yield higher responsiveness than 100 unpersonalized ones. When I look back, I’ve only had serious job-related conversations with startups that either come my way via an introduction from someone I trust, or from a personalized note from a recruiter or hiring lead.
- Equity shouldn’t be an elephant in the room. If you’re going to tout equity as part of your “holistic comp package,” you better be prepared to discuss what it means and how I should be thinking about it. Equity is a motivating concept for a lot of candidates, and sometimes joining a startup means you make some sacrifices in anticipation of that ownership. I’ve thought a lot about why this topic is so cagey in most interview processes. I presume some hiring managers are scared of making ‘promises’ about equity that can’t necessarily be kept. Or that the value and nature of that equity are subject to change in the future based on things like fundraising. But neither of those are good reasons to be unexplicit about what you’re offering. Too often, equity is simply offered as a number — a number of shares or basis points — and candidates are expected to believe blindly that it’s a reasonable one. There’s no open dialogue around total outstanding shares, valuation, fundraising plans, dilution risk, why you picked that number, and so on. Why should I as a candidate get excited about ownership in your company if I can only conceptualize the value of it by using my own imagination? Paint the picture for me. Candor is reflective of your culture.
- I want to know what’s real today. It’s great to hear about and to discuss the upside of joining your company. TAM, the product roadmap, your pipeline, your goals. I love it and hopefully there’s no ceiling in sight! But let’s spend a lot of time talking about what’s real right now. What evidence do you have to prove the reach and appetite that your product has in the market? Why are your existing customers paying you money today? My long term goal is to help transform your business into a household name. But my short term goal is to know why the product has legs today so I feel confident that I’m going to make an immediate impact (and, well, money).
- Give me space to do my own diligence. You’re highly invested in figuring out if I’m the right candidate for the role you’re hiring for. Right back at ya! The perfect candidate will be game for hours of interviews to prove they’ve got the chops for your needs. And the right employer will do the same for the candidate. The general consensus is that joining a startup is a risky endeavor. I’m empathetic and cautious to that point of view, but I’ve developed my own diligence process that makes me feel confident and secure doing it. Personally, I want to assess your tempo — looking for goldilocks indications that you’re moving quickly but not recklessly. Good example: Veeva Systems. Bad example: WeWork. I want to hear about the milestones — macro and micro — that you have hit along the way. And further, what ‘next steps’ were unlocked by hitting those milestones? There must be at least some reasonable methods to the madness. Every candidate should have their own unique approach to diligence, and I would encourage you to experience it as a strength when it shows up. Diligence indicates a candidate is serious, curious, thorough, and solutions-oriented, which are four skills you’re hopefully vetting for in a rockstar sales candidate.
That’s my inside skinny on acquiring sales talent that will thrive and grow under your leadership. No doubt the list will change and mature over time, but I suspect these themes resonate with a lot of salespeople considering a jump into the startup trenches with you. I can say for sure that, had any of these boxes remained ‘unchecked,’ I wouldn’t have joined Proton. And I wouldn’t have joined Proton as prepared to win as I did. The investment that every person made in the hiring process was immense. My team painted the full picture of what it’s like to work at Proton, filling me in on what I’d missed in the 2.5 years since the company’s inception (including how exactly the product and customer base had evolved over time). And they were never shy about sharing the unique characteristics I brought to the table that they found specifically exciting and applicable to the business. It made my (admittedly autonomous) onboarding feel faster, happier, and made it so I could build processes and close major deals within 6-months on the job.