Best Practices for Hiring Your First Sales Employee

After hiring early sales reps across multiple companies, I’ve learned what works—and what definitely doesn’t. Most founders don’t approach it systematically. They post a job, interview a few folks, and pray it works out. That’s expensive guessing. I’ve made the same mistake. But over time, I’ve developed a repeatable approach that actually delivers 👇 🎯 Step 1: Wait for market pull — not market hope Don’t hire a rep because you think they’ll figure out your GTM. Hire when you have more demand than you can handle. At Clarify, we had more inbound than we could convert. That’s your signal. ⸻ ⚡ Step 2: Hire for traits that predict success I’ve stopped obsessing over resumes. I look for: • Ex-athletes or Ironman types — competitive spirits • Great question-askers • People who always do their homework • Relentless, disciplined executors You can’t coach hunger. ⸻ 📊 Step 3: Align comp with the actual problem What’s your bottleneck? Leads? Or process? For us, it wasn’t lead gen. We needed help running discovery, managing follow-up, and tightening the pitch. So we paid for that: more base, less commission. If you need lead gen? Flip it. Don’t copy someone else’s comp plan. Solve your own problem. ⸻ 📝 Step 4: Build the playbook together Your first rep won’t inherit a manual. They’ll help write it. Every startup has a sales process — even if it only lives in your head. Extract it. Scale it. Then expect your rep to own and evolve it. ⸻ 👥 Step 5: Hire with the next hire in mind Your first AE might not become your future VP of Sales. Different skill sets. Different jobs. Execution vs. management. But don’t rule it out. Some reps grow into operators — if you give them the path. ⸻ The right rep won’t just close deals. They’ll help you build the system that scales them.

Hiring your first sales team is like walking a tightrope🚶– very rarely you get that right, especially as a first-time founder. I've chatted with a couple of other founders recently, and all of them have shared these consistent hurdles, that I personally have experienced too: 1️⃣ Exaggerated Results: Candidates frequently inflate their past success – almost everyone has crushed their quota and was a top performer. Don't hesitate to dig deeper and ask for specific questions. Do the math on the fly for their ACV, their Win Rate, # of deals they were handling every month, etc., and you'll actually get real numbers. Remember, stories sell, but details tell. 🔍 2️⃣ Evaluating Potential: Determining potential from an interview is tough, especially for Salespeople – as they're great at talking and selling themselves. Don't hesitate to run role-play scenarios and ask situational questions. I personally like to give take-home assignments, which are the same for everyone so you're not putting them on the spot and letting them prepare a bit, but also get to compare candidates for the same scenarios and situations. Remember, "show and tell" is better than "talk and sell". 👩🏫 3️⃣ Cultural Fit: Most often, it's not about whether the individual candidate is good or not – it's mostly about – if they are a good fit for your culture. Don't ignore to look beyond achievements and assess for cultural fit. This is definitely hard to assess, but if you care about transparency, see how candid the conversation is vs. how fabricated it is. If you care about hard work and hustle, then see if the candidate optimizes for personal and career growth vs. work-life balance. Remember, skill sets can be learned, but attitude can’t!💡 4️⃣ Startup Uncertainties: Startups bring risks unknowns to the job, that could scare off some reps. Don't shy away from sharing an honest picture of your culture, values, challenges, and vision. The right person would embrace them. And it's better for them to realize they're not a fit during the interview stage vs. 3 months after joining the company. Remember, it's better to break up sooner than later! 💔 --- I have made my fair share of mistakes in hiring sales reps. And I've learned a lot and getting better in hiring. But I'm sure I still can learn from others' experiences. Appreciate any thoughts or advice on this topic. 🙏 Feel free to share your experiences below or DM to continue the conversation.👇 #startups #saleshiring #teambuilding #leadership

I can always tell when someone is hiring sales people for the first time. They typically make 3 rookie mistakes: 1) Hiring a VP as their First Salesperson Good VPs want to build teams, manage them, set strategy, and help with the most important deals. Good VPs DO NOT want to do the dirty out bounding, follow-ups, contract redlines, etc…that come with early stage sales. If you need help building some operations or strategy, then hire a good sales consultant. They’re going to help you avoid some very costly mistakes. And make sure your first hire is a full cycle AE that can prospect and close. 2) Complicated Commission Plans I’ve built dozens of sales compensation plans. I used to worry about every scenario…how do I protect the company? How do I protect the reps? The plans got complex. It cost the company company countless hours of expensive time trying to calculate every detail and manage the one off scenarios with the team. Don’t do this. Instead, keep it simple. - Your first plans should not include escalators, just flat rates For SDRs specifically: - Start with a commission for each meeting held and try to add a commission for each deal closed (if you can) - In the beginning, don’t penalize them for bad meetings set, but monitor it closely. Eventually you can add variable that measures the % of their meetings set that AEs mark as Sales Qualified Opps 3) Missing Obvious Red Flags in the Hiring Process A bad first hire will cost your executives a lot of time and a lot of actual money for the company. At a bare minimum, your first hires should be excellent with the small details around communication — good formatting, proactive, professional. You’re hiring sales because you need to get it off your plate. So while you’re juggling everything else, you don’t have time to train someone on the fundamentals of client communication. How they communicate with you during the interview process is a reflection of how they communicate with customers. Even if the candidate has good logos on their resume, don’t drop your standards on communication. The reason this is top of mind? We've been hiring a bunch of overseas SDRs for our clients and I've been having these exact conversations with founders and early stage managers.

I'm helping a company hire their first sales person.  They are looking for a great mid-market seller.  HMU if you want some more information, but we were talking about some of our favorite interview questions. For this type of role (2nd sales role, few years of closing experience, mostly mid-market / SMB type of SaaS deals) - here is what I'd focus on and the questions that I'd ask and why. I focus on three things for these types of candidates - curiosity, attention to detail, and grind.  If you have these three things, somewhat early in your career, you're likely going to go far in life. Curiosity: Do they ask more questions than you? - - - Remember, 2-ears, 1-mouth for a reason. Do they ask smart questions about the business, the space, the buyer?  - - - Or do they ask less smart things about enablement, OTE, holidays, stock, whatever. Attention to detail: Explain the product that you’re currently selling to me like I was 5 years old. - - - Can they articulate complex topics in an easy way?  Is it a bunch of word salad or do they actually do this?  Does their description pass the grandma test? Tell me about the ideal buyer you sell to. Why is that person ‘ideal’? - - - What do they actually know about their customers and why it’s important to sell to that customer?  Do they understand their customers' pain points or are they just processing orders? If you were CEO of your current company, what would you change starting tomorrow? What would be the impact of that? - - - Shows that they know about their own business and how they think. Tell me about the deal you closed that you’re most proud of? Give me all the details about it. - - - Every good sales person knows all the details of the best deals that they closed. If they can’t describe details about their deals, they aren’t real Grind: Tell me about where you grew up and how you got here.  - - - Shows what they came from, where they want to be. - - - Are they a silver spoon person or did they hustle to get to that interview? - - - You're looking for hunger What is the most difficult challenge, personally or professionally, that you’ve ever had to overcome and what did you do?  - - - No joke, I once had a candidate tell me that the biggest professional challenge that they ever had was that they had to work on a Sunday to get ready for a customer meeting Outside of work, tell me what you do competitively? - - - Every sales person will tell you that they are competitive, but very few actually are - I’ve heard everything from competitive sailing to competitive birdwatching - red flag if they’ve not done anything in a few years Will those give you the most ideal candidate?  No guarantee.  But, anyone can fake questions like “Tell me about your strengths and weaknesses.” and other BS things to ask.  These are a bit tougher to fake and give you better insight into how the candidate is going to work on a day to day basis.  Good luck.  LMK if I can help.