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Hiring Your First Sales Leader


The default for most startups is founder-led sales, but as the team and company grows, you will eventually need to hire your first sales leader. Hiring a VP of Sales or CRO will depend on which milestones you've hit that are defined by the CEO and the Board. This typically starts at a specific revenue target, pipeline metric, and/or user-counts for a product-led-growth model after you've found some form of product-market fit (PMF).


There are several elements to consider that determine the type of sales leader you would need. We’ll touch more on this in a future post, but there are some common traits every sales leader should have and which you should vet for throughout the interview process.


Here’s the interview process and questions we use at Unusual, working alongside our portfolio companies to ensure a successful sales hire at the seed stage.

Interview Schedule (separate days)

  • Session 1: 45min Interview with the founder(s)
  • Session 2: 45min Interview with VC/Board Member
  • Session 3: 1 Hour Interview with the founder and cofounder or other senior team member
  • Session 4: 2 Hour meeting (with strategic 5-10min breaks) with Founders to walk through the Challenge deck and 30-60-90
  • Session 5 (optional): 30min meeting with founders/VC to discuss any remaining details or issues

Interview Structure

Start with some personal questions (learn about them as a person, care about getting to know them): 5-10min

  • Where do they live?
  • Where are they originally from?
  • Kids? Family?
  • How would your friends describe you?

Transition into the career questions (listed below): 15min and/or 60% of the allotted time

End by letting them ask you any/all questions they have + next steps: 10min and/or 20%-30% of the allotted time

Sales AE/Manager Interview Questions

This is a big decision and one that’s very personal for both parties, the worst thing either of us can do is oversell the other, so I’m going to be very transparent and just ask that you do the same if that’s ok with you

  • Answer: I like to open with this to set a tone of transparency, especially since salespeople love to oversell when it comes to interviews

Take me back to (University, a specific job, etc) and walk me through how you got to where you are now and why you made those moves

  • Answer: They should have a narrative for their career and clear answers as to why they joined/left companies. Things you don't want to hear: My friend started working there and it seems interesting, I left because I hated my boss, they changed the comp plan, etc. It should have been a thought-out decision.

When it comes to sales at X, what’s your process?

  • Answer: Simple question on its face, but they should dive into the way they approach pipeline generation, the sales methodology they follow / that the company prescribes, how they qualify deals, think about territory management, etc.

What’s the most difficult feedback you’ve received and how did it change you/your approach?

  • Answer: They should be able to tell you a concrete example which will show that they aren't perfect and are coachable

Who are the three most influential people in your life? Why?

  • Answer: This is a great way to get to learn about someone on a deeper level and tap into their motivation/drive

Who was the best manager you ever had? Why? Worst manager and why?

  • Answer: This will give you insight into how they like to be managed and/or how they will manage others. You can also get a glimpse into red flags like, "I like to be left alone to call my own shots", "My old manager was an idiot", etc

What’s your current breakdown between inbound/outbound?

  • Answer: They should know this % and it should reflect what what you're striving for in the next 12-24 months

Where do you rank currently on the team? If number 1, what are you doing that others aren’t? If not, what are they doing that your not?

  • Answer: They should have a clear answer for this, red flags are any type of excuse.

Out of the following, which is the most important thing to focus on (only one right answer):

  • Closing deals
  • Building relationships
  • Building pipeline (this is the only answer)
  • Answer: building pipeline trumps everything and good reps/managers know this.

We're looking at a lot of candidates for this role, why are you the best fit for it based on where the company is in its journey?

  • Answer: They should sell you on themselves and close you at the end of the meeting (AKA they should ask directly for the job or ask you if they have any hesitations moving you forward to the next step)

What deal sizes have you sold to, on average, and range? (If it’s not a similar fit to you, pass. If he/she can’t answer fluidly, pass).

  • Answer: they deals and motions they have the most experience around should be what you're looking for. Hard to learn on the fly if selling up/down market.

Tell me about the teams you’ve directly managed, and how you built them. (If he/she can’t describe how they built a team — pass).

  • Answer: This should weed out people that have only inherited teams or have very little management experience.

How big a team do you think we need right now, given what you know? (If he/she can’t answer — right or wrong — pass).

  • Answer: they should ask you what ARR you're at now and where you want to be in 6 months, a year, etc. Then, take the basic math (ARR/quota= of reps)

What sales tools have you used and what works for you? What hasn’t worked well? (If they don’t understand sales tools, they aren’t fit to be a VP of Sales).

  • Answer: this is a bit of a trick question. Most people will say SFDC or Outreach, but a lot of candidates will have only used those tools, and probably not well. They need to be able to detail all the tools in their desired stack and how they work in conjunction.

Who do you know right now that would join you on our sales team? (All good candidates should have a few in mind). Tell me about them, by background, if not name.

  • Answer: Any good VP of sales will want to bring up and comers with them in order to hit the ground running since recruiting is so hard. If they say, "will use recruiters", that's the wrong approach.

How should sales and client success/management work together? (This will ferret out how well he/she understands the true customer lifecycle).

  • Answer: They have to have an understanding of this in order to be a leader at your company since they will play a role in the foundational approach to these teams.

Tell me about deals you’ve lost to competitors. What’s going to be key in our space about winning vs. competitors?

  • Answer: If they have worked at a larger company and they aren't in a truly competitive environment, pass. They have to be familiar with the hand to hand combat at the early stages to beat out the competition.

How do you deal with FUD in the marketplace? (This will ferret out if they know how to compete — or not).

  • Answer: Again, this will speak to how they beat out the competition and think about positioning.

Do you work with sales engineers and sales support? If so, what role do they need to play at this stage when capital is finite? (This will ferret out if he/she can play at an early-stage SaaS start-up successfully — and if he knows how to scale once you scale).

  • Answer: If they have had tons of help in their current role, they aren't going to get it at the early stage so how will they cope?

What will my revenues look like 120 days after I hire you? (Have him/her explain to you what will happen. There’s no correct answer. But there are many wrong answers).

  • Answer: How much ARR do you have now? How much have you grown in the last 6 months? How many reps do you currently have? They should be able to give you a realistic estimate. Anyone who says, "it's too early to tell", wrong answer.

How should sales and marketing work together at our phase? (This will ferret out if he understands lead generation and how to work a lead funnel. Believe it or not, most candidates don’t understand this unless they were really a VP Sales before).

  • Answer: They should have an opinion of how this should work, what type of role they would suggest (marketing vs demand gen). If they give a vague answer here, pass.

Walk me through the deal you're most proud of - (Similar to "What deal sizes have you sold to, on average, and range?") - The best reps will walk you through a complex deal with a high price tag, and tell you notable milestones or the adversity they overcame. Strong examples lead to good conversation and naturally highlight the areas in where they spike and areas where they need improvement.

  • If the deal is weak or not in the range you expect, then you can ask more questions about their average deals and sales process. Usually the way they approach this uncovers a ton of threads to pull on in the conversation.

First interview question: "Why are you interested in this role, and why this company?" (Did this person do their research? How much? If they aren't willing to sell themselves or express genuine interest in the interview process, how will they do selling your product?)

  • Answer: You want to avoid people who answer "I just want to work at a startup" or "this is a really exciting company because it makes data useful." The best candidates will prove they did research about the role and how it either relates to their previous experiences or why this transition is so exciting to them. In regards to the company, most will give a pitch and highlight a case study or example that most excited them about the solution they want to sell.

What to watch for:

How many questions did they ask you?

  • Answer: They should be qualifying this opportunity just as hard if not more than a deal

How did they differentiate themselves from other candidates?

  • Answer: Was the interview memorable (for good reasons)? Were they able to articulate why they are the best person for this role right now at your companies stage of growth?

How much research did they do on your company/space coming into the call?

  • Answer: They should be able to articulate what your company does at a high level (assuming you're public facing at this point) and have an opinion on the market you're in and know at least 1-2 of your competitors.

Did they make any excuses, blame others, or bash co-workers during the interview?

  • Answer: Examples of why a deal was lost, identifying weak-links, or showing lack of collaboration are red flags for reps at any stage company. Selling is a team sport and successful reps will interact with many functional teams at your company.

Set of interview questions to vet for a successful VP of Sales or CRO hire

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