We’ve received great feedback from our post on “Hiring a kickass VP of Sales”, and often get asked about a similar set of questions for hiring individual Sales Account Executives. There is some crossover between interviewing for an AE and a VP of Sales; however, I thought I would expand a bit and share some of the best input I’ve had on this over the years.  Special thanks to Jeff Jenkins at Blue Ridge, Scott McCarthy at XOi, and Chris Larson at Hive for their contribution.

I will raise the same disclaimer that I noted on our VP Sales post – I am just outlining sales specific questions in this post, and am not focused on other important interview topics, such as values, raw ability/intelligence and culture fit (a blog post in and of itself).

When getting to know a Sales Account Executive candidate, I typically cover the following topics:

  • What got you interested in speaking with us? Tell me about what are you looking for in your next company and role?  How does this compare to your current company and role?
  • Commentary – As you enter the interview process, it’s helpful to understand why the candidate is even speaking with you about a new opportunity. What’s happening in her current role / situation / life events, that initiated the sales interview? If the response is “well, I’m always opens to hearing about a better job”, that is a red flag.  If an AE is satisfied with her current company, products, culture, etc, she shouldn’t waste time and get distracted.  Only a solid answer here should keep things rolling.  Also, don’t settle for softball answers on what they want next (e.g. I want an organization where I can grow). Drill in and try to understand if this candidate is running to you or running away from something else. If the later, make sure you understand the circumstance and why that wouldn’t be the case at your company.  Push for what isn’t a fit with where they are and what a great fit really looks like in her mind.


  • What’s your perception of our [product/service/solution] at this point? To the best of your ability, describe what we do.  Are you aware of who we typically compete with?  How do you think we stack up?  What’s your perspective on the overall [insert your market] sector?  Where do you see things going over the next few years?  In your current role, what reading and research do you typically do outside of what your company has provided you.  What’s the last business book you read?  What did you take away from it?  How have you applied a concept from it in your work?
  • Commentary – this block of questions is about testing the candidate’s level of curiosity and prior homework.  If she’s done very little homework and thinking about your space, that is a significant red flag.  If she is willing to interview with you for a job without prepping, how do you think she will handle sales calls with your prospective clients?  As you progress in these questions, does she ask intelligent, probing questions to learn more about you?  In addition to asking the candidate about your company and market, try asking some of these same questions about her current (or immediately prior) company and market.  Drill into specifics to see how real their answer is. They should have their product pitch down cold, but are they able to talk with confidence and some level of specificity about their outside learning and the bigger picture in the market? Are they proactive about learning on their own and bringing new information into the company? Consider providing the candidate with industry research and training materials related to your company after the 1st interview, and then testing them in the second interview to see how well they absorbed it. 


  • Tell me about the products you’ve sold in the past. What was the price of these products? Walk me through an example of one of your best sales wins. Describe the typical buyer journey in purchasing your product(s). How mature is the market?  Is your product a new category or rip-and-replace solution? Based on what you know about our product, how were your prior products similar or different in type/price/buyer journey? Have you ever worked in our industry before?
  • Commentary – experience in our industry is a significant plus, but I draft for talent over position. A rock star seller is better than a B player from our industry who claims to have a rolodex. Even if the rolodex is real, it will run out and then we are left with a mediocre sales person. That said, experience with similar product types/price points/buying experiences is very important. If our product is a six to seven figure price point, complex enterprise sale with a 12 month sales cycle, then an AE who has worked only in low five figure, two call, 30 day sales cycles is not likely to bring the experience we need.  Draw out the full story on the best sales win.  Use the discussion to better understand the complexity of their prior sales processes.  Also, do they go ‘cowboy’ on their own or use company processes and help (and acknowledge this help)?  Was it all about the commission or about helping a customer achieve success?


  • Tell me about the roles you have held in the past.How many people were in the sales/marketing organization of your current/prior company? Describe the reporting structure – who did you report to, who did they report to? What were you specifically accountable for in the marketing and sales process?
  • Commentary – job titles are often inflated in sales, so I seek to understand what the prior team structure was like and her role within it. Get past the ‘we’ answers and get to the ‘I’ answers – what was her specific accountabilities/focus and how does this compare to the role we would be hiring her for?  How many accounts did she handle?  Did she close deals fairly independently or was her VP of Sales or CEO still heavily involved in the sales process? Dig especially hard on this question, as I’ve had top sellers at our own companies that were really B- players propped up by a boss that co-sold with them. Was she accountable for new logo acquisition or growth within existing accounts or both (if later, than what was the mix)? How does this compare to what you need in your role?


  • What were the company’s sales and marketing goals during each year of your tenure at [prior company] and what were your specific goals?  How did the overall team perform relative to these goals?  How did you perform relative to your individual goals?  If you exceeded quota, over what period of time and was this performance consistent over time?  How did your performance compare to other sellers within your group, within the company overall (if you worked in a large organization)?  What honors or awards did you receive during your tenure?  What honors or awards were regularly given out?
  • Commentary – sales is probably the most quantifiable job to hire for. Drill into the answers you get and map out quota attainment for each year (or even quarter) of his prior jobs within the last 5 years.  It is possible that he was in a bad situation, but if this is the case, then he should have a track record that reflects top performance in prior roles. Don’t stop at just individual attainment.  Push up to understand overall team attainment to better understand the environment and his performance relative to the team and company.  If this is an entry level sales role, then drill into prior work experience or school experience, seek similar examples of prior success. If he doesn’t have a demonstrated track record of prior success, pass and move on. 


  • How did you develop new leads at [prior company]? Were leads generated by marketing, partnerships, or were you responsible for generating your own leads?  What % from marketing, partners, yourself? Of the new business you just recently closed (last quarter/last year), how many came from leads you initially generated?  What was your approach to developing new leads?  Tell me about your weekly cadence.  How do you organize your work and prioritize your day/week?
  • Commentary – as an entrepreneur or sales leader, when you started your business/current role, did you hire a marketing lead or engage a channel partner and sit back to wait for them to give you a lead? No, you likely hustled your ass off and didn’t wait to be fed.  So, be careful you don’t hire sellers with an expectation that led gen is entirely someone else’s job.  The advent of sales development teams have been great accelerators for sales, but they have also created some lazy account executives that wait around to be fed by SDRs or marketing or partners. It’s not typically an efficient use of an AE’s time to do all their own prospecting (if it was we wouldn’t have marketing or channel partners), but consider your own go-to-market strategy as you discuss top of funnel with the candidate.  Typically, you will want to see a demonstrated track record of rolling up sleeves and doing at least some of their own outreach.  As you explore this topic, you can get a better understanding of how they organize their work. A great answer is “Well on Sunday night, I look at the week and…”.  It tells you they are hitting the ground running on Monday am.  A story that starts with “it depends” is not good.


  • Describe your prior sales processes.What were the stages involved and how did these evolve over time? Walk me through a recent deal you won.  Who did you meet with?  What steps were taken?  Who was involved in the process on your side?  Tell me about a deal you lost that was late in the cycle…one that you were forecasting to close, but got away.  What sales tools does your team use? How did your team measure success? What KPIs were tracked and how did you and your manager generate insights on your sales process? Give me an example of a few of these insights and how you applied changes as a result.
  • Commentary– Influencing people can be an art, but sales process is very much a science. Weak candidates will answer these questions at a high level and will likely just quote whatever sales methodology framework they were trained on in the past (Challenger Selling, Spin Selling, Sandler, Target Account Selling, etc). Stronger candidates will be able to share their metrics in detail, discuss the pros/cons of tools their team used, describe how they analyzed results, and be able to give specific examples of where their manager’s (or their own) analysis led to actionable insights.  By drilling into their wins, you can understand if they are feature selling or really identifying business challenges and presenting their product as a solution.  You can also get a sense if their manager is closing deals for them, and whether they take ownership for mistakes or blaming others.  The best AEs take a strong ownership of their own success and do not have a victim mentality. Beyond evaluating the candidate, this series of questions can also be an opportunity to collect relevant best practices.   


  • Let’s run a 10 minute discovery call of your existing product. Consider me a prospect for your current company, and let’s role play an initial call.
  • Commentary: This would typically be done after the first interview. Send directions ahead of the meeting and ask the candidate to run a 10 minute discovery call of the current product they are selling. The evaluation in the role play isn’t on new product knowledge. The goal is to see how well they follow the sales process they mentioned earlier in their interviews. Do they follow directions?  Do they manage the time?  Is there an up-front contract established in the call?  Are they prepared with company research? Are they asking questions trying to understand the buyer’s goals or selling features and functionality? If the interview goes well, provide feedback to the candidate and ask them to be spend the first 10 minutes of the next interview going through the same exercise and incorporate the feedback you shared with them. During the next interview, did they incorporate your feedback?  Do they send a follow up email? This series of role plays gives an opportunity for real-time coaching and an understanding of how well they absorb and incorporate feedback.


  • How was the sales team compensated at [prior company]?  What worked well with this approach and what didn’t?  What compensation structure would you advocate in the future?
  • Commentary – I try to use every interview as an opportunity to learn about successful approaches to sales process and sales compensation.  If the candidate has experienced prior success, dive into the details and seek to understand how compensation was aligned to motivate the team.  Would these structure(s) work at our company – why or why not?


  • What will you need to be successful at my company? What helped you be successful in your current/prior role?  Who is the best sales leader you have worked with in the past?  What made this person great to work with?  How would you think about organizing your first 90 days? What type of impact can you make on our sales in the first 180 days?  Our quota for this role would be [$XXX].  How long do you think it would take you to scale to quota?  How does that compare with the time it took you to scale at your current [last] role?
  • Commentary – it’s important to make sure your expectations align with the candidates expectations and that your leadership style will be a good match. Asking open ended questions about what they need to be successful and what led to success for them in the past can help uncover any misalignment. Think about what type of individual works well with your approach to managing a team.  Do you get the best results with team players that value and leverage one on one strategy sessions, brainstorming, and positive engagement with the rest of the team?  If so, then screen out the cowboy types that don’t value or appreciate a full team effort and a sales leader that engages regularly to keep things moving. If this is an experienced candidate, it can be helpful to understand how she thinks about her first 90 days and how she handled it in her prior company.  Make sure she can make a logical, cohesive argument for the time and training needed to attain quota and what near term outcomes she believes can be achieved.      


In addition to the questions above, keep track of how your candidate manages the overall process:

  • Do they return calls quickly?
  • Are they thorough in their follow up?
  • Does every interviewer get a follow up thank you which reiterates some of the key themes the candidate was emphasizing in that interview?
  • Are they well prepared with well thought out, probing questions?
  • Do they seek to ‘close’ the interviewer at the end of each interview (seek feedback and objection handling for anything that might block them from achieving the next interview or the offer)?

If the candidate doesn’t do the things above in pursuit of the job, how likely are they to handle these critical components in pursuit of your prospective customers?

If you are making your first sales hire, I typically recommend hiring two at the same time (or three if you can afford it).  If you hire only one, and he/she struggles, you won’t be certain if you made a bad hire or have a broader process or go-to-market problem.  If you hire more than one initially, and one seller excels while another struggles, then you can be more confident that you just have a correctable hiring issue. You also gain some efficiency when combining the training of more than one seller, and can benefit by creating some positive competition between your new sellers.

When the time comes for a hiring decision.  Be decisive.  If you feel yourself justifying the decision because you have seats to fill or find yourself saying “I can coach her up on that skill”, it’s often best to pass and continue searching for your A-Player. Typically, you will have very little doubt about your best hires, and you will find your worst mistakes come when you rationalize away a concern identified in the interview process.

Also, if you haven’t read Mark Roberge’s book – Sales Acceleration Formula – I recommend picking up a copy.  You can also watch a recent SaaStr talk by Mark here. Mark’s hiring formula (developed during his time at Hubspot) emphasizes establishing a theory of the ideal sales characteristics for your account executives, then defining an evaluation strategy for each characteristic and a model to score candidates against the ideal.  As an example, Hubspot’s ideal characteristics were coachability, curiosity, prior success, intelligence, and work ethic. I am a fan of his approach, and you will see his influence in my questions above.

Happy hunting!