January 31, 2023

Top 5 qualities of your best sales hires

Long before joining Cherubic, I spent years cold calling local businesses from a phone book, generating lead lists by driving up and down 101 and 280 in San Francisco with a tape recorder naming billboards and businesses, and selling an undifferentiated product in a saturated market – broadcast air time. I was a commission only account executive who quite literally wasn’t welcome at weekly sales meetings unless I brought with me a newly signed contract. It was completely ruthless.  

Later in my career, I joined Google where I built and led new business sales teams in the US and LATAM. I interviewed, hired and trained hunters for years. We weren’t farming in existing books of business or nurturing legacy relationships. We hunted for net new logos/customers ready to spend 6 figures on our ad platform. It wasn’t broadcast, but it wasn’t a walk in the park either. 

After eng, sales is likely your next hiring category. Flexport’s first hire, Anthony Chen, told me recently “sales solves all problems.” For the most part, I agree. What good is your product if nobody is using it? Sales is a critical early hire that you’ll likely get wrong at some point. Interviewing effectively, designing compensation correctly, tracking the right metrics etc all contribute to the success of your sales hires. But it ultimately starts with the interview – your screening process. Below are the top 5 qualities in sales people I optimized for when I was a hiring manager:

  • Resilient
  • Even Keeled
  • Disciplined 
  • Discerning 
  • Storytellers

Let’s dive into each with a sample interview question to help reveal these traits.


A good salesperson is not discouraged when they hear “no” from a prospect. They manage rejection well, and are tolerant of change (territory, commission, support structure, resources etc…). This is especially important for startup sales hires as the product, ICP, and competitive landscape are likely to evolve without notice. 

  • Tell me about your best and worst sales quarter. What was the outcome? What actions did you take that led you to that success/failure? Looking back, what would you have done differently to have been more successful? What was your key take-away?

Even Keeled

Alternatively, a good salesperson is not overly excited when things go right. They have a healthy dose of skepticism with their pipeline, discount their projections conservatively and always work the top of the funnel (ie cold call new leads) even when they’re feeling confident about later stage deals. 

  • Tell me about a time when you missed quota – why did you miss and how would you have done that quarter over again knowing what you know now (people who are self aware, even keeled, and proactive will not blame their circumstances – like the product or market – and will be metrics focused to know how to course correct). 


Outreach is important, but without follow up, it goes to waste. The best salespeople know how to balance their pipeline with new daily outreach, and timely client follow up. Balanced momentum across the pipeline – not just at the top or bottom – is critical. 

  • What metrics tell you you’re on track to hit your targets? How do you use them in your day to day? 


Not everyone is your ideal customer. Knowing who not to sell to is incredibly important as your team is building with limited time and resources. Optimize for discerning sales people who know how to acutely identify a customer’s pain, and assess how deeply your solution can solve it. Having them spin wheels on weak leads, and drain the resources of your technical and support teams, will distract and derail your progress. 

  • You have a target of closing 15 new deals at the end of this quarter for our company, and a prospect list of 1000 leads. How would you prioritize/filter these leads to maximize your chances of meeting this goal? Who would you pursue first, second, etc…What additional data would you ask for to inform your next steps?


Your sales hire will likely sell remotely. This means they need to have exceptionally strong written and verbal communication skills. They must also ask good questions & attentively listen. Most of all they need to sell you. Do you believe them? If you gave them a metaphorical phone book, would they know how to select, pursue, and close your most loyal customers? 

  • Take some time to familiarize yourself with our product and come prepared to roleplay and pitch our team. We’re less interested in your ability to memorize all our product features, and most interested in how you persuade and engage with potential customers. 

Sales hires are not easy. And if you’re struggling with sourcing good candidates, or with a recent hire, you’re in good company. The qualities above are ideally assessed early on before you make an offer. But if you’re managing performance right now, you can perhaps gain some clarity grading your existing hire(s) against the above!

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