After interviewing thousands of FinTech salespeople—and prepping hundreds more for interviews—I’ve noticed something consistent:
Sales hiring is still mostly done on gut feel.
It’s easily one of the least objective hiring processes. I’ve been guilty of it myself when hiring recruiters—overvaluing feedback like “they’re energetic” or “they’ve got charisma,” instead of focusing on tangible things like process, problem solving, and target attainment.
That said, I don’t think instinct is always wrong. Communication style and chemistry will always matter in sales, unless we fully outsource hiring decisions to AI. But if you’re a hiring manager, I hope this post helps you create a more structured, insightful process. If you’re a candidate, use this to prep and knock your next interview out of the park.
Part 1: Commercial & Role-Specific Questions
These are all about understanding the candidate’s current sales environment and how they operate.
- What does the product you sell do? What’s the value proposition?
- What is your exact role?
- What percentage of your work is new business vs. account management?
- What are your sales targets? How have you performed over the past 3 years?
- How many deals did you close to hit your number last year?
- If you were over/under target – what was the reason?
- Who are your competitors? What are your product’s strengths/weaknesses versus theirs?
- What types of clients do you sell to? (e.g. hedge funds, banks, trading firms)
- What countries are you selling into, and how do you split your time?
- Who uses your product, and how do different users benefit?
- Who’s the economic buyer? (CTO, Head of Engineering, etc.)
- How do you adapt your messaging for different roles/seniority levels?
- What’s the range and average of first-year ARR in your deals?
- How is your product priced? (Per user? Usage-based?)
- What negotiation tactics have you used? Any pricing levers you rely on?
- What’s your average sales cycle length?
- What steps do you take from lead to close? (e.g. outreach, discovery, demo, PoC, contract)
- What’s your lead generation approach? Cold calling? Events? Content?
- Where are you strongest/weakest in the sales process?
- Who else is involved in the sales cycle and when do they come in?
- Do you follow any sales methodology? (SPIN, MEDDIC, Challenger, etc.)
- How big is your team? Where have you ranked in the last two years?
- What other KPIs are you measured on?
- How does your manager know if you’ve had a strong or weak week?
- What tools do you rely on? (CRM, data finders, notetakers, etc.)
Part 2: Personal, Motivational & Relational Questions
This is where you get to know what really drives someone—and how they work with others.
- Why did you get into sales?
- Is that reason still what drives you today? If not, what is?
- What do you love most about your job?
- When do you get into a flow state?
- What parts of the job don’t you enjoy?
- How do you prefer to be managed?
- When do you usually go to your manager for help?
- Walk me through the deal you’re most proud of.
- Walk me through a recent deal you lost—what would you change?
- Talk about your top 3 client relationships. How did you build them?
- What’s your overall approach to building and maintaining relationships?
- What’s your general closing/negotiation style?
- Have you ever had to completely adapt that style to suit a client?
- What personal development have you done in the past 12 months?
- What would your customers say about you?
Wrap-Up
Great FinTech salespeople know their numbers and process—but also bring emotional intelligence, curiosity, and resilience. Whether you’re hiring or interviewing, this list is a great place to start if you want to raise the bar.
