Block Sales Development Representative (SDR/BDR) Interview Questions

1.Tell me about a time you had to sell or pitch something to two very different audiences — maybe a buyer and an end user — with competing priorities. How did you handle both?

2.Describe a time you made an error in something detail-oriented — a spreadsheet, a report, a client communication — that had real consequences. What happened and what did you change afterward?

3.Have you ever had to learn a new payment method, financial product, or fintech concept on the fly because a prospect or customer brought it up? Walk me through what you did and how you got up to speed.

4.Tell me about a time you pushed back on a process, a script, or a directive from a manager that you thought wasn't working. What did you say and what happened?

5.Imagine you're prospecting into a small business — say, a food truck owner — who's currently using a competitor's card reader and doesn't think they need Square. What's your opening, and how do you get them to care?

6.You're three weeks into a new outreach sequence for Square's banking products — loans and instant transfers — and your conversion rate is half what the team expects. You don't have a manager immediately available. What do you do, and what do you actually change?

7.If Square has roughly 4 million active sellers in the US, and the average seller processes about $70,000 a year, what's a rough estimate of the total payment volume flowing through Square annually? Walk me through your math.

8.Imagine you've been given a territory of 200 small food and beverage businesses in a single metro area. How would you estimate how many of them are realistically winnable in your first quarter as an SDR?

9.Square's attach rate for add-on products — things like payroll, loyalty, and banking — is higher among sellers who've been on the platform for more than a year. If you were asked to build an outreach list targeting those expansion opportunities, what data would you want and what would you prioritize?

10.Cash App has over 50 million monthly active users — mostly younger consumers — but Square serves small business owners. If Block wanted you to do outreach to Cash App users who might also be small business owners, how would you think about identifying and approaching that overlap?

11.Square loses some small business prospects to free or low-cost alternatives like Venmo for Business or Zelle — tools that charge nothing per transaction. If you had to estimate how much Square's ecosystem value would need to be worth to a seller for it to justify paying Square's processing fees instead, how would you frame that math?

12.Your team's SQL conversion rate drops 25% in a single month — from 20% of discovery calls to 15%. Nothing obvious changed in the market. How do you diagnose what happened, and what would you actually do about it?

13.If I handed you a list of 50 small business leads in Square's target market — coffee shops, salons, food vendors — what's the first thing you'd do to prioritize who to call first?

14.What's the difference between a lead, a prospect, and a qualified opportunity — and how would you know a Square merchant inquiry has crossed from one stage to the next?

15.You've sent 80 cold emails in a week to restaurant owners pitching Square for Restaurants, and your open rate is 40% but your reply rate is under 2%. What does that gap tell you, and what do you change?

16.Walk me through how you'd build a simple 30-day outreach cadence for a new campaign targeting Square Banking prospects — sellers who might want a business loan or instant transfer. What touches, what channels, what spacing?

17.Your manager gives you a weekly call quota of 50 dials. Halfway through Wednesday you're at 20 dials and have 0 conversations. Do you just hit the number, or do you do something different — and why?

18.A Square seller you've been working to qualify tells you they're happy with their current processor because of a lower interchange rate. You know Square doesn't compete on interchange — it competes on ecosystem value. How do you handle this objection without lying or over-promising?

19.You just wrapped a discovery call with a nail salon owner who seems genuinely interested in Square but says she needs to 'think about it.' You have no next steps scheduled. What do you do before you hang up — and what do you do in the next 24 hours?

20.You're on a prospecting call with a food truck owner, and halfway through your pitch he interrupts and says, 'I already tried Square two years ago and it was a nightmare — I'm never going back.' How do you handle the next 60 seconds of that call?

21.You're working a list of leads and you get a response from a Cash App business user who's curious about Square — but they're asking questions about crypto and Bitcoin features, and you have no idea what to tell them. What do you do?

22.Your team just got a new outreach script from marketing for Square for Retail, and your first two days using it produce zero responses. Your tablemate is having the same problem, but your manager says to 'trust the process' and stick with it for two more weeks. What do you do?

23.You're mid-sequence on a prospect — a local retailer — who suddenly goes cold. No replies to three emails, two calls, one LinkedIn message. You check their social media and see they just posted about a major flood that damaged their store. What do you do with this account, and when if ever do you re-engage on the sales side?

24.A mid-sized restaurant group reaches out inbound — they're interested in Square for Restaurants for all six locations, which would be one of the largest deals your team has seen at the SDR level. You know this is above your typical deal scope, but it's in your territory and your AE is on PTO for three more days. What do you do right now?

25.Have you ever needed information or help from someone who had no reason to prioritize you — a teammate in another department, a professor, anyone? How did you get them to move?

26.Tell me about a time you had to deliver bad news to someone — a customer, a teammate, a manager — and they didn't take it well. What did you say, and how did the conversation go?

27.You're working a prospect — say, a multi-location salon owner interested in Square — and the AE you're supposed to hand off to keeps deprioritizing your handoff meetings. The lead is going cold. What do you do without going over the AE's head?

28.Marketing just ran a campaign targeting Cash App business users, and some of those leads are now in your Square SDR queue. But the leads came in with almost no context — no company size, no industry, no stated need. How do you work with marketing to make the next batch of leads actually usable?

29.You're shadowing a senior AE on a Square Banking demo — loans and instant transfers — and partway through you realize the AE has made a factually incorrect claim about how quickly funds settle. The prospect seems to be making a decision based on it. What do you do in that room?

30.Imagine a small business owner you've been nurturing for weeks finally gets on a call — but they want to talk to 'someone more senior' because they don't trust that you can answer their questions. You have no AE available right now. How do you handle the next five minutes of that call?