Twilio Sales Development Representative (SDR/BDR) Interview Questions

1.Tell me about a time you had to figure out how to do something with almost no guidance — maybe a new job, project, or assignment where no one handed you a playbook. What did you do first?

2.Tell me about a time you helped a peer or classmate who was struggling with something you'd already figured out. How did you approach it, and what did they walk away with?

3.Tell me about a time someone's perspective or idea was being overlooked by your team or group. What did you do about it?

4.Tell me about a time you had bad news to deliver — to a manager, a teammate, or a customer — and you had to decide how and when to say it. Walk me through what happened.

5.Tell me about a time you finished something that everyone said was good enough — but you weren't satisfied. What did you go back and change, and why?

6.You're asked to prospect into a new industry or persona you've never sold to — no ICP doc, no talk tracks, no one to shadow. What's your game plan for the first two weeks?

7.Twilio charges per SMS, per call minute, and per active user for products like Flex. If a prospect asks you 'how much will this cost us?' on a cold call, how do you handle that?

8.Estimate how many businesses in the U.S. could realistically be target accounts for Twilio's Programmable Messaging product. Walk me through how you'd think about it.

9.You're prospecting into a healthcare company that would be a perfect fit for Twilio Verify — their patients need appointment reminders and 2FA for a patient portal. But every contact you reach says 'we have to go through procurement and IT security' before any new vendor is even considered. How do you move this forward?

10.Your open rate on cold emails is great, but your meeting conversion is flat. A teammate using a simpler, shorter sequence is booking twice as many meetings. How do you figure out what's actually going on?

11.Twilio is expanding into a new market segment — let's say mid-market logistics companies. There's no established playbook, limited case studies, and your AE has never sold into logistics before. How do you build a prospecting strategy from scratch in the first three weeks?

12.You've spent a week prospecting a list of 50 accounts in the e-commerce space. After 10 conversations, 8 of them mention they're waiting to see how Apple's messaging policy changes affect their SMS strategy. You've never heard of this and you don't know if it's real or a brush-off. What do you do with the next 40 accounts?

13.What's the difference between an MQL and an SQL, and how would you know when a Twilio prospect is ready to hand off to an Account Executive?

14.Walk me through how you'd research a prospect account before your first cold call — what sources would you check and what would you actually be looking for?

15.You've sent 50 cold emails this week using a sequence your manager gave you. Your open rate is 40% but your reply rate is under 2%. What do you look at first, and what do you change?

16.A mid-market VP of Engineering picks up your cold call, listens for 30 seconds, then says 'We already use Twilio for SMS — why are you calling me?' How do you handle the next 60 seconds?

17.Your manager shows you two SDRs' numbers: one books 20 meetings a month with a 15% SQL conversion, the other books 10 meetings with a 50% SQL conversion. Same quota. Which SDR is performing better, and what would you want to know before you answer?

18.You've been working a prospect for six weeks — they've attended a demo, replied to emails, but keep pushing the next meeting. You think they're stalling. How do you diagnose whether this is a real deal or a dead one, and what do you do differently?

19.You're on your third call with a prospect and they casually mention they had a bad experience with Twilio's support team last year. They're still on the call, but the energy shifted. What do you do right now?

20.Your manager just handed you a list of 200 accounts to work this quarter. There's no tier ranking, no priority guidance — just a spreadsheet. How do you decide where to start?

21.You're three weeks into a quarter and your pipeline is healthy on paper, but you have a gut feeling several of your 'meetings booked' aren't going to show. What do you do before those no-shows actually happen?

22.You get an inbound lead from a director at a major retail brand — exactly Twilio's ICP. But when you look at their tech stack, they're deep into Salesforce Marketing Cloud, which has messaging built in. How do you approach this conversation?

23.You've been grinding on a target account for two months — multiple touches, a demo booked, good conversations. This morning you find out a competitor just announced they signed this exact company as a customer. What's your next move?

24.Your AE asks you to book 15 meetings in two weeks for a new vertical Twilio is pushing into — fintech — but every talk track you've been given is built for e-commerce. You have no fintech contacts, no case studies, and two weeks. How do you execute?

25.Think about a time you needed someone to do something for you — a favor, a resource, a decision — but they had no real reason to prioritize you. How did you get them to move?

26.Tell me about a time you were new to something — a job, a team, a project — and a more experienced person gave you feedback you didn't fully agree with. What did you do?

27.You've booked a meeting for your AE with a good prospect — but the day before the call, you find out the AE hasn't prepared and might walk in blind. You can't run the meeting yourself. What do you do?

28.Marketing just launched a new campaign that's driving inbound leads your way — but the messaging is way off from what you're hearing prospects actually care about. How do you address it?

29.A prospect goes dark after three strong touchpoints — they were engaged, asked smart questions, and then just stopped responding. Your manager wants to close the opportunity. You think there's still something there. How do you make your case?

30.Imagine you're the first SDR covering a new territory or vertical at Twilio — no one has mapped the accounts, there's no established relationship with the regional AE team, and they're skeptical of SDR support. How do you build credibility with that AE team in the first 30 days?