How we hire at Liberate.
No black boxes. We build AI that takes the mystery out of insurance, so it would be a little rich to make our own hiring process a mystery. This is your guide to exactly how we hire — stage by stage, role by role — so you can prepare with confidence and show up as your best self.
The one thing we keep confidential is the specific questions inside each interview; that’s how we make sure everyone gets the same fair, consistent shot. Everything else is right here. And remember: a great interview goes both ways, so this is your chance to get to know us, too.
Our promise on timing: we read every application within 3 business days, and after your final interview you’ll hear back within 2 — a clear yes, no, or a specific why. Silence isn’t an answer, and we don’t do it.
Enterprise Account Executive
You’ll bring Liberate to the insurers and agencies who need it, and own those deals end to end. Here’s how we hire for it: four conversations, including a live pitch where you get to do what you do best.
At a glance
- Hiring manager interview — 45 min, video or onsite
- Alternative sales leader interview — 45 min, video or onsite
- CRO interview — 45 min, video or onsite
- Final presentation — ~30 min, live pitch + Q&A
Step 1 — Application Review
A real person reads every single application - no keyword filter, no black hole. If it looks like there’s a fit, we’ll reach out about next steps. And if the timing isn’t right, we’ll still tell you. Either way, you won’t be left wondering.
Step 2 — Recruiter Screen
30 minutes · phone
A conversation about your story so far - your average deal size, yearly quota and what’s pulling you toward Liberate. We’ll leave plenty of room for your questions, and cover the practical things together, like the role and timeline.
Step 3 — Hiring Manager Interview
45 minutes · with the hiring manager
A conversation anchored on your track record - your quota attainment, the deals you’ve owned, and how you’ve navigated complex, multi-stakeholder sales cycles. Expect to get specific: deal size, cycle length, who was in the room, and what you personally drove.
Step 4 — Alternative Sales Leader Interview
45 minutes · video or onsite, with a different sales leader
A second, independent conversation with a sales leader who isn’t your hiring manager - covering similar ground on your track record and approach, plus how you build trust with senior technical and business stakeholders.
Step 5 — CRO Interview
45 minutes · video or onsite, with our CRO
A conversation about fit - your read on the market we’re in, how you think about pipeline and forecasting, and your own conviction about the opportunity in front of us.
Step 6 — Final Presentation
~45 minutes · live pitch and Q&A with a panel
Bring a real pitch or demo of something you sell today, and treat the panel like a real prospective customer. We’re not testing your recall of a new product, we want to see your actual, practiced selling motion, including how you handle questions and objections live.
How to prepare
- Come ready to talk through your track record in specifics; quota attainment, deal size, sales cycle, and the stakeholders involved.
- Prepare a real pitch or demo of something you currently sell, you’ll present it live, as if the panel were a genuine prospect.
- Think about how you build trust with both business and technical stakeholders inside a single deal.