Job Search Retro: Customer Success Lead
Updated: January 6, 2026
Mary landed an Enterprise Customer Success Lead role at a late stage fintech company.
Hedgy Member Background
- Previously an Engagement Manager at a growth stage B2B company and a Strategic Accounts Director at a well known market research company.
- Was exploring both startups and late stage companies primarily in CS roles where there would be ownership over onboarding and activating enterprise clients.
- Received two offers on the same day (1 via a Hedgy intro and the other through an old colleague’s intro).
Key Insights
Finding the right job is a team effort
- Even before her job search, Mary had kept biannual 1:1s with a few trusted former co-workers. This made it easier to talk through who it may make sense to reach out.
- In one conversation, a former co-worker had mentioned a recruiter reached to them but it wasn’t a fit and ended up connecting Mary with the opportunity.
- She also leveraged Hedgy to review other opportunities and have another “thought partner” during her search.
The best prep is knowing the product
- Mary spent the majority of her time using the product of the company she was interviewing at and reading as much as she could on their website on what they offered. This helped her understand the pain points of their customers and what solutions were already available in the product.
- As part of her prep she would also think through her top 4 experiences at each of her previous jobs. Focusing on impact and how it drove $$ (particularly relevant in a CS role). This allowed her to draw on them as needed in qualitative interviews.
Simulating what the role would be like
- For both companies a significant part of the interview process was simulating what it would be like in the role. Either a case study presentation or a live simulation where she was asked to interpret metrics or feedback.
- The company she ended up joining gave her a week to prepare an 8 slide presentation that she would use to help activate an existing customer. Much of the discussion during her presentation was to see how she would handle objections, keep the conversation on track and ultimately be able to map solutions to pain points.
This post is part of our job search retro series where Hedgy members who have recently started a new job share learnings from their search. If we can be helpful as you navigate your search, email us at founders@hedgy.works