Latest / The Comeback Career Podcast with Fexingo: Returning After a Gap, Stay-at-Home Re-Entry / How a Career Gap Led to a Customer Success Manager Role
Transcript
- Lucas: So Luna, we’ve covered a lot of specific roles on this show — data analyst, paralegal, even cybersecurity. But one job that’s quietly exploded in the last five years is customer success manager. Luna: Right — it’s become this critical bridge between sales and support. But for a returning parent, is it actually accessible without a technical background? Lucas: That’s exactly what I wanted to dig into. I talked to a woman named Maya who took four years off to raise twins, and she came back as a CSM at a 50-person SaaS startup. She’d previously been an account manager at a mid-size software company, so she wasn’t starting from zero — but the gap was real. Luna: Four years is a sizable gap. How did she handle that on her resume? Lucas: She didn’t try to hide it. Instead, she framed those four years as a period of intentional skill development. She took free online courses — not from big-name platforms, but from the Customer Success Association — and she stayed current by reading industry blogs and joining LinkedIn groups. When she applied, her cover letter literally said, ‘I spent four years managing the most important relationships in my life. Now I’m ready to manage your most important client relationships.’ Luna: That’s a smart reframe. And it’s not just a line — the empathy and patience you build as a parent really do transfer. Did she target any specific type of company? Lucas: She deliberately avoided big enterprises. She went after startups and smaller scale-ups — companies with fewer than a hundred employees. Her reasoning was that those companies care more about attitude and relationship skills than a pristine five-year run at a Fortune 500. And she was right. Luna: Smaller companies are also less likely to have an automated HR filter that trashes your resume the moment it sees a gap. Lucas: Exactly. And speaking of which — if you’re a parent listening and this conversation is helping you think about your own return, I want to quickly mention that listener support is what keeps this podcast ad-free and independent. If you find value in episodes like this one, you can support the show at buy me a coffee dot com slash fexingo. It’s a simple way to say thanks, and it genuinely helps us keep making episodes that focus on real stories, not hot takes. Luna: Yeah, I love that we can keep it ad-free. And Maya’s story is a perfect example of why — no fluff, just a practical path. Lucas: So back to Maya. She landed a CSM role at a company that provides project management software for creative teams. Her title is Customer Success Manager, and she manages about 20 accounts with a combined annual recurring revenue of roughly two million dollars. Luna: Two million in ARR — that’s significant. And she does that from home, right? Lucas: Completely remote. She started in 2025, so the company was already distributed. She told me her onboarding was entirely virtual, which actually helped because she could flex around her kids’ schedule — do training modules during naptime, then shadow calls after they were in bed. Luna: That flexibility is huge for a returning parent. But what about salary? Did she have to take a big step back? Lucas: Surprisingly, no. She asked for the market rate for a CSM with her level of experience — which, based on her pre-gap account management years, was about five years total. She got an offer at sixty-five thousand base plus variable comp, which is right around the median for a CSM at a company that size. She told me the gap didn’t come up as a reason to offer less, partly because she had a concrete answer for what she did during those years. Luna: So the key is having a narrative. Not just ‘I took time off’ but ‘I used that time to develop these specific transferable skills.’ Lucas: Exactly. And Maya went a step further — she started a blog during her gap, not about parenting, but about customer retention strategies she was learning from books and case studies. She published six posts over two years. It wasn’t a huge audience, but when interviewers Googled her, they found active, thoughtful writing about exactly the field she was applying for. Luna: That’s brilliant. It turns the gap into a portfolio. And it works because customer success is a field that values continuous learning and communication. Lucas: Right. She also leveraged her network — not for job leads, but for informational interviews. She reached out to five former colleagues who had moved into customer success and asked each one, ‘What’s the biggest challenge you face?’ and ‘What tool do you use daily?’ That gave her vocabulary she could drop in interviews. Luna: So she basically did a mini-market research project on the role before applying. That’s the kind of preparation that separates someone who’s just eager from someone who’s actually ready. Lucas: And it worked. She got two offers in three months. One from a well-known unicorn — which she turned down because the culture felt too ‘always-on’ — and one from the startup she chose. She said the deciding factor was that the CEO said in the interview, ‘We hire for mindset and train for skill.’ Luna: That’s the kind of line every returning parent wants to hear. Did she feel any imposter syndrome at first? Lucas: Absolutely. She told me the first month she was constantly checking her own messages three times before sending. But within three months she had her first client win-back — a customer who was about to churn, and she turned them around by listening and offering a personalized onboarding session. That was the moment she felt fully legitimate. Luna: And that’s the thing — customer success is fundamentally about listening and problem-solving, which are skills parents practice every single day. Lucas: Exactly. Maya’s advice to other returning parents is simple: don’t underestimate the organizational skills you built managing a household schedule, and don’t be afraid to lean into the empathy you’ve developed. Those are exactly the traits that make a great CSM. Luna: And if you’re a parent listening, you can start today — read one article on customer success, set up a LinkedIn profile, and think about one story from your gap that shows resilience or problem-solving. Lucas: That’s the takeaway. Maya’s story is proof that a career gap doesn’t have to be a liability — it can be a different kind of training ground. And customer success is a field that’s built to recognize that.