Latest / The Comeback Career Podcast with Fexingo: Returning After a Gap, Stay-at-Home Re-Entry / How a Career Gap Helped One Parent Pivot to Tech Sales
Transcript
- Lucas: Today, I want to talk about one of the most intimidating pivots you can make coming off a career gap: moving into tech sales. It’s a field where everything seems to hinge on recent, relevant experience — quotas, cold calls, CRM data — and if you’ve been out of the workforce for two or three years, the assumption is you start at zero. Luna: And yet, the stereotype of the tech sales rep is this young, hungry recent grad. So where does a parent re-entering after a gap fit in? Lucas: That’s exactly the question. And I’ve got a concrete example that flips the script. I was talking to a woman named Maya Rodriguez — she’s a former elementary school teacher who took a three-year career gap to raise her two kids. When she decided to re-enter, she didn’t go back to teaching. She set her sights on a sales development role at a mid-market SaaS company. And she got it. Luna: I love that — teaching to tech sales. That’s a big leap. How did she frame it? Lucas: So Maya’s key insight was this: managing a classroom of 25 energetic six-year-olds is, in a lot of ways, exactly like managing a sales pipeline. You’ve got to prioritize. You’ve got to handle objections — try convincing a first-grader to eat broccoli. You’ve got to track progress, follow up, and maintain enthusiasm even when things aren’t working. Luna: Right — the parallel is actually stronger than most people realize. A teacher’s day is a constant cycle of outreach, persuasion, and data tracking. Lucas: Exactly. And Maya didn’t just rely on that analogy in interviews. She used her gap year to actually learn the tools. She took a free Salesforce trailhead course — that’s Salesforce’s online learning platform — and got herself certified as a Salesforce Administrator. She also spent time on LinkedIn learning learning about cold outreach and sales methodology. Luna: So she didn't just talk about transferable skills — she built new ones during the gap. Lucas: That’s the critical move. The gap isn’t a blank space. It’s an active period where you can acquire exactly the credentials hiring managers are looking for. In Maya’s case, she targeted the tools that every sales team uses: Salesforce, Outreach for email sequencing, and LinkedIn Sales Navigator. She actually got a 30-day free trial of Sales Navigator and practiced finding decision-makers at companies she was interested in. Luna: And when she started applying, did she lead with the teaching background or the new skills? Lucas: She led with the new skills, but she anchored everything in the story of why she wanted to move into sales. She said, 'I spent years convincing parents to support their kids’ education. I want to spend my days convincing people to invest in a product that solves real problems.' That narrative is powerful because it shows intent, not desperation. Luna: I think that’s the part returning parents underestimate. They worry the gap looks like a weakness, but it can actually show that you’re deliberate — you took time, you figured out what you really wanted, and you went and got the skills. Lucas: Right. And when Maya started sending cold emails to hiring managers, she didn’t hide the gap. She put it right in the subject line: 'From classroom to sales floor — 3 years later.' She said that line got a 40 percent open rate, which is double what most cold emails get. Luna: That’s smart. You’re turning the potential objection into a hook. Lucas: Exactly. And the response she got from one VP of Sales — the one who ended up hiring her — was, 'I’ve never seen anyone so transparent about a gap. I figured if you can handle a classroom of second-graders, you can handle a few grumpy prospects.' Luna: So the gap actually became a signal of resilience rather than rust. Lucas: That’s the phrase right there. Resilience. Because if you’ve been out raising kids or caring for a family member, you’ve been developing patience, adaptability, and the ability to manage chaos. Those are gold in a sales role. Luna: But there’s a trap here, right? Some people might over-apologize for the gap. They might feel like they need to explain it away. Lucas: Absolutely. And Maya told me she made that mistake in her first few interviews. She’d say things like, 'I know I’ve been out for a while, but I’m a quick learner.' She realized that framing puts you on the defensive. Instead, she started saying, 'I took three years off to focus on my family, and during that time I built a foundation for this next chapter.' That’s ownership. Luna: Ownership — that’s a good word. You’re not a victim of the gap; you’re the author of it. Lucas: And look, not every company is going to be open to that story. Maya applied to about 30 roles before she got her first interview. But the companies that did interview her, she said, were usually more open-minded and less obsessed with pedigree. They were willing to bet on potential. Luna: So the strategy isn’t to convince everyone. It’s to find the employers who value the specific combination you bring. Lucas: Exactly. And one tactic Maya used that I loved: she identified companies where the VP of Sales or the founder had a non-traditional background herself. She’d look on LinkedIn for people who came from teaching, or nursing, or the military — people who made a big pivot. And she’d target those companies because they already understood that the best salespeople don’t always come from sales. Luna: That’s a great filter. It saves you from wasting time on companies that won’t see your value. Lucas: Right. And then there’s the interview itself. Maya prepared a 'Sales Scenario' — she called it her 'Lesson Plan.' She had a five-minute pitch that started with her teaching background, moved into her gap year learning Salesforce and cold outreach, and ended with a mock discovery call. She actually practiced it on her husband and her former teaching mentor. Luna: A mock discovery call — that’s so specific. What did that look like? Lucas: She took a product — say, a project management tool — and she role-played asking questions about a prospect’s workflow, their pain points, their budget. She recorded herself and listened back to see where she was stumbling. She told me that doing that five times made her feel more confident than any book she read. Luna: That’s the kind of preparation that actually bridges the gap between where you are and where you want to be. Lucas: Yeah. And I think there’s a bigger lesson here. The career gap gives you something that a lot of early-career salespeople don’t have: perspective. You know what it feels like to be on the other end of a pitch — to be the busy parent who doesn’t have time for another cold call. That empathy is a massive advantage. Luna: You can hear it in the way she frames her outreach. It’s not 'buy this thing.' It’s 'I know you’re busy, here’s a specific reason this might matter to you.' Lucas: Exactly. And that’s the kind of thing you can only learn from lived experience, not from a sales playbook. Luna: This has been so practical. If someone listening is thinking about making this pivot, what’s the one thing you’d tell them to do this week? Lucas: Pick one sales tool — Salesforce, HubSpot, Outreach — and get a free certification. Most of them take less than ten hours. Then write a cold email to three hiring managers at companies you admire, and put the gap in the subject line. See what happens. Luna: And don't apologize for it. Just own it. Lucas: Exactly. And if today’s episode gave you a concrete idea or a new way to think about your own career gap, that’s the whole goal here. These episodes stay free because listeners find value in them. If you want to support that, you can head to buy me a coffee dot com slash fexingo. It’s a simple way to say 'this helped'. Luna: Yeah, and it really does keep the lights on. Plus it's way more rewarding than a random podcast ad. Lucas: So back to Maya — I actually asked her what surprised her most about the whole process. She said it was how many recruiters told her they were impressed that she’d taken the initiative to learn Salesforce during her gap. They said, 'Most candidates we see have sales experience but haven’t bothered to get certified.' She had the certification and no direct experience, and they saw that as a sign of drive. Luna: So the gap, combined with intentional learning, became a differentiator. Lucas: Exactly. And that’s the message I want to leave listeners with: a career gap doesn't have to be a hole you climb out of. It can be a platform you build on. It just takes some intentionality about what you learn and how you tell your story. Luna: Thanks, Lucas. And thanks to Maya for sharing her story. For anyone thinking about tech sales, I hope this gave you a real blueprint. Lucas: Next time, we’re going to look at how a career gap can help you land a role in customer success — which is another great re-entry path. Until then, keep building.