From Layoff to Startup: Jess Chen's Journey to Reinvent Offboarding

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From Pink Slip to Product Demo: An Unexpected New Chapter

Jess Chen never pictured herself walking out of an office with a cardboard box. As the head of talent operations at a once-high-flying SaaS startup, she’d weathered her share of pivots and restructures. But the sweeping tech layoffs of 2025 weren’t something anyone could outrun. Her team was dissolved, her access card deactivated, and her LinkedIn flooded with “Open to Work” badges overnight[1]. Jess found herself staring at the ceiling, questioning not just her next move, but her place in an industry where the ground seemed to be shifting weekly.

Unearthing a Problem Waiting to be Solved

With rent due and a resume that suddenly felt heavier than helpful, Jess did what she’d coached dozens of candidates to do—reach out, listen, and learn. Over lattes and Zooms with fellow HR leads who’d also been let go, a pattern emerged. Companies were scrambling to handle offboarding more humanely, but most tools were built for recruiting, not caring for the people who were leaving. Those affected by layoffs felt lost in impersonal transition portals, desperate for support, dignity, and real connection.

“I realized I’d spent my whole career optimizing for how we bring people in, but there was almost nothing out there to help them land softly when they’re out. It didn’t seem right to leave it broken.”

The earliest days were messy. Jess sketched workflows on the back of takeout receipts, notepads, and slide decks recycled from her old job. Ideas felt huge, but her resources were thin. She taught herself basic no-code tools, sought part-time contract work to keep the lights on, and reached out to engineers she’d worked with before, promising little more than a mission and a revenue split if things worked out.

First Customers, First Wins, First Pivots

After three months of hustle, she launched a scrappy prototype—an offboarding portal aimed at tech companies needing to lay off employees with empathy and legal rigor. Cold emails met polite rejections, but one former colleague at a Series B fintech gave it a shot, needing to offboard 20 team members quickly and compassionately.

Nothing about the launch was smooth. The server crashed fifteen minutes into the rollout. Templates for severance paperwork had bugs, and email notifications hit spam folders. Still, exit surveys rolled in showing employees appreciated the clear, caring communication. The CTO of her pilot customer called it “the first offboarding experience I didn’t feel ashamed about.” That team paid her first $1,000 invoice by week’s end.

• First paid customer: A small win that proved people would pay for a better exit process.
• First partnership: A local outplacement agency reached out to integrate their reskilling workshops, opening new revenue streams.
• Pivot: Initial focus on large enterprise gave way to mid-market firms after feedback that “giants were too slow to move.” Jess narrowed in on companies with 50-500 employees processing layoffs for the first or second time.

Revenue trickled in, small teams signed up, and Jess slowly built a volunteer team into a full-time remote crew. Customer testimonials led directly to three new clients by the end of month six. Churn stayed low because layoffs, while unpredictable, never seemed to go away.

Three Practical Lessons for Founders in the Trenches

1. Backchannels are your superpower. Jess’s earliest users and advisors came not from job boards, but from word-of-mouth through Slack communities, alumni groups, and contacts she’d helped in the past. These relationships led to honest feedback and warm intros when she needed them most.
2. Build for the pain you know best. Offboarding wasn’t just an HR pain point; it was Jess’s own lived experience. Solving a problem she’d felt personally kept her motivated during the slow stretches when progress felt invisible.
3. Don’t romanticize the pivot, but be ruthless about it. Early on, Jess spent weeks chasing enterprise leads before realizing her fastest-growing users were actually smaller HR teams handling layoffs alone. Course corrections felt embarrassing at first, but focusing on speed and fit got her to product–market fit faster.

“Being let go turned out to be the unlikely gift that pushed me to finally solve the thing I’d been secretly complaining about for years. Founding something doesn’t erase the anxiety, but every real problem you solve puts you back on firmer ground—even if it’s just one customer at a time.”

Looking Back, Looking Forward

Within twelve months, Jess’s startup had helped dozens of companies lay off staff more mindfully, landed $100,000 in annual recurring revenue, and caught the eye of a major HR platform interested in partnership. The journey wasn’t linear, and the scars of uncertainty linger. Yet, each tough call—every bug fixed at midnight, every hard feedback session with users, every awkward cold call—became the backbone of both a new business and a new sense of purpose.

Jess likes to say the “comeback” is less about bouncing back to what was, and more about building something that feels right for what’s next.

What is your biggest takeaway from this journey? Share your thoughts in the comments below!

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