For decades, COBRA compliance has been one of those “necessary evils” for employers — a regulatory requirement buried in HR checklists and legal manuals. Under federal law, employers offering group health plans must allow eligible former employees and their families the option to continue coverage when employment ends or hours are reduced. Employers must notify departing workers and ensure the paperwork is handled correctly — or face compliance risk.
But once that obligation is met, the experience has traditionally ended abruptly.
A health plan continuation notice. A severance package. Laptop access terminated. Key cards turned in. And then — goodbye.
For many employees, especially those who have spent years or even decades with an organization, this moment feels less like a transition and more like being cut loose. After long careers of contribution and loyalty, they are suddenly left to navigate healthcare, income uncertainty, and job transition entirely on their own.
The Human Side of Off-Boarding Has Long Been Ignored
Historically, COBRA administration has been treated as a purely transactional exercise. Employers — even thoughtful, well-intentioned ones — have focused on compliance while overlooking the emotional and practical complexity of what happens next.
Yet the COBRA election window often coincides with one of the most stressful periods in a person’s life:
- Confusion around deadlines and eligibility
- Sticker shock when premiums shift from employer-subsidized to employee-paid
- Lack of clarity around alternatives like the individual market, Medicare, or Medicaid
- No support for related coverage decisions such as dental, vision, or life insurance
Compliance may have been satisfied, but support was not.
A New Model Emerges: COBRA Compliance Meets Employee Assistance
That dynamic is starting to change.
A new category of solutions is emerging that reframes off-boarding as more than an administrative ending. Companies like Kept.io are helping redefine what COBRA support can look like by combining compliance with education, guidance, and practical transition support — something that closely resembles an Employee Assistance Program for departing employees.
Instead of simply handing someone a COBRA notice, this approach provides:
- Clear, understandable guidance around COBRA mechanics and timelines
- Support in evaluating alternatives such as exchange plans, subsidies, Medicare, or Medicaid
- Help identifying gaps in coverage, including dental, vision, and life insurance
- Resources that extend beyond insurance, including job placement and transition support
This creates a bridge — not just between employment and healthcare coverage, but between one chapter of a career and the next.
Why This Matters to Employers
The way an organization treats employees at the moment they leave often leaves a deeper impression than how they were treated while they stayed.
A more thoughtful off-boarding experience:
- Preserves dignity during a vulnerable moment
- Reduces confusion and poor decision-making around healthcare
- Strengthens employer brand and long-term reputation
- Aligns compliance obligations with cultural values
Former employees don’t vanish. They become future hires, referral sources, customers, and ambassadors — or detractors. How they experience their exit matters.
CorpStrat’s Perspective
At CorpStrat, we spend every day working with employers on benefits strategy, risk management, and workforce planning. We also see firsthand where systems fall short — particularly at moments of transition.
That’s why CorpStrat principals have chosen to invest in Kept.io
Not simply as a vendor relationship, but because we believe in the concept: that terminated employees deserve more than a packet and a deadline. We believe COBRA electees should be supported, educated, and treated as consumers navigating complex decisions — not as administrative loose ends.
We also hope insurance carriers and the broader benefits ecosystem continue to move in this direction, embracing more consumer-centric thinking around COBRA elections and post-employment coverage.
Looking Ahead
COBRA was designed as a safety net — not a roadmap. But today’s workforce demands more clarity, more support, and more humanity at moments of change.
Startups like Kept.io represent an important cultural shift — one that moves off-boarding from cold compliance to thoughtful transition. While the path of any startup may evolve, the direction here matters.
The future of employee benefits will be shaped not only by how companies care for people while they are employed — but by how they help them move forward when they are not.
