Customer Story
Chicago-Based Technology Consulting Firm
How a Chicago Tech Consulting Firm Saved $1.4M in Three Months by Replacing COBRA Subsidies with a COBRA Alternative
Location
Chicago, IL
Industry
Business & Technology Consulting
$1.4M
saved in 3 months
Background
This client is a Chicago-based technology consulting firm with a leadership team that treats how people leave as seriously as how they arrive. Workforce transitions were not a one-time event: like any firm of its size, employees departed throughout the year, and each departure carried both a coverage decision for the employee and a cost decision for the company. The firm’s standard approach, a subsidized COBRA offering, was not delivering the best outcome for anyone involved.
The Challenge
The firm needed an offboarding solution that was both cost-effective and compassionate, and traditional COBRA was neither. COBRA continuation coverage is priced at the full, unsubsidized group premium, making it expensive for the departing employee and a quiet liability for the company: every employee who elects COBRA stays on the group plan, in the population where claims run highest. A COBRA subsidy that looks like a fixed severance line item compounds into real, recurring claims exposure with every transition.
Just as important, the default did not match the firm’s values. Leadership wanted departing employees to feel genuinely supported, not handed the most expensive option and a deadline. The firm saw offboarding as the last, lasting impression it makes: done well, it preserves alumni relationships, protects the employer brand, and keeps the door open for boomerang talent and future collaboration. Done by default, it does the opposite.
The Solution
The firm partnered with When, the workforce transitions platform, to replace costly COBRA subsidies with a When Benefit — a flexible, cash-based COBRA alternative each departing employee could apply to the health plan that actually fit them. Alongside the benefit, employees received on-demand guidance from When’s non-commissioned, licensed agents and access to resources tailored to their career transition.
Implementation moved fast: in just 14 days, When integrated with the firm’s HRIS platform, Workday. From there, outgoing employees were engaged automatically — a co-branded resource portal, one-on-one support from licensed agents, unbiased advice with no commissions steering it, and consistent communication with timely reminders for application deadlines and benefit status updates. One departing employee described the experience:
“I thought I knew insurance from my previous job, but navigating it now left me stumped. Dana was a lifesaver. She walked me through everything, explaining just enough without overwhelming me, and I actually felt good about my choices.”
Departing Employee
The Results
In three months, the firm saved $1.4 million. The savings compounded at every level: about $5,624 per exiting employee across the board, and $23,947 for every employee who converted away from COBRA onto coverage that fit them better.
“Partnering with When transformed our offboarding process and reinforced our core values. By shifting away from costly COBRA subsidies, When is helping us achieve significant savings while elevating the overall experience for departing colleagues. We have always believed in empowering our people, and this approach provides peace of mind during their transition and allows us to maintain healthy relationships with them.”
Company Executive
The employee side of the ledger was just as strong. Over 93% of departing employees agreed with the value of the approach. 61% chose plans more affordable than COBRA, saving an average of $226 per month on premiums — about $2,300 in total premium savings per employee — while the average When Benefit of $1,900 covered roughly three months of premiums in full.
“I ran into system issues and the healthcare.gov support team struggled to help me, but one call with Dana and she unblocked me, and helped me get my application across the finish line!”
When Member, following enrollment
With When’s help, this client set a new standard in employee care — proof that financial prudence and genuine employee support aren’t competing priorities. The firm is fostering positive alumni relationships, strengthening its reputation as an employer of choice, and signaling to prospective talent that it values its people at every stage of their careers.
Not a Matter of If, but When
Workforce transitions are inevitable for every company. Build your offboarding plan before you need it, estimate your own numbers with our savings calculator, and connect with our team to learn how you can do right by your employees while protecting your bottom line.
