About this role
The OpportunityEvery year, tens of millions of Americans go through a coverage transition: a layoff, a resignation, a move into retirement, a 65th birthday while still working. It is one of the most consequential financial decisions a person makes, and it usually arrives as a twenty-page packet during the worst week of their professional life. Nobody owns it. COBRA makes the event compliant; it does not make it managed. That gap is expensive for employers and genuinely hard on people.
When is the enterprise platform for guided health insurance decisions at every qualifying life event. Through When Choice, When Medicare, and When ICHRA, we combine an intelligent decision-support experience with licensed, non-commissioned agents so every person understands their real options and lands somewhere good. We have supported more than one million employees and managed over 204,000 qualifying events for Fortune 50 and Fortune 500 employers, reducing COBRA enrollment by up to 80% while improving the experience for the people leaving. Doing right by employees and taking cost out are usually opposing forces. Here they are the same action.
The roleHealth plans are our highest-leverage distribution channel and, today, our least built out. A single national or regional plan relationship can put When in front of hundreds of employer groups at once, and the plan's own economics point the same direction ours do: the sickest members electing COBRA with no guidance is a problem the carrier feels directly.
We are hiring a VP of Health Plans to own that channel end to end. You will build the health plan and carrier partnership motion from strategy to signed agreements to revenue, and you will own the relationships after they close.
This is a senior individual-contributor-plus role to start: you sell, you build the playbook, and you grow a team behind you as the channel scales.
What you'll ownChannel strategy
Build the health plan partnership strategy: which plans, in what order, with what value proposition and what commercial construct
Segment and prioritize the landscape across national carriers, regional Blues, provider-sponsored plans, TPAs, and level-funded and self-insured blocks
Define the economic model for each partnership type (referral, reseller, embedded, revenue share, per-eligible-life) in partnership with Finance and Legal
Bring a clear point of view on where When sits relative to the plan's existing vendor and stop-loss strategy
Origination and closing
Own the full cycle: source, qualify, run the executive relationship, navigate the buying committee, and close
Sell to the people who own the exposure: Chief Actuary, VP Underwriting, Chief Medical Officer, heads of Employer/Commercial segments, Product, Network, and Strategic Partnerships
Build the business case in the plan's own language: claims exposure on terminated members, catastrophic claim frequency, risk-pool composition, MLR and trend impact
Own a defined annual new-partnership and channel revenue number
Relationship ownership and expansion
Serve as the executive relationship owner post-signature; drive from signed agreement to actual employer group activation, because a signed partnership that doesn't launch groups is not revenue
Build joint go-to-market plans with partner sales, account management, and underwriting teams so When shows up in their employer conversations, renewals, and RFP responses
Enable partner-facing teams: train their sellers, arm them with the narrative and the data ask, and make it easy for them to bring us in
Expand from initial pilot or segment into the full book
Cross-functional leadership
Feed carrier and plan requirements into Product and Operations so what we build is sellable through this channel
Partner with Legal, Compliance, and Security on contracting, data-sharing, HIPAA and SOC 2 requirements, and carrier-specific vendor diligence
Partner with the ICHRA team where plan relationships intersect our broker-aligned motion
Represent When credibly at industry forums and with consultant and reinsurance intermediaries
Hire and lead a partnerships team as the channel proves out
What you bringRequired
10+ years in health plan, carrier, or health tech commercial roles, including 5+ years selling to or partnering with health plans and carriers
Demonstrated record closing complex, multi-stakeholder enterprise partnerships with health plans, with names and outcomes you can speak to
Real fluency in health plan economics: risk pools, medical trend, MLR, underwriting, stop-loss, self-insured versus fully insured mechanics
Working knowledge of the employer benefits ecosystem: COBRA administration, benefits admin platforms, consultants and brokers, and where each one's incentives sit
Executive presence with actuarial, medical, and commercial leadership. You can hold a room where the smartest person is thinking about your claim in basis points
Comfort building a channel that does not exist yet, including the deck, the model, the diligence packet, and the first three deals
Strongly preferred
Direct experience inside a health plan or carrier
Experience with Medicare (MA, Med Supp, Part D) and the coordination questions facing Medicare-eligible active employees
ICHRA, individual market, or exchange distribution experience
Prior early-stage or scaling-company experience where you carried a number and built the motion at the same time
How you work
Analytically honest. You would rather show a plan its real exposure than oversell a projection
Long-horizon patient, short-horizon urgent. Carrier deals take time; you keep them moving anyway
Collaborative across Product, Compliance, and Operations, because this channel gets built by more than sales
Compensation, Location, and Travel
We offer a competitive salary, we pay 100% of your health insurance, stock options and more. This role is remote, with minimal travel for company and occasional client meetings.