The Opportunity
Every 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 role
Our commercial results depend on one thing after the contract is signed: whether the eligible population actually engages. Every point of engagement lift moves member outcomes, client savings, and renewal economics at the same time.
This role owns that. You will build and run the marketing engine that reaches eligible employees and members at their moment of decision, gets them to engage, and moves them through to enrollment. You will own the funnel from eligibility file to enrolled member across email, SMS, direct mail, print, landing pages, and inbound call flows, for both When Choice and When Medicare.
This is a builder role with real measurement discipline attached. Engagement rate, contact rate, enrollment rate, and cost per enrollment are your numbers.
What you'll own
Lifecycle and campaign execution
Design, build, and run multi-channel outreach programs (email, SMS, direct mail, print, digital) that reach eligible populations at the right moment in the qualifying event window
Own the When Medicare 64½ outreach journey end to end: proactive education sequences that reach employees before they have to ask
Own the When Choice separation journey: reaching departing employees during the election window with decision support, not a compliance notice
Build segmentation and cadence logic that reflects real timelines (election deadlines, Medicare enrollment windows, plan year dates)
Conversion and optimization
Own engagement and enrollment KPIs; report on them weekly with a clear read on what moved and why
Run a continuous testing program on creative, subject lines, channel mix, send timing, and offer framing
Partner with the licensed agent team to tighten the handoff from outreach to one-on-one guidance, and close the loop on where members drop
Improve landing page and inbound flow conversion in partnership with design and product
Client-facing engagement programs
Build the co-branded engagement playbook clients use to introduce When to their population, including HR-ready toolkits, manager talk tracks, and internal comms templates
Work with Customer Success on launch communications for new clients and on engagement lift plans for underperforming accounts
Tailor programs to segment realities: large self-insured employers, Medicare-eligible active populations, and broker-sold ICHRA groups
Compliance-aware creative
Write and manage copy that is clear, plain-language, and compliant. Medicare-facing material is subject to CMS marketing rules: we educate and enroll, we do not incentivize or coerce
Route Medicare and insurance-facing copy through compliance review as a standard step, not an exception
Maintain accessibility and readability standards across every member-facing asset
Systems and reporting
Own the marketing automation and campaign stack for member engagement; keep data flows between eligibility files, CRM, and outreach tooling clean and auditable
Build dashboards leadership can trust without asking a follow-up question
What you bring
Required
5+ years in lifecycle, growth, or engagement marketing with direct ownership of conversion metrics, not just program delivery
Demonstrated experience running multi-channel campaigns at scale (six figures of contacts or more) with documented lift
Hands-on with marketing automation and CRM (HubSpot, Marketo, Braze, Iterable, or similar); comfortable building the campaign yourself rather than briefing it out
Strong writer. You can produce plain-language copy about a confusing, high-stakes topic without making it sound like a legal notice
Analytical fluency: you can build the segmentation, read the funnel, design a valid test, and defend the result
Strongly preferred
Healthcare, health insurance, benefits, or regulated-industry marketing experience
Working familiarity with COBRA, ACA, Medicare, or ICHRA mechanics, or clear evidence you can learn a complex regulatory domain fast
Experience marketing to a population reached through an employer or partner channel rather than direct-to-consumer paid acquisition
Experience working alongside a licensed sales or agent team
Experience with Klaviyo and Claude is a plus
How you work
You care about the person on the other end of the campaign. Most of them are having a bad month, and the outreach should feel like help
You are comfortable operating in a fast-moving environment where you define the process as you build it
You bring a point of view and hold it with data
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.