Engagement Marketing Manager

USA (Remote)

Salary Not AvailableMid Level5+ years expFull time

Posted 1 day ago

Job Summary

Own end-to-end lifecycle campaigns and multi-channel outreach for Medicare-related programs, from segmentation and cadence design to optimization, reporting, and agent handoffs. Drive engagement and enrollment KPIs, run continuous tests, and tailor programs to segment realities while ensuring compliance and accessibility.

  • End-to-end campaign ownership across Medicare and related journeys.
  • Manage engagement metrics, weekly reporting, and continuous testing.
  • Collaborate with licensed agents, design, product, and compliance.

Job Description

Responsibilities

  • 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

Requirements

  • 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

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

Benefits

  • We offer a competitive salary, we pay 100% of your health insurance, stock options and more.
When logo

When

When is a comprehensive, AI-driven technology platform and healthcare severance solution that provides unparalleled support for employees navigating offboarding, life changes, and the complex health insurance market, all while saving your company time and money.

Founded in 2020
Chicago, Illinois, USA
26 employees (1 in marketing)

Marketing Team

Marketing Team Size
1 (4% of company)
Median Tenure
1.1 years
Marketing Roles Posted (Last 30 Days)
1

Funding

Total Funding
$17.3M
Last Raise
$10.2M
Series A, 2 months ago

Funding History

  • Jan 2026
    Series A • $10.2M
  • Apr 2025
    Seed
  • Aug 2024
    Seed • $4.6M

Traffic Signals

Monthly Visitors
734
Traffic Source Mix
Search
28%
Direct
47.5%
Referral
5.8%
Social
17.1%
Paid
1.5%

Headcount Trend

Current headcount: ~26
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Engagement Marketing Manager

When · USA · Remote