### Carly Keller

### VP of Client Operations

Naval Academy graduate and former Navy officer who led Operations at ApartmentJet through its Expedia acquisition, where she then built and managed large client service teams at Expedia. Carly brings military discipline combined with expertise in scaling customer success operations, having achieved 42% lead-to-lease conversion rates at Rentgrata. Her proven track record in SaaS implementations, client onboarding, and building high-performing service organizations positions her to ensure When delivers exceptional experiences that transform offboarding from liability to competitive advantage.

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Insight\
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Jun 17, 2026\
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**Your Aging Workforce Is a Benefits Cliff. Here's the Data.**\
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[Carly Keller](/content/explore/blog/aging-workforce-medicare-benefits-cliff/index.html)

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Insight\
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Apr 14, 2026\
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**"Our Plan Is Too Rich. They'll Always Choose COBRA."**\
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[Carly Keller](/content/explore/blog/health-insurance-plan-is-too-rich/index.html)

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Insight\
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Feb 9, 2026\
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**Why Proactive Medicare Support Delivers ROI**\
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[Carly Keller](/content/explore/blog/why-proactive-medicare-support-delivers-roi/index.html)

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News\
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Nov 5, 2025\
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**When CEO Andy Hamilton Featured in "All the Cool Girls Get Fired"**\
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[Carly Keller](/content/explore/blog/when-ceo-andy-hamilton-featured-in-all-the-cool-girls-get-fired/index.html)

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Stories\
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Sep 16, 2025\
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**A When Story - Meet Nicole**\
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[Carly Keller](/content/explore/blog/a-when-story-nicole/index.html)

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News\
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Apr 22, 2025\
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**When Partners with Iowa State University, Helping Graduates Navigate Health Insurance**\
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[Carly Keller](/content/explore/blog/when-partners-with-iowa-state-university-helping-graduates-navigate-health-insurance/index.html)

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Insight\
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Nov 10, 2024\
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**Client Saved $1.4M in 3 Months with When’s Workforce Transitions Platform**\
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[Carly Keller](/content/explore/blog/chicago-tech-consulting/index.html)