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Dearest Care

Tech-enabled patient advocacy and navigation platform

Head of Performance Marketing

Full-Time
No salary listed
Mid
Remote in USA
Remote
Growth & MarketingPerformance & Paid Marketing

About the job

Requirements
  • You have 3–6+ years of hands-on paid social experience, including managing substantial budgets for Meta and Google campaigns.
  • You have experience with significant monthly or annual spend, ideally in high-growth startups, consumer healthcare, insurance, lead generation, marketplaces, fintech, or other high-consideration categories.
  • You have an in-depth understanding of Meta and Google campaign architecture, optimization mechanics, budget pacing, bidding, creative testing, and audience strategy.
  • You have a track record of optimizing toward true business outcomes, not just low CPAs or cheap clicks.
  • You have strong creative judgment and the ability to analyze, critique, and suggest improvements for ad messaging and targeting.
  • You are proficient with both quantitative performance signals, including data and funnel metrics, and qualitative signals, including patient feedback, call outcomes, and creative insights.
  • You have experience managing tracking and measurement, including Meta Pixel, CAPI, UTMs, attribution windows, event definitions, and funnel reporting.
  • You can communicate results and strategy clearly to non-marketers without jargon.
  • You demonstrate proactive ownership, continuous improvement, and willingness to move quickly and iterate.
  • You have excellent taste, clear written communication, and demonstrated empathy for patients, caregivers, older adults, and families navigating healthcare.
  • You must be based in the United States.
Responsibilities
  • Lead paid social performance across Meta through campaign strategy, account structure, audience testing, budget management, creative testing, and ongoing optimization.
  • Build a system connecting message, creative, audience, landing page, lead quality, and downstream conversion for optimization beyond platform metrics.
  • Transform Dearest Care’s positioning into scalable ad concepts that convey advocacy as clear, urgent, trustworthy, and accessible.
  • Work with creative and brand teams to identify resonant messages, breakthrough hooks, and creative themes to expand, retire, or refine.
  • Establish a repeatable creative testing process by developing briefs, reporting performance, capturing learnings, and making recommendations.
  • Analyze the full funnel, including impressions, click-through rate, cost per click, conversion rate, lead quality, booked appointments, show rates, enrollment, retention, and lifetime value.
  • Partner with analytics to maintain clean tracking, consistent key performance indicator definitions, valid attribution, and disciplined reporting.
  • Own paid social measurement hygiene, including Pixel, CAPI, event mapping, UTMs, conversion signals, and quality feedback loops.
  • Align with conversion, lifecycle, and product teams to ensure a seamless experience from ad to post-click.
  • Diagnose performance issues such as creative fatigue, audience saturation, landing page issues, lead quality, tracking, and offer or message mismatch.
  • Test new paid social channels such as TikTok, Snapchat, YouTube Shorts, or other channels and evaluate their performance potential.
  • Translate channel performance into actionable recommendations for leadership and cross-functional teams.
  • Establish reporting rhythms, testing priorities, documentation, and decision rules for paid social.
  • Manage and mentor junior team members or external partners as needed as the team grows.
Desired Qualifications
  • A background in lead generation, healthcare, Medicare, insurance, benefits, home care, financial services, or other trust-heavy consumer sectors is preferred.
  • Paid social experience on TikTok, Reddit, YouTube, or similar channels is a bonus.

About the company

Dearest Care provides technology-enabled patient advocacy to help people navigate healthcare, especially Medicare patients, with a dedicated human advocate who guides them through diagnoses, medical bills, and care plan coordination. A proprietary platform blends AI tools, clinical workflows, and operational systems so advocates can deliver support at scale. The service is offered through B2B partnerships with health systems, IDNs, and regional provider groups, and direct-to-consumer access, combining personal human connection with technology to speed, empathize, and ensure consistency in care navigation. The company’s goal is to close gaps in healthcare access and navigation by giving every patient a determined advocate—“everyone deserves a fighter.”

Company Size

1-10

Company Stage

N/A

Total Funding

N/A

Headquarters

San Francisco, California

Founded

2025

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Simplify Jobs

Simplify's Take

What believers are saying

  • October 2026 site update shows 27,000 patients and same-day appointments, evidence of demand.
  • Series A backing from Omada, Oscar, and UnitedHealthcare improves credibility with providers.
  • September 2026 hiring for operations, data, and sales shows active expansion across functions.

What critics are saying

  • June 2026 and September 2026 job posts signal repeated hiring, not proven enterprise contracts.
  • Fewer than 15 employees in August 2026 makes scaling health-system sales brutally constrained.
  • If Medicare pricing or access rules shift in 2026, Dearest loses its core acquisition channel.

What makes Dearest Care unique

  • Dearest pairs Medicare patients with human advocates backed by proprietary workflows and AI tools.
  • September 2026 site claims nationwide Medicare coverage across all 50 states.
  • October 2026 careers page lists 103+ advocates, 29-year average experience, and 24-hour support.

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Benefits

  • Remote Work Options
  • Company Equity