Dearest Care

Jobgether
·2 days agoJobgether
·2 days agoHead of operations
Location
remote, United States
Salary
$225k – $245k/yr
Commitment
Full Time
Level
Director
Required skills
Job Description
This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Head of Operations based in the United States.
This is a senior, hands-on leadership role responsible for building and running the operating engine of a fast-growing healthcare technology company. You will oversee the full operational ecosystem, spanning clinical operations, revenue cycle management, sales, growth, quality, compliance, finance, HR, and the end-to-end patient journey. The role has direct ownership of the metrics that determine scalable growth, including unit economics, gross margin, LTV/CAC, conversion, and retention. You will work closely with founders and senior leaders, combining data-driven decision-making with practical execution. This is an AI-native environment where you are expected to identify manual processes, deploy technology, and build systems that improve efficiency and patient outcomes. With significant autonomy and broad scope, you will have a direct influence on operational excellence, product decisions, growth, and the company’s readiness for its next stage.
Accountabilities:
- Own the core business metrics, including LTV/CAC, gross margin, contribution margin, cost to serve, patient growth, conversion, activation, and retention, ensuring growth is supported by healthy and improving unit economics.
- Identify operational and financial leaks across the patient funnel, care delivery, and revenue cycle, develop corrective actions, and drive measurable improvements in profitability and gross margin.
- Run the company’s operating cadence across clinical operations, advocates, providers, call center operations, RCM, contracting, credentialing, claims, sales, growth, quality, compliance, finance, and HR through structured weekly scorecards, monthly reviews, and quarterly targets.
- Diagnose operational breakdowns quickly, identify root causes, implement practical fixes, and establish repeatable processes that prevent recurring issues and reduce dependence on individual heroics.
- Own the end-to-end patient funnel from initial contact through onboarding, first physician and advocate interactions, ongoing engagement, and retention, with deep visibility into conversion rates and points of patient drop-off.
- Optimize speed-to-lead, channel economics, pipeline quality, activation, and retention through continuous experimentation and close collaboration with product and commercial teams.
- Build and operate a world-class advocate organization, including capacity planning, staffing models, service levels, productivity, quality assurance, and the systems advocates rely on every day.
- Improve advocate workflows so teams can spend more time supporting patients and less time navigating inefficient internal processes.
- Drive AI adoption across operational workflows, partnering with technology and product teams to apply AI to call quality assurance, summarization, follow-up, documentation, RCM, credentialing, reporting, and other manual processes.
- Measure the business impact of AI initiatives, ensuring technology meaningfully lowers costs, increases operational capacity, improves quality, increases conversion, or enhances the patient experience.
- Champion the patient experience by monitoring critical moments across the journey and resolving dropped calls, missed handoffs, delayed follow-ups, and unresolved issues before they negatively affect patients.
- Work directly with founders and senior leaders to influence product, go-to-market strategy, operational priorities, major contracts, and preparation for the company’s next growth stage.
- Establish scalable systems across credentialing, contracting, claims, compliance, finance, HR, and quality so critical functions operate through clear processes, data, and accountability.
Requirements
- 7+ years of operations experience in telehealth, technology-enabled care, consumer health technology, or a comparable healthcare environment, including experience leading functional leaders rather than only individual teams.
- Demonstrated ownership of a patient or customer funnel, with the ability to understand and manage each stage, conversion rate, operational constraint, and improvement opportunity.
- Hands-on experience running contact center or high-volume care operations, including staffing models, service levels, productivity, and quality assurance.
- Direct exposure to revenue cycle management, credentialing, payer enrollment, or related healthcare financial operations, with an understanding of how these functions affect growth and unit economics.
- Strong data-driven operating mindset, with the ability to know the critical numbers, detect when performance is deteriorating, identify root causes, and move quickly from insight to execution.
- Demonstrated ability to build scalable processes and operating systems in environments where ambiguity is high, priorities shift quickly, and resources are limited.
- Strong AI fluency and enthusiasm for applying AI to real operational workflows, with the ability to identify high-value automation opportunities and evaluate their measurable impact.
- Excellent judgment, prioritization, and execution skills, with a willingness to operate hands-on rather than manage exclusively from a distance.
- Strong communication skills and the ability to work effectively with diverse stakeholders, from patients and care teams to health plan, contracting, and executive leadership.
- Comfortable partnering directly with founders and senior executives and influencing product, growth, go-to-market, and strategic decisions.
- Entrepreneurial mindset, high ownership, resilience, and a willingness to operate in a demanding, high-velocity environment where significant responsibility comes with the mandate.
- Experience working with Medicare or Medicaid populations is a strong plus.
- Experience helping an early-stage company scale from Series A toward Series C is advantageous.
- Experience leading operations for a senior patient population or working closely with founders and executive teams in a high-growth healthcare company is a plus.
Benefits
- Competitive annual base salary of approximately $225,000–$245,000 USD.
- High equity ownership in a rapidly growing company.
- Fully remote work environment, with the leadership team meeting periodically in the San Francisco/Bay Area.
- Significant autonomy and direct ownership of the company’s operating engine, with authority to shape how the organization runs.
- Direct partnership with founders and senior leadership, with meaningful influence over product, go-to-market, growth, and strategic execution.
- Opportunity to build scalable healthcare operations at a critical stage of company growth.
- Mission-driven work focused on improving healthcare navigation and helping patients and families manage complex healthcare journeys.
- High-growth, high-ownership culture emphasizing rapid execution, thoughtful problem-solving, accountability, and continuous improvement.
- Distributed working environment primarily aligned with the Americas time zones.
- Culture centered on conscious leadership, healthy human connection, creativity, excellence, direct communication, and customer impact.
- Opportunity to work at the intersection of healthcare, technology, AI, operations, and patient experience.
How Jobgether works: We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best!
Why Apply Through Jobgether? Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.
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