Manager / Director of Enrollment (Series A Healthtech)

Reporting to the VP of Operations, you will own the enrollment KPIs — scheduled calls, attended calls, and converted, enrolled families — and the quality that has to come with them. You will manage, coach, hire, and performance-manage a team of ~15 specialists (growing over the coming year), and partner with product, engineering, and data on the AI systems that increasingly drive the funnel.

What You'll Do

Team Leadership & Coaching

• Line-manage a remote, hourly team of ~16 enrollment specialists — setting the coaching cadence, running 1:1s, and building the day-to-day performance-management rhythm that keeps a distributed team engaged and accountable.
• Own hiring, onboarding, training, and performance management for the team, scaling it thoughtfully as enrollment volume grows.
• Build the training and call-coaching program that lifts the whole team — not just the top performers — using motivational interviewing and objection-handling techniques suited to a free program families have never heard of.

Performance & Conversion

• Own the enrollment funnel by the numbers: scheduled calls, show rate, on-call conversion, and booked-call-to-enrolled conversion — and relentlessly improve them.
• Diagnose where the funnel leaks and why, and design the coaching, training, and process changes that move conversion.
• Set clear targets, hold the team to them, and make the funnel legible to leadership.

Quality & Compliance

• Own the quality of enrollment, not just the volume: ensure every enrollment is compliant with Medicare rules and that the application rejection rate stays below target.
• Run a HIPAA-compliant outbound-calling operation, with proper consent and eligibility captured before any information is collected.
• Build the QA and monitoring that lets you push conversion without ever trading away compliance.

AI & Systems

• Own the metrics for our AI outbound-calling and AI compliance/coaching systems, in close collaboration with product, engineering, and data.
• Understand the workflows deeply, monitor them closely, and recommend improvements — defining what "good" looks like and driving the roadmap, without needing to engineer it yourself.
• Ensure Carespaces, DialPad, cal, and the AI toolkit work together to make specialists faster and enrollments cleaner.

Process & Continuous Improvement

• Take a functioning team from good to great through structured, continuous improvement — redesign workflows, roll out changes to a live team, and prove the lift.
• Identify the constraints worth fixing first, and sequence quick wins ahead of bigger bets.

Cross-Functional Collaboration

• Partner with Sales and Account Management, who own the partner-clinic relationships that generate patient referrals, to make sure referrals convert.
• Work closely with Product, Data, Operations, and Compliance so the enrollment engine supports the whole care motion.
• Represent Enrollment with rigor and credibility in cross-functional and leadership settings.

You'll Love This Role If

You see leverage in people and systems. The team you build and coach multiplies how many families get the support they need. A tighter coaching loop that lifts the whole team is more satisfying to you than any single great call.

You improve what already works. You'd rather take a functioning team and make it measurably better than stand something up from a blank page. You love finding the constraint and fixing it.

You balance the number and the mission. You can push conversion hard while never losing sight of compliance, quality, or the fact that these are vulnerable families — and you know the two aren't in conflict when the system is built right.

You lead from the numbers. You're fluent in data, you coach against it, and you make a complex funnel legible to the people who depend on it.

You foster a feedback loop. You're coachable, you iterate quickly, and both share and receive feedback freely.

What We're Looking For

Experience and skills

• 3 to 8+ years of total experience, including direct management of a remote, hourly, W2 call-center or contact-center team of comparable size (~15+ reps), with hiring and performance management at that scale.
• A track record of owning conversion or funnel metrics and moving them — you diagnose from the data, not from anecdote, and you're genuinely strong with numbers.
• Demonstrated ability to coach call craft and build training that lifts a whole team, ideally including motivational interviewing, objection handling, or QA-driven coaching.
• Experience running a compliant, HIPAA or other regulated industry call center operation, and owning a quality or error-rate metric alongside a conversion metric.
• A clear good-to-great story: you've taken a functioning team or process and measurably improved it through coaching, training, or process change.
• Excellent written and verbal communication, with the ability to make a complex funnel legible to a cross-functional team and leadership.

Preferred qualifications

• Healthcare, value-based care, or benefits-enrollment operations experience — a member-services, patient-intake, or enrollment background is ideal.
• Familiarity with Medicare-reimbursed care models (GUIDE, PIN/CHI, CCM/PCM) or comparable healthcare enrollment structures — though no specific GUIDE knowledge is required.
• Experience partnering with product or data teams on AI-driven or automated workflows, or running conversation-intelligence and QA tooling.
• Bilingual English/Spanish, or experience running a bilingual enrollment or member-services team (a plus, not a requirement).

A meeting lands on your calendar

If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.