We partner with MSK provider groups and specialty clinics to help them grow, operate more efficiently, and deliver better longitudinal care across patient acquisition, clinical workflows, and ongoing patient engagement. Our platform sits at the intersection of care delivery and clinic operations, helping providers capture more value across the full patient lifecycle.
We’ve recently raised our Series B and are entering our next phase of growth. We’re hiring a Head of Marketing to build and scale the marketing engine that will drive that growth.
This is a pipeline and revenue role. Success means generating high-quality pipeline from the right provider groups, and helping convert that into revenue in a complex, trust-driven market.
We are looking for a hands-on VP, People & Talent to be the first dedicated hire owning recruiting, people operations, and culture at Flagler Health. This is a foundational role. You will not inherit a team, a playbook, or a set of processes. You will build them. You will directly own full-cycle recruiting across engineering, product, GTM, clinical, and G&A functions while simultaneously standing up the people systems (onboarding, performance, compensation, compliance) that a company at this stage needs to scale with intention.
This role reports directly to the CEO and is expected to be in-office at least three days per week in New York City.
Own Recruiting End-to-End: Run the full lifecycle for every open role, from intake and role design with leadership through sourcing, screening, interviews, offer negotiation, and close. You are the recruiting engine for the company.
Build Diverse, High-Quality Pipelines: Act as your own headhunter. Design and execute creative outbound sourcing strategies that reduce dependency on agencies and inbound volume. Healthcare AI talent is niche, and you know how to find people who are not actively looking.
Raise the Interview Bar: Design and coach leadership on structured, evidence-based interviewing that evaluates for mission alignment, adaptability, and long-term potential, not just resume pattern matching.
Close with Conviction: Navigate complex offer negotiations including equity education and comp benchmarking in a competitive market. Maintain a high acceptance rate by ensuring candidates feel informed, respected, and genuinely excited about Flagler.
Scale the Hiring Plan: Partner with the CEO and department leads to translate business goals into a hiring roadmap. You will help the company move from 28 to 50+ headcount this year. That means prioritizing which roles to open, sequencing searches, and moving fast without sacrificing quality.
Build the Foundation: Stand up core people infrastructure from scratch: onboarding programs, an employee handbook, compliance frameworks, benefits administration, and HRIS/ATS workflows. You will choose and implement the tools.
Performance & Growth: Design and launch a lightweight, stage-appropriate performance management framework. Ensure feedback loops are real, calibration conversations happen, and the bar for performance stays high as the team grows.
Compensation & Equity: Own compensation philosophy and benchmarking. Build a comp framework that is competitive, fair, and sustainable at the company's current stage, including equity education for candidates and employees.
Leadership Coaching: Serve as a trusted advisor to leaders across the company on team dynamics, personnel decisions, org design, and how to manage effectively as roles and teams evolve.
Culture Stewardship: Be the person who protects and shapes Flagler's culture as headcount doubles. Help define values, rituals, and norms that scale without becoming performative.
Compliance & Risk: Ensure Flagler stays ahead of employment law requirements across all operating states. Build policies that protect both the company and its employees.
You are a builder who thrives on ownership. You have done this before at an early-stage company, likely as the first or second people/talent hire, and you know what it feels like to simultaneously run five searches, troubleshoot an onboarding gap, and advise a founder on a tough personnel call. You have an investigative instinct for talent: you look past polished resumes to find the real evidence of high performance, adaptability, and mission fit. You treat every candidate with dignity and every leadership conversation with candor. You are energized, not overwhelmed, by the pace and ambiguity of a company scaling this fast.
8+ years of experience in a high-growth startup environment, with significant time spent owning full-cycle recruiting across technical and non-technical roles at all levels.
Direct experience as the first or early people/talent hire at a company scaling from ~20 to 75+ employees. You have built recruiting and people operations infrastructure, not just inherited it.
Strong sourcing chops. You know how to build pipelines through outbound strategies, warm networks, and creative channels, and you do not default to agencies.
Comfort operating as a generalist across recruiting, people ops, and HRBP responsibilities. You understand employment law basics, performance management, compensation benchmarking, and compliance.
Experience with Ashby or a comparable modern ATS, and a strong point of view on how to build efficient recruiting workflows and reporting.
Exceptional judgment and communication. You can advise a CEO, coach a first-time manager, and close a skeptical candidate in the same day.
A genuine interest in healthcare, AI, or the intersection of both. You can speak fluently about what Flagler does and why it matters.
Based in or willing to relocate to the San Francisco Bay Area. This is a hybrid role with at least three days per week in office.
Experience recruiting in healthtech, health systems, or a regulated industry where compliance and credentialing intersect with speed.
Familiarity with multi-state employment compliance, particularly as it relates to remote or distributed team members.
Experience building employer brand from scratch, including careers pages, candidate-facing content, and presence at industry events.
Prior exposure to venture-backed environments and comfort communicating with investors and board members on people metrics.
Rare growth trajectory. $0 to $9M in revenue in 18 months, $29M CARR closed in the last quarter alone. The product works, the market is pulling, and the team needs to grow to meet it.
Foundational impact. You will not be optimizing someone else's system. You will build the people function from the ground up and shape how this company grows.
Direct access to the CEO. This is not a role buried three layers deep. You will have a seat at the table and real influence on company decisions.
Mission that matters. Flagler's AI is improving patient outcomes and reducing provider burnout across 36+ states. The work you enable has downstream impact on real healthcare delivery.
This is what you can expect of your teammates at Flagler:
Persistence + ownership of outcomes: We wear many hats and aren’t afraid to run through walls to solve hard problems.
Personal + professional growth: We push ourselves to learn new things and embrace challenges, even if it means that we sometimes fail.
Don’t take things personally: We value and react quickly to constructive feedback.
Speed is our ally: In the fast-paced world of startups, we understand the value of moving swiftly. We thrive on the adrenaline of working rapidly.
Be Right: We are highly detailed oriented and try to be right, a lot.