Head of Marketing

Flagler Health is a fast-growing healthtech company transforming how healthcare organizations deliver care through AI-powered workflow automation, remote patient engagement, and chronic care programs. Our platform has already served over 1.5 million patients and is trusted by providers and payers to improve efficiency, lower costs, and drive better outcomes. With a unique freemium model and minimal direct competition, we are poised to capture a large share of the $4.5T U.S. healthcare industry.

Role

We are making our first Marketing leadership hire to build the company’s brand, narrative, and demand engine from the ground up. This is a full-stack role, with a primary emphasis on Product Marketing (messaging, positioning, content, sales enablement, category leadership) and a strong secondary focus on Growth/Demand Generation (campaign execution, funnel optimization, marketing ops).

As our Head of Marketing, you’ll refine Flagler’s narrative to stand out in a crowded digital health market, position the company as a thought leader in AI-enabled care, and deliver measurable impact on pipeline and revenue. This is a rare chance to join a company at an inflection point and directly influence growth and market leadership.

Key Responsibilities

• Product Marketing: Refine and own Flagler’s story; translate technical capabilities into differentiated, buyer-friendly value propositions.

• Content & Thought Leadership: Produce case studies, one-pagers, white papers, videos, and impact stories that position Flagler as a category-defining AI leader.

• Sales Enablement: Build collateral including pitch decks, battle cards, objection-handling guides, and executive messaging to help Sales close more accounts.

• Narrative Development: Ensure consistent messaging for the exec team, customer-facing teams, and external channels.

• Demand Generation: Design and execute multi-channel campaigns (email, LinkedIn, Google, conferences) that drive qualified leads and accelerate pipeline.

• Account-Based Marketing: Partner with Sales to execute targeted outreach campaigns supporting key deals.

• Brand & Events: Establish Flagler’s presence at conferences, industry events, and across digital channels.

• Analytics & Funnel Optimization: Stand up a marketing tech stack, track CAC, LTV/CAC, MQL→SQL, campaign ROI, and report KPIs directly to the CEO.

• Cross-Functional Alignment: Work closely with Sales, Product, and leadership to ensure marketing strategy directly supports revenue growth.

Requirements

• 6+ years of experience in B2B healthcare marketing, with ~2 years in a player/coach leadership role.

• Proven expertise in Product Marketing (messaging, positioning, sales enablement, category leadership).

• Skilled operator in Growth/Demand Generation, with hands-on experience running multi-channel campaigns.

• Deep familiarity with analytics and funnel metrics (CAC, LTV/CAC, MQL→SQL, ROI).

• Strong product marketing storytelling skills—able to translate complex AI/tech into buyer-ready messaging.

• Knowledge of AI applications in healthcare.

• Experience building a marketing tech stack and analytics dashboard.

• Background in brand and content development as well as conference/event presence.

• Exceptional storyteller who can simplify complex ideas into compelling narratives.

• Scrappy and resourceful—thrives in an early-stage environment.

• Ruthlessly focused on outcomes; knows how to separate noise from true conversion opportunities.
  

Reasons to join Flagler Health:

1. Massive Problem, Massive Market: U.S. healthcare is broken; providers are overwhelmed, and Flagler is building the AI co-pilot to fix workflows at scale.

2. High-Impact Mission: Free up clinicians’ time, improve patient experiences, and strengthen provider finances.

3. Early Traction: Already working with leading health systems and specialty groups; strong foundation to build from.

4. Zero-to-One Ownership: First marketing leader with full ownership to create the brand, messaging, and GTM playbook.

5. Executive Visibility: Work directly with the CEO and leadership team; your work is core to company strategy.

6. Career-Defining Role: Chance to build the marketing engine for a high-growth Series A startup in one of the world’s most important industries.

• OTE (cash): $225K–$275K (base + variable bonus)

• Equity: Competitive stock option package

• Benefits: Health, dental, vision insurance

• PTO: Flexible paid time off policy

Our values

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.