Medicare Agency Director (Fintech)

TL;DR

Medicare Agency Director (Fintech): Leading a new line of business, Willoughby, through its post-incubation scaling phase to build a digital Medicare brokerage with an accent on financial performance, member service, and applying modern consumer technology. Focus on defining strategy, driving enrollment growth, owning P&L, and scaling efficiently through AI and automation.

Location: Remote (US) or Downtown Brooklyn office. Must be based in one of the following US states: California, Colorado, District of Columbia, Florida, Georgia, Illinois, Maryland, Massachusetts, New Jersey, New York, Oregon, Pennsylvania, Texas, Virginia, and Washington.

Salary: $180,000 - $220,000 USD

Company

hirify.global is a venture-backed technology company on a mission to empower low-income Americans by simplifying access to government benefits with modern technology, focusing on government benefits and Medicare services.

What you will do

• Set and execute Medicare agency strategy, partnering to define a 3-year plan, annual OKRs, and GTM strategy to drive enrollment growth.
• Own financial performance, including P&L, budgeting, and long-range financial modeling.
• Build and scale the brand and growth engine, driving top-of-funnel demand across digital and partner channels.
• Lead cross-functional operations and execution, aligning product, operations, and growth roadmaps, scaling efficiently through automation and AI.
• Drive product strategy and platform expansion, championing an AI-first roadmap and leading mobile-to-web expansion.
• Ensure regulatory excellence by defining compliance strategy and overseeing development of an in-house compliance program.
• Build and lead a high-performing team, fostering a culture of ownership and empathy for low-income beneficiaries.

Requirements

• 7+ years of product, project management, operations, and/or business development experience.
• Experience leading teams through projects from incubation to mass scale.
• 3+ years of experience in Medicare, with tech, product design, or agency operations experience a plus.
• Exhibits extreme ownership and acute attention to detail.
• Experience working directly with a founder team and/or managing key executive leadership stakeholders.
• Highly motivated by helping low-income Americans on government sponsored healthcare programs.

Culture & Benefits

• Meaningful work and a strong shared sense of mission.
• Remote-friendly work environment with an optional dog-friendly office in Downtown Brooklyn, with optional in-person retreats.
• 20 Days of PTO.
• 4% 401K match.
• $10k lifetime spend towards Carrot Fertility.
• Excellent Medical, Dental and Vision options, plus other health and mental health benefits.
• Commitment to building a diverse and inclusive team.