Regional Vice President, Health Plan Sales (Medicare Advantage)

Sword Health is shifting healthcare from human-first to AI-first through its AI Care platform, making world-class healthcare available anytime, anywhere, while significantly reducing costs for payers, self-insured employers, national health systems, and other healthcare organizations. Sword began by reinventing pain care with AI at its core, and has since expanded into women’s health, movement health, and more recently mental health. Since 2020, more than 700,000 members across three continents have completed 10 million AI sessions, helping Sword's 1,000+ enterprise clients avoid over $1 billion in unnecessary healthcare costs. Backed by 42 clinical studies and over 44 patents, Sword Health has raised more than $500 million from leading investors, including Khosla Ventures, General Catalyst, Transformation Capital, and Founders Fund. Learn more at www.swordhealth.com.

The Regional Vice President, Health Plans (Medicare Advantage) is responsible for driving growth within the health plan segment by securing, expanding, and deepening strategic partnerships with leading payers, with a dedicated focus on the Medicare Advantage (MA) and Managed Care markets. You will own regional market development, build a high-quality pipeline, and lead end-to-end deal execution for Sword’s most complex opportunities within the government programs sector.

As the primary commercial representative for Medicare Advantage, you will cultivate executive-level relationships, positioning Sword’s AI Care platform as a category-defining solution to improve member outcomes, reduce medical spend, and enhance Star Ratings. You will accelerate enterprise adoption specifically within Medicare Advantage, Dual-Eligible (D-SNP), and Medicare Supplement lines of business.

This role is ideal for a high-impact, consultative seller with deep payer expertise, strong executive presence, and the ability to navigate and influence complex, multi-stakeholder buying processes.

You will join a high-caliber team of five Regional Vice Presidents on the Health Plan side, serving as a strategic peer group to scale Sword’s presence across the payer landscape. This role emphasizes heavy collaboration within this cohort to share market intelligence and align on national account strategies to collectively accelerate growth within the Medicare and Government sectors.

What you’ll be doing:

• Prospect, educate, accelerate, and close complex enterprise deals with regional and national health plans, focused primarily on the Medicare Advantage market.
• Develop and articulate compelling value propositions tailored to payer economics, clinical performance, and total cost-of-care impact.
• Build, nurture, and expand senior executive relationships with health plan decision-makers and industry influencers.
• Partner with SMEs to build strategic collateral, refine financial models, and solve complex payer-specific challenges.
• Build and maintain a robust, accurate pipeline—including forecasting, dashboards, and performance reporting.
• Collaborate cross-functionally to ensure seamless deal execution and long-term account success.
• Serve as a spokesperson for Sword at industry events, conferences, and partner forums.
• Leverage deep payer relationships and market knowledge to gain access to new accounts and accelerate multi-line expansion.
• Influence regional go-to-market strategy and contribute to continuous improvement across the Health Plans sales motion.
• Champion a culture of curiosity, collaboration, and high performance—supporting peers and contributing to broader commercial team development.

What you need to have:

• 10+ years of Sales or Business Development experience, with 5+ years selling directly into the Medicare Advantage space.
• Deep understanding of the payer landscape and the Medicare Advantage and adjacent markets.
• Proven track record of exceeding quota and closing complex, multi-year enterprise agreements.
• Experience leading executive-level relationships, negotiations, and financial modeling.
• Ability to launch and scale new markets with limited guidance.
• Entrepreneurial mindset with strong ownership, resilience, and an action-oriented approach.
• Excellent communication, storytelling, and relationship-building skills.
• Comfort operating in a fast-paced, hyper-growth environment with changing priorities.A collaborative, proactive, and growth-oriented mindset—paired with a willingness to roll up your sleeves.
• High integrity, low ego, and a genuine desire to help patients, clients, and teammates succeed.

To ensure you feel good solving a big Human problem, we offer:

•  A stimulating, fast-paced environment with lots of room for creativity.
• A bright future at a promising high-tech startup company.
• Career development and growth, with a competitive salary.
• The opportunity to work with a talented team and to add real value to an innovative solution with the potential to change the future of healthcare.
• A flexible environment where you can control your hours (remotely) with unlimited vacation.
• Access to our health and well-being program (digital therapist sessions).
• Remote or Hybrid work policy.
• To get to know more about our Tech Stack, check here.

Total compensation range

$390,387 - $565,000 a year

*This range includes base, variable and equity

These compensation bands are just the starting point. Once someone joins and proves they’re outlier talent, we adjust quickly to ensure their compensation aligns with their impact.

Our job titles may span more than one career level. Actual pay is determined by skills, qualifications, experience, location, market demand, and other factors. Compensation details listed in this posting reflect the base salary and any potential variable, bonus or sales incentives, and the Company’s estimation of the value of private company stock options, if applicable. The pay range is subject to change, future value of company stock options is not guaranteed, and compensation may be modified in the future. In addition to our total compensation, Sword offers a number of benefits as listed below.