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.