Associate Director, Medicare Advantage Bid Strategy & Analytics

Devoted Health • Waltham, MA

4d • $129,000 - $193,000 • Remote

About The Position

We are seeking a highly skilled and analytically driven Medicare Advantage Bid Strategy & Analytics Associate Director to join the team responsible for designing, pricing, and optimizing Devoted Health’s MA benefit portfolio. This individual will play a critical role in benefit design, financial modeling, competitive positioning, and the analytical work that drives sound bid decisions across a large, complex, multi-state plan portfolio. This role reports to the Senior Director, Medicare Product Strategy and Analytics. This is true end-to-end product ownership — from 1,000-foot strategic framing all the way down to the individual benefit parameters on individual plans — and you need to be excellent at both. The ideal candidate thrives in a fast-paced, analytically demanding environment, is eager to make a meaningful impact, and is equally at home building a financial model, writing production SQL, and presenting a recommendation to the executive team. This role will play an integral part in our annual plan bid and will collaborate regularly with executive leadership, actuarial, and finance on product design strategy, financial sustainability, and competitive positioning. You will take direct ownership of the benefit design and financial analytics workstreams that sit at the heart of what we bring to market each year. Devoted is an AI-forward company in the most practical sense of the term: we are actively rebuilding how the bid cycle works using agentic workflows, AI-assisted code generation, and automated pipelines that turn what used to be weeks of manual work into something that runs overnight. This team is at the center of that build. Every person on the team — regardless of role — is expected to use AI tools fluently, push them into new territory, and help shape how we work. If you find the intersection of Medicare Advantage and AI-powered analytical infrastructure genuinely exciting, you will fit right in.

Requirements

• Direct Medicare Advantage bid mechanics experience — you understand BPTs, how the bid math works, what MCR means and how it constrains benefit decisions. This is the foundation of the role and hard to teach; you need to come in with it.
• 5–8 years of relevant experience at a Medicare Advantage health plan or actuarial/consulting firm (Milliman, Wakely, Oliver Wyman, or similar).
• Able to operate independently from day one, demonstrating strong business judgement and comfort with ambiguity
• Strong modeling skills: you build analytical frameworks from scratch, interpret complex bid and actuarial data, conduct benefit scenario analyses, and translate findings into strategy — pairing technical depth with executive-level “so what”
• SQL fluency — you write complex queries, debug multi-CTE pipelines, and reason about data architecture in the context of a benefit calculation system
• Python proficiency — you build scripts, automate analytical workflows, and work with structured data without hand-holding
• A proactive and adaptable mindset; the ability to thrive in a fast-moving, entrepreneurial environment where the work is rarely fully defined before it starts

Nice To Haves

• Familiarity with MA benefit design: cost-sharing structures, benefit category logic, and how individual benefit decisions interact with plan economics and CMS requirements
• Familiarity with Stars, QBP eligibility, and the downstream plan portfolio implications of rating changes
• Experience building or working within automated benefit generation systems, cascade pipelines, or large-scale bid tooling
• ASA or FSA designation is not required, but candidates with actuarial training who have decided they want strategy and product work over pure pricing are a strong fit and a profile we actively welcome

Responsibilities

• Develop and maintain bid financial models connecting benefit decisions to plan economics: MCR analysis, PMPM normalization, plan-absorbed benefit value estimation, and version-over-version delta tracking across pricing iterations
• Pressure-test benefits across markets to identify pockets of adverse selection risk; quantify the financial exposure and recommend design adjustments to improve risk posture and protect plan performance
• Monitor CMS regulations, payment methodologies, risk adjustment updates, and Stars payment changes for downstream impact on benefit strategy and plan economics; provide executive-level interpretation of what changes mean for our portfolio
• Build and refine the algorithms that generate benefit values across hundreds of PBPs — translating high-level strategic intent into precise, implementable benefit logic at scale, and identifying and resolving the edge cases those algorithms surface
• Support new product and plan flavor development from opportunity sizing and financial viability assessment through full benefit build-out: doing the analytical groundwork that makes leadership decisions possible, then executing implementation once direction is set
• Evaluate plan portfolio decisions with full financial and competitive context: plan terminations and crosswalks, Stars implications, market entry and exit tradeoffs, and the member impact of structural product changes
• Synthesize analytically complex findings into clear, decision-enabling recommendations for senior leadership and the executive team
• Write and maintain production SQL (Snowflake) supporting the benefit cascade system: multi-CTE pipelines for plan benefit calculations, lead/non-lead enforcement logic, MCR-driven benefit deterioration and enrichment, and bid review outputs
• Build Python scripts and automation workflows that reduce manual effort in the bid cycle — benefit workbook generation, data validation, and analytical tooling that scales with a growing plan portfolio
• Use AI tools — including agentic workflows and AI coding assistants — as a core part of how you work; actively contribute to how the team evolves its use of AI to automate, scale, and improve bid operations

Benefits

• Employer sponsored health, dental and vision plan with low or no premium
• Generous paid time off
• $100 monthly mobile or internet stipend
• Stock options for all employees
• Bonus eligibility for all roles excluding Director and above; Commission eligibility for Sales roles
• Parental leave program
• 401K program
• And more....

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed