Sr. Technical Program Manager

About the Role

Bringing two companies — and their platforms, products, and teams — together into one seamless Member experience is one of the most ambitious and consequential technical programs our company is taking on. This is not a single-team delivery role. You will lead a massive, org-wide program spanning our AI/WayFinding products, core platform and integration infrastructure, and the unification of Transcarent and Accolade systems into a single, coherent product. You'll work in close partnership with engineering and product leads across many teams, and your stakeholders will extend to the most senior levels of the company — engineering, product, clinical, security, and go-to-market leadership.

Your first job is to make this program ship: sequenced, de-risked workstreams with honest timelines and no surprises. Where ownership is ambiguous, you create clarity. Where dependencies collide, you broker the tradeoff. And where executives need the truth about program health, you deliver it — crisply, early, and with a recommendation.

Responsibilities

• Drive delivery with rigor. Structure the program into workstreams with clear owners, milestones, and exit criteria. Own the cross-team dependency map and critical path. Anticipate risks before they become escalations, surface tradeoffs early, and keep timelines honest as capacity, client commitments, and priorities shift.
• Manage release readiness across teams — dates, approvals, documentation, and communication — in a HIPAA-regulated environment where quality and compliance are non-negotiable.
• Lead at the executive level. Own program-level communication to senior leadership: status, risks, tradeoffs, and decisions needed. Build trusted relationships with VPs and C-level stakeholders across engineering, product, clinical, and business functions. Frame decisions so leaders can make them quickly — and drive them to closure when they stall. Represent the program with clients and partners when integration work touches their implementations.
• Operate with real technical depth and product perspective. Partner with engineering leads and architects on integration and unification strategy — service consolidation, data migration, identity and eligibility unification, and API and event contracts. Pressure-test technical plans, understand the architecture well enough to spot hidden dependencies and sequencing risks, and translate fluently between deep technical detail and executive-level narrative. Identify gaps in product scope across dispersed teams and domain ownership.
• Work AI-natively. Use AI tools and agentic workflows as a core part of how you operate — program tracking, documentation, analysis, and communication — and help raise the bar for how the broader organization uses them. Bring genuine curiosity about how AI changes program management itself, not just the products we build.
• See beyond delivery into operation excellence and continued quality and scalability into the future.

Requirements

• 8+ years as a Technical Program Manager, Engineering Program Manager, or similar, with at least 3 years leading large, multi-team programs with company-wide scope and visibility.
• A proven track record driving complex platform integration, migration, or post-merger technical unification programs from ambiguity to launch, with disciplined risk management and dependency tracking at scale.
• Demonstrated success managing executive stakeholders: you've owned the room with senior leadership, delivered hard news well, and driven decisions across organizational boundaries.
• Strong technical fluency — you can read an architecture diagram critically, engage credibly in design discussions, and challenge engineering plans constructively. A software engineering background is a plus.
• Exceptional written and verbal communication; your program docs and status updates create alignment on their own.
• Comfort operating in a fast-moving environment with competing priorities, incomplete information, and high stakes.

Preferred Qualifications

• Experience in healthcare or employer benefits, HIPAA-regulated environments, or shipping AI/LLM products.

About Us

We are looking for teammates to join us in building our company, culture, and Member experience who:

• Put people first, and make decisions with the Member's best interests in mind
• Are active learners, constantly looking to improve and grow
• Are drivers, unafraid to take ownership and accountability for outcomes
• Communicate directly and honestly, and assume good intent in others
• Are laser focused on delivering results, and proactively problem-solve to get there

Transcarent is the One Place for Health and Careᵀᴹ, bringing medical, pharmacy, and point solutions together with the WayFindingᵀᴹ experience, the first and only generative AI-powered health and care platform for health consumers. Our WayFinding experience, paired with transparent and consumer-driven pharmacy care, 2nd.MD expert medical opinions, and virtual primary care, works seamlessly with comprehensive Care Experiences – Cancer Care, Surgery Care, and Weight Health – to support people with all of their health needs, simple or serious. More than 1,700 employers and health plans rely on us to provide information, guidance, and care, empowering health consumers with more choice, an experience they love, access to higher-quality care, and lower costs for 21 million Members.

Values

• People First: We prioritize our Members, clients, and each other in every decision
• Care: Every decision starts with improving health and care for our Members
• Resilience: We push boundaries and take the uncharted path to change an industry
• Results: We take ownership, solve with speed, and deliver for our people and each other
• Humble and Human: We lead with humility, bring fun to tough moments, and go further together

Pay

Individual compensation packages are based on factors unique to each candidate, including primary work location and an evaluation of a candidate’s skills, experience, market demands, and internal equity.

Benefits

• Competitive medical, dental, and vision coverage
• Competitive 401(k) Plan with a generous company match
• Flexible Time Off/Paid Time Off, 13 paid holidays
• Protection Plans including Life Insurance, Disability Insurance, and Supplemental Insurance
• Mental Health and Wellness benefits
• Corporate bonus program or sales incentive (target included in OTE)
• Stock options