About Us

We are a profitable healthcare technology company on a mission to transform and build the operating 

system for post-acute care. Each year, millions of seniors transition out of hospitals into skilled nursing 

facilities, home health, or back home — and far too often, that handoff fails them. Readmissions, 

medication errors, missed follow-ups, families left in the dark. Our products sit at the seams of that 

journey, giving providers, payers, and caregivers the visibility and tools to get the right care to the right 

person at the right time. Our Anna™ platform, through clinical intelligence, deep datasets, and 

connected technology, empowers providers & payors to collaborate to deliver exceptional outcomes, 

streamline care coordination, and enhance patient experience. 

What makes PAA distinctive isn't the funding or the growth curve — it's how we work. Autonomy and 

ownership are non-negotiable: AI amplifies expertise, it doesn't replace it. User trust is infrastructure, 

not a metric. Architecture is product strategy, not engineering's problem.   

The Opportunity

We’re hiring Head of Product to own the strategy and execution across our product portfolio. You’ll be 

our most senior product leader, reporting directly to the CEO, participating in Board room discussions, 

and serving as a peer to the heads of Engineering, Clinical, Commercial, and Client Success. You’ll 

inherit a strong foundation — real customers, real revenue, real product-market fit scaled across million 

of lives / 40+ states / industry’s most marquee payors and providers — and your charter is to take us 

from a multi-product company to a coherent platform that compounds across the post-acute continuum.  

What You'll Own  

Product strategy across the portfolio. You’ll define how our individual products work together as a 

system, where we invest next, and how we sequence bets against a long-term platform vision. You’ll 

bring clarity to tradeoffs between deepening current products and expanding into adjacent post-acute 

workflows.    

Product operations. You’ll inherit and grow a team of PMs and designers, set the operating cadence, 

setup clear and timely communication channels, and build a top quartile product execution organization 

performing customer discovery, outcome-driven road mapping, capacity planning, and resource 

allocation. You will clearly articulate the ROI that our products and features deliver for our customers.  

Expect to make hires, develop the team, and define how product partners with engineering, clinical, & 

customer success. 

Executive engagement with our payer and health system clients. You’ll build direct relationships 

with senior leaders at our largest customers — CMOs, COOs, VPs of Utilization Management, and 

population health executives. You’ll get into the room to understand their strategic priorities and 

operational pain points, then come back with crisp, compelling presentations that articulate what we’re 

going to build for them, why it matters to their business, and how we’ll deliver. These conversations 

should sharpen our roadmap and deepen the trust that our customer partners have come to expect. 

Customer and market intelligence. Furthermore, you’ll spend meaningful time with our users that we 

ultimately serve. You’ll translate what you learn about their workflows and pain points into a roadmap 

that results in high adoption of Anna™ and clinicians at our customers trusting Anna’s 

recommendations.   

Commercial partnership. You’ll work closely with sales and customer success to understand what’s 

winning deals, what’s stalling them, and where product can unlock the next layer of growth. You’ll help 

shape pricing, packaging, and go-to-market motions for new offerings. 

Cross-functional leadership. You’ll be a core member of the executive team — contributing to 

company strategy, board materials, and the cultural tone of how we build.

Ten-plus years in product, with at least three to five leading product orgs (Director, Sr. Director, or 

VP). You’ve managed managers and built teams from roughly 5 to 20+ people. 

Deep experience in healthcare — ideally in post-acute, care coordination, value-based care, 

population health, or related provider/payer workflows. You understand the realities of HIPAA, EHR 

integrations, clinical workflows, and the operational pressures on the people who use our software. 

We’ll consider exceptional candidates from adjacent healthcare segments, but generic enterprise SaaS 

backgrounds won’t be a fit. 

Multi-product or platform experience. You’ve owned a portfolio, not just a single product, and can 

speak to how you handled prioritization, shared infrastructure, and the org design questions that come 

with it. You have a track record of taking products from early traction to scale. 

Strong customer instincts. You’re comfortable in a discharge planner’s office, on a virtual call with a 

payor CMO, or sitting with a front line clinician. You don’t outsource discovery. You understand what it 

takes to have clinicians adopt new software, workflows, and recommendations.   

Proven ability to influence C-suite buyers. You’ve sat across the table from health system and payer 

executives, diagnosed what they actually care about, and built the kind of executive-grade narratives 

and presentations that move enterprise decisions forward. You can hold a room of senior clinical, 

operational, and financial leaders and leave them with a clear answer to “why this, why now, and why 

you.” 

Executive presence. You can hold your own in a board meeting, write a crisp strategy doc, and have a 

hard conversation with a peer without burning the relationship. 

A genuine pull toward the mission. The seniors we serve are often at the most vulnerable point of 

their care journey. We want a leader who feels that and lets it shape the work. 

Who You Are 

• A mission-driven builder who gets genuinely energized by improving outcomes for vulnerable 
• seniors 
• A confident communicator who can present to clinicians in the morning and to the board in the 
• afternoon 
• Comfortable with ambiguity — you can make good decisions with imperfect information and 
• adjust quickly 
• An empathetic leader who listens deeply, builds trust across disciplines, and advocates fiercely 
• for the user 
• Commercially astute — you understand the business model and can connect product decisions 
• to ARR, retention, and NPS 

Why This Role

You’ll be the Head of Product at a company that’s past the riskiest early stages but still nimble enough 

that your fingerprints will be on everything we build for years. You’ll work directly with a CEO who wants 

a true partner on product strategy, not a roadmap manager. And you’ll do it in a corner of healthcare 

where the work matters — measurably — to the people on the other end of the software. 

 What We Offer 

• Compensation - Competitive base salary + equity, annual performance bonus.
• Flexibility - Flexible PTO policy. Frequent team offsites
• Benefits - Comprehensive medical, dental, and vision. 401(k) with employer match
• Growth - Commitment to growth. Learning & development budget. Direct access to company leaders and clinical leadership. 

Our Commitment to Diversity 

We are an equal opportunity employer committed to building a diverse and inclusive team. We believe 

that diverse perspectives make us better product builders and better advocates for the patients we 

serve. We welcome applicants of all backgrounds, lived experiences, and identities.