Transforming Complexity Into Coordinated Care

Alice Massey

Chief Strategy & Operating Officer

Transforming Complexity Into Coordinated Care

Alice Massey

Chief Strategy & Operating Officer

POP Recovery Systems

The role of the Chief Operating Officer has rapidly evolved—no longer confined to operational oversight, today’s COOs are hybrid leaders. They borrow tech foresight from CTOs, strategic insight from CEOs, and people-centric thinking from CHROs. Leading this new era of operational leadership is Alice Massey, Chief Strategy & Operating Officer at POP Recovery Systems. With over 15 years in healthcare IT and enterprise systems, Alice is transforming how recovery happens. At POP, she’s pioneering a Recovery-as-a-Service platform that integrates mental health, nutrition, and concierge wellness-logistical post-op planning, cutting hospital readmissions and setting new standards in post-surgical care using the human touch as well as AI predictive analytics. Alice’s career is marked by game-changing milestones. At Capital One, she was honored as an “Uncompromising Operator” for aligning resiliency frameworks with enterprise architecture—a move that impacted systems company-wide. She led critical metadata overhauls, drove cross-functional process reforms, and played a central role in the high-impact “Get to Platinum” initiative. Earlier, she saved $1M in a nationwide telecom migration at Bowlmor AMF and $5M in asset management at Performance Food Group. In an exclusive conversation with TradeFlock, Alice reflects on the strategies that shaped her journey, the challenges she’s conquered, and why operational excellence is ultimately about empowering people.

What does being an "Uncompromising Operator" mean to you, and where does that mindset come from?

I’ve always believed that “excellence isn’t just a goal—it’s a responsibility.” Being an Uncompromising Operator means I don’t trade integrity for convenience. In healthcare, cutting corners isn’t just risky—it’s reckless. That mindset came from years inside complex hospital systems, where I saw what happens when execution falters—patients suffer, data is exposed, and trust erodes. At POP Recovery Systems, I lead with structure, purpose, and zero tolerance for shortcuts because in this field, how we deliver matters just as much as what we deliver.

What’s the toughest strategy-toexecution gap you’ve closed—and how?

The toughest gap I’ve closed looked like a compliance issue, but it was really a culture problem. We were chasing 100% software certification across the enterprise—a goal that had failed for years. So I flipped the approach: brought engineers and architects into the strategy early, listened closely, and uncovered deep-rooted blockers no one had truly addressed. By co-creating the solution, we didn’t just fix a process—we changed the way execution worked. That’s what made it 100% possible for the first time.

“The real breakthrough wasn’t just operational; it was shifting the execution model from compliance enforcement to collaborative enablement.”

What’s the most meaningful compliment you’ve received —and why?

It wasn’t a spotlight moment—it was trust in action. Being chosen to lead the ‘Get to Platinum’ rollout in Enterprise Architecture meant more than a title. It meant someone saw how I turned complexity into clarity. We delivered major changes with zero rollbacks, in a system where rollbacks were the norm. But the compliment that stayed with me was this: “You made it simple.” That meant everything—because real mastery lies in clarity, not complexity. That mindset guides me daily: de-risk the unknown, test rigorously, and make the hard parts feel effortless—for everyone.

What’s the most important leadership lesson you've learned in your career so far?

I’ve learned that leadership often starts where no one’s looking. As an admin assistant in HR, I focused on doing every task—no matter how small—with care, consistency, and what I call “Keeping Things Simple.” That mindset quietly set me apart.

“Never underestimate the value of the tasks you’re doing today— they could be the foundation of something extraordinary.”

While many followed the traditional path of school, then work, mine went in reverse. I gained hands-on experience first, then earned my MS and MBA to sharpen what I’d already lived. Years of consulting taught me how organizations rise or fall, and roles in cloud tech, enterprise risk, and data challenged me to think big and lead purposefully. When I was asked to lead POP Recovery Systems, I realized I hadn’t just prepared for the role—I’d been living it all along.

If not ops, what career would you love—and why?

Honestly? I think I would’ve made a great lawyer. People have told me that for years—and I can see why. I’m wired for structure, precision, and advocating for what’s right. Law would have allowed me to serve people through representation. Operations allow me to serve them through transformation. That sense of fairness is at the core of how I work. I don’t cut corners, I follow through, and I care deeply about doing things the right way—especially when the outcome matters. That’s what pulled me toward healthcare and why I love what we do at POP Recovery Systems: building systems that lift burdens so clinicians can focus on care. In the end, law and ops aren’t so different. Both demand clarity, discipline, and a drive to improve the lives of others.

What’s your strategy when everything feels like it’s on fire?

When everything’s on fire, I don’t rush—I assess. I rely on data, not drama, to guide decisions. That mindset comes from years in healthcare IT, where reacting without clarity causes more harm than good. I zoom out, separate signals from noise, and focus on what moves the needle first. Then, I rely on the right people, listen deeply, and build a structure where chaos exists. Mastering a crisis isn’t about doing more—it’s about doing what matters, with calm, precision, and purpose.

How did you align stakeholders with conflicting priorities during 'Get to Platinum'?

I’ve learned that alignment doesn’t start with answers— it starts with who’s in the room. For ‘Get to Platinum,’ I brought IT, risk, and business leaders together and shifted the conversation from gut feel to facts. The real shift happened when we moved the conversation from opinion to evidence. By defining clear, risk-based criteria and co-building the standards, we turned resistance into ownership. I led the rollout across architecture and governance, and because people shaped the path, they walked it with conviction.

How do you build resilience without slowing innovation?

I’ve never believed resilience and innovation are at odds. When done right, resilience doesn’t slow innovation—it builds the confidence to scale it. The key is weaving it into the innovation lifecycle from the start, not bolting it on later. I design risktiered governance that lets teams move fast on low-risk features, while reinforcing what truly matters. Some things need a fortress, others just need a seatbelt . By automating controls in CI/CD, aligning engineering with business continuity, and avoiding overengineering, I build systems that are fast, stable, and ready for the unexpected. That’s how resilience becomes a growth engine, not a brake.

What legacy are you building at POP Recovery Systems?

I’m building a legacy where recovery is designed, not left to chance. “Recovery shouldn’t be improvised—it should be intentional.” At POP Recovery Systems, I’ve embedded that belief into our Recovery-as-a-Service model, fusing clinical operations, IT resiliency, and patient engagement into one unified system. After years across hospital admin, rehab, outpatient care, and healthcare IT—from Bon Secours to Anthem—I saw a common thread: when systems lack structure, people get lost. Now, I’m closing those gaps—making recovery coordinated, compassionate, and scalable. Because real healing demands more than treatment, it needs continuity, clarity, and lasting care.

In your opinion, what’s the least visible but most impactful work you do as a COO?

Some of the most powerful work I do as a COO never appears in a headline. It lives in the space between ideas and outcomes, where execution quietly determines success. At POP Recovery Systems, I’ve helped build the operational backbone—HIPAA compliance, standardized clinical workflows, SOPs, and enterprise-level systems that make scaling possible. I bridge strategy with real-world execution, often behind the scenes: aligning departments, templating operations, leading seamless hospital rollouts while ensuring innovation and transformation is at the helm of all we do. Coming from hospital IT and consulting, I know that defining the real work, sequencing it right, and getting it done are what set highperforming teams apart. It’s not glamorous, but it makes everything else possible.

What do people misunderstand most about being a COO?

People often think a COO just “keeps things running.” But the truth is, we’re the architects behind the scenes —turning strategy into systems that actually work.

“COOs don’t just manage processes—they build cultures of accountability and resilience that allow great ideas to thrive.”

At POP Recovery Systems, I’ve seen firsthand how critical this role is. If operations slip—if workflows, tech, or communication break down—it doesn’t just affect teams internally. It impacts patients, surgeons, and hospital partners directly. The COO role demands more than efficiency. It requires strategic agility, emotional intelligence, and the ability to lead from the middle—aligning vision with execution, and people with purpose. We might not be in the spotlight, but we always ensure the mission moves forward