Executive Director of Architecture

We’re building a world of health around every individual — shaping a more connected, convenient and compassionate health experience. At CVS Health®, you’ll be surrounded by passionate colleagues who care deeply, innovate with purpose, hold ourselves accountable and prioritize safety and quality in everything we do. Join us and be part of something bigger – helping to simplify health care one person, one family and one community at a time.

CVS Health is looking for an Executive Director of Architecture to lead a team driving broad technical initiatives across multiple CVS Health portfolios — all in pursuit of a unified set of technology capabilities.

We're hunting for a rare species: an architecture leader who thinks in systems but dreams in possibilities. You're the kind of person who gets bored drawing boxes and arrows the "correct" way and instead asks why the boxes exist  can sketch wild, unconventional ideas with engineers one minute, then walk into a room of executives and translate them into business outcomes the next — without losing nuance, just real clarity.

You're fluent in the bleeding edge — not because it's trendy, but because you're genuinely curious what's coming next and you've already been tinkering with it. You lead teams not by hovering, but by making people want to build something ambitious with you.

This isn't your typical architecture team, and that's the point. We're not a group of theorists sketching diagrams from a tower somewhere above the actual work — we're builders who happen to also think in systems. We prototype, we get our hands dirty with bleeding‑edge tech, and we measure our ideas by whether they actually work, not by how good they look in a deck.

If you've spent your career frustrated by architecture teams that hand down mandates instead of rolling up their sleeves, this is the opposite of that.

* This role can work remotely from anywhere in the continental USA.

• You've led at scale — you can turn messy, competing business requirements into technical solutions that actually hold up in a large, complicated organization.
• You've driven technology strategy and architecture decisions across a large, complex enterprise spanning multiple business domains — not just one product or platform.
• You know how to influence senior executives: you can walk into a room with the CIO or CTO and translate complex technical tradeoffs into strategic recommendations they can act on.
• You've architected large-scale, cloud‑native applications and know your way around the full stack, including cloud infrastructure (GCP, AWS, or similar).
• You can talk to anyone — business leaders, product managers, UX designers — and actually understand what they need, not just what they said.
• You communicate like it's a craft, not a checkbox.
• You're genuinely passionate about technology, with the technical range to prove it.
• You go both broad and deep, and you'd rather take on strategic technology leadership across a large org than stay in one lane.
• You've managed highly technical teams — and you've also led other leaders, including senior architects and architecture managers, and helped grow their careers.

• Lead and shape technical architecture initiatives that span the enterprise application portfolio — not just review them.
• Build real relationships and real collaboration across teams, not just alignment on paper.
• Help set the architectural strategic direction for CVS Health.
• Lead and guide a team of highly technical architects who expect to be challenged, not managed — including senior architects and architecture leaders, developing their leadership skills along the way.
• Help build CVS Health's reference architecture — and make sure it reflects how things…