Executive Director of Architecture

CVS Health•Work At Home-Massachusetts, MA

11d•$175,100 - $334,750•Remote

About The Position

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 at all. You 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.

Requirements

15+ years as a software developer/architect (20+ preferred).
A track record leading large technical architecture initiatives that touch multiple value streams (e.g., multiple Release Trains) across a large, complex enterprise.
Recognized expertise across multiple technical domains — the kind of person other architects go to when they're stuck.
Demonstrated ability to influence and align senior executives around technology strategy, translating deep technical detail into business outcomes.
Experience leading leaders — not just individual technical contributors, but senior architects and architecture managers — and a track record of developing leadership talent within an organization.
Strong collaboration, influence, negotiation, coaching, and coalition-building skills — you can move a room without pulling rank.
Excellent written and verbal communication

Nice To Haves

Experience in health care and/or insurance.

Responsibilities

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 actually get built, not just how they're supposed to.
Bring an architect's eye to identifying the right technology partnerships.
Serve as a trusted technical voice to senior executives, translating complex architecture decisions into clear business impact and strategic direction.