Director, Software Engineering

Chewy Chewy · Retail · Boston, MA

Director of Software Engineering to lead B2B Vet Clinics organization, delivering scalable, secure, and intelligent SaaS solutions. This leader will shape the technology vision that enables clinics to operate more efficiently, deliver better patient outcomes, and grow their businesses through modern, AI-enabled software platforms. The role requires owning the technical vision and strategy, building and developing high-performing teams, driving a culture of innovation, and implementing with operational excellence. Requires experience leading engineering organizations that have built and scaled B2B SaaS platforms, with an AI-first mindset and experience embedding AI/ML capabilities into products.

What you'd actually do

  1. Own the Technical Vision & Strategy: Define and execute a 3–5 year technical roadmap for our PIMS platform used in Vet clinics. Architect scalable, secure, multi-tenant systems that support veterinary practices across digital and physical environments. Ensure seamless workflows across in-clinic experiences, e-commerce, and partner ecosystems. Champion AI-first solutions that enhance workflow automation, clinical insights, and operational efficiency.
  2. Build and Develop High-Performing Teams: Lead an organization of approximately 40, including Associate Directors and senior ICs. Hire and retain top-tier talent with SaaS, platform, and omnichannel systems experience. Foster a culture of technical excellence, operational rigor, and customer obsession tailored to B2B software delivery.
  3. Drive a Culture of Innovation: Empower your teams to experiment, learn, and deliver breakthrough solutions. Be a key sponsor and driver for internal innovation programs that fuel events like our company-wide Innovation Days.
  4. Implement with Operational Excellence: Partner closely with product, design, and business partners to translate ambitious goals into concrete, well-managed execution plans. Own key business objectives, proactively de-risk complex projects, and communicate progress, risks, and trade-offs with absolute clarity to senior leadership.

Skills

Required

  • Demonstrated experience leading engineering organizations that have built and scaled B2B SaaS platforms, including full lifecycle ownership from architecture to rollout and adoption.
  • Proven experience building and successfully rolling out SaaS software, including multi-tenant systems, subscription models, enterprise integrations, and customer onboarding.
  • Experience building software that supports omnichannel environments (online and brick-and-mortar retail), including integration across digital commerce, in-store systems, and operational workflows.
  • AI-first mindset, with experience embedding AI/ML capabilities into products to drive automation, intelligence, and differentiated customer value.
  • 12+ years of experience in software engineering, with a significant portion in a leadership capacity, including proven experience managing other managers.
  • A track record of leading through ambiguity, creating clarity from complexity, and delivering measurable results on multi-faceted, strategic problems.
  • Deep technical expertise with the ability to operate at depth, guide teams through complex architectural challenges, and maintain an exceptionally high bar for quality.
  • Proven experience authoring strategic documents and technical proposals for executive-level consumption.
  • Bachelor's degree in Computer Science, a related field, or equivalent experience.

Nice to have

  • Experience building software for healthcare, veterinary, or regulated industries.
  • Experience with AI-driven workflow automation or clinical decision support systems.
  • Experience in high-growth B2B SaaS, platform-as-a-service, or omnichannel retail technology organizations.

What the JD emphasized

  • AI-first solutions
  • AI-enabled software platforms
  • embedding AI/ML capabilities into products

Other signals

  • AI-first solutions
  • AI-enabled software platforms
  • embedding AI/ML capabilities into products