Director of Engineering Operations

Whoop • Boston, MA

24d • $200,000 - $245,000 • Onsite

About The Position

At WHOOP, we're on a mission to unlock human performance and healthspan. WHOOP empowers members to understand their bodies through continuous measurement of physiological data, enabling them to sleep better, train smarter, and live healthier lives. WHOOP is scaling rapidly, with ambitious growth ahead for the software organization. To sustain this momentum, WHOOP is hiring a Director of Engineering Operations to drive the systems, processes, and visibility that enable our teams to deliver at scale. Reporting directly to the SVP of Software, this leader will serve as the operational backbone of WHOOP's engineering organization - building the mechanisms that drive productivity, consistency, and clarity across all teams. You'll work closely with Engineering, Product, Recruiting, QA, and Platform leadership to align people, processes, and data, ensuring WHOOP continues to deliver software with excellence and efficiency for our members.

Requirements

• 5+ years of experience in software operations, technical program management, or engineering leadership within high-growth technology organizations.
• Proven success scaling engineering teams.
• Deep understanding of software development lifecycles (SDLC), Agile/DevOps practices, and incident management frameworks.
• Demonstrated experience defining and operationalizing engineering metrics (e.g., DORA, cycle time, developer experience).
• Strong analytical and data-driven mindset, with the ability to build dashboards, measure outcomes, and inform decisions through data.
• Exceptional communication and collaboration skills, with experience influencing across all levels of an organization.
• Hands-on operator who thrives in ambiguity and can build systems from the ground up before scaling them.
• Experience managing budgets, vendor relationships, and cross-functional programs.
• Strong commitment to embracing and leveraging AI tools in day-to-day tasks, ensuring AI-assisted work aligns with the same high-quality standards as personal contributions.

Responsibilities

• Engineering Metrics & Continuous Improvement - Define, implement, and manage engineering performance metrics (e.g., DORA, delivery throughput, cycle time). Translate insights into action through reviews, tracking, and reporting to leadership. Partner with Platform and QA teams to ensure data pipelines and dashboards are accurate and actionable.
• Hiring, Onboarding & Growth Enablement - Collaborate with Recruiting and leadership to improve hiring velocity and maintain quality. Build and continuously refine the engineering onboarding experience to reduce ramp-up time and increase new hire satisfaction. Design systems that help new engineers quickly understand WHOOP's tools, systems, and culture.
• Incident Management & Reliability - Oversee the incident lifecycle - ensuring consistent classification, escalation, postmortems, and follow-through. Build accountability for reducing repeat incidents and improving reliability metrics. Collaborate with Platform and SRE teams on root-cause visibility and operational readiness.
• Operational Excellence & Cadence - Own and facilitate the operational rhythm of the software organization, including leadership syncs, Engineering Manager forums, quarterly reviews, and Software All-Hands. Establish feedback systems that promote alignment, accountability, and clear communication across teams. Identify organizational bottlenecks and develop scalable, data-driven solutions to improve flow and focus.
• Governance, Compliance & Communication - Serve as a bridge between Software and GRC, Legal, and Finance to ensure operational alignment on compliance, documentation, and governance. Own the Builder (Engineering) Blog and internal communications, maintaining transparency through dashboards, documentation, and reports.
• Financial & Vendor Management - Manage budgets for developer tooling, DX platforms, and operational vendors. Partner with Finance and Legal on procurement, ROI analysis, and vendor strategy. Ensure investments deliver measurable improvements in productivity and quality.

Benefits

• WHOOP compensation philosophy is designed to attract, motivate, and retain exceptional talent by offering competitive base salaries, meaningful equity, and consistent pay practices that reflect our mission and core values.
• At WHOOP, we view total compensation as the combination of base salary, equity, and benefits, with equity serving as a key differentiator that aligns our employees with the long-term success of the company and allows every member of our corporate team to own part of WHOOP and share in the company's long-term growth and success.
• In addition to the base salary, the successful candidate will also receive benefits and a generous equity package.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Industry: Computer and Electronic Product Manufacturing
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees