Software Operations Jobs in Massachusetts (NOW HIRING)

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.

• 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, post‑mortems, 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.

• 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.

This role is based in the WHOOP office located in Boston, MA. The successful candidate must be prepared to relocate if necessary to work out of the Boston, MA office.

The U.S. base salary range for this full‑time position is $200,000‑$245,000. Salary ranges are determined by role, level, and location. Within each range, individual pay is based on factors such as job‑related skills, experience, performance, and relevant education or training. In addition to the base salary, the successful candidate will also receive benefits and a generous equity package.

WHOOP is an Equal Opportunity Employer and participates in E‑verify to determine employment eligibility. It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.