Whoop5mo ago

Director of Software Operations

BostonFull Timeexecutive

OtherSoftware Operations

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Overview

WHOOP is scaling rapidly, with ambitious growth ahead for the software organization. To sustain this momentum, WHOOP is hiring a Director of Software Operations to build the systems, workflows,

Technical Tools

OtherSoftware Operations

WHOOP is scaling rapidly, with ambitious growth ahead for the software organization. To sustain this momentum, WHOOP is hiring a Director of Software Operations to build the systems, workflows, and insights that help our teams operate with greater speed, clarity, and effectiveness.

Reporting directly to the SVP of Software, this leader will sit at the intersection of engineering, data, process design, and operational strategy. They will serve as the operational backbone of WHOOP’s software organization — not only driving visibility through metrics and dashboards, but also identifying friction, redesigning workflows, and building practical internal tools and automations that help teams move faster and work more effectively.

This role is ideal for someone who understands how modern software organizations scale: through strong operating mechanisms, trustworthy data, thoughtful process design, and the smart application of AI and automation to reduce manual work and improve decision-making. You’ll work closely with Engineering, Product, Platform, QA, Recruiting, GRC, Legal, and Finance to improve how the software organization hires, plans, executes, communicates, and continuously improves.

Operational Efficiency, Tooling & Insight: Drive the systems that improve the efficiency and effectiveness of WHOOP’s software organization. Define and evolve key operational metrics, dashboards, and reporting that provide clear visibility into delivery health, reliability, team capacity, and organizational bottlenecks. Identify friction across the software development lifecycle and design practical solutions — including improved workflows, internal tools, automations, and AI-assisted processes — that reduce manual effort, improve consistency, and help teams move faster with greater confidence.

Organizational Effectiveness & Team Enablement: Build the mechanisms that help the software organization scale effectively. Partner with Recruiting and software leadership to improve hiring operations and reduce friction in the hiring process while maintaining quality. Build and continuously refine onboarding systems that help new engineers ramp quickly and understand WHOOP’s tools, systems, and ways of working. Create feedback loops, documentation, and lightweight operational frameworks that strengthen alignment, improve accountability, and increase overall team effectiveness.

Reliability, Governance & Cross-Functional Operations: Oversee and improve the operational systems that support incident management, reliability, compliance, and cross-functional coordination. Ensure consistent incident processes, strong postmortem follow-through, and better visibility into root causes and repeat failure patterns. Serve as a bridge between Software and functions such as Platform, QA, GRC, Legal, and Finance to improve governance, planning, documentation, vendor management, and operational decision-making. Ensure investments in tooling and vendors drive measurable improvements in productivity, quality, and organizational effectiveness.

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.