Director of Engineering Operations at Whoop

Boston, Massachusetts, United States

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Not SpecifiedCompensation

Senior (5 to 8 years), Expert & Leadership (9+ years)Experience Level

Full TimeJob Type

UnknownVisa

Technology, Healthtech, WearablesIndustries

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

Responsibilities

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
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
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
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
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
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

Skills

Key technologies and capabilities for this role

Engineering MetricsDORAContinuous ImprovementData PipelinesDashboardsHiringOnboardingIncident ManagementPostmortemsSREReliability MetricsPerformance MetricsCycle TimeDelivery Throughput

Questions & Answers

Common questions about this position

What is the reporting structure for the Director of Engineering Operations?

The role reports directly to the SVP of Software and serves as the operational backbone of WHOOP’s engineering organization.

Is this position remote or does it require office work?

This information is not specified in the job description.

What salary or compensation is offered for this role?

This information is not specified in the job description.

What key responsibilities define success in this role?

Key responsibilities include defining engineering metrics like DORA and cycle time, improving hiring and onboarding, overseeing incident management, facilitating operational cadence, ensuring governance and compliance, and managing financials and vendors.

What experience makes a strong candidate for this position?

Strong candidates will have expertise in engineering operations, including metrics like DORA, incident management, hiring processes, operational cadence, governance, and financial management, with the ability to collaborate across Engineering, Product, Recruiting, QA, and Platform teams.

Whoop

Wearable fitness tracker with personalized insights

About Whoop

WHOOP offers a fitness membership that focuses on improving personal health and performance through a wearable device called the WHOOP Strap 3.0. This device continuously collects physiological data, including heart rate, sleep patterns, and recovery levels, to provide users with personalized recommendations on their daily activity, sleep needs, and readiness for performance. Unlike many competitors, WHOOP operates on a subscription model, where users pay a fee to access the membership, which includes the device and continuous insights through the WHOOP app. This model not only provides a steady revenue stream but also fosters a strong community among users, encouraging engagement through teams, challenges, and social features. The goal of WHOOP is to help users optimize their health and performance while minimizing injury risk.

Boston, MassachusettsHeadquarters

2012Year Founded

$393.7MTotal Funding

SERIES_FCompany Stage

Data & Analytics, HealthcareIndustries

501-1,000Employees

Benefits

Take Time Off: Time outside of the office is important for sleep, strain and recovery! Our PTO plan encourages members to take time off in order to come back refreshed.

Live a Healthy Lifestyle: Our competitive benefits package includes premium medical, dental, and vision coverage for employees and their dependents. Life and disability insurance are also available.

Feel Invested: In addition to a competitive base salary and 401k, you're eligible to receive stock options to share in the future of WHOOP. Work means more when you have personal stake. You have ownership in what we are building.

Eat Well: Keep hunger at bay with endless snacks in our fully stocked kitchen. Enjoy catered team lunches on Friday, and even a cold brew keg.

Know The Product: We want you to understand and experience the product firsthand. We offer you a WHOOP strap and membership at no cost.

Be Active: Take advantage of our office gym and on-site showers! WHOOP also offers a $500 yearly wellness perk for fitness classes and memberships.

Be Present: It’s important to be present when bringing home a new family member. Take care of your loved ones with 12 weeks paid parental leave, plus an additional 2 weeks to gradually return to work.

Love Where You Work: Sitting in the heart of Fenway, our beautiful office overlooks Fenway Park. A prime location for great food, not to mention catching a Sox game, too!

Work Hard, Play Harder: If we don't already have a club here that fits your lifestyle and interests, you're encouraged to start one. Share your passions with others at work, or discover new ones!

Risks

Increased competition from brands like Oura and Fitbit threatens market share.

Privacy concerns over data collection could lead to regulatory challenges.

Economic downturns may affect consumer willingness to pay subscription fees.

Differentiation

WHOOP offers 24/7 physiological data tracking with its WHOOP Strap 3.0.

The company provides personalized health insights for athletes and fitness enthusiasts.

WHOOP's subscription model includes a community aspect for user engagement.

Upsides

WHOOP's partnership with Cristiano Ronaldo boosts brand visibility and credibility.

Expansion into 56 markets enhances WHOOP's global presence and growth potential.

Collaborations with brands like Assos strengthen WHOOP's position in sports technology.

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