Head of Operations, Data Programs

Workstream • Menlo Park, CA

8d • $170,000 - $190,000 • Onsite

About The Position

Workstream is a mission-driven company building the all-in-one HR, payroll, and hiring platform for managing the hourly workforce. There are 2.7 billion hourly workers, making up 80% of the global workforce, but this market has been heavily underserved by technology and deserves better. Workstream has been purpose-built for the hourly workforce from day one so that these businesses and their employees can thrive.
Our customers include leading brands from multiple sectors, including Burger King, Carl's Jr./Hardee's, IHOP, KFC, and Culvers. We are a high growth series B company and quickly expanding our product portfolio to deliver on our vision. We are backed by legendary VCs and industry experts like Founders Fund, BOND, and Coatue.
Grow With Us
We are looking for a highly driven, analytical, and execution-oriented Head of Operations to lead one of Workstream's fastest-growing strategic initiatives: large-scale data collection and workforce operations programs.
In this role, you will operate as the business leader for a rapidly growing data platform operation, overseeing workforce management, operational execution, process design, quality control, and scaling initiatives. You will be responsible for building and managing the systems, teams, and operational infrastructure required to collect, organize, and deliver high-quality data at scale.
This is a highly visible leadership role that sits at the intersection of operations, technology, workforce management, and business strategy. You will partner directly with executive leadership and cross-functional teams to define operational strategy, drive execution, and scale programs from hundreds to thousands of contributors.
The ideal candidate combines exceptional operational rigor with entrepreneurial instincts. You thrive in ambiguity, move quickly, make decisions with incomplete information, and are excited to build from zero-to-one while simultaneously scaling existing operations.
This is a full-time role requiring presence of up to 5 days per week in our Menlo Park office.

Requirements

• 8+ years of experience in operations, strategy, consulting, finance, marketplace businesses, or high-growth startup environments
• Proven experience leading large-scale operational teams and workforce programs
• Strong track record of building and scaling operational systems from zero-to-one
• Experience managing complex, cross-functional initiatives with measurable business impact
• Exceptional analytical and problem-solving skills with strong business judgment
• Ability to make high-quality decisions in fast-moving and ambiguous environments
• Experience managing large contributor, contractor, marketplace, gig economy, or workforce operations programs
• Strong executive communication and stakeholder management skills
• High ownership mindset with a bias toward action and accountability
• Comfortable operating both strategically and tactically when needed
• Proven ability to attract, develop, and lead high-performing teams

Nice To Haves

• Experience at Uber, DoorDash, Mercor, Handshake, Airbnb, Instacart, or similar marketplace businesses
• Background in investment banking, private equity, management consulting, or business operations leadership
• Experience managing large-scale data collection, labeling, AI operations, or workforce platforms
• Familiarity with operational excellence methodologies and workforce optimization systems
• Experience building and scaling businesses from early-stage growth through operational maturity
• Exposure to AI, data infrastructure, robotics, or technical services delivery

Responsibilities

• Own and lead Workstream's data collection and workforce operations programs across the United States
• Manage and scale a network of hundreds to thousands of contributors participating in video and data collection initiatives
• Build the operational systems, processes, and infrastructure required to support large-scale data programs
• Drive day-to-day business operations, workforce planning, capacity forecasting, quality management, and program execution
• Partner closely with executive leadership to define strategic priorities and translate them into operational plans
• Design and optimize contributor acquisition, onboarding, engagement, retention, and productivity systems
• Build and manage operational teams responsible for recruiting, scheduling, workforce management, quality assurance, and program coordination
• Develop reporting frameworks, dashboards, and operational metrics to drive decision-making and accountability
• Analyze operational performance to identify bottlenecks, improve efficiency, and increase output quality
• Lead large-scale cross-functional initiatives across Operations, Product, Engineering, Recruiting, and Program Management
• Establish scalable playbooks and operating procedures that enable rapid growth while maintaining quality standards
• Serve as the primary operational leader for new program launches, expansions, and strategic initiatives
• Communicate business performance, operational insights, and recommendations to executive leadership

Benefits

• Competitive salary and equity
• Comprehensive health coverage: medical, dental, and vision. We pay 95% of your premiums for our employees and 85% for dependents
• 401K Plan
• Pre-tax commuter benefits
• Learning/development stipend
• Flexible PTO

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed