Head of Operations, Workstream
Data Programs
$170-190k
+ Equity
More information about location
Office located in Menlo Park, CA
HR and payroll solutions built specifically for restaurants
Be an early applicant
HR and payroll solutions built specifically for restaurants
201-500 employees
Be an early applicant
$170-190k
+ Equity
More information about location
Office located in Menlo Park, CA
201-500 employees
Company mission
To help businesses hire faster and smarter, so they can focus on supporting their team and serving their customers.
Role
Who you are
- 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
- 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
Desirable
- 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
What the job involves
- 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
- 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
Our take
Recruiting new staff can be a slow andf frustrating process for HR teams, especially in industries that rely on hourly workers. Roles often need filling quickly, turnover can be high, and managers don't always have time to sit at a desk sorting through applications and emails. So, chasing candidates, scheduling interviews, and keeping people engaged can take hours each week, often delaying businesses , leaving them short-staffed when they need people most.
Workstream is a HR and hiring platform built specifically for hourly workers, with text messaging at the centre of how it works. Instead of forcing candidates to apply through long online forms or emails they may never check, Workstream allows people to apply, communicate, schedule interviews, and even complete parts of onboarding directly through their phone. And for employers, the platform automates most of the hiring process, so managers can source, screen, hire, and onboard staff with ease.
Whilst the company operates in a competitive HR software market, its carved out a strong position by focusing on deskless and hourly workers, a group often overlooked by traditional HR tools. Its growing list of customers also span quick-service restaurants, retail, logistics, and other hourly-heavy industries, and the company has attracted significant investor backing as a result. Competition may remain strong but Workstream's clear focus, steady expansion, and continued product adoption give it a strong foothold in the market.
Kirsty
Company Specialist at Welcome to the Jungle
Insights
4% employee growth in 12 months
Company
Funding (last 2 of 3 rounds)
Sep 2022
$60m
SERIES B
Aug 2021
$48m
SERIES B
Total funding: $118m
Company benefits
- Health and wellness: We care about the physical and mental health of each of our team members. We offer every employee comprehensive medical, dental and vision plans, and access to a generous number of fully-paid counseling sessions with licensed therapists every year.
- Competitive compensation (and equity): As a company, we have ambitious goals with a high-potential financial upside—and we share that with every employee through competitive market compensation and generous stock.
- Flexible time off: We believe team members do their best work when their life feels balanced. We promote work-life harmony through flexible PTO and paid parental leave.
- Professional development: We believe in becoming 1% better each day. That’s why we offer a quarterly learning reimbursement that can be used toward continuing education, books, subscriptions and more.
Company HQ
SoMa, San Francisco, CA
Leadership
Desmond Lim
(Co-Founder & CEO)Prior to co-founding Workstream in 2017, Desmond was a Product Manager at MIT Media Lab and WeChat.
Max Wang
(Co-Founder & CTO)Previously, Max co-founded VC.CN where he served as the CTO for 5 years.
Lei Xu
(Co-Founder & CSO)Lei previously co-founded Emote where he served as the CTO for 2 years. Prior to that, he spent 3 years at Google in Revenue Acceleration and Software Engineering roles.
Salary benchmarks
We don't have enough data yet to provide salary benchmarks for this role.
Submit your salary to help other candidates with crowdsourced salary estimates.
Share this job
View 7 more jobs at Workstream