Chief of Staff
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 analytical, proactive, and execution-oriented Chief of Staff to report to our CFO and partner directly with the C-level Executive Team.
This is a highly visible, cross-functional role that works across the Executive Team and departments to help prioritize and drive the company’s most important strategic and operational initiatives. You will operate at the intersection of strategy, operations, and execution—translating company priorities into action, creating alignment across teams, and ensuring critical initiatives move forward with clear ownership and accountability.
As a key partner to the CFO and C-level Executive Team, you will work across Finance, Product, Engineering, Sales, Customer Success, Marketing, People, and Operations. You will help identify the highest-impact opportunities, structure complex problems, coordinate stakeholders, and drive projects from initial definition through execution and measurable outcomes.
This is a high-ownership role for someone who thrives in ambiguity, learns quickly, and is comfortable moving between strategic problem-solving and hands-on execution. The ideal candidate is an exceptional generalist who can quickly understand complex business challenges, bring structure to ambiguity, and help leaders make informed decisions and execute against company priorities.
You should be comfortable operating with limited direction and stepping into whatever problem is most important to the business at a given time.
Day In The Life
Partner directly with the CFO and C-level Executive Team on company strategy, priorities, and execution
Drive high-priority, cross-functional initiatives from problem definition through execution and measurable outcomes
Work across departments to identify, prioritize, and drive operational projects based on business impact and organizational priorities
Translate strategic priorities into clear action plans, owners, timelines, milestones, and accountability mechanisms
Serve as a central point of coordination across leadership and functional teams to maintain alignment and momentum on critical initiatives
Develop analyses, business cases, and recommendations to support strategic and operational decision-making
Establish and manage operating rhythms, including company goals, KPIs, business reviews, and executive follow-ups
Work across Finance, Product, Engineering, Sales, Customer Success, Marketing, People, and Operations to identify and resolve organizational bottlenecks
Identify opportunities to improve company performance, efficiency, and organizational effectiveness
Lead special projects that span multiple functions and require rapid execution in ambiguous environments
Conduct market, competitive, and business research to inform strategic and operational decisions
Help the CFO and C-level Executive Team prioritize resources, initiatives, and projects based on business impact
Ensure critical decisions, action items, and initiatives are followed through to completion
Prepare materials, analyses, and recommendations for leadership meetings and other critical business discussions
Act as a trusted thought partner to the CFO and C-level Executive Team , providing clear analysis, structure, and perspective
Step into operational problems directly when needed, taking ownership rather than simply delegating
Help build scalable processes, systems, and operating mechanisms as Workstream continues to grow
Who You Are
4–8+ years of experience in strategy, operations, consulting, investment banking, product, or a high-growth technology company
Proven track record of owning complex, cross-functional initiatives with measurable business outcomes
Exceptional analytical and structured problem-solving skills
Ability to quickly understand unfamiliar industries, businesses, and technical concepts
Strong business judgment and ability to make decisions with incomplete information
Exceptional written and verbal communication skills
Ability to influence senior executives and cross-functional teams without direct authority
High ownership mindset with a strong bias toward action
Comfortable operating in a fast-paced, ambiguous, and constantly changing startup environment
Ability to manage multiple high-priority initiatives simultaneously while maintaining strong attention to detail
Strong proficiency with spreadsheets, presentations, and modern productivity tools
Must be based in or willing to relocate to San Francisco, CA and work onsite 5 days per week
Nice To Have
Experience working directly with a CEO, founder, or executive leadership team
Background in management consulting, investment banking, private equity, or venture capital
Experience at a high-growth, venture-backed technology company
Experience leading strategic planning, annual planning, or company operating processes
Exposure to board and investor relations processes
Experience in SaaS, HR technology, payroll, workforce management, or marketplaces
Experience managing or launching 0→1 initiatives
Strong technical or data background and ability to work closely with engineering teams
What We Offer
A mission-driven and value-based company dedicated to empowering deskless workers and local businesses
An early employee opportunity at a Series B hyper-growth startup with over $120M in funding
Work directly with the founding team and industry veterans to accelerate your career
Competitive salary and equity
Comprehensive health coverage: medical, dental, and vision. We pay 95% of premiums for employees and 85% for dependents
In-office amenities and stocked kitchen
401(k) Plan
Flexible PTO
Salary Range
The base salary range for this role is $150,000 and $170,000 annually, depending on experience and qualifications. In addition to base salary, this role includes participation in Workstream's stock option program, offering meaningful equity ownership in the company.
Know More About Workstream
https://www.workstream.us/blog/funding-series-b
https://techbuzz.news/buzzworthy-august-27-2021/
Additional Information
Workstream provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training.
We are committed to the full inclusion of all qualified individuals.