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
- 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
- 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
The base salary range for this role is $160,000 and $180,000 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://techcrunch.com/2021/08/26/workstreams-text-based-recruitment-tool-gets-a-48m-bet-from-bond-and-beyond/
- 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.
Skills Required
- 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
- Comfort 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, California, and work onsite five days per week
- 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 zero-to-one initiatives
- Strong technical or data background and ability to work closely with engineering teams
What We Do
Workstream (www.workstream.us) is a text recruiting and hiring tool for local businesses, especially restaurants. We help you to hire faster with texting / SMS, cutting in half the time to engage, hire and onboard hourly workers. We save companies 30+ hours every week by making your hiring process streamlined, automated and finding you the right talent when you need it. We have helped business owners and operators from Jamba, Chick-fil-A, McDonald's, Dunkin', Applebee's, Auntie Anne's, Cinnabon and more to increase efficiency by over 150%, increasing their bottom line and creating significant cost savings. We are a team from MIT, Google, Yelp, Stanford, Cornell, and backed by investors including Peter Thiel's Founders Fund, Charles River Ventures, CEO Zoom, Jay Z, CEO DoorDash, Joe Montana, James Harden, COO Yelp, CEO Logitech, Chairman Louis Vuitton (LVMH), Chairman JetBlue, Peterson Ventures, GGV Capital, CEO Intercom, and more.
