Chief of Staff

Workstream; San Francisco, Northern (CA, KY); On-site; USD 150,000 - 170,000; Full time

Benefits offered by this job

Competitive salary and equity

Health coverage

Onsite work in San Francisco

Job summary

Workstream is seeking a Chief of Staff to partner with the CEO and executive leadership, translating priorities into action, and driving cross-functional initiatives to strengthen operating cadence across the company.

As a generalist with strong judgment, you will own complex problems, move from strategy to execution, and work onsite in San Francisco, CA five days a week. You’ll influence senior leaders, manage timelines, and deliver measurable outcomes through data-driven analyses.

Qualifications

• 4–8+ years of experience in strategy, operations, consulting, investment banking, product, or a high-growth technology company.
• Proven track record of owning cross-functional initiatives with measurable outcomes.
• Exceptional analytical and structured problem-solving skills.
• Able to quickly understand unfamiliar industries, businesses and technical concepts.
• Strong business judgement and decision-making under uncertainty.
• Exceptional written and verbal communication skills.
• Ability to influence senior executives and cross-functional teams without direct authority.
• High ownership mindset with bias toward action.
• Comfortable in fast-paced, ambiguous startup environments.
• Willing to relocate to San Francisco, CA and work onsite 5 days/week.

Responsibilities

• Partner with the CEO on strategy, priorities, and execution.
• Drive high-priority cross-functional initiatives from definition to outcomes.
• Translate priorities into clear action plans with owners and timelines.
• Prepare the CEO and executives for leadership, board, and investor meetings.
• Develop analyses, business cases, and strategic recommendations.
• Establish and manage operating rhythms with KPIs and reviews.
• Work across Product, Engineering, Sales, Customer Success, Finance, People, and Operations.

Skills

Strategy

Operations

Cross-functional leadership

Analytical thinking

Communication

Influence without authority

Ownership mindset

Startup environment

Excel / PowerPoint

Tools

Spreadsheets

Presentations

Productivity tools

Job description

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 work directly with our CEO and executive leadership team.

In this role, you will serve as a force multiplier for the CEO and help drive the highest-priority initiatives across the company. You will operate at the intersection of strategy and execution—helping translate company priorities into action, driving cross-functional alignment, and ensuring critical initiatives move forward with urgency and accountability.

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. You will work closely with the CEO, executive team, and leaders across the organization on everything from company strategy and operating cadence to special projects, business analysis, and organizational priorities.

The ideal candidate is an exceptional generalist who can quickly understand complex problems, structure them clearly, make sound decisions, and drive teams toward outcomes. 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 CEO on company strategy, priorities, and execution
• Drive high-priority cross-functional initiatives from initial problem definition through execution and measurable outcomes
• Translate the CEO’s priorities into clear action plans, owners, timelines, and accountability mechanisms
• Prepare the CEO and executive team for leadership meetings, board meetings, investor discussions, and other critical engagements
• 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 Product, Engineering, Sales, Customer Success, Finance, People, and Operations to identify and resolve organizational bottlenecks
• Identify opportunities to improve company performance, efficiency, and organizational effectiveness
• Lead special projects that may span multiple functions and require rapid execution in ambiguous environments
• Conduct market, competitive, and business research to inform strategic decisions
• Help the CEO and executive team prioritize resources and initiatives based on business impact
• Ensure critical decisions and initiatives are followed through to completion
• Act as a trusted thought partner to the CEO and executive team, providing candid analysis and perspective
• Step into operational problems directly when needed rather than simply delegating them to others
• 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 without losing 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.

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.