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