Chief of Staff
About the role
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.
Responsibilities
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
Build scalable processes, systems, and operating mechanisms as Workstream continues to grow
Requirements
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
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
Strong proficiency with spreadsheets, presentations, and modern productivity tools
Qualifications
Must be based in or willing to relocate to San Francisco, CA and work onsite 5 days per week
Skills
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
Benefits
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
Pay
Salary Range: $150,000 - $170,000 annually, depending on experience and qualifications
Schedule
Work onsite 5 days per week