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 01 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://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