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Salary: USD 160,000 - 180,000 / annual
Workstream is a mission-driven, high-growth Series B company building an all-in-one HR, payroll, and hiring platform for the hourly workforce. With 2.7 billion hourly workers making up 80% of the global workforce, Workstream is purpose-built to serve this underserved market. The company is backed by top-tier VCs including Founders Fund, BOND, and Coatue, and counts leading brands like Burger King, Carl's Jr./Hardee's, IHOP, KFC, and Culvers among its customers.
The Chief of Staff will report to the CFO and partner directly with the C-level Executive Team in a highly visible, cross-functional role. This position operates 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.
Key responsibilities include:
- Partnering directly with the CFO and C-level Executive Team on company strategy, priorities, and execution
- Driving high-priority, cross-functional initiatives from problem definition through execution and measurable outcomes
- Working across departments (Finance, Product, Engineering, Sales, Customer Success, Marketing, People, Operations) to identify, prioritize, and drive operational projects based on business impact
- Translating strategic priorities into clear action plans with owners, timelines, milestones, and accountability mechanisms
- Serving as a central point of coordination across leadership and functional teams to maintain alignment and momentum
- Developing analyses, business cases, and recommendations to support strategic and operational decision-making
- Establishing and managing operating rhythms, including company goals, KPIs, business reviews, and executive follow-ups
- Identifying and resolving organizational bottlenecks
- Leading special projects that span multiple functions and require rapid execution in ambiguous environments
- Conducting market, competitive, and business research to inform strategic decisions
- Ensuring critical decisions, action items, and initiatives are followed through to completion
- Preparing materials and analyses for leadership meetings and business discussions
- Acting as a trusted thought partner to the CFO and C-level Executive Team
- Stepping into operational problems directly when needed, taking ownership rather than delegating
- Helping build scalable processes, systems, and operating mechanisms as the company scales
The ideal candidate is an exceptional generalist who thrives in ambiguity, learns quickly, and is comfortable moving between strategic problem-solving and hands-on execution. This role requires someone with high ownership mindset, strong bias toward action, and ability to operate with limited direction.
**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
- 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 priorities and adapt to shifting business needs
