Chief Operating Officer Insurance Jobs in California

Grow With Us

We are looking for a world-class Chief Operating Officer (COO) to serve as the primary strategic and operational partner to our CEO, helping scale Workstream from a high-growth Series B company into a category-defining global enterprise.

In this role, you will oversee and unify the company's core business operations-bridging the gap between strategy, product, go-to-market (GTM), and corporate functions. You will ensure Workstream scales efficiently while maintaining speed, quality, and a high-performance culture.

This is a high-impact executive leadership role for an exceptional operator who thrives on complexity, drives organizational accountability, and translates visionary goals into repeatable, company-wide business performance. You will work closely with the CEO, Executive Team, Board of Directors, and investors to align global strategy with flawless execution.

The ideal candidate is a visionary builder and a disciplined executioner-equally comfortable setting corporate direction, driving executive alignment, and stepping into day-to-day operations to clear roadblocks.

Why This Role Is Different

This is not a traditional, back-office administrative role. At Workstream, the COO will act as the company's chief execution architect-owning the organizational design, cross-functional synergy, and governance needed to transform high-level strategy into market-defining execution.

As a vital force multiplier for the CEO, you will focus on scaling not just our market footprint, but the executive leadership team and organizational machine behind it.

The ideal candidate is an elite enterprise operator who combines high-velocity startup agility with world-class operational discipline-a leader who can build resilient systems, accelerate corporate growth, and help shape Workstream as the definitive platform powering the global hourly workforce.

Day In The Life

• Executive Leadership & Partnership: Serve as the primary strategic partner to the CEO and executive team, co-designing the company's operating cadence and ensuring total alignment on corporate priorities.
• Cross-Functional Orchestration: Drive synergy and alignment across traditionally siloed functions-Product, Engineering, GTM, Finance, and People-to accelerate product-to-market velocity and business growth.
• Corporate Scale & Governance: Build and scale company-wide operating models, including long-term corporate goal setting (OKRs), business reviews, and the infrastructure required for global expansion.
• Organizational Efficiency: Identify macro operational bottlenecks and design organizational structures, workflows, and resource allocation models that improve decision-making speed.
• Strategic & Financial Planning: Partner with the CEO and Finance leadership on the annual operating plan, corporate budgeting, and resource optimization.
• Board & Investor Relations: Support the CEO in board meeting preparation, investor relations, and high-level corporate reporting.
• People & Culture Leadership: Mentor, scale, and inspire a world-class operational team while fostering a culture of high ownership, accountability, and psychological safety.
• Special Initiatives & Ambiguity: Spearhead critical corporate initiatives, market expansions, or ambiguous business challenges, driving them from concept to execution.

• 12+ years of executive leadership experience across business operations, corporate strategy, or general management within high-growth technology companies.
• Proven track record scaling a B2B SaaS or technology company through critical growth inflection points (Series B through Series D, IPO, or major scale).
• True multi-functional oversight: Experience managing complex organizations that span commercial, operational, and corporate functions.
• Exceptional business & financial acumen with a deep understanding of SaaS metrics, corporate governance, and capital allocation.
• World-class stakeholder management with the ability to command a room, influence executive peers, and align diverse global teams.
• High-velocity execution mindset paired with the strategic patience required to build for the long term.
• Comfort in ambiguity: A history of thriving in fast-paced, evolving startup environments by bringing order to chaos.

• Previous COO, President, General Manager (GM), or VP of Operations experience at a high-growth SaaS company.
• Experience in HR tech, payroll, workforce management, or vertical SaaS.
• Experience scaling global, distributed teams and managing international corporate entities.
• M&A, corporate development, or fundraising experience.

• 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
• Pre-tax commuter benefits
• Flexible PTO
  

Salary Range

In compliance with the California Pay Transparency Law, the base salary range for this role is between $200,000 to $250,000 base in San Francisco areas. This range is not inclusive of our discretionary bonus or equity package. When determining a candidate's compensation, we consider a number of factors including skillset, experience, job scope, and current market data.