About Opportunity@Work

Opportunity@Work is a national nonprofit organization dedicated to unlocking career opportunities for the more than 70 million workers in the United States who are Skilled Through Alternative Routes (STARs) rather than a bachelor’s degree.

Through research, employer engagement, technology innovation, and narrative change, we work to eliminate the “paper ceiling” — the invisible barrier limiting economic mobility for talented workers without four-year degrees.

With an annual operating budget of approximately $20 million and a distributed, remote workforce headquartered in Washington, DC, Opportunity@Work partners with leading employers, policymakers, and ecosystem leaders to create a labor market where skills — not pedigree — determine opportunity.

About the role

The Chief Operating Officer (COO) is the architect of Opportunity@Work’s enterprise operating model and the executive responsible for transforming People, Finance, and Enterprise Systems into a unified engine for scale, innovation, and mission impact.

Reporting to the CEO and serving as a key member of the five-person executive leadership team, the COO elevates the organization’s internal capabilities to evolve in step with strategy — building the operating discipline, digital fluency, and performance systems required to scale impact nationally. The full-time team is 65 FTE today. 

As Opportunity@Work enters its next phase of scale and national influence, the COO will play a pivotal role in modernizing the organization’s operating systems, aligning enterprise capabilities, and preparing the institution for sustained impact and leadership continuity. The COO will directly manage the People & Culture team of 3 + contractors, the CFO and finance team of 3, Enterprise IT of 1 FTE supported by an MSP, and an outsourced legal team. 

This role is fully remote, though we anticipate at minimum, quarterly travel to the Washington, DC office, and bi-annual leadership and team retreats.

What you'll do

1. Executive Leadership & Organizational Stewardship

• Serve as a senior member of the Executive Leadership Team, contributing to enterprise decision-making, financial management, organizational design, and long-term capability building.
• Hire and develop new and existing talent to fill key operations functions; ensure team continues to build capabilities and drive excellence throughout their respective functions. 
• Act as a thought partner to the CEO and executive peers on operational feasibility, organizational readiness, and enterprise tradeoffs.
• Strengthen and lead efforts to achieve administrative excellence and accountability, institutional integrity, and operational reliability during periods of growth and change for the entire organization.
• Lead delivery and develop senior leaders across the core business functions reporting to the COO, ensuring performance, collaboration, and results.
• Build and run accountability mechanisms that track execution and follow‑through for the entire organization.
• Lead continuous improvement efforts around communication of policies, updates, and organizational priorities managed by the COO, working with the Chief of Staff to embed needed communications into overall org-wide communications mechanisms. Support ELT members to cascade communications, change management and cross‑team alignment.
• Drive cross-functional enterprise transformation initiatives that increase organizational agility, reduce friction, and expand institutional capability beyond current scale.

2. Performance of People & Culture function (Human Resources, People Operations, Organizational Effectiveness)

• Elevate the People & Culture strategy, systems, and operations in partnership with the VP/Sr leader of People & Culture.
• Ensure the organization has equitable, transparent, and mission-aligned people practices across the employee lifecycle, including hiring, onboarding, performance management, development, and offboarding.
• Steward performance management and accountability systems (e.g., goal-setting, OKRs, feedback cycles), ensuring they are clearly defined, consistently applied, and effectively supported by managers.
• Support leaders in continuing to build and inspire high-performing teams through strong management practices, role clarity, and organizational design.
• Ensure compliance with employment laws, HR policies, and people-related risk management.
• Guide HR policies, benefits administration, employee relations, compliance and employee lifecycle processes

3. Performance of Finance & Administration functions

• Oversee the organization’s financial management and administrative infrastructure, ensuring fiscal discipline, transparency, and compliance.
• Orchestrate strong budgeting, forecasting, financial reporting, and resource allocation processes that support strategic priorities and operational needs.
• Supervise corporate governance processes, including fiduciary reporting to the board, and ensure adherence to nonprofit regulations.
• Steward internal controls, audit processes, insurance, and financial risk mitigation in partnership with finance leadership.
• Oversee contracts administration, grant compliance, and regulatory obligations associated with funding and partnerships.
• Integrate finance and administrative systems to enable timely decision-making, accountability, and organizational learning.

4. IT, Enterprise Systems & AI Enablement

• Own the enterprise technology and systems strategy that underpins internal operations, cross-team collaboration, and organizational effectiveness.
• Operationalize IT governance, security, access controls, and systems permissions to uphold reliable, secure, and compliant operations.
• Lead the strategy for internal or external IT partners to sustain a stable, scalable, and resilient technology infrastructure.
• Ensure enterprise systems are well documented, integrated, and continuously improved to meet evolving organizational needs.
• Lead the evolution of Opportunity@Work’s operating model to support a human and AI-enabled workforce, ensuring leaders are equipped to deploy advanced tools responsibly while preserving the uniquely human capabilities central to the mission.
• Build executive fluency across People, Finance, and Systems in AI-enabled decision-making, productivity, and performance management.

5. Legal, Compliance, Risk & Governance

• Serve as the organization’s lead for legal, compliance, and risk management functions.
• Oversee contracts, regulatory compliance, corporate governance processes, and fiduciary reporting to the Board.
• Maintain compliance calendars and validate timely filings, renewals, and reporting obligations.
• Coordinate legal counsel, auditors, and advisors as needed to protect organizational integrity and manage risk.

6. Workplace Operations, Facilities & Procurement

• Align facilities, workplace operations, and vendor management to ensure a productive, safe, and mission-aligned work environment.
• Manage office operations, leases, space planning, and vendor relationships. 
• Hone, improve and ensure strong procurement standards, purchasing policies, and contract administration practices.
• Orchestrate ethical, cost-effective, and compliant procurement and supplier management across the organization.

7. Systems for Accountability, Performance & Continuous Improvement

• Design, steward, and continuously improve the systems that hold teams and leaders accountable for results.
• Partner with the Chief of Staff and executive leaders to architect organizational planning, reporting, and performance systems are well supported by strong infrastructure and clear ownership.
• Ensure operational data, dashboards, and reporting mechanisms provide leadership with clear visibility into organizational health, risks, and performance.
• Identify systemic bottlenecks and operational risks, and lead corrective action through the appropriate departments.

Qualifications & Experience 

• 15+ years of progressive leadership experience, ideally with at least 3 years of professional service experience
• Senior executive experience transforming complex operations across 2 or more key functional areas: people, technology/IT, legal, and finance.
• Demonstrated capacity to operate as an enterprise-level leader with the strategic judgment and institutional perspective required to steward mission-driven organizations at scale.
• Strong track record of building scalable systems, controls, and infrastructure in mission-driven organizations.
• Deep understanding of organizational accountability, performance management, and operational excellence.
• Strong understanding of talent, strategic planning, budgeting, compliance, IT and finance functions. 
• Excellent communication, leadership, and cross‑functional collaboration skills. 
• Comfort operating as a senior thought partner while maintaining clear operational boundaries.
• Commitment to equity, transparency, and mission-aligned leadership.