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

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.

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

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.

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.

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.

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.

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.

Compensation

200,000 - 250,000 USD/year (Remote)

Due to the high volume of interest, we kindly ask that candidates apply through this portal only. No emails or direct outreach to the Opportunity@Work team, please.

Opportunity@Work

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