Jun 03, 2021

Chief Operating Officer

  • Generation USA
  • Remote
Full-Time Administration/Operations

Job Description


Generation is a nonprofit that transforms education to employment systems to prepare, place, and support people into life-changing careers that would otherwise be inaccessible. The global pandemic has led to an unprecedented surge in unemployment. Even before the pandemic, more than 75 million young adults were out of work globally, and three times as many were underemployed—and 375 million workers of all ages needed to learn new skills by 2030. At the same time, certain jobs remain in high demand, and 40 percent of employers say a skills shortage leaves them with entry-level vacancies. To date, more than 38,000 people have graduated from Generation programs, which prepare them for meaningful careers in 14 countries. Generation works with more than 3,900 employer partners and many implementation partners and funders.


Generation USA is seeking a Chief Operating Officer to play a pivotal role in a time of rapid growth. Reporting to the Chief Executive Officer, the Chief Operating Officer will play a key role in leading and optimizing Generation’s finance, data, evaluation and learning, and operations functions to deliver the best possible outcomes for 500,000 learners over the next 10 years. In addition to serving as a vital thought partner to the CEO and other executive leaders, the Chief Operating Officer will manage the teams charged with delivering exceptional finance, operations, data systems, evaluation and learning, and legal across Generation’s 15 sites and 100+ employees. 

The COO will play a critical role in establishing a sophisticated understanding and application of financial policies, practices, and strategies within the organization while leading all financial, budget, audit, and compliance aspects of Generation’s operations. Collaborating closely with cross-functional team leads, the COO will capitalize on this opportunity to refine and update Generation’s financial systems, processes, and reporting capabilities to reflect an organization that has undergone rapid, massive growth and increased complexity in funding. The COO will set the financial strategy for Generation’s $20M operating budget while also continuing to build and coach the finance team to design and deliver the financial processes/systems needed to support Generation’s ongoing growth and evolution, scaling to a projected budget of $46M in 2025.

The ideal candidate believes that robust data systems, financial oversight, and strong operations are core foundations for organizational success. They are experienced in growth and scale and looking for an opportunity to drive systems to change through organizational growth. This is an ideal opportunity for a proven leader to apply their finance and operations expertise towards Generation’s mission.

This is a full-time and fully remote position.



People Management & Organizational Leadership

  • Provide leadership, guidance, and coaching to organizational leaders responsible for finance, operations, data systems, evaluation and learning, and legal; build systems to support all those functions
  • Directly manage a team of five Managing Directors (Budgeting and Forecasting, Finance, Operations, Data Systems, Evaluation, and Learning) and one Special Advisor (Legal), who in turn collectively manage and/or support full functional teams
  • Provide exceptional coaching and development, constantly modeling what it means to grow talent and establish leadership pipelines
  • Act as a thought partner to the CEO and work closely with other members of the executive team to craft an overall organizational strategy and goals, with specific ownership of financial and operational objectives
  • Routinely represent the organization to financial and operational partners, including financial institutions, investors, foundations, auditors, lawyers, partners, public officials, and board members

Financial Planning and Management

  • In consultation with the CEO, define the organization’s financial strategy; communicate financial requirements and implications of business decisions to leadership and the Board of Directors
  • Provide high-level oversight of the annual budgeting process, monthly close process, and quarterly forecasting, working closely with the Managing Director of Budgeting and Forecasting and Managing Director of Finance to minimize actual vs. forecast quarterly variances
  • Manage and direct the selection, implementation, and integration of financial and accounting software and systems
  • Manage the organization’s cash flow; support business planning with sophisticated financial models and accurate revenue forecasts
  • Oversee the approval and processing of revenue, expenses, general ledger, account maintenance, data entry, and financial recordkeeping
  • Oversee cash, investment, and asset management as well as financing strategies and activities and banking relationships
  • Develop and utilize forward-looking, predictive models and activity-based financial analyses to provide insight into the organization's business plans
  • Oversee internal/external reporting, including ensuring compliance with GAAP and all applicable local, state, and federal laws
  • Oversee annual financial audit, collaborating with the Managing Director, Finance on audit preparation, fieldwork, and preparation of audited financial statements and 990
  • Continue to optimize tools and systems to provide critical financial and operational information to the executive team, departmental managers, and the Audit and Finance Committee of the Board
  • Mentor and lead the finance team, with an eye towards meeting organizational goals and developing the team as professionals

Business Operations and Systems Development and Management

  • Identify, develop, and implement operational systems improvements that will support highly efficient and effective operational performance at Generation USA, both improving upon the current state of operations and moving good systems to great ones
  • Oversee risk management and legal activities such as memorandums of understanding, contracts, leases, and other legal documents and agreements, in consultation with legal advisor and Managing Director of Operations
  • Collaborate with Managing Director of Operations to strengthen procurement policy and procedures
  • Provide guidance and oversight for facilities and office management; lead process of re-entry to onsite work when it is deemed safe to return to the office
  • Partner with the Managing Director of Operations and the IT Lead to implement key IT initiatives to ensure Generation continues to provide best-in-class IT infrastructure to support its mission
  • Serve as a thought partner for the Chief People Officer and Equity Director  on employment policies and practices, benefits, and regulatory compliance
  • Manage relationships with retained and pro bono legal counsel as necessary

Knowledge, Learning, and Data Systems

  • Oversee the Learning and Evaluation team and Data Systems team through weekly coaching, professional development, and process creation and oversight;
  • Work with the Managing Directors to create and continuously improve a comprehensive strategy for collecting, managing, and using data;
  • Ensure the development, maintenance, and dissemination of role-specific training for all staff members on utilizing data systems, tools, and reports;
  • Collaborate with C-Level staff to develop and implement data cycles that drive continuous improvement
  • Ensure a culture of data where we accurately track information that reflects program operations, key performance metrics, and outcome data
  • Collaborate with Managing Director of Data Systems to optimize database systems and ensure coordinated use of 3rd-party database vendors
  • Oversee the design, development, and management of report and dashboard solutions to ensure that Generation staff at all levels of the organization have the information they need to make effective decisions;
  • Oversee the knowledge management strategy, framework, and tools for the organization, ensuring that key policies, data resources, and clarification of roles and responsibilities are widely documented and available to staff

Hiring Organization

Generation USA



You are a visionary, strategic and passionate leader energized at the thought of taking Generation into the next phase of growth. You have the ability to create organization-wide systems and processes that drive consistently strong outcomes. You have a knack for getting things done and the ability to mobilize a team to reach organizational goals. You have extensive experience managing teams and overseeing large-scale programs from inception to completion.

Specific requirements include, but not limited to:

  • A deep commitment to the mission of Generation USA
  • An unwavering commitment to anti-racism, diversity, equity, and inclusion, with an ability to serve as an exemplar for the organization's values and foster an inclusive and respectful workplace
  • 10+ years of progressively increasing operational leadership experience for a growing, multi-site organization;
  • 10+ years of progressively increasing financial leadership experience of a budget size of at least $30M annually
  • Holds high standards for project management while empowering others to proactively and creatively problem-solve, and model versatility and collaboration for the organization
  • Ability to exercise excellent judgment in decision-making by leveraging stakeholder input and data
  • Thoughtfully considers the impact of decisions, and facilitates resolutions that protect the organization's interests, and prioritizes mission/values when conflict or disagreements arise
  • Demonstrates integrity, both in words and actions, and encourages ethical behavior and decision making
  • A collaborative approach to executive leadership, and the ability to work effectively and flexibly with cross-functional teams to meet goals and improve organizational performance
  • Extensive experience working with and/or developing complex accounting systems with multiple funders, multiple cost centers, and complex allocation models
  • Extensive experience overseeing financial operations including budget development and scenario planning
  • Experience building different business models and relying on analysis to inform strategic decisions
  • Demonstrated ability to build and lead effective, high-performance teams within a high-growth and fully remote environment

Generation is an equal opportunity employer and actively encourages applications from people of all backgrounds. 

“In compliance with federal law, all persons hired will be required to verify identity and eligibility to work in the United States and to complete the required employment eligibility verification document form upon hire.”

Industry/Service Area

Education, Employment



Application Instructions

Please apply using this link here: https://grnh.se/c9edcd2c2us 

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