Chief of Staff

Stradaeducation

United States

Posted November 25, 2025

Full-time 275000 - 325000 USD per-year-salary

Job Overview

The Chief of Staff (COS) is a trusted strategic partner to the CEO, enhancing CEO effectiveness by strengthening organizational alignment, tackling special projects, and accelerating progress on priority initiatives. Reporting directly to the CEO, the COS brings strong judgment, synthesis, project management, problem-solving, and execution skills to support decision-making, communications, and cross-functional coordination.

The COS serves as an advisor, integrator, project manager, and communicator – a “utility player” offering clear analysis, anticipating needs, and ensuring the CEO is prepared for the highest-impact internal and external engagements. The COS will work primarily with the leadership and broader team at Strada to advance this agenda. The role requires exceptional professionalism and interpersonal skills, discretion, and the ability to work fluidly across both strategic and operational tasks.

Working closely with the CEO, the COS develops a strong understanding of both short-term and long-term priorities and partners with Strada team members, including the Senior Leadership Team, to ensure effective execution. This will include delegating tasks, tracking and monitoring progress, and personally executing priority actions.

The COS is a member of Strada’s Senior Leadership Team and oversees a small team responsible for the CEO’s key administrative functions (i.e., schedule, internal communications, and event planning), ensuring seamless coordination of these functions to enable the CEO to maximize time spent on strategic priorities. Specifically, the COS shares an executive assistant with the CEO (who oversees the office managers at Strada’s headquarters in Indianapolis and its Washington, D.C. hub) and oversees three additional direct reports: the Director, Internal Communications; the Senior Manager, Board Engagement, Events, and Outreach; and an additional shared executive assistant who supports several Strada teams.

The COS is based in Strada’s Washington, D.C. hub, co-located with the CEO. While Strada maintains a hybrid work environment, the COS will generally be in the office on the days the CEO is present (typically 3-4 days per week) to support close coordination and real-time collaboration

Context

Strada Education Foundation supports programs, policies, and organizations that strengthen connections between postsecondary education and employment in the U.S., with a focus on helping those who face the greatest challenges. Our strategic plan centers on five keys to strengthen the link between education and opportunity: Clear Outcomes, Quality Coaching, Affordability, Work-Based Learning, and Employer Alignment. We leverage several impact lever teams to advance our work, including actionable research, catalytic grantmaking, nonpartisan policy solutions, strategic communications, strategic investments, and affiliates (e.g., CredLens). We work collaboratively with hundreds of partners across the U.S., including educators, employers, policymakers, learners, and other nonprofits and trade associations. Strada offers a dynamic, collaborative professional environment that provides many learning and professional development opportunities.

Key Responsibilities

The COS has six core responsibility areas, listed below with the approximate time required.

Context

Key Responsibilities

The COS has six core responsibility areas, listed below with the approximate time required.

Area 1: Strategic Advisor (20%)

Develop and maintain a strong understanding of short-term and long-term CEO priorities and projects on both the mission and operations sides of Strada.
Serve as a thought partner to the CEO on strategic, operational, and organizational issues.
Maintain regular touchpoints with senior leaders and other colleagues to gather insights, identify obstacles, monitor progress, and surface opportunities.
Provide concise synthesis, context, and recommendations to support CEO decision making.
Strengthen coordination and communication across teams by helping clarify decision rights, facilitating alignment, and improving information flow.
Build trust-based relationships across Strada to enable collaborative problem-solving and accurate “pulse checks.”
Protect the CEO’s time by filtering, prioritizing, and routing issues requiring CEO attention.

Area 2: Execution and Monitoring of CEO’s Key Priorities and Projects (25%)

Manage a variety of special projects, large and small, at the CEO’s request to ensure the CEO can focus on the highest-impact strategic priorities.
Conduct research, analysis, and structured problem-solving to inform strategic recommendations.
Where helpful, convene and coordinate cross-functional working groups to advance priority initiatives.
Identify operational or strategic barriers and work with stakeholders to resolve issues and maintain momentum.
Ensure follow-through on commitments emerging from CEO and leadership meetings.
Develop and maintain trackers or dashboards to monitor progress and completion of priorities and projects that require CEO engagement or for which the COS is responsible.
Drive execution by delegating tasks, tracking and monitoring progress, ensuring clarity of roles and expectations, and personally completing priority actions when appropriate.

Area 3: Executive Communications and Board Support (15%)

Draft and develop high-quality communications for the CEO, including slide presentations, talking points, memos, and internal updates.
Synthesize complex or diffuse information into clear, compelling narratives for senior internal and external audiences.
Working collaboratively with the CEO and relevant team members, coordinate all aspects of the annual retreat of the Strada Board of Trustees.

Area 4: CEO Meeting Preparation, Prioritization, and Calendar Strategy (10%)

Manage executive team meetings, including agenda setting, coordinating or preparing materials, clarifying objectives, and ensuring timely and effective follow-up on decisions and action items.
Support prioritization of the CEO’s time, including meetings, speaking engagements, and requests for external participation.
Ensure the CEO is fully prepared for key engagements by coordinating and reviewing pre-reads, briefing materials, objectives, and anticipated follow-up needs. ▪ Coordinate with executive team members and other stakeholders to ensure timely and accurate information reaches the CEO.
Manage information flows to and from the CEO’s team with clarity, discretion, and efficiency.

Area 5: Issue Spotting and Problem Resolution (15%)

Identify and elevate emerging issues, risks, or organizational tensions that may require CEO attention. Where appropriate, resolve issues that do not require CEO engagement, ensuring only the right matters reach the CEO.
Provide balanced, discreet counsel to the CEO on sensitive or urgent matters.
Respond quickly to unexpected challenges with a calm, solution-oriented approach and drive toward resolution.
Clarify issues, propose recommended actions, and ensure follow-through in fast-moving or high-stakes situations.

Area 6: Management of CEO’s Direct Team and its Key Functions (15%)

Lead and oversee the CEO’s direct team that includes an Executive Assistant, Director of Internal Communications, and Senior Manager of Board Engagement, Events, and Outreach.
Work closely with the Executive Assistant and Senior Leadership Team members to ensure the CEO’s schedule is optimized for mission impact and seamless internal operations.
Partner with the Director of Internal Communications to ensure Strada’s internal communications are effective, timely, responsive to employee interests, and aligned with CEO priorities.
Partner with the Senior Manager of Board Engagement, Events, and Outreach to ensure effective planning and execution of Board of Trustee meetings, Strada-hosted events, and key engagements.

The Person: Qualifications and Experience

Education: Bachelor’s degree required; MBA or similar advanced degree strongly preferred. An additional advanced degree in higher education, economics, public policy, or another field relevant to Strada’s work is a plus.
Progressively responsible experience in management consulting, strategy, finance, operations, or similarly analytical and cross-functional work, including experience leading teams and leading complex, cross-organizational projects and workstreams
At least three years of management consulting experience with interactions at senior levels of large client organizations strongly preferred
Experience working directly with or supporting a CEO or senior executive(s) strongly preferred
Experience in mission-driven environments, high-intensity roles, and/or complex cross functional organizations is preferred
Experience working in partnership with executive team members and colleagues at multiple levels to advance initiatives across an organization
Plus for experience in postsecondary education, workforce development, economic development, and/or economic mobility

Key Skills & Competencies

Excellent project management skills: ability to drive multiple high-profile projects, effectively leverage all resources to drive results, and create excellent (and simple) processes
Ability to translate innovative, strategic ideas into tangible, actionable steps, as well as to effectively monitor progress and partner with others on identifying improvements during implementation to increase the likelihood of successful execution
Strong business acumen, financial skills, and analytical abilities, including proficiency with Excel modeling
Ability to drive change management and influence change across teams ▪ Well-honed written, verbal, and creative communication skills, including ability to translate insight into content, create compelling slide presentations, create internal communication plans, and present to board members
Ability to effectively utilize a hypothesis-driven approach to problem solving, including taking on broad-reaching and sometimes ambiguous questions while working collaboratively and cross-functionally with colleagues across an organization
Exceptional interpersonal skills and judgment, including the ability to build trust quickly and influence across teams without relying on positional authority
Ability to quickly learn about and tackle new topics

Personal Attributes & Values

Passion for Strada’s mission of connecting education with opportunity, especially for those who face the greatest challenges
Comfort and alignment with Strada’s values
Friendly, collaborative, and inclusive approach
Comfort juggling and executing a diverse variety of projects, often with tight time constraints
Grace and kindness even under pressure – maintaining composure, steadiness, and empathy in moments of urgency or conflict
Strong sense of curiosity, as well as commitment to read broadly to stay on top of important developments in our space

Mission and Values Alignment:

Committed to providing equitable pathways to opportunity through PSET, particularly for individuals who have faced significant barriers. Demonstrated alignment with Strada's guiding values, commitment to building a strong and healthy workplace culture, and working in a collaborative environment.

Strategy and Innovation Leadership:

Adept at operationalizing strategy and effectively communicating strategic endeavors within the organization and in external contexts, both verbally and in writing. Particular skill in designing annual plans, monitoring progress, and refining plans as needed. Adaptable with tolerance for ambiguity. Able to problem-solve and navigate varied viewpoints. Capacity to refine efforts based on evidence that change is needed. Ability to lead efforts to visualize and monitor change. Capability to see and support innovative ideas and opportunities across the organization, and to embed innovation within operational plans. Capabilities in taking the perspective of others and adapting an agenda and approach – toward a shared aim - accordingly.

Strategic Problem Solving:

Ability to effectively utilize a hypothesis-driven approach to problem solving, with effective quantitative and communication skills. Ability to take on broad-reaching and sometimes ambiguous questions while working collaboratively and cross-functionally with Strada team members across the organization.

Execution and Operations Leadership:

Ability to translate innovative, strategic ideas into tangible, actionable steps, as well as to effectively monitor progress and partner with others on identifying improvements during implementation to increase the likelihood of successful execution.

DEI Commitment:

Commitment and professional experience advancing diversity, equity, and inclusion within and organization, including incorporating stakeholder perspectives in the design, implementation, and evaluation of strategic efforts.

Relationship Building and Collaborative Capabilities:

Demonstrated ability to cultivate, grow, and manage positive, mutually beneficial relationships at all levels of an organization and with partners outside the organization. Strong communication, interpersonal and relationship management skills—including identifying and working through challenges—underscored by strong judgment and emotional intelligence. Proven collaborator, able to work with colleagues at all levels in the organization.

Diversity, equity, and inclusion are central to Strada’s organizational vibrancy, employee experience, and mission. Strada is Diversity, Equity, and Inclusion Workplace-certified by Diversity for Social Impact, a strategic professional and organization development company dedicated to promoting diversity and inclusion to drive social impact worldwide. We strongly encourage applicants from people of color/the global majority, immigrant, bilingual, and bicultural individuals; people with disabilities, members of the LGBTQIA2S+ and gender nonconforming communities; and people with other diverse backgrounds and lived experiences. We believe every member on the team enriches our workplace by exposing us to a broad range of ways to understand and engage with the world, identify challenges, and discover, design, and deliver critical insights and solutions.