CEO Chief of Staff

Location: Washington, D.C.

About Opportunity@Work

Opportunity@Work is a nonprofit social enterprise with a mission to expand access to career opportunities so that all Americans can work, learn and earn to their full potential in a dynamic economy. Our work aims to leverage and build the collective capacities of employers, educators, tech innovators, social entrepreneurs, and civic institutions to unlock opportunity for over 1 million Americans in the next decade. By transforming hiring practices, expanding learning pathways and pioneering talent financing, Opportunity@Work and our partners will equip Americans currently overlooked by today's labor market practices to build skills, demonstrate them and be hired into well-paid, in-demand jobs across the country.

About the Role

Opportunity@Work’s CEO is looking for a Chief of Staff to support him in maximizing his time, energy and focus across a range of internal and external responsibilities. This includes clarifying and framing communications across multiple media and audiences and coordinating information and opportunities across stakeholders. This highly organized, business-savvy professional will also help track, prepare for and follow up on all of the CEO’s projects and deliverables. We seek a multi-talented professional who is collaborative, mission-oriented and a strong multi-tasker.

Your Responsibilities

Business Alignment. Capture and organize CEO’s requirements, content development, decision making and communication for company deliverables. Coordinate with staff on process definition and improvements related to the CEO’s activities. Project manage the CEO’s deliverables, liaising between the CEO and key stakeholders to ensure they are complete and on time.

Idea Synthesis and Translation. Intensive listening to CEO’s vision and plans, capturing many ideas quickly and pressure testing for efficacy. Organizing and sequencing ideas and plans into clear, professional outputs for specific deliverables. Act as the CEO’s sounding board for ideas, asking questions to uncover any gaps in ideas and/or help connect thoughts into holistic, clear themes and communications.

Front-line Liaison & Strategic Scheduling. Screen, manage and direct incoming and outgoing requests via phone, email and in-person with staff, business executives, nonprofit leaders, media, or government officials. Work with the CEO’s Executive Assistant to: establish and oversee strategic scheduling and time management protocols to prioritize and focus CEO’s time in the most effective way; track and respond to correspondence, maintaining timely engagement across entities and contacts; prioritize meetings and resolve thorny schedule conflicts; ensure the CEO’s meetings, interviews, appearances, and travel are consistent with professional obligations as defined in the CEO’s quarterly goals and priorities. Ensure appropriate time allocation across: Opportunity@Work strategic initiatives, organization, people, and partnerships; collective impact efforts to make the U.S. labor market more inclusive.

People, Task and Project Management. Develop, improve, and implement routines to capture and track CEO’s priorities, tasks, communications, and follow-ups. Ensure that all deliverables are assigned, resource, monitored, prepared, and executed - or explicitly triaged out - so that no idea or deliverable is unaddressed. Maintain and adjust priorities to ensure deadlines are met; use required travel to strategically maximize CEO’s time and opportunities to develop and deepen relationships with existing and prospective partners. Capture and share out new or recently engaged contacts, discussion summaries, agreed upon next steps and owner(s) to relevant team members.

Meeting Event Preparation and Support. Prepare CEO for meetings and events by clearly identifying the purpose of each meeting, assemble background material, do relevant research and prepare “message points” and/or “who’s who” briefings as needed. Assist in coordinating and compiling presentations and other communications. Attend business meetings, take notes, disseminate and ensure follow-ups are completed.

Speaking and Media Support. Collaborate with the Marketing and Communications team to manage intakes or requests, evaluate opportunities with relevant staff against goals, thought leadership themes, and scheduling tradeoffs. Negotiate logistical details to ensure CEO’s needs are met and presentations and panels run smoothly. Coordinate A/V, tech rehearsals, collateral, collecting business cards and follow-ups. Provide marketing/PR team social media “chirps” and posts tied to schedule and appearances.

Contact and Information Management. Work with the CEO’s Executive Assistant and other staff on protocols to maintain and leverage his professional contact database, as well as keep the organization’s CRM system fully updated with new or recently engaged contacts, discussion summaries, agreed next steps and owner(s). Partner with Customer Acquisition & Success to define and manage contact-related reports in support of CEO’s success. Ensure maintenance of highly organized digital and paper files for easy retrieval, and coordinate resolution of any technical issues.

Ad Hoc Tasks (as needed). Assist with special projects, ad hoc research assigned by CEO.

About You

Executive presence. You are poised with a positive and confident presence, able to represent the CEO’s interests while making others feel taken care of. You get along with a wide variety of people, influence colleagues and contacts at all levels, and create win-win’s. You are comfortable in ‘managing up’ and have proven experience supporting a senior executive while maintaining a high level of workplace discretion.

Communicator. You are a precise and professional communicator across mediums, personalities, and roles. You assimilate wide ranges of information and act as ‘translator’, summarizing other’s ideas into organized themes and thorough summaries. You understand the nuances of communication and presentation and uphold the highest standards of excellence, accuracy, and completion.

Business savvy. You grasp the CEO’s organization, goals, responsibilities, and activities, able to understand how critical aspects interconnect and what is needed to move the CEO’s work forward. You exercise good judgement when facing new opportunities, conflicting priorities, and difficult decisions.

Organized. You are able to track, manage and prioritize multiple short, medium, and long-term projects in parallel, with nothing falling through the cracks. You have meticulous attention to detail. You translate ideas into processes that drive execution, manage deliverables across parties, and ensure deadlines are met. You are technically proficient with Microsoft and Google tools, email calendar, and file management platforms.

Proactive. You are self-motivated and can manage your own workload, producing results without needing reminders or daily supervision. You plan ahead and keep an eye on the future, anticipating needs, opportunities and conflicts, making appropriate adjustments to ensure things run smoothly.

Flexible and Adaptable. You are comfortable working in the midst of fluidity and ambiguity, able to read other people and situations. You are willing to tackle tasks with enthusiasm and adapt rapidly and calmly to changes in priorities, direction or information. You are a good team player, respectful of others roles and contributions, able to delegate, collaborate or take direction. You are responsive to CEO’s time-sensitive needs.

How to Apply

In line with our mission and values, we will hire for this role based on your demonstrated ability to do the job. As such, here’s what we want you to submit with your application:

  1. Please submit a resume and short cover letter in PDF.

  2. In your cover letter, address why you are a good fit for this role and our organization.

Email your application to
Subject line should read “Opportunity@Work, Chief of Staff”

You may also mail your application to:

Development Resources, inc.
1820 N. Fort Myer Drive, Suite 702
Arlington, VA 22209
Attn: Opportunity@Work, Chief of Staff

Compensation and Benefits

Opportunity@Work offers competitive salary and a comprehensive benefits package. Some of our benefits include medical/dental/vision, life insurance, both short and long-term disability, flex savings accounts, pre- and post-tax retirement accounts with company match, commuter benefits, professional development funding, flexibility to work remotely when necessary, paid parental leave and generous paid time off.


Accommodations are available for applicants with disabilities in all phases of the application and employment process. Please email or call 202-847-4470 to discuss your needs.

Opportunity@Work is an equal opportunity employer committed to hiring a diverse workforce at all levels of the organization. We value and encourage the contributions of our employees and strive to create an environment where everyone can reach their full potential and drive outstanding results. All qualified applicants will receive consideration for employment without regard to race, national origin, age, sex, religion, disability, sexual orientation, marital status, veteran status, gender identity or expression, or any other basis protected by local, state, or federal law. This policy applies with regard to all aspects of one’s employment, including hiring, transfer, promotion, compensation, eligibility for benefits and termination.