Chief of Staff

Program Management Solutions LLC•Reston, VA

7d•$120,000 - $140,000•Hybrid

About The Position

pmdigital is a growing government contracting and consulting company supporting mission-focused customers with practical, high-quality services and technology-enabled solutions. We operate in a fast-moving environment where disciplined execution, strong customer relationships, sound business judgment, and dependable delivery matter. We are seeking a high-performing Chief of Staff to serve as the CEO’s execution partner and help build the management systems that enable pmdigital to scale effectively. This is not an administrative-assistant role. It is a hands-on leadership position for an organized, analytical, trusted operator who can turn executive priorities into clear plans, accountable owners, timely decisions, and measurable results. The Chief Of Staff will work directly with the CEO and leadership team to improve company-wide execution, operating discipline, strategic alignment, and decision-making. The successful candidate will serve as the connective tissue across business development, finance, operations, proposal/capture, delivery, and corporate initiatives. They will lead the company’s executive operating rhythm; prepare decision-ready information for leadership; track strategic initiatives and critical actions; surface risks early; and help ensure that important work moves forward without requiring constant CEO intervention. This role is ideal for a professional with 6–10 years of experience in government contracting, consulting, professional services, program management, business operations, PMO leadership, capture/proposal operations, or executive operations.

Requirements

Bachelor’s degree or equivalent relevant professional experience.
6–10 years of progressively responsible experience in government contracting, consulting, professional services, program management, business operations, PMO, corporate operations, capture/proposal operations, or a related environment.
Demonstrated experience leading cross-functional initiatives involving multiple stakeholders, shifting priorities, and incomplete information.
Strong understanding of the government-contracting lifecycle, including opportunity identification, capture, proposal development, award, contract startup, delivery, and customer management.
Strong project and program management skills, including planning, milestone management, issue/risk management, action tracking, and stakeholder communication.
Ability to develop concise, high-quality executive materials, including decision memoranda, dashboards, presentation content, meeting briefings, and status reports.
Experience working with financial and operational information, including revenue, backlog, pipeline, margin, staffing, project performance, or cash/AR metrics.
Excellent written, verbal, and interpersonal communication skills.
High degree of professionalism, judgment, discretion, and comfort handling sensitive business, personnel, financial, and customer information.
Ability to operate independently, prioritize effectively, and maintain momentum in a fast-paced small-business environment.
Experience in a small or mid-sized government contractor, professional-services firm, or growth-stage consulting organization.
Eligibility to work in the United States.

Nice To Haves

Experience supporting a CEO, president, COO, executive office, or senior leadership team.
Prior experience as a Chief of Staff, Director of Operations, PMO Lead, Program Manager, Operations Manager, Capture Manager, Proposal Operations Lead, or business operations leader.
Familiarity with federal acquisition, IDIQ/GWAC/task-order environments, subcontractor/teaming management, proposal processes, contract transition, and delivery startup.
Experience supporting corporate growth activities, including pipeline reviews, bid/no-bid decisions, pricing inputs, strategic partnerships, and organizational readiness.
Experience developing executive dashboards and operating reports using Microsoft Excel, Power BI, SharePoint, Teams, CRM systems, project-management platforms, or comparable tools.
PMP, CAPM, Lean Six Sigma, MBA, or other relevant business, operations, or program-management credentials.
Experience implementing workflow automation, AI-enabled processes, knowledge-management systems, or data-driven operating improvements.

Responsibilities

Partner with the CEO to translate strategic priorities into execution plans, workstreams, milestones, accountable owners, decision points, and measurable outcomes.
Manage the CEO’s priority portfolio, including strategic initiatives, corporate projects, customer/partner commitments, major pursuits, and internal transformation efforts.
Prepare concise executive-ready decision briefs, meeting materials, agendas, talking points, follow-up communications, and action trackers.
Triage incoming issues and requests; resolve matters within delegated authority; and elevate only those decisions, risks, or tradeoffs that require CEO attention.
Ensure meetings lead to clear decisions, assigned owners, deadlines, and reliable follow-through.
Act as a trusted thought partner to the CEO while maintaining confidentiality, sound judgment, and appropriate discretion.
Lead 2–4 CEO-designated strategic initiatives each year, from definition through implementation and results tracking.
Develop charters, project plans, success measures, stakeholder maps, risk logs, communication plans, and implementation roadmaps for priority efforts.
Drive cross-functional coordination across business development, finance, operations, delivery, proposal/capture, recruiting, and technical teams.
Identify obstacles, dependencies, resource constraints, and decision gaps early; recommend practical solutions and facilitate timely resolution.
Support annual planning, quarterly operating reviews, and periodic strategy updates.
Help translate growth objectives into practical operating requirements, including staffing, delivery readiness, financial planning, process maturity, and organizational capability.
Establish and maintain a disciplined leadership operating cadence, including weekly leadership meetings, monthly business reviews, quarterly planning sessions, and executive action reviews.
Maintain a centralized executive action register that tracks commitments, due dates, dependencies, owners, status, and escalation needs.
Drive timely closure of leadership actions and strategic commitments.
Build and maintain executive dashboards and scorecards that provide a clear view of company performance, including pipeline, bookings, backlog, revenue, margin, cash/AR, staffing, delivery health, major proposals, customer risks, and key initiatives.
Partner with the CFO and operations leadership to ensure management reporting is timely, accurate, relevant, and decision-oriented.
Improve the quality of internal meetings by implementing clear agendas, decision logs, action tracking, and concise post-meeting summaries.
Coordinate business-development, finance, operations, technical, and delivery inputs for significant pursuits, bids, and strategic opportunities.
Help operate and improve the company’s bid/no-bid, pursuit-governance, and capture-review processes.
Ensure major opportunities receive appropriate consideration of strategic fit, delivery capacity, staffing, teaming, contractual risk, financial implications, pricing inputs, and operational readiness.
Support clean handoffs from capture and proposal activity into contract startup, staffing, delivery planning, and customer management.
Work with the Director of Business Development and other leaders to maintain visibility into the opportunity pipeline, priority pursuits, proposal readiness, and associated business risks.
Facilitate win/loss and project after-action reviews, ensuring lessons learned translate into process and performance improvements.
Identify recurring operational friction, unclear decision rights, duplicated work, communication gaps, and process weaknesses that consume executive time or create delivery risk.
Design and implement practical process improvements that increase accountability, speed, visibility, and consistency.
Help define and document roles, operating procedures, decision authorities, and cross-functional workflows as the company grows.
Support appropriate adoption of automation, AI-enabled workflows, collaboration tools, dashboards, and knowledge-management practices where they produce measurable business value.
Create scalable templates, playbooks, reporting formats, and management routines that reduce reliance on ad hoc CEO direction.