Program Manager

Program Manager (Key Personnel)

Fearless is seeking a senior Program Manager to lead a large-scale federal workforce training and learning management program supporting a national health and safety mission. This role serves as the single, trusted partner to federal leadership and oversees a nationwide training ecosystem that supports thousands of federal and state users. The work directly impacts regulatory effectiveness, workforce readiness, and public health outcomes. This is not a typical project management role. We're looking for someone who wants to steward a mission-critical program for the long term, someone steady, thoughtful, and confident enough to operate at both strategic and detailed levels without losing sight of the people behind the work. This position is designated as Key Personnel and requires executive presence, consistency, and long-term commitment.

Responsibilities:

• Serve as the primary interface with federal Contracting Officers, CORs, and program leadership, maintaining clear, consistent, and trusted communication.
• Provide end-to-end management of a complex federal contract, ensuring compliance with FAR requirements, federal security standards, accessibility regulations, and all contractual obligations.
• Oversee the planning, execution, and integration of multiple workstreams (including learning management system (LMS) operations, instructional systems design (ISD), curriculum development, help desk support, data analytics, and large-scale training events) into a unified program strategy.
• Maintain holistic visibility into the status of all training initiatives and platform enhancements, participating directly in prioritization discussions with stakeholders. Ensure operational excellence across the learning management ecosystem, including system uptime, SLA performance, reporting accuracy, and long-term records management compliance.
• Provide Agile program oversight across cross-functional teams while maintaining disciplined project controls, integrated schedules, and performance baselines.
• Manage program budgets and financial performance, monitor burn rates, and ensure responsible stewardship of federal funds.
• Identify, assess, and mitigate program risks and dependencies; implement proactive mitigation strategies to protect delivery commitments.
• Lead multidisciplinary teams of instructional designers, developers, analysts, help desk personnel, and event coordinators, fostering accountability and high performance.
• Maintain sufficient technical fluency to speak confidently about cloud-hosted platforms, DevSecOps practices, reporting infrastructure, and system enhancements without heavy reliance on escalation.
• Provide strategic insight and recommendations to federal leadership regarding modernization, process improvement, and long-term program sustainability.
• Contribute to account stability and growth through proactive engagement and consistent delivery excellence.

The Impact You Will Create in this Role:

• A successful Program Manager will independently operate at an advanced level, provide practical ideas and support, and break down complex concepts. The Program Manager will support Fearless' customers and organizational goals by:
• Achieving long-term customer retention and expanding account opportunities by effectively managing client relationships.
• Ensuring projects are delivered on time, within budget, and in compliance with federal regulations, contributing to exceeding overall client satisfaction and program success.
• Enhancing team performance and operational efficiency, leading to measurable improvements in program outcomes, cost management, and resource allocation.
• Increasing account growth by X%, reducing project costs by Y%, and ensuring X% of project milestones are achieved on schedule.
• Ensure that Fearless positively impacts our customers' missions and the lives of the people they serve by consistently delivering world-class products and services on time and within budget.
• Serve as the primary point of contact for all program activities, ensuring the cohesive execution of multiple projects under the program.
• Present Fearless capabilities to potential customers in detail, highlighting how those capabilities could impact the potential customer to meet the previously identified requirements.

Place of Performance & Travel Requirements:

• While this role is primarily remote, the individual must be available to attend in-person customer meetings at the client's headquarters in Baltimore, Maryland, as needed.
• The individual in this role will lead approximately three in-person events annually within the greater Baltimore metropolitan area. These events range from one to five days in length and require full on-site participation.

Qualifications Required for this Project:

• Minimum of 8-10 years of progressive leadership experience managing federal government programs or contracts.
• Experience managing programs and projects at Center for Medicare and Medicaid Services (CMS).
• At least 7 years of experience managing federal training, instructional systems design (ISD), learning management systems, or enterprise workforce development initiatives.
• Demonstrated experience serving as the primary client interface on a federal contract, with direct communication experience supporting COs, CORs, and senior federal leadership.
• Proven experience managing multidisciplinary teams across technical, instructional, and operational functions.
• Strong understanding of federal contract management principles, FAR compliance, performance management, and financial accountability.
• Demonstrated experience overseeing enterprise Learning Management Systems (LMS) or similarly complex digital platforms.
• Experience managing large-scale workforce training programs and curriculum lifecycle oversight is strongly preferred.
• Experience operating within structured process maturity environments (e.g., CMMI or equivalent) is a plus.
• Experience in Agile delivery environments integrating scaled Agile practices with traditional program controls is highly desirable.
• Project Management Professional (PMP) certification is required. Additional certifications such as PMI-ACP, ITIL, or SAFe are a plus.
• Master's degree in Instructional Design, Education, Organizational Development, Public Administration, or related field is preferred.
• Ability to obtain and maintain required federal background clearance.
• Extensive experience leveraging Learning Management Systems (LMS) is required.
• Proven experience in instructional design is required.

Qualifications We Require at Fearless:

• Minimum of 7 years of experience in program management, including experience managing government contracts.
• Experience with government procurement processes, contracts, and compliance regulations (e.g., FAR/DFAR) is a plus.
• Experience with IT project delivery, software development, or digital transformation programs is highly preferred.
• Understanding of cybersecurity and data privacy regulations in federal contracts.
• PMP or similar project management certification preferred.
• Other relevant certifications (e.g., Lean Six Sigma, Agile, ITIL) are highly desirable.
• Proven track record of managing large, complex programs with multiple work streams and budgets exceeding $5M.

Skills and Competencies Needed for Success in this Role:

• Communicating with Credibility & Influence: Builds credibility as a subject matter expert within the customer's organization. Promotes buy-in among organizational stakeholders for initiatives. Motivates staff and other stakeholders to support vision and goals. Serves as an advocate for the organization or team members to advance the organization's strategic direction and goals. Shares opinions about important issues, regardless of risk or discouragement from others. Promotes the role of their function in achieving the organization's mission, vision, and goals. Builds credibility for themselves and Fearless within the customer's organization as an expert in their field. Serves as an influential voice for strategies, philosophies, and initiatives within the organization. Advocates for the implementation of evidence-based solutions. Inspires staff, customers and executive-level organizational stakeholders to support and pursue the organization's strategic direction, vision and long-term goals. Builds consensus among leaders about the organization's strategic direction and long-term goals. Uses knowledge and skills to influence business strategy.
• Technology Awareness: Wholistic knowledge of technology developments and new applications (hardware, software, telecommunications), emerging technologies and ability to apply to business processes and implementation of information systems to meet organizational requirements.
• Project Management for Gov Contracts: Applies project management principles and practices to plan, execute, and close government projects, ensuring timely delivery, budget adherence, and compliance with federal regulations.
• Account Growth & Retention: Nurtures, grows and maintains existing accounts by monitoring, measuring, and ensuring customer satisfaction; leveraging existing contracts for up-selling and cross-selling opportunities, actively troubleshooting and resolving issues, countering competitive threats, and expanding customer networks and champions.
• Government Procurement Rules, Regulations & Methods: Uses knowledge of contracting officers, acquisition regulations, procurement levels, and government contracting methods-including contract types, IDIQ, GSA schedules, socio-economic categories, and teaming agreements-to identify opportunities and secure funding that align with the organization's strategic priorities, ensuring successful outcomes for both the organization and its customers.
• Evaluating Business Challenges: Partners with stakeholders to understand current and future challenges, and identify needs and opportunities for improvement. Informs stakeholders about current and future threats and liabilities that jeopardize successful outcomes. Advises stakeholders through collaboration and recommends solutions to ensure attainment of business outcomes and support the organization's strategic direction and long-term goals.
• Advising on Solutions: Provides guidance to other professionals, managers, and business unit teams on the implementation of related solutions. Works with business partners to overcome obstacles to implementing solutions. Provides follow-up to and ongoing support for the implementation of solutions to ensure their continued effectiveness. Ensures that the implementation of solutions adheres to defined goals and outcomes. Provides ongoing support and solutions to business unit leaders on the organization's strategic direction. Encourages staff and leaders to provide input on strategic business decisions. Works with leaders to overcome obstacles to implementing initiatives. Integrates solutions with related organizational processes, systems, and other business or management initiatives.
• Stakeholder & Partner Management: Knowledge of the concepts, practices, and techniques used to identify, engage, influence, and monitor relationships with individuals and groups connected to a work effort, including those actively involved, those who exert influence over the process and its results, and those who have a vested interest in the outcome (positive or negative).
• Team Management: Manages the team by analyzing team data (such as forecasts and progress to goals), ensuring achievement of metrics, allocating resources and managing budgets, attracting, selecting, onboarding, developing, coaching, motivating, promotin,g and terminating team members. Conducts performance reviews and career planning, removes demotivating factors in the environment, and enhances collective team competencies.
• Focus on Performance: Ensures high performance standards and accountability across the organization by focusing the team on results, ensuring accountability, using metrics to measure performance, and applying continuing improvement.
• Cost Estimation & Budgeting: Develops accurate cost estimates and budgets for government projects, ensuring compliance with federal financial management regulations and guidelines.
• Environmental & Customer Awareness: Maintains awareness of agency and other external dynamics, power structures within client environments as well as functional/domain knowledge, regulatory trends and contract requirements that influence service delivery and company expansion/growth.
• Complex Solution & Definition Positioning: Translates business requirements into technical solution requirements, coordinating technical expertise, sizing, scoping and defining delivery and deployment approach timelines, identifying required resources, coordinating demonstrations of proof of concept supporting internal deal acceptance.

Required Level of Proficiency:

• Advanced Application: You can perform the actions associated with a skill without assistance. You are recognized within your immediate organization as "a person to ask" when difficult questions arise about required skills.

Physical Requirements:

• Ability to sit for extended periods while working on a computer or during meetings.
• Must be able to travel occasionally to client sites or company meetings, which may involve driving or flying.
• Ability to communicate effectively via phone, email, and in-person, requiring clear speech, listening, and written communication skills.
• Ability to move within an office environment, including reaching for files, using office equipment, and occasional light lifting (up to 10 pounds).

Life at Fearless

We're a digital integration consultancy on a mission to build a better tomorrow. At Fearless, we combine technology, people, and organizational development to solve meaningful problems. Through iterative development, we deliver smart, user-friendly solutions that make tech work better-for everyone.

But great tech is just part of the story. What really makes us Fearless is our Purple Culture.

What Makes Us Purple?

Being Purple means you:

• Are valued as a whole person-not just a job title
• Get matched with work that plays to your strengths and passions
• Are supported by coaches, not micromanagers
• Have the autonomy and clarity to make decisions and drive impact
• Join a community that celebrates equity, curiosity, and innovation
• Do work that matters-every day

We believe in flexibility, growth, and balance. Our benefits and culture are designed to support you in doing your best work-while making space for what matters to you outside of it.

We're proud to be an equal opportunity employer. At Fearless, we're building a workplace that welcomes and respects everyone-across race, gender, age, religion, identity, background, and ability.

Compensation at Fearless

Fearless is committed to providing a competitive compensation package that will meet your current and future needs. Our philosophy is aimed at rewarding team member contributions, supporting long-term financial growth and security, and overall well-being.

We believe in paying people fairly, so we've established a compensation model aimed to ensure everyone at Fearless - regardless of race, ethnicity, gender, sexual orientation, disability, religion, age, nationality, or willingness/ability to negotiate - is consistently paid fairly based on alignment to the needs and requirements of the role.

The salary range for this position is:

Minimum Salary: $128,453

Salary Midpoint: $170,200

Maximum Salary: $211,947

Hiring Range for Role: $128,453 - $175,000

*This position is eligible for a discretionary bonus based on individual and company performance criteria.

Benefits at Fearless

At Fearless, we take care of our team-because when you're supported, you can do your best work. We offer a flexible, family-friendly environment with benefits designed to support your health, growth, and life outside of work.

For Full-Time Team Members (Starting Day One):

• Flexible, life-friendly schedules
• 100% coverage for our medical HSA plan + HSA contributions
• Dental & vision covered 100% for you and your dependents
• Competitive premiums for HMO/PPO and dependent coverage
• 401(k) with 4% match & immediate vesting
• Paid Parental Leave and 12 weeks paid FMLA
• Generous PTO, 11 Federal Holidays, a Birthday Holiday, and Sick Leave
• Up to 15 days for Jury Duty and Bereavement Leave
• Education, wellness, and tech allowances
• Referral bonus: $6K-$12K for each successful referral
• Pet insurance & discount plans
• Employee Assistance Program (EAP)
• Legal support, life insurance, disability coverage

Reasonable Accommodations

Fearless is committed to providing reasonable accommodations for applicants and candidates with disabilities. If a reasonable accommodation is needed to participate in the job application or interview process, please contact the Human Resources Department at hr@fearless.tech.

So, What's Next?

We've refined our hiring approach to make sure every team member is a great fit for Fearless-and that we're a great fit for you, too. If there's alignment, we'll reach out to kick off the interview process. Depending on the role or project, your experience may vary slightly, but it typically includes:

Introductory Interview

You'll connect with a recruiter to:

• Build rapport and get to know each other
• Review your experience and skills
• Talk through salary expectations and role details
• Set expectations for the rest of the process

Skills + Business Fit Interview

This is where we dig deeper to:

• Review findings from any technical assessments
• Walk through situational and values-based questions
• Explore how your approach aligns with Fearless culture and project needs

Some roles may also include customer interviews based on specific project requirements in addition to background check and security clearance requirements.