Program Manager

Skyward IT Solutions, LLC • Maryland, MD

19d • $150,000 - $180,000 • Hybrid

About The Position

We are Skyward, a people-centered business focused on human advancement through information technology. We are diverse, unified, creative, and collaborative, driven by a civic tech mission. Our values include Integrity, Compassion, Inquisitiveness, Unconventionality, and Authenticity. This role is contingent upon contract award. We are seeking an individual who is passionate about managing Risk Management Programs, including continuous monitoring, security authorization, and risk-based asset management. Ideal candidates will have experience managing federal cybersecurity programs, fluency in NIST RMF and FISMA, and the ability to align stakeholders including CISOs, CORs, and technical teams. We encourage motivated individuals eager to learn and contribute to a future-looking, growth-oriented team.

Requirements

• BA/BS and a minimum of five (5) continuous years of Program Management experience in cybersecurity (or equivalent area) leading federal IT or cyber programs of similar scope.
• One active PMI certification: PMP, PgMP, or PMI-RMP.
• An active ISC2 CISSP, CISM, or comparable professional cybersecurity certification.
• An active Agile certification: PMI-ACP, SAFe Agilist, Scrum Alliance CSM, or comparable.
• Demonstrated experience leading multi-stream cybersecurity programs (10+ FTEs across cyber compliance, continuous monitoring, vulnerability/configuration management, or similar).
• Working knowledge of FISMA, the NIST RMF, OMB Circular A-130, and DHS 4300A.
• Experience managing federal contract performance.
• Strong writing skills for executive briefings, memos, SOPs, policy, and decision papers.
• A track record of running cross-functional, remote, and collocated teams in dynamic environments using Agile/SAFe practices.
• Comfort with the program manager’s tool belt: MS Project or Jira, MS Teams, SharePoint, and reporting/dashboarding tools.
• Excellent stakeholder management instincts.

Nice To Haves

• Prior experience supporting USCIS, DHS components, or other federal civilian agencies on continuous monitoring, security authorization, or Ongoing Authorization (OA) programs.
• Hands-on familiarity with GRC tooling - CSAM, DHS Fenix, RegScale - and SIEM platforms like Splunk.
• Direct exposure to Vulnerability Management (Tenable/Nessus, Prisma Cloud), Configuration Management (per NIST SP 800-128), or Database Hardening using DISA STIGs and CIS Benchmarks.
• A sense of humor that survives a Friday afternoon data call.

Responsibilities

• Serve as the single point of accountability for task order management and execution.
• Act as the primary liaison to the Government Program Manager, COR, and federal team leads.
• Plan, execute, and track all program activities across three task areas: Program Management & Project Support, Risk Management Operations, and Risk-Based Asset Management.
• Integrate management and technical activities across the task order so Cybersecurity Assurance, Continuous Monitoring & Analytics, Vulnerability, Configuration, and Database Management are all moving in the same direction.
• Manage corporate resources, supervise contractor staff and subcontractors, and review the work of team members for quality, accuracy, and alignment to performance standards.
• Own the program’s deliverable engine: Project Management Plan, Risk Management Plan, Quality Control Plan, Weekly Status Reports, Monthly Program Management Reviews, Risk Register, Roadmaps, Ad hoc reports, and a Telework Plan.
• Develop written recommendations, executive briefing materials, and oral presentations for stakeholders.
• Drive risk identification, validation, and response in alignment with the NIST Risk Management and Cybersecurity Frameworks.
• Champion continuous improvement: stand up automation, refine SOPs and playbooks, and use metrics to make the program measurably better quarter over quarter.

Benefits

• Medical, dental, vision insurance (fully paid for employees)
• 15 days of paid leave
• 7 days of sick leave
• 2 days bereavement leave
• 11 paid Federal holidays
• Up to 40 hours for jury duty
• 401K with 4% employer contribution (and no vesting period)
• Up to 4 weeks of paid paternity and maternity leave
• Company provided laptop
• $5,000 per year for professional development
• $600 per year for technical supplies and equipment
• $2,000 referral bonus
• Life and disability insurance
• HSA and FSA
• Legal Shield and ID Shield Voluntary Benefits
• Opportunity to work in a collaborative, motivated team focused on modernizing government services with cutting-edge technology and innovative solutions.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior