SkyePoint Decisions is a leading Cybersecurity Architecture and Engineering, Critical Infrastructure and Operations, and Applications Development and Maintenance IT service provider headquartered in Dulles, Virginia with operations across the U.S. We provide innovative enterprise-wide solutions as well as targeted services addressing the complex challenges faced by our federal government clients. Our focus is on enabling our clients to deliver their mission most efficiently and effectively – anytime, anywhere, securely. We combine technical expertise, mission awareness, and an empowered workforce to produce meaningful results.

This is a contingent position based upon customer approval.

SkyePoint Decisions is seeking a Lead ISSO Manager to join our team supporting the Department of Education’s (DoED) Federal Student Aid (FSA) Cybersecurity and Privacy Support Services (CPSS) in Washington, DC.

This is a remote position.

Responsibilities:

Serve as the principal advisor to senior SSD leadership on all cybersecurity and compliance matters for an assigned portfolio of major applications, general support systems, and/or cloud environments (FISMA-based, FedRAMP, Guaranty Agency, and Partner systems, etc.).
Lead, mentor, and supervise the contractor team of ISSOs and junior security analysts
Oversee the full Risk Management Framework (RMF) lifecycle (NIST SP 800-37) for all assigned systems, including categorization, control selection, implementation, assessment, authorization, and continuous monitoring.
Develop, maintain, and enforce the organization’s System Security Plans (SSP), Security Assessment Reports (SAR), Plans of Action & Milestones (POA&M), Contingency Plans, Incident Response Plans, and Configuration Management Plans.
Coordinate and manage independent Security Controls Assessments (SCA) performed by third-party assessors (3PAO) and internal red/white teams; review and approve final assessment reports and evidence artifacts.
Track, validate, and drive remediation of all POA&Ms to closure within FSA and DOED established timelines; escalate overdue high/critical findings to executive leadership.
Ensure 100% compliance with federal mandates including FISMA, Executive Order 14028, OMB M-22-09 (Zero Trust), CISA Binding Operational Directives (BODs), and NIST SP 800-53 Rev 5 baseline, inherited, and common controls where applicable.
Review and approve all change requests, configuration changes, and new technology introductions from a security and compliance perspective.
Act as the primary liaison with the FSA and ED Security Operations Center (FSA SOC and ED-SOC), CISA, auditors, GAO, and other oversight bodies during audits, penetration tests, and incident investigations.
Prepare and deliver executive-level briefings, dashboards, and attestation letters (e.g., annual FISMA report, EO 14028 attestation, FedRAMP Significant Change Requests).
Manage the organization’s continuous diagnostics and mitigation (CDM) program integration, vulnerability management program, and endpoint detection & extended detection and response (EDR/XDR) operations.
Develop and maintain security policies, standards, procedures, and guidelines; ensure flow-down to subcontractors and cloud service providers.
Oversee secure software supply chain practices (SBOMs, NIST SSDF, EO 14028 §4 requirements) for all custom and COTS software in the portfolio.

Required Qualifications:

Bachelor’s degree in Cybersecurity, Information Technology, Computer Science, or related field (Master’s preferred).
Minimum 10 years of progressive cybersecurity experience, with at least 5 years serving in an ISSO or senior security control assessor role on federal systems.
Minimum 3 years of direct supervisory or team-lead experience.
Active certification(s) (one or more required):
- CISSP (must be current)
- CISSP-ISSMP or CISM (highly desired)
- CAP or CGRC (Certified in Governance, Risk and Compliance)
- CCSP or CCSK (for cloud-heavy environments)
Demonstrated expert-level knowledge of:
- NIST SP 800-53 Rev 5 (High baseline), 800-37 RMF, 800-137 Continuous Monitoring
- FedRAMP and/or DoD RMF processes
- Executive Order 14028 and CISA directives
- Zero Trust Architecture (NIST 800-207, OMB M-22-09)
Experience obtaining and maintaining ATOs at appropriate FISMA or FedRAMP impact levels.
U.S. citizenship and ability to obtain/maintain a NACI public trust.
Excellent written and verbal communication skills with proven ability to brief C-level executives and non-technical stakeholders.

Preferred Qualifications:

Experience with automated compliance tools (e.g., Tenable, Splunk, ServiceNow GRC, Xacta 360, CSA CCM).
Prior federal agency or 3PAO experience.
Project Management Professional (PMP) or equivalent.

Compensation:

Salary Range: $90,000-$120,000

The SkyePoint Decisions salary range for this position is a general guideline only. It represents an estimated range for this position and is just one piece of our total compensation package.

Salary at SkyePoint is determined by various factors, including but not limited to location, work schedule, the candidate’s combination of education, knowledge, skills, competencies, and experience, as well as contract-specific affordability, market data and business considerations.

In addition to a competitive salary, SkyePoint offers benefits including a certification incentive program, PTO, floating federal holiday options, several insurance options including HMO and High Deductible plans with Health Savings Accounts [HSAs], Flex Spending Accounts [FSAs], Full Dental Plans, Vision, ST/LT Disability, Life Insurance, and 401k matched.

What We Can Offer You:

At SkyePoint, we go B.I.G. (beginning in GRATITUDE) by recognizing all we have and giving back to our employees, families, and communities. It instills a positive mindset that permeates all we do. By beginning in gratitude, SkyePoint can continue to spread living in gratitude each day.
Great Benefits: Several insurance options including HMO and High Deductible plans with Health Savings Accounts [HSAs], Flex Spending Accounts [FSAs], Full Dental Plans, ST/LT Disability, Life Insurance, floating federal holiday options, and 401k matched
Certificate Incentive Program: To promote professional development, we recognize and reward employees who obtain new certifications aligned with business needs.
Flexible Work Environment

SkyePoint Decisions is an established ISO 9001:2015 and ISO/IEC 27001:2013 certified small business and appraised at CMMI Level 3 for Services and Development. We possess a common vision of excellence and foster a collaborative team culture built upon individual performance and accountability. We invest in our people and systems to create value for our clients. It is the SkyePoint Way. We are grateful for the opportunity to work with exceptional people and give back to the communities we serve. Our employees value the flexibility at SkyePoint that allows them to balance quality work and their personal lives.

SkyePoint Decisions is a participating E-Verify Employer.

U.S. Citizenship is required for most positions.

Equal Opportunity Employer/Veterans/Disabled.

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