Lead ISSO Manager

SkyePoint Decisions

1d•Remote

About The Position

SkyePoint Decisions is seeking a Lead ISSO Manager to join their 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, contingent position based upon customer approval. 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. They provide innovative enterprise-wide solutions as well as targeted services addressing the complex challenges faced by their federal government clients. Their focus is on enabling their clients to deliver their mission most efficiently and effectively – anytime, anywhere, securely. They combine technical expertise, mission awareness, and an empowered workforce to produce meaningful results.

Requirements

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.

Nice To Haves

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.

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.

Benefits

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
401k matched