Federal Chief Technical Advisor

GuidePoint Security • Herndon, VA

7h • Remote

About The Position

GuidePoint Security is seeking a highly experienced and technically exceptional individual to join their Federal presales engineering team as a Chief Technology Advisor (CTA). This role is the most senior customer-facing technical authority within the company, serving as a trusted CTO-level advisor embedded within strategic federal agency accounts. The CTA will partner with federal agency leadership, including CIOs, CISOs, and CTOs, to understand their mission environments, identify complex technology challenges, and architect solutions using GuidePoint's cybersecurity portfolio. This is a genuine advisory role focused on building sustained relationships based on technical credibility and mission understanding, rather than a vendor-pitch position. The CTA will operate as an individual contributor, collaborating with the SVP & Chief Engineer, Federal to provide customer-derived technical intelligence that informs the company's federal growth strategy, service development, and vendor portfolio priorities.

Requirements

• 12+ years of progressive experience in federal cybersecurity, federal IT strategy, or federal technology advisory roles, with a demonstrated track record of operating at the senior technical advisory level with federal agency leadership.
• Proven experience identifying complex technology challenges within federal customer environments and designing integrated, multi-vendor solutions that resolve them.
• Direct experience in a CTO, Chief Architect, Principal Technologist, or equivalent senior customer-facing technical advisory role within a federal agency, the federal government, or a federal professional services firm.
• Demonstrated track record of contributing to federal business development — growing accounts, identifying new opportunities, and supporting AE-led commercial growth through technical relationship development.
• Deep familiarity with the federal cybersecurity and IT technology vendor landscape across multiple domains including Zero Trust, cloud security, identity and access management, endpoint security, SIEM/SOAR, and GRC.
• Broad cybersecurity architecture competency across at least four major domains.
• Current knowledge of the federal cybersecurity regulatory and compliance landscape including FISMA, NIST SP 800-53, FedRAMP, DoD RMF, OMB cybersecurity memoranda, Zero Trust mandates, and relevant Executive Orders.
• Systems-level technical thinking — ability to understand how technology choices in one domain create constraints, risks, or opportunities in others, and to advise on enterprise-level architecture trade-offs.
• Exceptional executive presence — the ability to engage federal agency CIOs, CISOs, CTOs, and program leadership as a genuine peer advisor, not a vendor representative.
• Strong business development instincts — ability to identify revenue opportunities within customer relationships and partner effectively with Account Executives to convert them into wins.
• Self-directed with the discipline to manage a complex portfolio of senior customer relationships, internal coordination, and presales support activities simultaneously.
• CISSP required as the foundational senior cybersecurity credential.
• Active Secret clearance required at time of hire.
• Willingness to pursue clearance upgrade required given IC account responsibilities.

Nice To Haves

• Broad domain certifications reflecting technical range — CCSP, cloud security certifications (AWS Security, AZ-500), and relevant vendor certifications preferred.
• DoD 8570/8140 IAM Level II or higher baseline certification preferred.
• TS/SCI preferred.

Responsibilities

• Serve as a Trusted CTO-Level Advisor to Federal Customers, acting as a senior trusted technical advisor to federal agency CIOs, CISOs, CTOs, program managers, and mission owners.
• Develop and maintain a deep understanding of each assigned customer’s technology environment, legacy systems, security posture, compliance obligations, mission priorities, and strategic modernization roadmap.
• Provide strategic technology roadmap guidance to federal customers, helping agency leadership prioritize investments and build multi-year security programs.
• Conduct executive technology briefings, architecture workshops, and solution strategy sessions.
• Solve the most technically complex challenges within assigned customer accounts, requiring CTO-level systems thinking.
• Facilitate structured problem-solving sessions with federal technical teams.
• Develop solution concepts for complex challenges, including technology selection, integration architecture, implementation approach, and risk mitigation.
• Coordinate GuidePoint’s Technical Directors across various cybersecurity domains to bring domain depth into customer problem-solving.
• Produce executive-quality advisory outputs such as architecture decision briefs, technology evaluation summaries, and roadmap recommendations.
• Partner closely with Account Executives as the senior technical business development resource, contributing technical insight and credibility.
• Identify new revenue opportunities within existing federal customer accounts.
• Grow federal contracts through technology-driven account expansion.
• Drive product and technology solution sales growth by positioning GuidePoint’s vendor portfolio.
• Engage early in federal agency technology evaluation and acquisition planning to shape requirements and acquisition strategy.
• Build senior-level technical relationships with federal agency decision-makers.
• Provide senior technical presales support for strategically significant federal competitive opportunities.
• Develop technically differentiated solution approaches for major federal proposals.
• Participate in oral presentations and technical demonstrations for high-value federal competitive bids.
• Orchestrate Technical Directors into presales engagements when domain-specific depth is required.
• Provide regular intelligence from customer account engagement to the SVP & Chief Engineer, Federal on federal agency technology priorities, buying patterns, and emerging requirements.
• Flag vendor portfolio gaps identified in federal accounts and recommend new vendor evaluation actions.
• Mentor senior engineers and Solution Architects on customer advisory skills, executive engagement techniques, and systems-level thinking.

Benefits

• Group Medical Insurance options: Zero Deductible PPO Plan (GuidePoint pays 90% of the premium for employees and 70% for family plans (spouse/children/family) or High Deductible Health Plan with HSA (GuidePoint pays 100% of the employees premiums and 75% for family plans (spouse/children/family). If you choose the High Deductible / HSA plan, GPS will contribute in 4 equal quarterly installments: ($850 per EE annually / $1750 per family annually (includes spouse/children/family options)
• Group Dental Insurance: GuidePoint pays 100% of the premium for employees and 75% of family plans
• 12 corporate holidays and a Flexible Time Off (FTO) program
• Healthy mobile phone and home internet allowance
• Eligibility for retirement plan after 2 months at open enrollment
• Pet Benefit Option

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed