Federal Chief Technical Advisor

GuidePoint Security provides trusted cybersecurity expertise, solutions and services that help organizations make better decisions and minimize risk. By taking a three-tiered, holistic approach for evaluating security posture and ecosystems, GuidePoint enables some of the nation’s top organizations, such as Fortune 500 companies and U.S. government agencies, to identify threats, optimize resources and integrate best-fit solutions that mitigate risk.

About GuidePoint Security

GuidePoint Security is a leading cybersecurity solutions and services firm enabling federal government organizations to make smarter security decisions that minimize risk. With more than 800 vetted technology vendor partnerships and deep practitioner expertise across every major cybersecurity domain, GuidePoint serves more than half of the U.S. Government’s cabinet-level agencies across Civilian, DoD, and Intelligence Community segments, as well as Federal System Integrators and major defense prime contractors. We are growing our Federal presales engineering team and looking for technically exceptional engineers who thrive at the intersection of federal mission and cybersecurity technology.

About The Role

The Chief Technology Advisor (CTA), Federal is GuidePoint Security’s most senior customer-facing technical authority — the federal equivalent of a trusted CTO-level advisor embedded within our most strategic federal agency accounts. Where a company’s CTO looks inward to understand the organization’s technology landscape, challenges, and strategic direction, this role does that work externally, becoming a deeply embedded technical partner to federal agency leadership.

The CTA works across all federal segments — Civilian agencies, DoD components, Intelligence Community programs, and Federal System Integrators — partnering directly with GuidePoint’s Account Executives to understand each customer’s mission environment, identify complex technology challenges, and architect solutions that resolve those challenges using GuidePoint’s cybersecurity portfolio. This is not a vendor-pitch role. It is a genuine, sustained advisory relationship built on technical credibility, mission understanding, and the ability to think through hard problems alongside federal agency leadership.

This role is an individual contributor with no direct reports. It operates as a peer to the SVP & Chief Engineer, Federal — contributing customer-derived technical intelligence that informs GuidePoint’s federal growth strategy, service development, and vendor portfolio priorities

What You'll be Doing

Serve as a Trusted CTO-Level Advisor to Federal Customers

• Function as a senior trusted technical advisor to federal agency CIOs, CISOs, CTOs, program managers, and mission owners — the customer’s de facto CTO partner for cybersecurity technology strategy, architecture decisions, and complex problem-solving.
• Develop and maintain a deep, living understanding of each assigned customer’s technology environment, legacy systems, current security posture, compliance obligations, mission priorities, and strategic modernization roadmap.
• Provide strategic technology roadmap guidance to federal customers, helping agency leadership prioritize investments, navigate technology decisions, and build multi-year security programs aligned to federal mandates and mission needs.
• Conduct executive technology briefings, architecture workshops, and solution strategy sessions that translate complex technical concepts into mission-relevant executive guidance.

Solve the Hard Problems

• Engage directly in the most technically complex challenges within assigned customer accounts — multi-domain architecture conflicts, legacy modernization with mission continuity constraints, zero trust implementation blocking issues, cloud migration security architecture challenges — where CTO-level systems thinking is required rather than domain-specialist execution.
• Facilitate structured problem-solving sessions with federal technical teams, helping agencies work through technology decisions, vendor selection trade-offs, architecture design conflicts, and implementation approach questions that are stalling program progress.
• Develop solution concepts for complex challenges — technology selection rationale, integration architecture, phased implementation approach, and risk mitigation strategy — producing advisory outputs that federal agency leadership can act on.
• Coordinate GuidePoint’s Technical Directors across relevant cybersecurity domains (Zero Trust, Cloud Security, IAM, SIEM/SOAR, OT/ICS, DFIR, GRC, and others) to bring the right domain depth into customer problem-solving without requiring the agency to independently coordinate across multiple specialists.
• Produce concise, executive-quality advisory outputs including architecture decision briefs, technology evaluation summaries, solution option analyses, and roadmap recommendations.

Drive Federal Account Growth

• Partner closely with Account Executives as the senior technical business development resource across all assigned federal accounts — contributing technical insight and customer relationship credibility that enables AEs to identify, shape, and close larger and more complex opportunities.
• Identify new revenue opportunities within existing federal customer accounts by maintaining deep awareness of the agency’s full technology landscape, upcoming programs, budget cycles, and modernization priorities — surfacing opportunities that the commercial relationship alone may not reveal.
• Grow federal contracts through technology-driven account expansion — identifying where GuidePoint’s capabilities address adjacent requirements within active programs, recommending contract modifications or new task orders that extend GuidePoint’s scope and value.
• Drive product and technology solution sales growth by positioning GuidePoint’s vendor portfolio against specific customer requirements with technically credible recommendations that accelerate purchasing decisions.
• Engage early in federal agency technology evaluation and acquisition planning to shape requirements and acquisition strategy in ways that reflect GuidePoint’s capabilities, strengthening competitive positioning before formal solicitation.
• Build senior-level technical relationships with federal agency decision-makers that create long-term account loyalty and position GuidePoint as the customer’s cybersecurity technology partner of choice.

Support Competitive Federal Pursuits

• Provide senior technical presales support for the most strategically significant federal competitive opportunities — contributing customer-specific technical intelligence to proposal design that generic presales engineers cannot replicate.
• Develop technically differentiated solution approaches for major federal proposals by leveraging deep account knowledge to design architectures that precisely fit the customer’s environment and evaluation priorities.
• Participate in oral presentations and technical demonstrations for high-value federal competitive bids as GuidePoint’s most credible customer-relationship technical voice.
• Orchestrate Technical Directors into presales engagements when domain-specific depth is required, maintaining the coherent customer relationship throughout.

Contribute Market Intelligence Internally

• Provide the SVP & Chief Engineer, Federal with regular intelligence from customer account engagement on federal agency technology priorities, buying patterns, emerging requirements, and competitive dynamics that should inform GuidePoint’s federal growth strategy.
• Flag vendor portfolio gaps identified in federal accounts, recommending new vendor evaluation actions to strengthen GuidePoint’s solution capabilities.
• Mentor senior engineers and Solution Architects on customer advisory skills, executive engagement techniques, and the systems-level thinking required to operate as a trusted CTO-level advisor.

Required Qualifications

Experience

• 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 — not just executing against pre-defined requirements.
• 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.

Technical Depth

• Broad cybersecurity architecture competency across at least four major domains — sufficient to provide credible advisory guidance across the full scope of federal agency technology challenges without requiring specialist support for routine conversations.
• 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.

Interpersonal & Business Skills

• 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.

Certifications & Security Clearance

• CISSP required as the foundational senior cybersecurity credential.
• 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.
• Active Secret clearance required at time of hire.
• TS/SCI preferred; willingness to pursue clearance upgrade required given IC account responsibilities.

“Applicants selected will be subject to a security investigation and must meet eligibility requirements for access to classified information.”

We use Greenhouse Software as our applicant tracking system and Zoom Scheduler for HR screen request scheduling. At times, your email may block our communication with you. Please be sure to check your SPAM folder so that you don't miss updates on your application.

Why GuidePoint?

GuidePoint Security is a rapidly growing, profitable, privately-held value added reseller that focuses exclusively on Information Security. Since its inception in 2011, GuidePoint has grown to over 1,200 employees, established strategic partnerships with leading security vendors, and serves as a trusted advisor to more than 6,200 customers.

Firmly-defined core values drive all aspects of the business, which have been paramount to the company’s success and establishment of an enjoyable workplace atmosphere. At GuidePoint, your colleagues are knowledgeable, skilled, and experienced and will seek to collaborate and provide mentorship and guidance at every opportunity.  

This is a unique and rare opportunity to grow your career along with one of the fastest growing companies in the nation.

Some added perks….

• Remote workforce primarily (U.S. based only, some travel may be required for certain positions, working on-site may be required for Federal positions)
• 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