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.
The GuidePoint Security Information Technology Project Management Office (IT PMO) directly contributes to our internal customers’ success by ensuring IT initiatives are executed seamlessly. This position bridges the gap between enterprise strategy and technical execution across multiple modern disciplines, including Strategic IT Planning, IT Roadmaps, IT PMO, Business Analysis, IT Product Development and Experience Design, and IT Quality Assurance (QA). The Director of the IT PMO oversees the IT project management process including governance, team leadership, monitoring, prioritization, communication, and quality controls. The Director will cultivate an environment of continuous improvement, introducing robust quantitative and qualitative project performance measurements to ensure that IT initiatives deliver maximum business impact and peak customer satisfaction. This role requires a proven track record of successful project delivery, an ability to improve project management practices, and substantial team leadership experience. The Director will bridge the gap between business strategy and technology execution, spanning IT roadmaps, product development, business analysis, and quality assurance. Success in this role consists of: 1) Successful execution of IT Roadmaps and strategic planning that directly supports the overarching goals of the organization; 2) High satisfaction scores from business sponsors and end-users on project delivery quality, system usability, and change management support; and 3) Predictable project delivery schedules and low rework through the standardization of PMO, Business Analysis, and QA frameworks.
Roles and Responsibilities:
Strategic IT Planning & Roadmap Management
- Enterprise Alignment: Partner with executive leaders to translate corporate objectives into a comprehensive, multi-year IT strategic plan.
- Portfolio Roadmapping: Define, maintain, and publish the organization's IT Roadmap, ensuring cross-functional initiatives are prioritized based on resource capacity, financial return, and technical dependency.
- Demand Management: Establish a unified process to intake, evaluate, score, and approve new technology and product proposals. Work with project sponsors to define project priorities, opportunities, challenges and communicate project risks and opportunities.
IT PMO Governance & Continuous Improvement
- Process Excellence: Oversee the day-to-day operations of the IT PMO, enforcing uniform methodologies (Agile, Scrum, Waterfall, Hybrid) across the portfolio. Ensure pre-defined project management processes and practices are followed, driving simplification and improvement as necessary.
- Continuous Improvement Framework: Lead IT continuous improvement by institutionalizing post-project retrospective reviews into IT processes; responsible for monitoring and maximizing key cost, schedule, and performance metrics.
- Tools and Standards: Modernize and manage enterprise PMO software applications (i.e., Jira, Confluence) to enable clear portfolio visibility. Develop, implement, and govern project management processes, dashboards, templates, policies, and metrics; provide executive leaders with the information needed to assess and contribute to the resolution of high risk/ escalated projects.
Business Analysis, Product Development & Experience Design
- Business Analysis: Direct the Business Analysis function to guarantee user requirements are precisely defined, verified, and trace directly back to business value.
- Product Mindset Lifecycle: Manage IT project deliverables with an IT Product Development framework, overseeing digital products from discovery through deployment and feature refinement.
- Experience Design: Collaborate with design stakeholders to incorporate modern User Experience (UX) and Experience Design principles, validating that delivered software addresses real customer needs.
IT Quality Assurance (QA) & Delivery
- Release Excellence: Direct the IT Quality Assurance framework to implement automated and manual software validation, minimizing bug leakage into production environments.
- Risk & Change Management: Govern the organizational change management lifecycle to protect delivery timelines, business continuity, and system stability.
Portfolio Metrics, Analytics & Customer Satisfaction
- Quantitative Measurement: Define and track metric-driven operational KPIs, including Schedule Variance, Resource Utilization, Defect Leakage, and Budget Variance. Identify opportunities within in-flight projects to deliver additional value.
- Qualitative Measurement: Implement qualitative evaluation tools, such as project health scorecards and organizational change readiness surveys.
- Customer Satisfaction: Establish frameworks for the quantitative and qualitative measurement of IT projects to evaluate delivery efficiency, ROI, and technical health. Systematically capture internal and external stakeholder feedback through post-implementation surveys to optimize the Customer Satisfaction Score (CSAT) and/or Net Promoter Score (NPS) for delivered IT solutions.
Team Leadership:
- Coach and mentor direct reports and share knowledge of best practices.
- Grow the IT PMO organization structure, hire and manage project staffing requirements in line with service portfolio workload.
- Provide project deliverable QA and retrospective reviews with IT teams to identify potential improvement opportunities.
- Set annual performance targets for direct reports and conduct semi-annual performance reviews.
- Adhere to GuidePoint Security Core Values.
- Other duties as assigned.
Required Experience:
- Bachelor’s Degree in Information Technology, Computer Science, Business Administration, or Finance (Master's degree preferred).
- Minimum of 10 years of IT project/portfolio management experience (p. 3), with at least 5 years in an enterprise PMO leadership role.
- PMP (Project Management Professional), PMI-ACP, or Agile/Scrum Master certifications are highly preferred.
- Demonstrated experience overseeing digital software development, user interface design lifecycles, and modern software testing methodologies (QA).
- Exceptional interpersonal and communication skills required to maintain alignment with executive stakeholders and external vendor partners
- Strong analytical and problem-solving skills, particularly on challenging, complex, and difficult issues to develop solutions that address root causes.
- Ability to develop and deliver training to new Project Managers or candidates just entering the cybersecurity space.
- Ability to influence without authority.
- Flexible, adaptable, and resourceful when managing changing timelines and multiple deliverables.
- Demonstrated leadership ability to establish and manage a high-performance team.
- Motivated to build relationships at executive levels with customers, and vendor groups.
Travel Requirements:
- Willingness to travel up to 10%.
Physical Requirements:
- Sedentary work
- Substantial movement of the wrists, hands, and/or fingers for a minimum of 8 hours a day
- Required to have close visual acuity to view computer terminal and/or extensive reading for a minimum of 8 hours a day
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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
Skills Required
- Bachelor's Degree in Information Technology, Computer Science, Business Administration, or Finance (Master's preferred)
- Minimum of 10 years of IT project/portfolio management experience
- 5 years in an enterprise PMO leadership role
- PMP, PMI-ACP, or Agile/Scrum Master certifications
- Experience overseeing digital software development and QA methodologies
- Exceptional interpersonal and communication skills
- Strong analytical and problem-solving skills
- Leadership ability to establish and manage a high-performance team
GuidePoint Security Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about GuidePoint Security and has not been reviewed or approved by GuidePoint Security.
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Healthcare Strength — Company materials highlight fully covered employee premiums on a base medical plan, options including PPO and HSA, employer HSA contributions, and access to an EAP. These elements materially enhance the overall value of compensation for individuals.
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Flexible Benefits — A remote‑first model with telework/flex‑time and monthly phone/home‑internet stipends is emphasized. This flexibility and stipending increase the attractiveness of the total rewards across many roles.
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Leave & Time Off Breadth — Flexible Time Off, company holidays, and parental and other protected leaves are outlined in ESG materials and job postings. Such breadth supports work‑life balance and complements cash compensation.
GuidePoint Security Insights
What We Do
GuidePoint Security is an elite team of highly trained, top certified experts who cut through cyber chaos and confusion to put control back in your hands. We help you make the smartest, most informed decisions, choose and integrate products and services that are the best fit, and build the most effective cybersecurity posture. We provide organizations with holistic perspective on their cyber ecosystem to minimize gaps, vulnerabilities, and optimize resources, including: 1. Understanding the changing threat landscape, vulnerabilities, and gaps 2. New insights of how product decisions align with resource capacity 3. Insightful product comparisons and integration to save time, money, and mistakes
