Chief of Staff

Role Description

As the Chief of Staff, Product and Technology, you will serve as a strategic advisor and trusted partner to the CPTO and senior leadership, playing a pivotal role in driving operational excellence, aligning priorities, and enabling the leadership team to execute on business objectives. You are highly organized, have a growth-mindset, and are adept at navigating fast-paced, dynamic environments. You will lead high-impact projects, provide technical and strategic guidance, and ensure cross-functional coordination to support Deltek’s mission of delivering innovative, reliable, and competitive software solutions. This is a high-impact position at the center of the Product & Technology team.

Key Responsibilities

• Act as an extension of the CPTO, collaborating with leadership to address cross-functional and enterprise-wide challenges.
• Serve as the connective layer across Product & Technology leadership, driving alignment, accountability, and momentum to ensure strategic priorities are executed with focus and follow-through.
• Oversee and manage high-priority initiatives, ensuring timely delivery and alignment with company goals.
• Provide technical expertise and insights to support decision-making and problem-solving.
• Drive communication strategy by developing and delivering presentations, translating technology vision, strategic priorities, and complex technical concepts into clear, compelling messages to executive stakeholders and cross-functional teams.
• Establish and maintain operating cadence, including leadership meetings, goals, and metrics.
• Capture and synthesize key points from strategic meetings, distilling complex discussions into clear takeaways, documented decisions, and actionable follow-ups.
• Anticipate problems, provide diplomacy, and drive balanced perspectives to ensure success.
• Step into ambiguous, high-urgency problems and own them end-to-end.

Qualifications

• 10+ years of experience in fast-paced environment (start-up, software, consulting, etc.)
• Bachelor’s degree in technical or quantitative field.
• Demonstrated ability to engage deeply with technical teams and independently evaluate technical tradeoffs.
• Excels at operating in fast-paced, ambiguous environments with shifting priorities and rapid iteration.
• Deep understanding of enterprise technology trends, software development lifecycles, and emerging technologies, particularly AI and cloud infrastructure.
• High ownership mindset, comfortable making decisions under uncertainty.
• Ability to work independently while integrating tightly with leadership and technical teams.
• Demonstrated ability to operate strategically and execute tactically.
• Strong written and verbal communication skills, with the ability to translate strategic conversations into actionable outcomes across teams and stakeholders.
• Demonstrated success in facilitating cross-functional collaboration and driving measurable business results in matrixed organizations.
• Excellent project and program management skills, with a track record of managing complex initiatives using modern collaboration tools.
• Highly organized and detail-oriented, with strong problem-solving skills, and the ability to synthesize insights across multiple workstreams.
• Able to work independently and collaboratively, balancing long-term strategy with day-to-day execution.

Preferred Qualifications

• Experience in a Chief of Staff or similar strategic advisory role within a technology-driven organization.
• Advanced degree in a technical or business-related field.
• Experience with enterprise software, digital transformation, and AI-driven initiatives.
• Proven track record of driving operational excellence and organizational change.
• Strong stakeholder management and executive communication skills.

Compliance Requirements

Certain roles may have additional privacy, security and compliance requirements to the extent they support Costpoint GCCM or similar product offerings.