Chief of Staff to the CTO

Company Overview

Strong Private Equity Ownership

In December 2021 Genstar Capital invested in PA along with a large rollover from Bregal Sagemount and the management team.

Genstar Capital is a leading private equity firm that has been actively investing in high quality companies for over 30 years. Based in San Francisco Genstar has developed a strong market reputation of working in partnership with management teams and its network of strategic advisors to build industry-leading businesses while generating outsized returns. Genstars vision is to help build lasting impactful companies that will continue to succeed well beyond their ownership.

Genstar currently has approximately $33 billion of assets under management and targets investments focused on targeted segments of the software industrials healthcare and financial services 2020 Genstar was ranked 2nd worldwide in aggregate private equity fund performance (out of 529 PE firms) and ranked 3rd in 2019 (out of 497 PE firms) by HEC-Dow Jones. For more information please visit .

The Opportunity

The Chief of Staff to the CTO serves as a strategic partner and operational leader for the Technology organization. This role is responsible for ensuring strategic priorities are effectively planned funded governed and executed across all technology functions. Acting as an extension of the CTO the Chief of Staff drives organizational alignment execution discipline financial performance and cross-functional collaboration while enabling the CTO to focus on technology vision innovation and external leadership.

Key Responsibilities

Strategic Leadership

• Partner closely with the CTO to develop and execute the technology and AI strategy.
• Drive alignment across engineering data AI product and business teams.
• Translate strategic priorities into executable plans with clear milestones and accountability.
• Support long-term technology planning organizational design and investment decisions.
• Ensure technology initiatives align with broader corporate objectives and value creation goals.

Executive Effectiveness & Organizational Leadership

• Act as an extension of the CTO ensuring strategic priorities are translated into action across the organization.
• Manage executive communications leadership team operating rhythms and strategic planning processes.
• Prepare and facilitate leadership meetings ensuring decisions are documented communicated and executed.
• Coordinate organizational priorities and resolve conflicts across teams to maintain focus on key objectives.
• Drive transparency accountability and alignment throughout the technology organization.
• Technology AI & Agentic Transformation
• Coordinate the enterprise technology and AI portfolio across the architecture organization ensuring initiatives are sequenced resourced and governed against measurable business outcomes.
• Support the companys transformation toward agentic-driven workflows partnering with technology and business leaders to identify prioritize and scale opportunities to embed AI automation and advanced analytics into how the business runs.
• Partner with the architecture organization on roadmap evaluation gates and rollout planning the architects own the technical strategy in their domains; you own the operating cadence and cross-team alignment around it.
• Translate technical progress into business-facing milestones and help business leaders surface use cases worth investing in.
• Stay current on emerging AI data and product technologies competitive developments and industry trends and maintain enough fluency in the stack to pressure-test plans and represent the work to the executive team.

Financial Planning & Resource Management

• Own the annual technology budgeting process including operating expenses capital expenditures and strategic investment planning.
• Lead forecasting variance analysis and resource planning across engineering data AI infrastructure and security functions.
• Partner with Finance to develop business cases ROI analyses and investment recommendations for technology initiatives.
• Monitor technology spend and ensure alignment between strategic priorities staffing plans and financial commitments.
• Provide the CTO with regular reporting and insights on budget performance resource utilization and investment effectiveness.
• Drive resource allocation decisions to ensure investment is focused on the highest-value initiatives.
• Establish and run the operating cadence for the technology organization quarterly planning monthly business reviews roadmap governance and executive reporting with clear inputs owners and decisions at each step.
• Own governance of the technology portfolio: prioritization resourcing dependencies milestones and the decision log that ties them together.
• Hold technology leaders and cross-functional partners accountable for commitments surfacing slippage and resource constraints early enough to act on them.
• Serve as the central coordination point for cross-functional initiatives and prepare the executive-level communications dashboards and business reviews that come out of them.
• Drive continuous improvement of how the technology organization plans executes and reports.

Stakeholder Engagement

• Serve as a key liaison between the CTO executive leadership team and business stakeholders.
• Facilitate decision-making by providing analysis recommendations and strategic insights.
• Build strong relationships across departments to drive collaboration and alignment.
• Partner with functional leaders to remove barriers resolve conflicts and accelerate execution.

Team Leadership

• Lead coach and develop direct reports.
• Foster a culture of innovation accountability and continuous learning.
• Support talent development workforce planning and succession planning within the technology organization.
• Reinforce high-performance expectations and organizational accountability.

Success Measures

• The technology operating cadence quarterly planning monthly business reviews roadmap governance executive reporting is running on a published calendar with documented inputs owners and decisions.
• The annual technology budget is closed on schedule with variance against plan tracked monthly and explained.
• The AI initiative portfolio has named business owners defined success gates and a quarterly review against those gates with at least one initiative reporting measurable business impact.
• Roadmap commitments are landing within their committed quarter at a rate that improves measurably over the first year with slippage surfaced early enough to act on rather than reported after the fact.
• Executive reporting and board materials for the technology organization are produced on a regular cadence and require no rework from the CTO before they ship.

Required

• 8 years of experience in technology strategy operations consulting program management or a related field.
• Experience partnering with senior executives and leading enterprise-wide cross-functional initiatives.
• Demonstrated success managing complex programs involving multiple stakeholders and competing priorities.
• Strong business financial and technology acumen.
• Experience developing budgets forecasts business cases and investment analyses.
• Proven ability to influence senior leaders and drive accountability without direct authority.
• Excellent communication executive presentation and stakeholder management skills.
• Strong analytical problem-solving and project management capabilities.
• Ability to operate effectively in fast-paced high-growth environments.

Preferred

• Experience in digital transformation data analytics AI or technology modernization initiatives.
• Demonstrated fluency with AI tools (Claude ChatGPT or equivalent) as a daily working environment for analysis drafting and executive communications.
• Experience in a private equity-backed or high-growth company environment.
• Prior people leadership experience.
• Experience establishing governance frameworks operating cadences and performance management processes.
• MBA or equivalent business leadership experience.
• Understanding of AI data platforms and modern technology architectures.