Director, Technical Program Management – Planning

Jobtailor; California (MO); On-site; USD 180,000 - 240,000; Full time

Job summary

Jobtailor seeks a seasoned Technical Program Management leader to guide the CTO-aligned TPM function, defining intake, triage, and cross-functional handoffs. You will shape annual and quarterly planning cadences with Product and Engineering, manage headcount, and drive an AI-native operating model across the TPM organization.

You will partner with Analytics and other stakeholders to turn planning into a data- and AI-informed feedback loop, improving predictability and allocation across the

Qualifications

• 12+ years of relevant experience, with 4+ years leading TPM teams and cross‑group leadership.
• Proven track record running enterprise-scale annual and quarterly planning cycles.
• Strategic partner to Engineering and Product leadership, shaping portfolio investments.
• Experience scaling TPM craft, with mentoring and development pathways.
• Fluency with AI-driven systems and governance for responsible use.

Responsibilities

• Lead and develop the CTO-aligned TPM team to deliver AI-native outcomes.
• Own the TPM program slate, refining intake, triage, and handoff criteria.
• Architect planning cadences for annual/quarterly cycles with Product and Engineering.
• Allocate headcount and maintain visibility from strategy to delivery.
• Advance TPM standards and tooling, integrating AI/ML into workflows.
• Collaborate with Analytics to create data/AI-informed planning feedback loops.

Skills

TPM leadership

Strategic planning

AI/ML concepts

Cross-functional collaboration

Data-driven decision making

Education

Bachelor's degree

Master's degree

Tools

Program Management Tools

Data Analytics Tools

AI-enabled solutions

Job description

Responsibilities

• Lead and develop the CTO-aligned Technical Program Management team, setting the standard for AI-native TPM craft and ensuring delivery against scorecard, say-do ratio, and AI adoption outcomes.
• Own and curate the CTO TPM program slate, defining and refining intake, triage, and handoff criteria so the team focuses on the most complex, cross-cutting, and high-impact initiatives across Tech.
• Architect and run the planning and operating cadence for annual and quarterly cycles, translating top-level strategic priorities into clear, capacity-checked, initiative-level plans in close partnership with Product and Engineering.
• Manage engineering commitments and headcount allocation across subdivisions, building and maintaining the visibility layer that connects strategic goals to execution, including progress, scope, and delivery mix.
• Drive the TPM community of practice and cross-organizational standards, tooling, and development, advancing an AI-native operating model and safely integrating AI/ML-enabled solutions into TPM workflows to improve planning and delivery outcomes.
• Partner with Analytics and other stakeholders to turn planning into a continuous feedback loop, using data and AI-assisted insights to inform mid-quarter rebalancing, optimize resource allocation, and improve predictability across the portfolio.

Requirements

• 12+ years of relevant professional experience for Bachelor's or 10+ years for Master's, including at least 4 years leading TPM teams or a TPM function with Director-level people leadership scope across multiple engineering groups or equivalent experience.
• Proven experience running enterprise-scale annual and quarterly planning cycles, including capacity planning, commitment tracking, and headcount allocation across several engineering organizations or subdivisions.
• Demonstrated ability to operate as a strategic peer to Engineering and Product leadership, influencing where TPM and engineering investment is focused and shaping the portfolio rather than only executing assigned backlogs.
• Experience establishing or scaling a TPM craft/community capability, including defining leveling frameworks, competency standards, and mentorship or development pathways for TPMs.
• Fluency with modern AI-driven systems, tools, or workflows used in program management, including practical experience applying AI/ML concepts to real-world planning, risk prediction, or status synthesis, and defining governance for responsible use.

Core Competencies

Demonstrates expertise in leading Technical Program Management teams, with a strong focus on AI-native practices, strategic planning, and cross-organizational collaboration. Proven ability to influence engineering and product leadership while optimizing resource allocation and improving delivery outcomes through data-driven insights.

Tools & Technologies

• AI-Enabled Solutions
• Program Management Tools
• Data Analytics Tools