Technology Program Management Director

Leadout Capital; Chicago (IL); Presencial; USD 150.000 - 210.000; Jornada completa

Descripción de la vacante

Leadout Capital seeks a Technology Program Management Director to lead strategic program development, roadmap planning, and execution across our engineering organization. This leader will partner with engineering leaders and cross-functional stakeholders to translate strategic priorities into clear, executable programs and ensure measurable outcomes.

The ideal candidate combines strong technical fluency with exceptional program leadership, strategic planning, and organizational influence.

Formación

• Experience leading complex technology programs in large-scale software/infra environments.
• Proven ability to translate strategic goals into structured programs and actionable plans.
• Exceptional stakeholder management and executive communication skills.
• Ability to influence senior leaders and technical teams without direct authority.

Responsabilidades

• Partner with engineering leadership to develop and maintain multi-quarter strategic roadmaps aligned to priorities.
• Translate strategy into structured programs with milestones, dependencies, and measurable outcomes.
• Identify gaps, overlaps, sequencing, and cross-team dependencies across the portfolio.
• Facilitate prioritization discussions and help leadership trade off competing initiatives.
• Establish clear program charters, objectives, success metrics, and execution plans.

Conocimientos

Strategic roadmapping

Executive stakeholder management

Cross-functional leadership

Ambiguity to structure

Descripción del empleo

The Experience

We are seeking a Technology Program Management Director to lead strategic program development, roadmap planning, and execution across our engineering organization. This leader will partner closely with engineering leaders and cross-functional stakeholders to translate strategic priorities into clear, executable programs and ensure our most important initiatives deliver measurable outcomes.

The ideal candidate combines strong technical fluency with exceptional program leadership, strategic planning, and organizational influence. They are comfortable operating in ambiguity, bringing structure to complex initiatives, and driving alignment across multiple teams and stakeholders without relying on direct authority.

This is not a traditional project management role. The Technology Program Management Director will help shape what we prioritize, how initiatives come together into a cohesive roadmap, and how we execute against that roadmap at scale.

What You’ll Actually Be Doing

Program & Roadmap Development

• Partner with engineering leadership to develop and maintain multi-quarter strategic roadmaps aligned to organizational priorities.

• Translate strategy and broad objectives into structured programs, milestones, dependencies, and measurable outcomes.

• Identify gaps, overlaps, sequencing considerations, and cross-team dependencies across the portfolio.

• Facilitate prioritization discussions and help leadership make informed tradeoffs across competing initiatives.

• Establish clear program charters, objectives, success measures, and execution plans for strategic initiatives.

Strategic Program Leadership

• Lead complex, cross-functional technology programs from definition through execution and adoption.

• Drive alignment across Engineering, Product, Architecture, Operations, Security, Infrastructure, and other partner organizations.

• Establish program governance and operating mechanisms that provide transparency while minimizing unnecessary process and overhead.

• Proactively identify risks, blockers, and dependencies and work with leaders to drive resolution.

• Ensure programs remain focused on business and engineering outcomes rather than activity or milestone completion alone.

Portfolio & Operating Management

• Develop an integrated view of the organization's strategic portfolio, including priorities, timelines, dependencies, risks, and resource considerations.

• Establish consistent operating cadences for roadmap reviews, program reviews, and leadership decision-making.

• Track progress against strategic commitments and surface areas requiring leadership attention or intervention.

• Help evolve planning and execution practices as the organization scales.

• Drive accountability for decisions, commitments, and follow-through across participating teams.

Executive Communication & Stakeholder Management

• Serve as a trusted partner to senior engineering leadership.

• Create clear, concise executive-level communications that translate complex technical programs into outcomes, risks, decisions, and recommendations.

• Facilitate leadership discussions and drive decisions when priorities, ownership, or direction are unclear.

• Build strong relationships across organizational boundaries and influence stakeholders at multiple levels of the company.

• Ensure teams have clarity on priorities, decisions, ownership, and next steps.

Continuous Improvement

• Identify opportunities to simplify planning, governance, and execution processes.

• Develop repeatable frameworks and mechanisms that improve organizational effectiveness without creating unnecessary bureaucracy.

• Use program data and metrics to identify trends, execution risks, and opportunities for improvement.

• Champion an outcome-oriented, automation-first approach to program management.

You’re Our Person If…

• Significant experience leading complex technical programs within large-scale software engineering, infrastructure, platform, reliability, or technology organizations.

• Demonstrated experience developing and managing strategic technology roadmaps across multiple teams or functions.

• Strong understanding of modern software engineering and technology delivery practices.

• Proven ability to translate ambiguous strategic goals into structured programs and actionable plans.

• Experience managing large, cross-functional initiatives with significant dependencies and organizational complexity.

• Exceptional stakeholder management and executive communication skills.

• Ability to influence senior leaders and technical teams without direct authority.

• Strong analytical, problem-solving, and decision-making skills.

• Demonstrated ability to identify risks early, drive decisions, and maintain momentum across complex programs.

• Experience establishing effective planning, governance, and operating mechanisms for engineering organizations.

Even Better If…

• Experience working with Site Reliability Engineering, observability, cloud infrastructure, developer platforms, operational excellence, or enterprise-scale engineering organizations.

• Experience supporting engineering transformation or modernization initiatives.

• Familiarity with Agile development, product operating models, DevOps, and modern software delivery practices.

• Experience using data and metrics to evaluate program health, organizational performance, and business outcomes.

• Experience operating in a highly matrixed global organization.