Prin Tech Program Manager- Eng

UKG•Leavenworth, WA

About The Position

We are seeking a Sr. Staff Technical Program Manager- Eng to partner directly with the Chief of Staff, CTO, and senior engineering leadership on high-visibility, cross-company initiatives. This role is central to running the operational and strategic heartbeat of the technology organization—driving alignment, enabling execution at scale, and ensuring that the CTO’s priorities translate into measurable outcomes. You will lead multi-team, multi-discipline programs; build and refine organizational mechanisms; and serve as a trusted advisor to senior leaders. This role requires strong technical acumen, executive presence, and the ability to influence across a large, matrixed engineering environment.

Requirements

10+ years of technical program management, engineering operations, or relevant leadership experience in large-scale, cloud or enterprise software environments.
Proven ability to lead highly complex, multi-team programs with Director+ or VP-level stakeholders.
Strong technical depth across modern cloud, platform, or distributed systems engineering domains.
Exceptional communication skills—capable of synthesizing complexity and influencing at the executive level.
Demonstrated ability to create structure from ambiguity, build scalable mechanisms, and drive measurable outcomes.
Strong judgment, discretion, and leadership maturity; trusted to operate autonomously in a high-stakes environment.

Nice To Haves

Experience supporting senior engineering or CTO-level leadership strongly preferred.

Responsibilities

Drive execution of the CTO’s top strategic priorities, ensuring initiatives are measurable, well-structured, and aligned to long-term technology vision.
Shape and lead annual and quarterly planning processes, including engineering goals, resourcing strategy, and multi-year technology planning.
Partner with Finance, HR, and Engineering leadership on forecasting, staffing, and operational investments that support scale and efficiency.
Lead large-scale, multi-disciplinary technical programs with complex dependencies and senior stakeholders across engineering and product.
Define program architectures, operating mechanisms, and cross-team workflows that improve clarity, velocity, and accountability.
Anticipate risks, resolve high-impact blockers, and guide Director+ leaders through tradeoff decisions.
Own core engineering business rhythms: QBRs, CTO program reviews, portfolio updates, and organizational dashboards.
Build and refine metrics, telemetry, and insights that inform decision-making and surface organizational risks or bottlenecks.
Establish scalable processes that improve execution predictability, communication flow, and operational maturity across engineering teams.
Prepare high-quality briefings, narratives, and program updates for the CTO, Chief of Staff, and senior leadership forums.
Translate complex technical and organizational information into concise strategic insights.
Influence executive stakeholders by presenting clear recommendations, decision points, and data-driven rationale.
Build deep, trusted relationships with senior engineering, product, HR, and operations leaders.
Act as an extension of the Office of the CTO—driving clarity, alignment, and follow-through across multiple leadership groups.
Surface early signals on organizational gaps, execution risks, or strategic misalignments and partner to resolve them.