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Why UKG:

At UKG, the work you do matters. The code you ship, the decisions you make, and the care you show a customer all add up to real impact. Today, tens of millions of workers start and end their days with our workforce operating platform. Helping people get paid, grow in their careers, and shape the future of their industries. That’s what we do.

We never stop learning. We never stop challenging the norm. We push for better, and we celebrate the wins along the way. Here, you’ll get flexibility that’s real, benefits you can count on, and a team that succeeds together. Because at UKG, your work matters—and so do you.

About the Team:

The Office of the CTO sets the technology vision for UKG and ensures that our global engineering organization executes against it with clarity, discipline, and impact. Our team enables strategic alignment, operational rigor, and seamless cross-organizational coordination across complex, highly distributed engineering groups.

About the Role:

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.

Responsibilities

Strategic Leadership & Organizational Alignment

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.

Technical Program Excellence

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.

Operational Excellence & Mechanisms

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.

Executive Communication & Influence

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.

Stakeholder & Relationship Leadership

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.

About You:

Basic Qualifications:

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.

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

Company Overview:

UKG is the Workforce Operating Platform that puts workforce understanding to work. With the world's largest collection of workforce insights, and people-first AI, our ability to reveal unseen ways to build trust, amplify productivity, and empower talent, is unmatched. It's this expertise that equips our customers with the intelligence to solve any challenge in any industry — because great organizations know their workforce is their competitive edge. Learn more at ukg.com.

Equal Opportunity Employer

UKG is an equal opportunity employer. We evaluate qualified applicants without regard to race, color, disability, religion, sex, age, national origin, veteran status, genetic information, and other legally protected categories.

View The EEO Know Your Rights poster (https://www.eeoc.gov/sites/default/files/2022-10/EEOC\_KnowYourRights\_screen\_reader\_10\_20.pdf)

UKG participates in E-Verify. View the E-Verify posters here (https://www.e-verify.gov/sites/default/files/everify/posters/EVerifyParticipationPoster.pdf) .

It is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.

Disability Accommodation in the Application and Interview Process

For individuals with disabilities that need additional assistance at any point in the application and interview process, please email [email protected] .

The pay range for this position is $184,300 to $304,693, however, base pay offered may vary depending on skills, experience, job-related knowledge and location. This position is also eligible for a short-term incentive and a long-term incentive as part of total compensation. Information about UKG’s comprehensive benefits can be reviewed on our careers site at https://www.ukg.com/about-us/careers/benefits

It is the policy of Ultimate Software to promote and assure equal employment opportunity for all current and prospective Peeps without regard to race, color, religion, sex, age, disability, marital status, familial status, sexual orientation, pregnancy, genetic information, gender identity, gender expression, national origin, ancestry, citizenship status, veteran status, and any other legally protected status entitled to protection under federal, state, or local anti-discrimination laws. This policy governs all matters related to recruitment, advertising, and initial selection of employment. It shall also apply to all other aspects of employment, including, but not limited to, compensation, promotion, demotion, transfer, lay-offs, terminations, leave of absence, and training opportunities.