Chief of Staff, GTM

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 Role:

The Chief of Staff, GTM Leadership Program Management & Operations Leader is a senior operating partner to GTM leadership, responsible for translating go-to-market strategy into clear priorities, disciplined execution, and effective operating rhythms across UKG’s go-to-market organization. This leader serves as the connective tissue across Sales, GTM Operations, Marketing, Customer Success, Enablement, Product, Finance, HR, and other cross-functional partners to ensure the GTM leadership agenda is understood, operationalized, measured, and executed with pace, supported by clear and timely communications.

This role combines business operations, transformation program management, operating cadence design, stakeholder alignment, executive readiness, and team leadership, with communications as an enabling capability. The ideal candidate is a strategic operator who can simplify complex information, create executive-ready materials, drive accountability across matrixed teams, and manage high-priority field initiatives from concept through adoption.

The CoS supports strategic priorities including field execution, operating cadence, program governance, launch readiness, commercial effectiveness, process simplification, cross-functional alignment, and supporting communications. This leader will manage one professional focused on program coordination, executive content, operating rhythm support, and communication execution.

Responsibilities include:

Executive Partnership & Chief of Staff Leadership

• Serve as a trusted advisor and operating partner to GTM leadership, helping translate strategy into priorities, decisions, actions, and measurable outcomes.

• Prepare GTM leadership for executive meetings, operating reviews, leadership forums, customer-facing discussions, and cross-functional decision points.

• Anticipate business needs, identify risks and gaps, and proactively drive follow-through across leaders and workstreams.

• Create leverage for GTM leadership by managing priorities, synthesizing inputs, tracking commitments, and ensuring consistent execution against the operating agenda.

Communications Support & Executive Narrative

• Support GTM leadership communications by helping ensure priorities, decisions, and updates are communicated clearly and consistently.

• Develop executive-ready content including leadership messages, organizational updates, QBR narratives, operating review summaries, transformation updates, and field communications as needed.

• Partner with corporate communications, marketing, HR, and GTM leadership to align messaging across audiences and channels.

• Translate complex business initiatives into simple, compelling narratives that connect strategy, operational change, customer impact, and field execution.

• Maintain practical communication standards, planning routines, and feedback loops that improve message quality and consistency without creating unnecessary overhead.

Program Management & Operating Cadence

• Lead program management for GTM leadership-sponsored initiatives, ensuring clear charters, owners, milestones, decision rights, risks, dependencies, and success measures.

• Design and manage the GTM leadership operating cadence, including weekly staff meetings, monthly business reviews, quarterly business reviews, planning cycles, transformation reviews, and executive follow-ups.

• Create disciplined governance for strategic programs, including action trackers, dashboards, executive readouts, issue escalation, and decision logs.

• Drive cross-functional alignment across Sales, GTM Operations, Marketing, Customer Success, Product, Finance, HR, Enablement, and other partners.

• Support field transformation initiatives by coordinating stakeholder engagement, change plans, communications, adoption tracking, and business impact measurement.

Business Operations, Insights & Decision Support

• Develop executive briefing materials that highlight progress, tradeoffs, decisions needed and recommended next steps.

• Support annual planning, quarterly prioritization, transformation roadmap development, and resource allocation discussions.

• Ensure leadership forums produce clear decisions, accountable owners, and measurable follow-through.

• Identify opportunities to simplify processes, improve field experience, increase transparency, and accelerate execution.

People Leadership

• Lead, coach, and develop one direct report supporting program coordination, executive content, operating rhythm execution, and communication support.

• Set clear priorities, roles, standards, and development plans for team members.

• Build a high-accountability team culture grounded in clarity, trust, responsiveness, operational rigor, and continuous improvement.

• Model strong collaboration, judgment, discretion, and executive presence in all interactions.

Basic Qualifications

• 10+ years of experience in chief of staff, business operations, program management, executive communications, GTM operations, strategy, consulting, or related roles.

• Experience supporting senior executives in a complex, matrixed, enterprise environment.

• Proven ability to lead cross-functional programs with multiple stakeholders, dependencies, and executive-level visibility.

• Exceptional executive communication skills, including the ability to write clearly, synthesize complex topics, and create compelling leadership narratives.

• Strong business acumen with experience interpreting performance metrics, operating rhythms, transformation plans, and go-to-market priorities.

• Demonstrated ability to manage confidential information with sound judgment and discretion.

• Experience leading, coaching, or managing people.

• Bachelor’s degree or equivalent practical experience.

Preferred Qualifications

• Experience in B2B SaaS, HCM, workforce management, enterprise software, or a large-scale go-to-market organization.

• Experience working with Sales, GTM Operations, Marketing, Customer Success, Product, Finance, HR, or Enablement leaders.

• Background in executive communications, change communications, transformation program management, or management consulting.

• Experience building operating cadences, executive dashboards, leadership scorecards, governance models, and QBR materials.

• MBA or advanced degree preferred but not required.

Leadership Competencies

• Strategic operator: Connects strategy to execution and ensures priorities become measurable actions.

• Executive communicator: Creates clear, concise, persuasive narratives for senior leaders and broad field audiences.

• Program leader: Brings structure, governance, urgency, and accountability to complex initiatives.

• Trusted advisor: Builds credibility through judgment, discretion, follow-through, and business insight.

• Influencer: Drives alignment across teams without relying solely on formal authority.

• Field-centric thinker: Understands how decisions, processes, and communications impact sellers, leaders, customers, and partners.

• People leader: Develops talent, sets clear expectations, and creates a culture of ownership and excellence.

Success Measures

• GTM leadership priorities are clearly defined, communicated, and translated into actionable plans.

• Leadership operating cadence is consistent, efficient, decision-oriented, and supported by high-quality materials.

• Strategic programs have clear ownership, governance, milestones, risks, and measurable business outcomes.

• Executive communications improve clarity, alignment, and trust across the field organization.

• Cross-functional stakeholders understand decisions, dependencies, and next steps.

• The direct report operates with strong quality, responsiveness, ownership, and accountability.

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 $163,900 to $235,550. The actual base pay offered may vary depending on skills, experience, job-related knowledge and work location. In addition to base pay, employees may be eligible to participate in a performance-based bonus plan and to receive restricted stock unit awards as part of total compensation. Learn more about UKG’s benefits and rewards 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.