Sr Director, Technology Strategy & Portfolio Management

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Reporting Location: Chicago - 345 North Morgan

$200,000-$240,000

Workplace Type: Hybrid

ABOUT US

tms unites technology, marketing, and sourcing to drive transformational change for the world’s leading brands. With more than 1,400 employees across 28 countries., we offer an impressive range of solutions – from inspiration and innovation to category management and delivery.

Operating as a creative agency, a strategic consultancy, a sourcing business, and a technology provider, we engage with over 110 million customers every single day for our clients, including McDonald’s, T-Mobile, O2, Starbucks, and adidas.

Most importantly, we're a place where you can achieve great things, and be recognized as the best.

WHAT MATTERS THE MOST

Breakthrough, business-driving ideas come from extraordinary people with the freedom to be their most authentic selves at work. Authenticity and diversity are critical elements of our business. They can only be realized when we create access and equity for all. We foster a culture of inclusion and belonging and aspire to be ever-evolving.

tms is a place where brilliant people are better together. If you want your ideas to be heard and to contribute to a culture of inclusion and authenticity, bring us your voice! Visit us at tmsw.com.

WHY WE THINK YOU WILL LOVE THIS ROLE

The Senior Director, Technology Strategy & Portfolio Management leads enterprise technology governance, delivery coordination through program and project management, and technology vendor oversight to ensure disciplined execution, operational alignment, and visibility across the enterprise technology organization.

This leader will report to the CIO and partners with senior leadership to lead cross-functional enterprise technology initiatives, drive digital transformation, support security initiatives and align IT strategy with overall business and financial objectives. The role sets long-term planning frameworks, optimizes enterprise technology operations, and ensures the seamless integration of emerging enterprise solutions across the organization. It also identifies opportunities for process improvement, manages budgets and resource allocation for the corporate technology department, and mentors PMO and VMO teams to foster a culture of excellence and accountability.

What you will own:

Strategic Leadership

• Align technology investments with organizational strategy, developing budgets and program roadmaps in partnership with finance and business leaders
• Establish and maintain governance frameworks for technology programs to ensure alignment and accountability
• Define and execute the Technology PMO vision, mission, and strategy in support of enterprise goals
• Prioritize initiatives based on strategic impact, resource availability, and business need

Governance & Portfolio

• Lead technology governance processes to drive alignment, transparency, and decision-making.
• Oversee Corporate Technology portfolio health, reporting, and investment visibility.
• Govern intake, prioritization, and resource alignment across technology initiatives.
• Drive executive and steering committee governance, including reporting and decision support.
• Oversee strategic vendor performance, accountability, and service delivery.
• Govern vendor SLAs, contracts, and compliance with operational commitments.
• Lead resolution of critical vendor escalations and risks.
• Chair vendor operational and performance reviews to drive continuous improvement.

Delivery Coordination / PMO

• Establish and maintain project delivery standards, governance, and operating rhythms.
• Oversee cross-functional dependencies, risks, and execution alignment across initiatives.
• Ensure operational readiness and successful transition of technology capabilities into production.
• Coordinate enterprise technology change portfolios and delivery calendars with Infrastructure & Operations.

Executive Operations Support

• Provide executive-level KPI, dashboard, and portfolio reporting.
• Enable leadership team effectiveness through meeting governance and strategic planning support.
• Drive visibility and management of key risks, issues, and escalations.
• Oversee investment tracking, prioritization, and portfolio-level decision support.

Stakeholder Engagement

• Partner with C-suite executives, department heads, and cross-functional teams to align technology initiatives with business strategy
• Serve as the primary point of contact for business leadership on program status, risks, and issue resolution

Resource & Capacity Management

• Allocate and manage resources across the portfolio to optimize efficiency and delivery
• Identify and address skill gaps within the program and vendor management teams
• Build a culture of deep business alignment, accountability for outcomes, and continuous improvement

Risk Management & Quality Assurance

• Proactively identify, assess, and mitigate risks across technology programs
• Establish metrics and KPIs to measure program success and drive continuous improvement
• Build, mentor, and lead a high-performing PMO and vendor management team
• Foster a culture of collaboration, innovation, and accountability

Process Improvement

• Continuously refine methodologies, tools, and processes to improve delivery efficiency and effectiveness
• Promote adoption of industry best practices and emerging trends in technology management

WHAT YOU WILL BRING TO THE ORGANIZATION

• 10+ years of progressive experience in technology management, including 10+ years leading enterprise governance, PMO (technical and functional), and vendor management functions
• Demonstrated ownership of a technology portfolio, including intake, prioritization, and executive-level portfolio reporting
• Proven experience managing technology vendors: performance management, SLA and contract oversight, and escalation resolution
• Track record establishing project management standards and coordinating cross-functional delivery dependencies at enterprise scale
• Experience partnering directly with C-level stakeholders and preparing steering committee and executive materials
• Strong financial acumen, including budget ownership and resource allocation for a technology function
• Bachelor's degree in Computer Science, Information Technology, Business Administration, or a related field, or equivalent professional experience; Master's degree preferred
• Proven track record managing large-scale, complex technology programs in a global, fast-paced environment
• Budget ownership of up to $20M across global and business-line technology spend
• Strong understanding of technology development lifecycles and methodologies (Agile, Waterfall, hybrid) and delivery tools (e.g., Jira, Microsoft Project)
• Exceptional leadership, communication, and interpersonal skills, with demonstrated ability to influence stakeholders at all levels
• Excellent time management and organizational skills
• PMP, PgMP, or equivalent program management certification

SKILLS AND EXPERIENCE WE WOULD LIKE YOU TO HAVE

• Strategic thinking and planning
• Strong analytical and problem-solving skills, leveraging data to inform decisions and drive program success
• Ability to manage multiple priorities in a fast-paced environment
• Ability to foster innovation, encouraging teams to think creatively and challenge the status quo
• Commitment to diversity, equity, and inclusion
• Understands technology operations deeply
• Challenges leaders diplomatically
• Thinks in enterprise priorities—not project silos

Any of the following would be a plus

• Familiarity with infrastructure and operations change and release calendars
• Agile certifications (e.g., SAFe, CSM)
• Experience leading through change management and organizational transformation
• AI experience

Starting Salary between: $200,000-$240,000

Our total rewards philosophy integrates programs for compensation, benefits, recognition, learning and development, corporate culture, corporate citizenship and work-life balance. While individual program components may differ by country, some things remain constant:

• Our commitment to rewarding results
• Opportunities to work with talented and driven individuals at every level of our company who respect each other, treat each other fairly and hold one another accountable for our customers’—and our company’s—success

There's more ...

• Generous medical, dental, vision and other great benefits
• Paid parental and medical leave programs
• 401(k) with a company match component and profit sharing
• 15 days of paid time off plus company holidays
• Tuition reimbursement and student loan repayment assistance
• Inclusive employee resource groups

EQUAL OPPORTUNITY EMPLOYER

We are an equal opportunity employer, and we value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, sex, gender, gender expression, sexual orientation, age, marital status, veteran status, or disability status. We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform essential job functions, and to receive other benefits and privileges of employment. Please contact us to request accommodation.

RECRUITING AGENCIES

tms does not accept agency resumes submitted by third-party vendors unless a valid agreement has been signed and the tms Talent Acquisition Team has granted authorization for submissions for a specified position. Please do not submit or forward resumes to our site, tms employees, or any other company location. tms is not responsible for any fees related to unsolicited resumes.