Director, Marketing Strategy & Media (Hybrid/Remote: Madison, WI)

At TruStage, we’re on a mission to make a brighter financial future accessible to everyone. We put people first, and work hand in hand with employees and customers to create a diverse and inclusive environment. Passionate about building insurance and financial services solutions, we push the boundaries of what’s possible. We need you to help us shape what’s next. You’ll be encouraged to share your experiences, ideas and skills to help others take control of their financial future. Join a team that has received numerous awards for being a top place to work: TruStage awards and recognition Location Preference: This position requires flexibility to maintain a regular in-person presence at our Madison, WI headquarters on a regular and as-needed basis to support evolving business priorities. Remote candidates may be considered; however, preference will be given to those who can maintain consistent on-site engagement in Madison. Job Purpose: This position serves as the strategic backbone and central “brain” of the marketing organization—aligning enterprise marketing strategy, optimizing digital media investment, and ensuring measurable growth and ROI. As a member of the Marketing Leadership Team, the Head of Marketing Strategy and Media COE establishes disciplined planning, measurement, and decision‑making frameworks that connect marketing priorities and investments to business outcomes. This role reports directly to the SVP, Chief Marketing and Brand Officer. Role Overview We are seeking a senior marketing leader to serve as Head of Marketing Strategy and Media Center of Excellence. This role acts as a strategic partner, operational leader, and force multiplier for the CMO and Marketing Leadership Team—driving clarity, alignment, and execution across Growth, Brand, Creative, and Marketing Operations. The role owns enterprise marketing strategy, digital media investment, measurement, and AI enablement, while shaping the marketing operating model through planning cadence, agile execution, and performance governance. The ideal candidate brings enterprise‑level strategic depth, strong executive presence, and the ability to lead through complexity, ambiguity, and large‑scale transformation. Job Responsibilities: 1. Enterprise Marketing Strategy & Leadership Alignment Own and align enterprise marketing strategy, planning, and execution across Growth, Brand, Creative, and Marketing Operations Serve as a trusted advisor and thought partner to the CMO, providing strategic insight, identifying risks, and ensuring focus on the highest‑impact priorities Act as an extension of the CMO—representing marketing leadership in enterprise forums, working groups, and strategic initiatives as needed Partner with Corporate Strategy to ensure marketing OKRs clearly ladder to enterprise objectives 2. Digital Media & Investment Optimization Own enterprise digital channel strategy and media investment across paid, owned, and emerging channels Optimize media mix, allocation, and performance to maximize ROI and incremental growth Partner closely with Finance to drive spend transparency, forecasting, vendor management, and investment optimization 3. Measurement & Decision Intelligence Establish and own enterprise marketing measurement and attribution strategy in partnership with Analytics Define scorecards, KPIs, and performance reviews that link marketing investment to business outcomes Drive consistent, data‑driven decision‑making and continuous optimization across all marketing teams 4. Marketing AI Strategy & Agile Enablement Define and lead the enterprise marketing AI strategy, identifying high‑impact, outcome‑driven use cases Partner with teams to pilot, scale, and operationalize AI capabilities across the marketing organization Design and champion TruStage’s agile marketing operating model, including agile pods, sprint‑based campaigns, pre‑sprint testing, and test‑and‑learn measurement 5. Leadership & Enterprise Orchestration Lead and scale the Marketing Strategy and Media Center of Excellence, with deep expertise in digital marketing, media optimization and marketing strategy. Design and operate leadership forums, including weekly scorecards, planning reviews, and operating updates Create executive‑ready presentations, narratives, and business reviews that influence and align senior audiences Develop senior‑level talent with strong judgment, autonomy, and the ability to lead through ambiguity Foster a culture of accountability, disciplined execution, and measurable enterprise impact The above statement of duties is not intended to be all inclusive and other duties will be assigned from time to time. Job Requirements: Bachelor’s degree in Marketing, Business, Analytics, or a related field; advanced degree preferred 12+ years of progressive marketing experience, with at least 5 years in a senior leadership capacity Enterprise‑level marketing depth spanning strategy, media, analytics, and performance optimization Strong expertise in digital media investment, ROI measurement, and marketing effectiveness Demonstrated success advising, influencing, and partnering with senior‑level executives Exceptional written and verbal communication skills, with mastery in executive storytelling and executive‑ready deliverables Strong analytical, operational, and project leadership capabilities, including budgeting, forecasting, and KPI‑driven management Proven experience leading teams and developing senior‑level talent Preferred Experience Management consulting experience or experience leading enterprise transformation initiatives Hands‑on experience defining and scaling AI‑enabled marketing strategies Experience designing and operationalizing agile marketing models Background in regulated or complex industries such as financial services or insurance High tolerance for ambiguity with strong judgment and the ability to drive clarity in fast‑moving environments #LI-Remote #LI-LT If you’re ready to help make a difference, apply today. A resume is required to apply. TruStage may process applicant information using an Artificial Intelligence (AI) tool. This tool automatically generates a screening score based on how well applicant information matches the requirements and qualifications for the position. TruStage recruiters use the screening score as a guide to further evaluate candidates; the score is one component of an application review and does not automatically determine whether a candidate moves forward. Candidates may choose to opt out of this process. Compensation may vary based on the job level, your geographic work location, position incentive plan and exemption status. Base Salary Range: $128,500.00 - $239,000.00 At TruStage, we believe a sound, inclusive benefits program is of vital importance, along with a flexible workplace that allows for work-life balance, career growth and retirement assistance. In addition to your base pay, your position may be eligible for an annual incentive (bonus) plan. Additional benefits available to eligible employees include medical, dental, vision, employee assistance program, life insurance, disability plans, parental leave, paid time off, 401k, and tuition reimbursement, just to name a few. Beyond pay and benefits, we also recognize that flexibility, including working in a place you prefer, is essential to caring for our employees. We will continue to strive to offer flexibility and invest in technology and other tools that will make hybrid working normal rather than an exception, so that when “life happens,” you can focus on what’s most important. Accommodation request TruStage is a place where everyone can bring their best self and thrive. If you need application or interview process accommodations, please contact the accessibility department. We’re on a mission to make a brighter financial future accessible to everyone. Dedicated to helping more people — in more ways — make confident financial decisions at every stage. And we’re committed to delivering on this belief, together. Creating opportunities beside our partners, members of our communities and our employees.