August 8, 2025

From Specialist to Generalist with Carolyn Pollock, Previous CMO @ Tailored Brands

Having spent years deeply immersed in the complexities of marketing, I've come to recognize patterns that repeat themselves across businesses navigating significant transitions. My recent conversation with Carolyn Pollock, previous CMO at Tailored Brands, provided profound insights into precisely these challenges, and how to address them head-on.

One theme stood out immediately: the essential yet elusive balance between brand building and performance analytics. Carolyn's extensive experience at Tailored Brands vividly illustrated the power of marrying data-driven insights with brand initiatives. She recounted using media mix modeling (MMM), paired with incrementality tests across matched markets, to confidently increase investments in upper-funnel brand marketing. Her description resonated deeply, reflecting the exact iterative, hands-on approach that we at Exactius advocate and practice daily: using MMM as a dynamic tool for continuous experimentation, actively testing various marketing channels, and integrating those results back into the model for ongoing refinement.

Carolyn emphasized the necessity of aligning analytics closely with finance teams and organizational goals. She shared a pivotal lesson: involve finance leaders deeply, early in the modeling process rather than waiting until polished outcomes are ready to present. This inclusive approach builds crucial trust and helps secure alignment for brand-building investments, often seen as riskier, less measurable bets.

Our dialogue moved into an exploration of leadership through transformative moments. Carolyn offered a nuanced perspective on managing teams during periods of significant change. She highlighted the importance, and difficulty, of honestly assessing team capabilities, distinguishing between employees with the aptitude for rapid adaptation versus those resistant to change. Carolyn was candid about the tough conversations required when team members no longer aligned with a company's evolving needs. She reinforced that swift, clear actions benefit both the organization and the individuals involved, allowing each to pursue better-suited opportunities.

Reflecting on recent tumultuous years marked by macroeconomic volatility, Carolyn shared a particularly striking experience: navigating Tailored Brands through the COVID-19 pandemic, a crisis that decimated demand for suits overnight. Her strategy focused rigorously on "controlling the controllables." Carolyn led her teams through meticulous budget evaluations, trimming non-essential expenditures to preserve funds for high-impact media investments. This disciplined, detail-oriented leadership empowered her team, giving them tangible actions amid uncertainty.

We also delved into the evolving skillsets marketers will need in an AI-driven future. Carolyn convincingly argued that while specialist roles have dominated recent decades, the pendulum is swinging back towards generalists (those marketers who deeply understand how various channels and capabilities connect holistically). She sees the rise of generative AI amplifying this trend, predicting the most successful marketers will be versatile strategists capable of guiding and contextualizing AI's functional capabilities rather than merely executing specialized tasks.

To prepare for this shift, Carolyn actively encourages her teams to seek opportunities that round out their expertise. Her advice resonated strongly: marketers should intentionally pursue cross-functional projects to build the broader fluency essential for leadership roles.

Finally, Carolyn emphasized an enduring principle amidst technological disruption: successful marketing hinges fundamentally on human connection. Despite advances in AI, she underscored the complexity of human motivation and behavior as elements AI might never fully grasp. Companies that prioritize genuinely understanding their customers' emotional needs will continue thriving, regardless of technological shifts.

As we concluded our conversation, I felt an optimism rooted not only in Carolyn's wisdom but in her practical, human-centered approach to marketing. Her strategies provide a robust framework for leaders navigating inevitable change: leverage analytics thoughtfully, align deeply with organizational stakeholders, manage change decisively yet empathetically, and nurture versatile marketing talent ready to thrive alongside emerging technologies.

Carolyn's approach is a powerful reminder that amid transformation and uncertainty, the core of great marketing (authentic, insightful connection with customers) remains timeless and irreplaceable.

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