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Season 2 Episode 4: Wayfair’s CMO Reveals Their Approach to Data-Driven Marketing

Ft: Bob Sherwin, Wayfair CMO 

Bob Sherwin has spent his career building an expansive data-driven marketing toolbox, which he has applied to the category-creating Fortune 500 retailer Wayfair as their CMO.  

Hear the full episode wherever you listen to podcasts or read the highlights below.

A Career of Skill Building

Bob Sherwin started his career in consulting, using big data analytics to create algorithms that removed dataset waste and optimized the organization of assets. By helping transform businesses, he developed a foundation for the strategic and communication skills he has depended on in his marketing roles and he also developed the confidence needed for management positions working on a variety of teams and projects.

First joining Wayfair eight years ago as the Senior Director of Customer Acquisition, Sherwin moved up as the VP of Marketing and is now the CMO. During his tenure at Wayfair, he has helped shape the marketing strategy that has allowed Wayfair to expand into the largest online-only retailer for home furniture in the US and brought a data-driven marketing approach to the company using the skills he built throughout his career.

Sherwin’s Career Path Advice: Diversify Your Expertise Early

“Think about where you are going to develop technical skills, communication skills, analytical skills.”

Using his own growth as a marketer as an example, Sherwin emphasizes the importance of skill building early on in your career path. He believes developing hard skill sets in communication and data analysis provides the foundation for confidence in management roles. Instead of being concerned about the function, brand, industry or title of the job, Sherwin believes early roles should be focused on developing skills that can be used in various environments.

Developing this expertise also helps with future roles in a company—although your initial role might be on a specific team, companies want to recruit talent that will nail their role and be able to shift roles internally.

Combining Creativity with Data-Driven Marketing To Lead Better

Building these strong analytical skills early in his career allowed Sherwin to approach marketing at Wayfair with a “blend of art and science.” Optimizing a marketing strategy requires an analytical approach to improve customer targeting, the landing page experience and algorithm updates, but data-driven marketing is incomplete without understanding how the messaging relates to your customer’s needs. Being able to anticipate those needs and have the data to back up that intuition is crucial.

Developing Marketing Talent: Think Outside the Box

When looking for talent, the skill set needed is often role-dependent, but many roles have both creative and analytical aspects. His teams don’t have hard boundaries, so even data scientists are able to be creative with their work.

The Multi-Disciplinary Future of Marketing Executives

For Sherwin, this multi-rounded skill set even applies to management positions such as CMOs. He believes future successful CMOs will need to feel comfortable operating across all functional areas with customer insights, product management, data science and all other disciplines to guide decision-making. Having experience in these fields will allow executives to provide strong brand guidance as well as understand the limitations of the field.

If you’re interested in learning more about the future of marketing leadership, check out the Building Modern Marketing Organizations Panel from CommerceNext IRL, featuring Sherwin and other retail CMOs. 

Since the future of marketing functions will continue to evolve, Sherwin believes it is important to build a broader expertise now, because adapting to change requires executives to have a knowledge of all disciplines. While some aspects of the position may be outsourced, Sherwin still sees the importance of executives building a strong foundation in different disciplines in order to stay ahead of ever-changing landscapes like privacy.

Building a strong skill set early on and continuing to adjust to change will prepare marketers for the future of the field. Sherwin has been able to use his years of experience working with data analysis to strengthen his marketing team’s strategy and put data at the forefront of their decisions, ultimately reinforcing their intuitions and creating a powerful final result. 

Bob Sherwin provided great insight into what data-driven marketing looks like at Wayfair. Listen to the whole episode to hear more about developing analytical skills and making career decisions.