Jackson Jeyanayagam is an accomplished executive leader whose work has spanned across many industry sectors and a wide range of organizations. He began his career on the agency side, where he worked for 15 years before pivoting into digital marketing, P&L management, and DTC growth for top brands like Chipotle, Clorox, and AB InBev. Jackson also has experience on the startup side, having served as CMO for Boxed, a DTC startup. Most recently, Jackson was responsible for founding and scaling RTD brand Hey, Hei for AB InBev, helping to incubate the brand and develop a startup mentality under AB InBev’s larger corporate umbrella.

Jackson and Roy discuss the parallels between agency work and developing a startup, the necessity for widening the hiring funnel to better include outside strategies and perspectives, and the ways in which conventional interviewing methods are keeping brands from attracting and securing top tier talent.

Highlights from our conversation include:

• Jackson’s experiences at startups vs. more established brands (2:07)
• How he builds teams when coming into new organizations (5:11)
• Jackson’s process for determining opportunities for change (and what not to mess with when starting a new role) (8:19)
• Gauging intentional and unintentional toxicity within one’s team (13:21)
• The intersection between curiosity, vulnerability, learning, and hiring (16:07)
• How Jackson is intentional about influencing and shaping culture (21:58)
• His process for making executive-level hiring decisions and who’s involved (23:18)
• Ensuring the hiring process is equitable and attractive to a diverse range of talent (24:06)
• Talent market trends Jackson’s noticed from both the candidate and hiring sides (25:26)

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Ben Steele is a seasoned marketing and brand development leader, having most recently served as REI’s inaugural chief customer officer. Prior to carving out this new role at the Co-op, Ben began at REI in 2014 as chief creative officer. Over more than ten years at one of the country’s largest and most preeminent outdoor retailers, Ben has led brand stewardship and strategy, shepherded large-scale marketing initiatives, engaged and grown REI’s 24.5 million-strong worldwide membership, and connected essential merchandising, digital, and physical assets – amongst many other functions at the Co-op – all with the goal of sharing and facilitating a deep passion for the outdoors.

Ben and Roy discuss the inspiration for creating the chief customer officer role (as well as the challenges of being the first to occupy the position), navigating the ever-changing context of customer experience, and vital competencies he’s learned to nurture and develop within his teams.

Highlights from our conversation include:

• His initial action items upon joining REI (3:57)
• How Ben translated REI’s brand and culture through its employee base (6:07)
• The functions reporting into the chief customer officer role and the structure of Ben’s former team (9:55)
• Opportunities he’s had to bring the REI brand life for customers and members (12:35)
• Necessary adaptations and evolutions at REI in the past five years (17:42)
• The ways in which being a part of a co-op influenced Ben’s approach to leadership and collaboration (20:40)
• How to determine whether or not a company is serving their customers well (26:58)
• Ben’s predictions for the future of retail (32:03)
• Recommended resources for professional development, news, and networking (35:48)

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To kick off a new series of special episodes here at How I Hire, we’re taking a close look at the chief digital officer role. Throughout this series, we’ll hear from different C-level executives about their unique functions, responsibilities, and skill sets in order to learn just what it takes to successfully hire – or be hired as – top tier talent.

Jamaliya Cobine is an accomplished chief digital officer and digital marketing expert, having spent the past decade plus helping businesses develop their user experience, e-commerce platforms, and strategic digital initiatives. Jamaliya has an impressive track record, working for major brands like Urban Outfitters, Burton Snowboards, Wüsthof, and Topshop. She is currently the CDO of Omorovicza Cosmetics, where she continues her legacy of implementing consumer-centric business strategy, omni-channel technology, and transformative approaches to digital marketing. With in-depth experience across the apparel, outdoor, beauty, home goods, and fashion industries, Jamaliya is the perfect leader to help us learn everything there is to know about the chief digital officer role.

Jamaliya and Roy discuss the key functions of a CDO (and how they vary, depending on business structure), how competitive the market is for hiring CDOs, important trends affecting CDOs’ work, and much more.

Highlights from our conversation include:

• The scope and primary accountabilities of the CDO role (2:13)
• Strategy and goal-setting when starting at a new company (4:44)
• Challenges and opportunities facing CDOs today (6:30)
• How company structure affects a CDO’s functions and responsibilities (12:03)
• The structure of Jamaliya’s team (13:08)
• Competencies and capabilities necessary to be a successful CDO (17:15)
• What boards, investors, or CEOs should be aware of when initiating a CDO search (20:00)
• Common hurdles or barriers to success faced by incoming CDOs (21:28)

Visit HowIHire.com for transcripts and more on this episode.

Follow Roy Notowitz and Noto Group Executive Search on LinkedIn for updates and featured career opportunities.

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