Leaders of Change: Jason Eastman

JASON EASTMAN is the Vice President of eCommerce at Crayola. He started his career in Atlanta working for Coca-Cola in various distribution roles before making stops in Jacksonville, Tampa and Minneapolis. The majority of his career is grounded in customer management roles calling on or leading teams responsible for almost every major retail channel, predominantly in the Target ecosystem, most recently with Crayola. In 2017, he was asked to create and lead an eCommerce Business Unit for Crayola.

Jason is a graduate of Georgia Southern University and received his M.B.A. from the University of Minnesota in 2015. He is married with a 13-year-old boy and 10-year-old girl and has a love-hate relationship with the family’s pack of shih tzu’s.

Why did you choose to pursue eCommerce in your career? After my 20 years in the brick and mortar world, I was fortunate enough to be asked by our leadership to figure out the eCommerce space for our brand. I’m a sucker for a challenge and I’ve been lucky enough to be surrounded by a great team to help sort it out. The opportunity to be given such a fresh challenge at this career stage was exciting and I haven’t looked back since my transition.

What is your biggest strength, and how have you used it for your success in eCommerce? I’d like to think that my ability to synthesize large amounts of disparate information (functional, financial, analytical or technical) and turn into coherent strategic and tactical plans has enabled experts on our team to educate me and in turn enabled me to inform our organization on our path forward. This starts with my clear understanding that I don’t have all the answers but I also don’t fear working hard to find them either on my own or through others.

What is the weirdest skill or talent to come in handy in your eCommerce experience? I’ve had the opportunity to lead or be a part of several team-building efforts for multiple companies. My experience in developing strategy, establishing team culture, defining individual work and building processes to drive execution have come in wildly handy in starting up our eCommerce Business Unit.

How have you most successfully influenced change within your organization (or with your clients)? Focusing on win-win scenarios is always a good starting point. This includes having clearly communicated goals and strategies that involves or addresses all stakeholders’ interests while setting clear expectations on what is believed to be possible. If win-win is the starting point for influence then communication is the foundation for change.

What was your most “valuable” career failure, and why? Let me start by saying I fail all the time and I see failing as both an opportunity to learn and as another source of motivation to improve.

My most valuable failure is one that is a bit more personal and occurred over time. It came earlier in my career at a time when I believed great work and strong results were enough to drive organizational behavior (and change). As I advanced in my career and reached the inflection point where how communicating the message became more important than the validity or quality of the message itself, I was slow to evolve. What I learned through that process was the importance of managing the narrative more carefully for both myself personally and for my team’s work professionally. Bringing people along and winning buy-in became a learned skill that has enabled the leadership opportunities I’ve been able to chase the last 7-10 years. Now I rarely enter a situation with stakeholders where I don’t already know the outcome of a discussion because I’ve done my due diligence in advance. That experience informed the type of people I want to work for and with and the type of leader I want to be. 

In the last five years, what new belief, behavior or habit has most improved your life? I’ve worked hard at having a better work-life balance. Not always successfully, but I’m less apt to work once at home than I might have been earlier in my career.

What are you learning right now? Two of my big projects this year are about having a better understanding of requirements for our site and the capabilities we need to develop to enable a more dynamic supply chain. Both areas aren’t native to my experience so every engagement in either area is an opportunity to learn.

What are the 1-3 songs that would make up your career soundtrack today?

• Alive by Pearl Jam: As of this writing I still am….

What are the 1-3 books you’ve gifted the most or that have greatly influenced your life, and why?

• The First 90 Days by Michael Watkins: This is a favorite book to gift because I believe it describes a continued state of behavior for leaders to demonstrate in addition to behavior to adopt as a new leader. The lessons communicated, especially in a macro-environment like we are in today, never become stale.
• Team of Rivals by Doris Kearns Goodwin: This is not a book I’ve gifted but one I’d recommend in large part because it demonstrates how a great leader can nudge other bright leaders with divergent viewpoints and have them come together to accomplish amazing things. With so many opinions available about how best to win in eCommerce, the idea of synthesizing and executing varying (cross-functional) viewpoints as a leader appears wildly achievable when cast against such an epic point in time. 

If you could have a gigantic billboard for the world to see with anything on it, what would it say, and why?  My favorite quote is “…a man's reach should exceed his grasp, or what's a heaven for?” by Robert Browning. This simple, efficient phrase captures multiple ideas like perseverance, aspiration and hope and always reminds me to set goals, to always work to improve and to never quit.

What are the worst recommendations or advice you have heard related to eCommerce? “It’s new? Let’s put it on Amazon.” This can be true, but isn’t always. Channel strategies matter.

What advice would you give to a future leader of change about to enter business, or specifically the eCommerce field? My advice for any future leader of change would hit on a few fronts:

First, have a goal in mind regarding what you want to be or do. Leave the goal broad enough that you don’t limit opportunities that come your way but know your “North Star”. For me that was about leading teams.

Second, I wouldn’t be afraid to charge into challenges or situations that might make you uncomfortable, including taking calculated risks like moving companies, home locations or channels of business. It might feel like a lot of work in the moment to build/re-build your personal equity or solve a difficult problem, but any trial by fire earlier in your journey will leave you tempered for more difficult challenges when you are leading later. You’ll be glad for those early challenges when team members and/or company leaders are relying on your ability to navigate difficult circumstances.

Last but not least, I’d suggest leaving room for self-improvement. This might come in the form of spending more time with your family and becoming a more attentive parent, spouse or friend or it could be about going back to school to get a graduate degree or some other form of certification. Careers are long and to stop learning will likely result in a slow-down in professional growth. This is in part why I embraced the chance to enter eCommerce. 

What specific, industry-related change do you believe will happen that few others seem to see? I’m very interested in the inevitable (?) intervention of government regulation here in the U.S. and the impact it will have on vertically-integrated organizations such as Amazon or tech market leaders like Facebook and Google. If or when legislators get involved, will anything occur in time to allow the legacy market to catch up in terms of capability development? Will the rapid rate of disruption/destruction continue unchecked and should we care? What is apparent after watching leaders in Washington probe the Cambridge Analytica/Facebook flare up is that the digital economy is not fully understood by the general public or our legislators which may drive more severe consequences for our industry.

From a less macro-perspective, I’m curious as to when certain logistics capabilities like drop-ship will be table stakes for brands that are less productive (considering sales rate or turn) when compared to the cost of carried inventory. With store footprints getting smaller and evolving into places to pick up products vs. shop for products, some brands might be vulnerable if or when a retailer pushes them to an online only experience if they haven’t kept pace with capability benchmarks in the market for order fulfillment.

What is the last thing you bought online, and why? The last purchase I made online was apparel. As a near-weekly traveler and father of two busy kids making time to shop in a physical location represents another place to burn free time. The convenience of shopping from the airport gate or from kids sporting events is a much better use of relative downtime. It took me a while to get comfortable with buying apparel online in particular but I have 4-5 brands I trust and they’ve earned my continued loyalty. 

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Leaders of Change is a weekly interview series featuring select industry pioneers who are driving the evolution of commerce, the consumer and everything in between. If you would like to recommend a Leader of Change for consideration, please reach out to me on LinkedIn.