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Like many marketers, Jackson's career started on the agency side, where he held a variety of roles and worked with brands such as Microsoft, T-Mobile, Old Spice, Dentyne, Proctor & Gamble, Jordan Brand and NASCAR, among many others. Jackson then transitioned in-house, becoming the head of digital for Chipotle, followed by a CMO position at Boxed, where he was named to the Forbes CMO Next 2018 list, identifying the 50 CMOs redefining the role and shaping the future.
Listen to this podcast episode where you hear more insights from Jackson Jeyanayagam speaking with GaryVee and Shane Battier here - “Jackson Jeyanayagam chats with #GaryVee on #MarketingForTheNow episode #4”.
You’ve been a digital brand builder and growth guy for 15+ years in your various roles (both full-time and advisor) - what do you love about this kind of work?
I love being able to see the results of my (and my team’s) work; there’s something so fulfilling when you see all the long nights/weekends and hard work result in something better than what you started with. But perhaps more than that, I love that I get to do it with other people that I respect and admire and that experience is quite rewarding.
You started doing agency work which is typically not quite as quantitative and over time your roles seem to be increasingly more numbers-focused - how did you find this learning curve? Did you just learn on the job or were there any other things you did outside of work to educate yourself?
I did do some research on my own and asked a lot of people smarter me for advice along the way but no question that 80% of everything I know is from doing it…and honestly, failing a lot, to truly learn. I don’t have an MBA and found myself in a GM role after many years across many types of organizations and functions and throughout that entire process I was learning at every step. My first real glimpse into understanding the numbers was my job at Taylor, where I was building and managing a practice group trying to drive incremental revenue and growth for the agency while balancing a group that was 15+. I was forced to have a better understanding of the numbers and that’s where it really started. It wasn’t easy and I made a lot of mistakes but I am better for it.
You mentioned that it was difficult for you at times balancing family life with work - what advice would you give younger folks about this? Is this just a rite of passage in your career progression journey or would you do things differently if you were to do it all over again?
This is a tough question. I don’t know if I have a good answer for people. It definitely is a consequence of being driven and having big ambitions; that said, the only way to think about this I would say is prioritization. Figure out what's important to you – whatever that is – and prioritize around those things. It can’t be 20 things but it can be more than 1 or 2. For me, my career is very, very important. But nothing is more important than my family and my kids, in particular. So while I can’t be there for every moment and every event in their lives, I do prioritize the things that I know are important to them and the moments that are unique. Everything revolves around that. But to do this well, as I have learned, you have to be extremely self-aware about yourself; your working style; how much time you have to work with, etc. You can’t do everything and can’t be everywhere so being self-aware of what you can do and what you can sacrifice is critical….and the one thing you can’t sacrifice is your health so keeping that in mind and trying to maintain that as a priority is also important…so to simplify – it’s all about prioritization AND self-awareness 😊
You talked about the need to have more diversity in the C-suite and board level - what tangible steps do you think need to be taken for this to happen?
It starts at the top and needs to be made clear by words and actions that it’s a priority for the organization; then whatever those steps and KPI’s are, they need to be made a part of everyone’s performance review. Beyond that, more specifically I believe it’s:
1) Creating a better recruitment process to expand the talent pool and where firms recruit from and how (e.g., potentially removing names from resumes to address unconscious bias, etc.);
2) Building out formal and functional internal career progression plans for employees of color and in particular those that are the most underrepresented in the organization – give your people of color and women a reason to stay;
3) Increasing awareness and conversation of the issues and not sweeping it under the rug or just saying “well we donated to XX so we are good for the year” and give people a place to feel safe and be themselves as well as talk about these real issues that exist at every company;
4) Treat it like you might sustainability or another initiative that is considered top of the priority list at a company – which means putting resources against it and talking about I&D initiatives at every executive meeting and town hall. I think there are likely many more tangible things companies can do, but these are a few that I have been thinking about.
You’ve had a few Advisor roles (ie. BounceX, Miles, Dynamic Signal, etc.). What exactly does an Advisor do?
The role can vary but generally it’s to serve as a counsellor to the startups (the founders and/or other key functional leads) in specific areas of expertise. For me, it’s often around growth/marketing/brand building/ecommerce but sometimes it’s also about building & growing teams; people management; change management; strategic partnerships, etc. There are times it is solely reactive and you are just there be available whenever the team needs you and other times it can be more proactive where you are signing up to help them develop leads or facilitate introductions or even have conversations with prospective investors and/or employees. No matter what though, I find it very rewarding and an awesome experience. I highly recommend it for anyone in a position to give back and help fledgling businesses and entrepreneurs.
Do you have any mentors that have helped you in the progression of your career? Do you think everybody needs mentors? How does somebody find a mentor?
I do. I have been lucky enough to have multiple. Each one of them I found through my job. They were all my manager or group lead at some point in my career. I never set out to “find a mentor;” I think it just happens. I always go into any role open minded that I will meet great, smart people who I can learn from and I also try to look for roles, in general, where I am learning 30% of the job…on the job. That will naturally open up mentorship opportunities in any job. Then the key is finding someone who you respect and have a good rapport with. That’s not always obvious at first. The most important thing I think is keeping an open mind…but also seeking out people that are similar to you BUT also not similar to you. That’s when you can learn the most. If your mentor is EXACTLY like you, I struggle to understand how you will maximize that relationship. But finding someone you have a connection with but is uniquely different from you is when you can really learn a lot. FWIW, I don’t think everyone NEEDS a mentor by any means…but it sure does help as you progress through your career. To that end, I should also note that you may have different mentors at different stages of your career. I have mentors that are now just friends. I may not go to them for advice on my career but I am still very close with them.
You spoke about the value of your network - what is something manageable and tangible that somebody could do to increase the size and improve the quality of their network?
I am a HUGE advocate of LinkedIn…especially right now when in-person events are non-existent. LI is THE best career networking site. Anyone spending 10 minutes on IG should re-allocate 8 of those minutes to LI and continue to refine their profile and add as many connections as possible, while also trying to engage and build in establishing genuine connections with those people in your network while also providing unique and thoughtful postings. It’s such a wonderful platform that anyone can maximize for their career.
How do you think COVID has changed the direct-to-consumer market?
It’s accelerated DTC mass adoption by 3-5 years, easily. It’s been such a game changer and I think it will only continue to accelerate. DTC is here to stay and will be a big part of the consumer shopping experience for a long time.
Do you see yourself starting a start-up in the DTC space?
I’ve always thought about it but I truly have the worst ideas. I have never been the person to come up with a new venture/idea/concept. I’m usually the person to hear someone else’s idea and want to help them grow it…so if I ever do, it will likely be with someone who has a killer idea that I believe in and we would build it together. But I think about that question a lot, actually.
If you were given $1 billion, how would you allocate the money to change the world?
That feels like an impossible question. It’s hard to pinpoint one place to start but I would definitely invest in a few areas that I believe are sorely underserved and a foundation for larger change:
1) Education – across the board. In every sector; at every level and in every way (from programs to scholarships to improving public school teachers salaries);
2) Helping under-privileged youth in under-developed countries (e.g., Sri Lanka), to provide hope, opportunities and access;
3) And last but certainly not least – I am really passionate about anti-bullying so I would absolutely spend a lot of that money on creating awareness AND action plans to prevent bullying in schools.
What do you think you would tell 16-year Jackson looking back?
Everything I knew back then is wrong.
How would you describe your dream life?
To be confident and secure in myself; to have options in life; have a strong ethical and moral compass to always do the right thing, even if completely unpopular or ridiculed; and of course the most important thing – to be surrounded by people that genuinely love you.
What is your favourite book(s) you’ve read recently and why?
I am big on leadership and management books. Im not really into reading fiction. So all of my books are usually on self-improvement and leadership. I just finished Extreme Ownership – an amazing book written by two Navy Seals on taking ownership of your actions/decisions; I am halfway through Range, a book that was one of Kobe Bryant’s favorites apparently (which is why I started reading it), and it’s been really amazing thus far. It’s about why being a generalist is much better than being a specialist in today’s world. I have many others I would recommend but these are two that I have recently been reading.
What is a new belief, behaviour or habit that has most improved your life?
To be better today than I was yesterday…at something. Anything.
How would you describe the Tamil community in the US? (as you’ve moved quite a bit in your career)
Dispersed and connected through our parents/older generations. We need to get better at finding each other via social media …there’s no excuse in 2020.
What is your favourite Tamil food (meal or dessert)?
Oh man. Probably my mom’s eggplant/brinjal curry.
What is your favourite Tamil movie?
I don’t have one because I haven’t seen too many. My Tamil actually is very bad. I understand some of it but it has to be broken Tamil the way my parents spoke to me. So I’m not a very good Tamil because I can’t answer this question!
What does Tamil culture mean to you?
Storied; rich; resilient.
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