Career Rocket Episode #10: Cindy Dunkley

Cindy Headshot3.jpg

Insight looking back:

“ I never knew how much my public speaking would be a catalyst for my career.” - Cindy Dunkley

The goal of Career Rocket is to make an impact on people’s careers by sharing wisdom from successful folks with high integrity. You can also listen to the full recording of this post by clicking on the podcast options.

Target audience for this episode: aspiring professionals in digital analytics, growth, and entrepreneurship.

Today’s guest: Data enthusiast, inspiring leader, and just a good human being, Cindy Dunkley dives into her career journey and shares a lot of great perspectives on what it takes to be successful in various career stages. I have always admired how she engages with people, is present, humble, assertive, and confident. She is respected and loved by so many and I am grateful she took the time to share her wisdom with our audience.

Professional background and highlights 

  • In 2005, I started my career at Coremetrics, now a part of IBM, in Austin, TX as a data analyst working with Macy’s, JCPenney, Bass Pro, Paper-Source, and more. Those were the early days of tech and big data. Back then we focused more on ‘how to track data’ versus like today, where we have so much more focus on ‘what to do with all the data’.

  • I then moved to New York to work for Ogilvy and Mather, part of WPP, where I was an analyst measuring the effectiveness of our digital marketing and ‘microsites’ for Nestle, SAP, Time Warner, and more. Agency work is tough and it taught me a lot about finesse and elevating work to a new level.

  • In 2011, I worked for Brooks Brothers as Director of Analytics and was then promoted to VP of Direct, managing the P&L for Ecommerce and the Contact Center. It was an honor to work for a piece of American history and to have the experience running a large team for an enterprise brand. 

  • In 2015, I was CEO and founder of a venture backed tech startup, helping to bring together buyers and sellers of enterprise software. 

  • I now consult full time across venture capital, marketing and ecommerce

How many people have you managed (includes direct reports and their teams) over your career? In total, over 40 people across marketing, development, customer service, merchandising, buying and product.

For each career stage, please share the most important characteristics to have in the field of marketing.

  • Entry level: 1-3 years (8:00)

    • Top characteristic: Nailing down Time Management early on in your career. Work only gets more complicated as you grow in your career. Learn how to master work/life balance and get done what absolutely has to get done, and learn what can wait. This also means learning how not to procrastinate. 

      • Tip: create these buckets: doing now, never doing. Get OCD about the time you are doing work so you have time for non-work life. Get into work fully charged. You will be able to contribute more if you take care of yourself. Find ways to get rest. Check out Ariana Huffington’s sleep video

    • Other key characteristics: curiosity and thoroughness. Tech moves quickly, but the building blocks are pretty stable. It is important to learn the basics and be curious. If you take the time to understand ‘how things work’ and not accept them for face value, you’ll never regret it for the rest of your career. There are things I learned in my first job that I still use today.

  • Mid-career: 3-6 years (16:14)

    • Top characteristic: Networking

      • Networking is not handing out a business card. Networking is building lasting relationships and helping others whenever possible. We all grow by helping others. When you meet someone, you never know what they will mean to you 5, 10, 15+ years in the future. Make the time, invest, to network 3-5 hours per week. When you are younger and have the time, go to dinners, attend local events, sit in on webinars and constantly meet new people in the industry. A few people I met in my early 20’s have been in my life ever since, and it all happened by chance. 

        • Tip: bring a buddy to networking events. It makes events more comfortable and you can grow your network faster too

  • Mgr/Directors: (21:45)

    • Top characteristic: Being able to manage up and around you. I always say managing is like playing football, you can get hit from the side, top and bottom. Meaning, your peers, boss and team. Realizing that leading isn’t dictating to a team what has to get done, it’s about activating the ecosystem that you live in. You have to get the job done while also bringing the organization with you. 

      • Tip: find people and leverage their strengths, even if it’s building relationships you are having trouble with

    • Until you are a manager one-day, know that your boss has a hard job. It may not look like it from your position, but that’s because they are doing their job well. Cut them some slack, be supportive of your manager and treat your manager the way you want to be treated when you run a team one day. It will work in your favor and create a lasting relationship.

Looking back, please share what you feel have been your biggest drivers to a successful career? (34:00)

  • Be resourceful. Never wait for someone to teach you something. Be resourceful and teach yourself or ask for help. In tech today, you can learn almost everything by watching YouTube or reading a blog post/book. If you have an Excel question, Google it. If you don’t know how to use Keynote, Zoom, Mailchimp, Google it. Anyone I work with will tell you I’m fast at learning new software. When they ask how I know so much or learn how to use X,Y,Z, I usually can just say, “I google it and watch a video.” Also, to bring back networking. When I don’t know something, I call someone in my network and ask them. That’s what they are there for. We all need to help each other out.

    • Tip: Learn and actually do what you just learned right away to make it stick

  • Public Speaking. I never knew how much my public speaking would be a catalyst to my career. I attribute 30-40% of my success to this skill set. I was in theater at a very early age and have never been shy speaking/presenting. I’ve spoken at conferences, run meetings, spoken to CEOs, pitched for investor funding, have to make a case for my ideas/projects and more. There isn’t a day that goes by that I don’t have to use my public speaking skills.

    • Tip: the more you do it, the easier it gets. Highly recommend ToastMasters.

If there was one thing you would like to tell someone earlier on in their career that you wish someone had told you, what would it be?

  • Live it. I have always gotten great advice. It just took me many years later to have that “Ah-ha” moment. 

Looking ahead, where do you think are the upcoming hot spots in careers around your discipline? (40:49)

  • Data Science by far the top of the list

  • Graphic Design

  • Software Product Leads

What are the interesting challenges you anticipate will be coming up in your discipline in the coming years? (45:22)

  • Automation of jobs - so much of what used to require people is now automated with machine learning. I’ve seen what I used to do manually for analytics, paid search, reporting, insights all happen automatically. You have to adapt to the speed of change and constantly stay on top of what’s next. As you grow with automation, you’ll also understand WHY machines do what they do. What are the inputs that make it learn/think a certain why. Algorithms can be biased, just like people, if the wrong inputs are going in. :)

  • Creative variations - with more personalization, 1:1 targeting, real time need and increased number of marketing channels, creative is a constant challenge. You need more assets and NOW. Photography, graphic design, copy-writing, etc are all must haves in the digital age. 

The more I research and reflect, the more obvious it is that we have diversity issues among leadership in companies across the US. What are the challenges you have seen or faced to make this a reality in the near future? (48:40)

  • The biggest challenge is the lack of diverse resumes. It’s hard to hire diverse talent if they never come across your desk. It should start with feeder programs and internships to help expose others to new/unknown opportunities.

Do you have anything in particular you would like to tell future women leaders? (56:25) 

  • Read Lean In. You have a seat at the table. There is a seat at the table but you only get to sit in it if you RSVP. ;)

  • It’s yours if you ASK for it. ASK. Every job I’ve ever had I ASKED for, I knocked on doors and called people for. NETWORK, build relationships, be authentic and ASK. 

Not only do you have a successful professional career, you seem to be genuinely grounded and happy. What does living abundantly mean to you and how have you carried it out? (58:20)

  • “The best day of your life is the one on which you decide your life is your own. No apologies or excuses. No one to lean on, rely on, or blame. The gift is yours - it is an amazing journey - and you alone are responsible for the quality of it.”

  • Own your life. If you LOVE to work like I do, learn to LOVE yourself, your health, your friends and your family as much as you LOVE work. You do not have to work 80 hours a week your whole life to be great. You are worth more if you come to work rested, healthy and ‘FULL’ from life outside of work. If you don’t take care of yourself, you can’t be as easily successful at work. I can honestly say I’ve operated for years at an imbalance and looking back wish I spent as much time on myself as I did my work.


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Check out our full list of Career Rocket guests here

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