High Alpha Pilots: Meet Jeff Cunning

VP Product + Partnerships, Pattern89

Taken in: Kuang Si Falls in Luang Prabang, Laos

The world can be a lot smaller than it feels. For someone who has explored much more of the world than most of us ever will, Jeff Cunning has also had his fair share of “small world” experiences, especially in the world of tech. The current VP of Product and Partnerships at Pattern89, Jeff’s journey to this role has taken him around the world (literally). However, connections to folks in the Indy tech community have demonstrated the power people and relationships have, in addition to knowledge and skillset, to success.

Journey to Product Management

An Economics and English Writing major at DePauw University, Jeff had a professor throughout his college career that would always say the same thing: “You remind me of this other student I had. You have to meet him!” During his senior year, Jeff finally got connected with this elusive other student, R.J. Talyor.

Through R.J., Jeff learned about the Catapult Program at ExactTarget, and from 2009–2014 spent time in a variety of Product Marketing and Product Management roles at the company.

“I got to join at a time when there were about 400 employees and the company was taking off, expanding to London, San Francisco, and going public. Everybody worked hard and a lot of great things happened,” shared Jeff of his ExactTarget experience.

As he settled into life at ExactTarget, Jeff found himself working often on projects involving the emerging social media platforms of the time (Facebook, Twitter, etc.). When ExactTarget acquired social media management and analytics tool, CoTweet, he jumped at the opportunity to try something new — he moved to San Francisco to join the CoTweet team out west. A couple years later, ExactTarget went public and was subsequently acquired for $2.5B by San Francisco-based Salesforce.

After the Salesforce acquisition, Jeff was a product manager for social, web, and advertising products, and helped lead the team that won a Facebook innovation competition for a product that is now Salesforce Active Audiences.

After finding his niche in the world of social platforms and advertising with a passion for building teams and new products, Jeff made the leap to Twitter and joined the MoPub team. MoPub, an ad exchange platform Twitter acquired in 2013, had a unique, startup culture in the middle of the Twitter organization, allowing Jeff to move fast with a startup and utilize the resources of a large company.

Around the World in Eight Months

A sense of adventure brought Jeff, an Indiana-native, out to the Bay Area, and that same sense of adventure led Jeff and his wife on the trip of a lifetime in early 2016. They were working off a bucket-list of adventures they wanted to accomplish. The top 5 items on their list were:

  1. Buy a house in San Francisco
  2. Move to London for a year
  3. Start a company
  4. Quit our jobs and travel around the world
  5. Move to a new city in the US

Jeff and his wife decided to make the leap and check off number 4. After quitting their jobs, storing all of their possessions, canceling their phone plans, and leaving their car with a friend — the Cunnings set off on an 8-month adventure around the world. The story of their travels could make this article much longer—and I could never do it justice—so take some time to view their travel blog, The Cunning Travels.

One of many video recaps on the Cunning’s travel blog.

Journey to Pattern89

As Jeff and his wife were winding down their global adventure, it came time to determine what their next career adventures would be. For Jeff, R.J. Talyor’s name came back up when connecting with some old friends, so Jeff decided to draft an email to see what opportunities there might be to work with R.J. again. After drafting the email to R.J., Jeff decided to wait and send it the next day. Before he had the chance to reach out, a message was waiting in his inbox.

The message was from R.J. Talyor:

“Hey Jeff, starting this new business and we should talk!”

R.J. was in the process of founding Pattern89, a High Alpha Studio company focused on using AI and machine learning to uncover the best content for social ads, and needed someone to lead product.

With the partners and social platforms Pattern89 primarily works with being located in the Bay Area, Jeff signed on as VP of Product and Partnerships in February 2016, utilizing his home base of San Francisco strategically for the organization.

Despite traveling around the world, Jeff’s world has come full circle, working once again with R.J. Talyor.

Why Product Management

When chatting with our various “Pilots” in the High Alpha Family, I love to learn more about why they are passionate about their specific functional area.

“When I think of ‘Product Management’ I often think of Office Space….

We don’t sell the product; we don’t service customers; we don’t design the product; we don’t build the product; but we work on the product,” shares Jeff.

“It’s all about how do you take in all those inputs and be a curator of what we should do as a business based on the needs of all different types of ‘customers’ (paying, prospects, investors, internal teams, etc.).”

Jeff is a problem-solver. He loves working with his team at Pattern89 to best highlight the problems they are trying to solve, confident that by defining the problems really well, everything else will fall into place while working towards a solution.

Jeff’s journey to his current role with Pattern89 has afforded him a lot of opportunities to learn and grow along the way. His biggest pieces of advice for folks starting their product journey?

  1. Find what’s broken and go fix it.
“When something is broken and stays broken it’s because other people don’t know how or don’t want to fix it. Be the person that wants to fix it.”

2. Get points on the board.

“Find early opportunities in every role to make a concrete and measurable impact — no matter how big or small. Use those “points on the board” to gain credibility and trust from others to take on bigger projects.”

3. Ask questions and listen voraciously.

“The more context and information you have, the better and more positive decisions you can make. So focus an inordinate amount of time gaining context by asking questions and listening to everyone across the business.”

Jeff Cunning has been around the world and back, and as Pattern89 continues to grow, his perspective will surely be a large part of the company’s adventure.


High Alpha is a venture studio pioneering a new model for entrepreneurship that unites company building and venture capital. To learn more, visit highalpha.com or subscribe to our newsletter.

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