Ask a Leader: Interview with Deborah Reuben

Dave Walton

Learning from a Leader: Career Development Advice

Interview with Deborah Reuben, CEO of TomorrowZone®

October 2021


Interview conducted by Garland Brooks, Sr. Advisor Business Enablement & Sales Optimization, Dell Financial Services and edited by Harrison Smith, Vice President, Stonebriar Commercial Finance . Both are members of the ELFA Emerging Talent Advisory Council. Learn more about this interview series.

When did you first join the equipment finance industry and what has been the trajectory of your career?

I joined the industry in an Application Development role within Wells Fargo Equipment Finance after returning from the mission field. I worked at Wells Fargo for several years before moving to TCF Bank as part of their TCF Equipment Finance start-up. At TCF, I held a strategic role between business and technology and was responsible for designing, building and implementing TCF’s suite of front-end applications. I worked at TCF for seven years, but within the first year I started looking at ways to create scalable solutions and imagine new solutions that did not exist. Craving new growth opportunities, I left TCF to manage my own consulting firm for a couple years before being recruited to join HCL (now Linedata) as a Senior Product Manager for their end-to-end origination platform.

I quickly ran into similar creativity constraints I faced at TCF. Limitations in my ability to discover what’s possible now and what’s next and focus on my passion for technology innovation. My passion is exploring the future, imagining how we can do things better and avoiding getting stuck in status quo. Around 2012, I saw cloud-driven disruption on the horizon and I realized if I didn’t pivot, I would be obsolete in a few years. I started Reuben Creative, LLC in 2013 and have been “making awesome happen” ever since. I doubled down on my curiosity for experimenting, creating, building and being surrounded by brilliant people. In January 2020, I re-branded to TomorrowZone®; however, by April 2020, the impact of COVID-19 forced me to reimagine my business model. The impromptu push to virtual made a lot of companies uncomfortable, but that’s my turf. I have collaborated digitally for over a decade. There are lots of discussions about the importance of technology innovation and future readiness in equipment finance, but few opportunities exist to connect, collaborate and experiment—to go beyond the surface on cutting-edge topics. In December 2020, we launched the UnConference community and event series to inspire unconventional collaborations, spark fresh thinking and shape the future—together.

What has been the biggest challenge you’ve faced in your own professional development? How did you overcome it?

Really understanding myself and how I think, and recognizing that things some people interpret as weaknesses are strengths given the environment. I thrive in environments that let me operate within my strengths, a very futuristic, creative and strategic idea machine. Being in a super analytical and regimented organization stifles me and kills innovation. To fill my tank and get inspired I went outside of my organization. Being an innovator in a traditional finance environment can be a lonely place because your nature is to challenge the status quo that companies are designed to vigilantly protect. I built my network and friendships, and found fresh inspiration outside of the industry, which helped me bring fresh ideas back into the industry.

I did not wait for anybody’s permission to learn or follow my curiosity. I didn’t wait for someone else to say it was OK to invest in myself. I’ve always owned that. That’s probably one of the best decisions that I made in my personal development. I’ve always been a voracious reader who learns through application and experimentation. I prefer integrated learning, not just visual, tactile or auditory but a combination. I like to “tinker” to spark imagination and gain new insight.

Taking ownership of my personal growth was the first step. The second was making time to learn and framing these short-term actions as a long-term investment. I think we need to keep learning throughout our careers because the things we learn today can quickly become obsolete, especially technical skills. Tech is constantly evolving and the half-life of these skills gets shorter and shorter all the time, so you must constantly be in a cycle of reinventing yourself. That’s one of the things that I’ve done continually throughout my career and I think it’s helped me overcome feeling boxed-in and uninspired.

When did you first get involved with ELFA and how have you been engaged as a Member thus far? How has being in ELFA helped your career?

TCF Equipment Finance was founded in 1999 and the next year I attended my first Operations & Technology Conference—my introduction to ELFA. It was so cool and shortly after, I was asked to speak at the event. In 2007, I was invited to join the Operations & Technology Committee. I chaired the Awards subcommittee, leading the revamp of that program and eventually chaired the Operations & Technology Committee for several years. I loved the cross-industry collaboration. It fed my soul to network with people from all different companies and perspectives. I introduced new standards of collaboration and planning for events; some of my strategies are still leveraged by that committee today.

In 2017, I was engaged to facilitate the Equipment Leasing & Finance Foundation’s Industry Future Council. In collaboration with Andrew Cotter, I designed and facilitated a program to introduce executives to exponential technologies and their implications and opportunities for the future of our industry. That spawned participation in industry studies, more speaking engagements and some interesting workshops.

I also helped launch the ELFA Women’s Council and led the initial strategy session for ELFA Equality. Later I was invited to serve on the ELFA Board of Directors, where I currently serve. Shortly after joining the Board in 2018, Ralph Petta reached out with an idea to bring leaders together regularly to monitor technology and innovation trends and specifically what it means for the industry. In 2018 I launched the Technology Innovation Working Group, which influences content for ELFA, and in 2021 we launched a series of Innovation Roundtables [the next Innovation Roundtable will be held Nov. 18, 2021].

ELFA membership has opened many opportunities to speak and meet people. Many of my friends and clients came to me through my involvement with the association.

What is the most rewarding risk of your career?

Having the boldness to leapfrog into the unknown. Every time I’ve experienced something amazing in my career, it’s tied to facing my fears and leaping into something new and uncertain. Leaving employment entirely to serve on the mission field was my first big leap into adventures in Ukraine, Russia and Mongolia. It was both crazy and exciting. Returning to the US and joining Wells Fargo Equipment Finance was another leap. Then joining a startup with no guarantees was another leap that opened more doors for me than I ever thought possible. Where would I be now if I had stayed in a corporate job? I would have missed the opportunity to start my own consulting business.

Then I leaped into a different industry that I have never worked in before. Joining the software industry as a Senior Product Manager was a whole new world for me.  It was another really rewarding experience and I saw this industry from the service provider lens. The biggest leap was going back into business for myself in 2013 and that leap is still paying dividends.

If you had to pick one, which is more important when considering a hire—a soft or technical background? You can’t pick both, and please include which soft or technical skill is most beneficial to success.

Soft all the way for personality, character and ability. I can teach you the technical skills, but the ability to collaborate, lead and listen is invaluable. Tech is interesting because it’s part soft skills as well—the ability to learn, unlearn and relearn quickly.

This makes me think of one the key people in my organization who I recruited from an unlikely place. My sister-in-law invited me to an event where I saw this person leading a group. The way she facilitated the group made me realize that I needed someone like that in my organization. I didn’t know how she made a living, and I didn’t care. I was looking at her character, her ability to make decisions, her ability to show up as a leader, and her presence to manage tough discussions in a diverse group. I found out that her background is in psychology—a fantastic balance to my focus areas. We needed someone who is organized, bold and willing to challenge me and she turned out to be a fantastic addition to our team.

I am an idea machine, but not all ideas are awesome and I need someone more balanced and structured to help me prioritize and get stuff done. If I had my way, I would be in a secret lab, experimenting, learning and creating all the time like a mad scientist.

What are the top 3 pieces of advice you would give to someone just entering the industry?

  1. Something a mentor told me a long time ago: Always be a student of your business, whatever that business is, and never stop learning.
  2. Take ownership of everything in your career—your learning, associations and network—you own it and when you take ownership of that it changes everything because you stop waiting for someone else’s permission.
  3. Get involved, get to know people and get outside of your comfort zone to diversify your association.

Given that ELFA recently updated its mission statement and strategic plan to affirm its commitment to diversity and inclusion, can you give some perspective on what your organization has done or is doing to promote diversity and inclusion?

For me diversity of thought is vital if we want to truly innovate. What we’re doing at TomorrowZone is creating a virtual safe space for brilliant people to come together, explore new ideas, connect with each other and collaborate in new ways. We are very intentional about thought diversity and you will find people from different companies, backgrounds, age and experience levels, races, geographies, interests and even different industries at our virtual collaboration table.

This summer we completed our first industry level collaboration. A four-week design thinking sprint with people from 12 different companies on four different teams reimagining originations. They worked through various phases of the design thinking process: empathy, ideation, prototyping, testing and presenting solutions. The ideas that were coming out of these teams were incredible. We had people from the US and beyond, from different types of equipment finance companies, and other companies within our ecosystem. We had a wide range of experience and perspectives ranging from a management trainee to an experienced CEO generating fresh ideas together.

When it comes to inclusion, we are just as purposeful. Inclusion is an action, not just a nice thing you say in relation to diversity. Being virtual levels the playing field and provides a space for equality—you’re all the same size in a zoom screen grid. I was recently reminded of how short I am while attending an in-person event after a year and a half of being the same height as everybody that I’ve interacted with.

Creating a space that includes all voices comes from deliberate action. A lot of meetings are boring and exhausting because they’re not led well and are not designed for a good human experience. The feedback we hear most commonly from our event attendees is how they feel like human beings and leave energized. We are one of the few virtual events they can go to where they are addressed by name. We make sure they have a voice and feel welcomed.

Even a smidge of strategic planning and facilitation effort can make all the difference. We’re focused on it because we want to help people get to a new level and unbox their thinking through the exchange of ideas in a safe space without fear of judgement. Sometimes you must help people tear down or diffuse their wall of fear of rejection so they can say what they want to say—often leading to breakthrough thinking. Our success comes from carefully designing the interactions; recognizing that not everybody is the same.

Being virtual enables inclusion of people from different countries. It’s opening a whole new realm for us. I think virtual has great possibilities to level the playing field and help advance DEI initiatives.