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Catherine York Powers of Constant AI: “You will spend a lot more time raising capital than you imagined”

You will spend a lot more time raising capital than you imagined. An entrepreneur can’t grow a business without capital either in the form of investment or revenue. I have spent a lot more time cultivating relationships with investors over time and then raising capital from them than I thought I would. As part of my […]

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You will spend a lot more time raising capital than you imagined. An entrepreneur can’t grow a business without capital either in the form of investment or revenue. I have spent a lot more time cultivating relationships with investors over time and then raising capital from them than I thought I would.


As part of my series about “individuals and organizations making an important social impact”, I had the pleasure of interviewing Catherine York Powers.

Catherine York Powers started her career with the Democratic National Committee helping to register voters and working on major policy initiatives like the creation of Empowerment Zones in economically distressed communities.

Catherine is a former founding member of the investment banking division at SunEdison, a former managing director at Capital Group Investments and recent prior Vice Chair of Maine Angels, which invests in early-stage companies.

She co-founded Constant AI, a fast-growing provider of digitized, self-service technologies for banks and credit unions, in 2015 with her business partner, Carissa Robb.


Thank you so much for joining us in this interview series! Can you tell us a story about what brought you to this specific career path?

I started my career as a political and social activist at the Democratic National Committee. The work we did to support the creation of Empowerment Zones to promote economic growth in distressed communities really spoke to me. After a career that included M&A, finance and P&L management roles, I thought it would be fun to strike out on my own and create a company that would generally promote financial inclusion and access to capital.

Can you share the most interesting story that happened to you since you began leading your company or organization?

Not far into my journey, I knew I needed an experienced consumer loan servicing and collections professional — not an easy find since most work at large banks which aren’t based in Maine. I was at my cousin’s birthday party and ran into a friend of his who I often saw at family events. I asked what she did for work, and it turns out she was the SVP and Head of US Loan Servicing for TD Bank where she had spent her entire career. She lived five miles from me. I couldn’t believe it. I put on my recruiting hat and within a month, she had agreed to take the leap to join Constant AI.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Very early on when we were exploring approaches and moving down the fintech lending path, we built a complicated financial model that would be the basis of our consumer lending algorithms. As a gut check, I hired a consultant and put all of the assumptions and formulas on a white board. The white board was pretty full. He walked up and said you have made this way too complicated. It’s literally these three things which looked like 1 + 1 = 2. I felt a little foolish, but after a good laugh, I reminded myself that the simplest answer is often the correct one.

Can you describe how you or your organization is making a significant social impact?

We started as a fintech lender and held ourselves to the standard of a ‘responsible lender,’ which included no payment spike if you missed a payment on a 0% promotional offer, lower interest rates, etc. With our digital loss mitigation platform, we enable financially stressed customers to secure a payment accommodation or other workout option in minutes instead of days or weeks. Whether it’s COVID-19 or any other disaster or similar event, it’s a time when consumers need help fast. We’re the only company that can do this across all debt types.

How do you define “leadership?” Can you explain what you mean or give an example?

Leadership should be transformational. I believe a leader’s job is to inspire and encourage his/her team to see and work beyond their comfort zone and help them embrace change to ensure success. One of the best examples of this was President Barack Obama.

What are your “5 things I wish someone told me when I first started” and why? Please share a story or example for each.

  1. You will spend a lot more time raising capital than you imagined. An entrepreneur can’t grow a business without capital either in the form of investment or revenue. I have spent a lot more time cultivating relationships with investors over time and then raising capital from them than I thought I would.
  2. As a founder, you better be able to sell. An entrepreneur will gain the earliest traction by talking with and ultimately getting a handful of customers to say yes. Before you hire your first salesperson, you should know the customer questions and objections. Many first-time entrepreneurs are product or tech-focused, and sales may seem daunting.
  3. Early on, hire people who are curious doers and are highly trainable, not people who managed doers. As a fast-growing company, everyone has to chip in in a variety of ways. If you hire a senior person for their experience but they managed the doers in prior jobs, you won’t enjoy the benefits of your new hire — and probably overpaid.
  4. When you hire your VP of Sales make sure he/she understands how to manage people responsible for the entire sales cycle — and is data driven. Early on, I hired a VP of Sales with impressive sales results. I later learned this person was a fantastic individual contributor but didn’t know much about managing teams and making data-driven decisions to grow the business.
  5. Know your customer. You can’t be all things to all people. Focusing on delivering one great product to a well-researched ideal customer will drive traction.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

Make the best education accessible to all with a huge financial literacy component taught from a young age to give everyone the same chance to build wealth and close the net worth gap.

Can you please give us your favorite “Life Lesson Quote?” Can you share how that was relevant to you in your life?

Expectations are disappointments under construction. Asking questions and being clear about intention has resulted in stronger relationships and avoided a lot of conflict. Whenever you start a sentence with “I thought” or “I assumed” it usually leads to an outcome that was avoidable by open communication, even if that conversation was a tough one to have.

Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them.

The tennis legend and GOAT, Rafael Nadal. When he plays, he digs out every point and leaves it all on the court whether it’s a regional tournament or a grand slam. Commentators often say that he plays like he’s broke, and his work ethic is legendary. This is the mentality that I have when it comes to my business. Even on my toughest days, I refuse to close my laptop unless I feel like I did everything I could to hit key milestones. I also play tennis this way, but I’ll never compete at a level where it matters!

How can our readers follow you on social media? https://www.linkedin.com/company/constant-ai

This was very meaningful, thank you so much. We wish you only continued success on your great work!

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