Cynthia Whitfield-Story is a longtime business leader. Earlier this year, she was named to the board of Franklin-based Lineage Bank after years in multiple leadership roles at Allstate Insurance Company.
For more than 30 years, strengthening employee’s leadership skills was important to her. At the age of 16, she began a career working in insurance while still attending high school in New Jersey. Twelve years ago, Nashville became her home, and she retired from Allstate in 2020.
Although insurance is a large part of Whitfield-Story’s career, she wanted to find a way to serve the community.
About a month after she retired from Allstate, she launched consulting firm Inspire1, focusing on leadership coaching and strategy development.
“It’s really about advancing yourself, always learning and always being a student,” she said. “A lot of people stop learning after they get to a certain level, and I think that can be detrimental.
She spoke with the Post about her background and her love for leadership.
How did your upbringing prepare you to have leadership roles?
It was my parents who told me to go for whatever I wanted or whatever I wanted to learn, be able to learn as much as I can. That’s why you’ll see at Allstate I worked in a lot of different roles, because I’m a student at heart in everything I do. If there was a position available that looked different than what I was doing, and somebody said, “hey, you know, we think you can do that,” instead of being fearful I would just take a calculated risk. I would pursue it and if I got the position, then I would learn, study, practice and then do my job and perform.
You retired in 2020 from Allstate but soon after opened your leadership coaching and consulting firm Inspire1. Why?
I decided I needed to do something else. I said OK, what did I love doing in my previous career? It was really around leadership development. It was the coaching, helping people build a bridge from one place to another. I love strategy. But if you are saying, I want to go here, but I don’t know how to get there, if you came to me, we would build a strategy and an action plan to help you get there. The goal is really to build a bridge for people to achieve their goals. Everything I do now has to tie to what my core values are and my core value is servant leadership from a corporate perspective and serving other people. My business helps other people achieve their goals.
How do you hope your firm shapes the younger generation?
I’m trying to teach young people how to be successful early on so that they understand the landscape of the company. They’ve done their homework; They’ve done due diligence and they set up goals for themselves early on in their career. No. 1, is this the right place that they want to be, and No. 2, what is it that they’re trying to achieve? The youth are going to run the world one day and I want to help build a bridge to where they’re trying to get to.
Why did you choose to accept the board role at Lineage Bank, and what does it involve?
I decided when I left my corporate job that I still wanted to be involved in the business. I started talking to people about being on a board, whether it’s a private or corporate board, because I felt I could still help companies grow. … What I did was I told a lot of people that I’m interested in board work, so I joined a couple of organizations and talked to people. I got this opportunity from an organization called The Table here in Nashville. They’re trying to help minorities and have Nashville be the best place for minorities to be successful. That was the organization that connected me to the bank and from there I met with the president and the CEO of the bank, and my skillsets – accounting, finance, leadership management – were something that they needed, and they were also a new bank. … The bottom line is my goal was to help the bank be successful, to help it grow, to support it from a governance perspective and help fulfill the goals that we’ve identified.
What lesson do you hope your mentees learn from your journey?
To pay it forward, I’m on three boards. I’m on [the board of] Big Brothers Big Sisters, which is all about mentoring young people. I’ve been on that board for many years, and I’ve been the chair of it, so getting to help the community that we serve is important to me. … I’m going to be the co-chair of the Young Women’s Christian Association. The mission is to eliminate racism, empower women, stand up for social justice, help families and strengthen communities.
What kind of leader would you like to be remembered as?
As a simple servant who was always willing to learn. Learning and growing – I think that’s what servant leaders do.