Learning platform Guild is out to create upward mobility for frontline workers

Terrence Cummings says his career trajectory has been based on "serendipity."

"I'm a Black man and I was born in the wrong place with the wrong socioeconomic status. We didn't have a lot of money, and my father was in jail. That's a story that often just tells itself," he says. "So as I really look at what got me from there to here, it took being in the right place at the right time with all the right people, and not once, but again and again and again." 

Cummings was recently named the chief opportunity officer at education and coaching platform Guild, where he will focus his efforts on creating those serendipitous opportunities for members that lead to economic growth. Guild partners with major employers including Walmart, Target, Chipotle and many others to give workers access to education, coaching and upskilling. 

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While created in response to the challenges that lower-income workers have faced throughout the pandemic and the economic instability of the last year, the idea of a chief opportunity officer has been in the works since Cummings started with the team six years ago. 

Terrence Cummings, Guild's new chief opportunity officer

"Since Guild started, creating opportunity and driving economic mobility has been at the heart of what we do," Cummings says. "There has been a continuing conversation about how we take the career aspirations of our members and learners to the next level, and how we then marry that to the workforce goals of our employer partners." 

Cummings recently shared his plans for the role and what motivates him to mentor and coach others so all workers have an opportunity to excel. 

You started your own career working in restaurants and have worked your way up the ladder. How are you applying your background to the work you're doing today at Guild? 
I have a mom that had the love and strength to remove me from an abusive household and sent me to live with my aunt. She was not only my guardian but my first coach — she taught me through questions and exploration how to survive and thrive in this world as a Black man. That's a core reason why coaching is so critical to me. 

Later in life, I happened to work in a burger restaurant, and one day, I served a burger to Jim Collins, the famous business author of Good to Great and Built to Last. And through our conversations when he'd come into the restaurant, he happened to see something in me and gave me a job. He later introduced me to a leader at consulting firm McKinsey. The list goes on of these events, and I can't find a better word to describe it than serendipity. 

When I found Guild, whose mission is to connect people with talent working on the front lines, like restaurants, and to give them opportunities that help that talent rise in order to grow their careers, I just felt like, that's me. So now I think about, how do we package that serendipity for our members and learners? As a human being, it's core to me. 

The COO role is completely new for the C-Suite at Guild — what are your aspirations for what this role will accomplish for clients and employees? 
This role is looking at driving economic mobility for both our members and learners, as well as our own employees so that every single person has a clear path to the middle class. There are a number of important pillars to that — things like, having the compensation and benefits that makes you not have to be distracted by thinking about, how do I pay rent? It's making sure that there's equitable access to advancement opportunities for junior employees, as well as folks that are from more marginalized groups. 

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We'll be focusing on professional development programs that establish a baseline understanding of navigating business and developing your career, like resume writing, interviewing, networking, all those kinds of things. And coaching is big to me; when folks think about it out in the world, they think about executive coaches or leadership coaches. But the populations we serve are frontline American workers and I believe everyone in the world can benefit from having a coach. So how do we continue to evolve our coaching solution, such that it continues to evolve with the populations that we serve and matches their needs, in order for them to drive economic mobility. Those are some things I'm planning to focus on. 

The goal of economic mobility is obviously very challenging amid today's financial reality for many workers. Do you feel daunted by that? 
It's a challenging time, for sure. But I also think it's an opportunity. I believe a lot in humanity. And I believe that human beings and the systems that we end up creating are highly resilient. And so in the micro environment, day-to-day, it's very hard right now. But there will be another side to whatever we're getting through, and it's so important to invest during the challenging times and provide individuals with confidence and clarity such that they can see it within themselves to stick through it. 

From the employer standpoint, it's vital that employers invest in this area. The main reason individuals join an organization is because they see that organization as a way for them to better their lives and their family's lives. And the number one reason now that people leave an organization is because they see that promise not coming true. And so my advice is to one, recognize that, and if you want to better understand how to help that to become true, listen, and sit down and talk to folks and understand what it is that they want, what they need, and then how that maps to your own business.