In a crazy year wracked by viral pandemic, racial strife and political uncertainty, female entrepreneurs are doing what they do best: Carrying on. And thriving.
In this miniseries, EdSurge, with support of Peak State Ventures, talked with four leading female entrepreneurs all building business at the intersection of learning and working. Our first conversation is with Rachel Romer Carlson, co-founder and chief executive of Guild Education, headquartered in Denver. Carlson and Brittany Stich started Guild in 2015 to help working adults, particularly those without a high school diploma, gain education through tuition benefits from their employer. Today more than 3 million employees are eligible for Guild programs through their employers, including those at Walmart, Chipotle and the Walt Disney Company. Carlson has raised $228.5 million in funding and the company is valued at more than $1 billion. In May, Guild announced it had bought the consulting firm, Entangled, to accelerate its growth. In this first half of 2020, Guild added 200 employees, growing into a team of 700. In August, Guild placed number 23 on Inc Magazine’s list of the fastest growing private companies in the US.
EdSurge: You’ve been on an incredible journey. Given all the moving pieces, how do you prioritize what to do?
Carlson: That is the topic du jour. I would say planning within the days and the weeks has never been harder. We’re feeling the pain of that in large part because we’ve been thrown into the world of remote work. We did an acquisition in the pandemic—and we’re glad we did, but most of these people have literally never been in the same room together. Of course, Zoom works, but the power of accomplishing something with 100 people in a room and a standup—which Guild had for a long time—is really limited on Zoom. You’re down to webinars where you can’t even see your colleagues and you can’t see how they react, so it’s been hard.
What’s made planning, whether two or four or more quarters easier and why we’ve continued to be able to make big bets is because of our alignment around our mission. I know every company says and feels that. But at least for us, because we’ve been really crisp about the fact that our mission is to unlock opportunity for America’s workforce. We’ve done that to date through education, but we always knew that there might be an “&” behind that word. We’re thinking more about career services and other components that sit in and around an education and that ultimately unlock opportunity.
That’s been a really powerful north star. Sometimes “mission,” “vision” and “value” statements can feel like fixed assets that sit on the company wall. There probably were times in the past at Guild when those values just didn’t feel like they were living, breathing, pulsing. But throughout Guild right now, I’m hearing people use both the mission and the 2020 vision that we architected and slightly updated given the pandemic as guiding lights for making big bets.
We’ve got a lot of work to do. It’s harder than ever in a remote setting and in a period where we all are facing intense, well, a mix of anxiety, depression, concern, anger and frustration about what’s going on in the world. We have to step back and put on our “EQ” (emotional quotient) hats for a little bit and say: “This is hard because life is hard right now, because my family is sad, because we’re missing out on milestones and opportunities, and we miss people.”
You added 100 people with the acquisition this spring of Entangled. How do you integrate people into a deeply mission-driven environment, especially at a time like this when everyone is remote?
I don’t know how to describe it other than it takes enormous more intentionality and an enormous number of conversations.
Of our four company-wide objectives, two are more externally focused on our stakeholders and two are more internally focused on our foundations and our employees. We are doubling down on the investments internally. That’s work we want to do regardless of what happens in the economic climate and regardless of what happens on a day-to-day basis.
Even if we have, let’s call it, say, a slower quarter of growth than we might have anticipated when we were all in the bull market of January, those internal investments —in our technology and infrastructure, in our people, and in topics like diverse talent initiatives, and career paths for our employees, and in settling into being a 700-person company versus 500—those issues feel really relevant to us and really important.
What needs to change about how job placement happens?
We have the great benefit of having a window into the career paths within the companies that are our customers, so we understand which of our companies have accelerated career paths for their frontline employees who are going through Guild programs. We also understand when those don’t exist. Both are really important.
I’ll give you a unique example. The Walmarts and the Chipotles of the world have enormous opportunities for promotion. In fact, many of the folks who now lead Walmart worked in stores as team managers then as store managers. Now they’re corporate executives of the largest company in the world. The same thing is true at Chipotle. That’s because their workforce is structured such that there are lots of frontline managerial and career advancement roles.
We work with other companies in other industries, whether it’s hospitality or logistics, where there aren’t as many frontline supervisory people and project management roles. Those companies are mostly choosing to figure out how to be blunt with their employees. They’re saying things like: “Hey! We’ve got a great job for you for now that will last for two to four years—so we really want you to take advantage of this education opportunity and move on to a better job beyond our company.”
Workers really have to hear that seven to 10 times before they believe it. It sounds a little bit like, “I got you.” People are very nervous about admitting to their employer that they don’t want to be there for life. The conversations we’re having all the time involve helping workers better understand their upward paths, including their paths onward, beyond the current company. We want to help them match their academic and career goals, ambitions, and interests. That’s a conversation that just doesn’t happen in higher ed at all and rarely within corporate walls.
How does the perspective you bring as a female founder shape your leadership of Guild during this time of economic, racial and political uncertainty?
It’s always so hard to have this conversation and to avoid the platitudes. I’m not really a believer in gender platitudes, but I do believe that the experience you have had in any group of “other” — whether that’s gender, race, ethnicity, or sexual orientation — gives you a different perspective.
Perhaps the most useful perspective that I’ve brought to Guild from the beginning is the awareness that I don’t have the answers of how to match the incentives of our ecosystems. I’m just really interested in connecting the different parts. In the early days—and still today—I felt totally comfortable asking our clients: “What does it take for you to want to send your employees to school? Do we need to solve your recruitment problems or your retention issues? Do we need to solve your upskilling?”
We’ve been dynamic. We have different clients for whom we solve different problems. I don’t believe I’m an expert in any one of those problems. I just want to help their employees go back to school debt-free. I’m dogmatic about our mission, but not dogmatic about how we achieve that mission.
And here’s one more point: During this pandemic, the most crucial skill set that we can deploy as leaders is exercising empathy. A big part of empathy is being able to empathize with someone who’s going through something different than you, even though you haven’t experienced it before. I always have to work to do better on it. But if you’re a woman growing up in a man's world, you naturally build empathy skills because you see yourself and you notice differences.
At Guild, that’s manifested in trying to be incredibly supportive of our employees right now. We’ve introduced mental health benefits. We reopened our healthcare plan so that people could re-enroll into low-deductible plans. We tried to think about how to provide work-from-home reimbursements. Then we changed a lot of our company schedules to support our parents so that they didn’t have as many meeting conflicts. Changes like that have been relevant, but we also have tons of work to do on this dimension.
I think the conversations about race, equity in the United States, and injustice have opened up an incredible exercise for many companies, Guild included, to sit up and look at ourselves seriously in the mirror and say, “We’re behind on this work. We have work to do on this topic.”
How are you trying to live that practice within Guild?
In our core work—unlocking opportunity for America’s workforce—we see the clear role that education and learning play in addressing race inequity for our students. The plurality of our students identify as students of color. We’ve spent meaningful amounts of time tackling that structural inequity through our work with clients, and we will continue to do so.
What we’ve also realized is that we need to spend more time thinking about that internally. For example, without putting a lot of work into it, slightly over 60 percent of Guild’s leaders are female and 60 percent of our employees are female. That happened naturally. But I’m not proud of our numbers on racial and ethnic diversity. That’s a real wakeup call, like, “Hey, these things don’t happen because you sit back.” We need to now intentionally change the conversation about hiring from a racial and ethnic perspective within Guild and then ensure we’re continuing to create a culture of belonging for people of color.
What should entrepreneurs ask of their board and their investors to support intentional diversity?
That’s a great topic. We’ve been a participant in All Raise for a long time, mostly on the giving side. I’ve mentored a number of the All Raise seed-stage entrepreneurs. We’ve taken part in their forums.
We feel like real benefactors now because we’re a participant in All Raise’s diverse board search program: I actually talked to them today. They’re helping me do a search that’s exclusively focused on hiring our next board member from a diverse background and making sure that we do that search nationally with a really great network. Working with All Raise was suggested by one of our existing investors.
You also have to ground the tactical work in a holistic Diversity and Inclusion strategy. If you don’t have that strategy in place, you can make wrong turns even if you’re well intentioned. It’s a two-part conversation: Getting the strategy right and then putting in place the right programs, tactical choices, training and other changes that need to happen.
You have a deep political background. What should edtech entrepreneurs be thinking about as we go toward the November elections? Is there a role they should play? Should they just try to stay out of the way?
A couple of things. One, I think all entrepreneurs should care more. Silicon Valley and tech across the country has gotten away with pretending the government sector didn’t matter for too long. It’s very clear right now that the government sector matters tremendously in fields of innovation and entrepreneurship. No one wins when those two entities don’t coordinate.
In terms of very tactical approaches: Part of our conversation earlier this summer was around race inequity, along with civil discourse and protests. Sowe gave everyone at Guild five days off to volunteer for any cause that they feel is important to their values. Some Guilders are using that time for voter registration and get-out-the-vote efforts. Those can be non-partisan efforts. You’re simply giving your employees the opportunity to engage.
My politics are on my LinkedIn profile, but I do think it’s important that companies take non-partisan approaches—but just support activism. Everyone in tech should be more active in the political discourse.
We’re also giving employees time off to vote, though, hopefully we’re all voting by mail this time around. We’ve also created election forums and conversations where people can share details on local and national initiatives. But broadly, my takeaway is that tech needs to be more engaged in political discourse. We all benefit if that’s the case.
What advice do you have for other, earlier stage entrepreneurs?
I would say continue to refine and focus on your mission as your north star because that is serving me better than ever before — I’m glad we did the early work — and it’s more important than ever. Yeah, that would be my one-liner.
