10x growth in just 5 years at Carta: the strategic HR lessons learned

Managing change and growth is a table-stakes capability for any HR leader today. However, overseeing the people function at an organization whose workforce grew 10-fold in just five years demands strategic steps on everything from agility to humility, and an ongoing willingness to put people at the center of business strategy.

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That’s what Paige Bailey brings to the table as chief people officer of Carta, a software company that helps organizations manage capitalization tables and valuation. The San Francisco-based business has seen rapid growth in recent years, and, with 30,000 companies now relying on the software, had to quickly dial up hiring. But, says Bailey—who joined Carta in 2018 after holding HR positions at InsideSales and One on One Marketing—the expansion hasn’t put any distance between Carta’s business strategy and its culture. That could be why 90% of employees say they’re proud to work at the company.

Bailey recently spoke with HRE about the work that’s behind that statistic.

HRE: During your tenure with Carta, the workforce has grown from 200 to nearly 2,000 employees. How have you had to shift your approach to leadership to keep up with that growth?

Paige Bailey, Carta; Rapid growth at Carta: strategic HR lessons learned
Paige Bailey, Carta

Bailey: What works for 200 employees doesn’t work for 2,000. The first thing we had to do was quickly create new systems, tools and processes that could grow with us. Today, that experience is a reminder to think proactively, instead of reactively. This kind of mentality helps to get you out of the weeds, too.

I also found that the smaller a company, the easier it is to dive in deep and be really hands-on with employees individually. The work is more tactical than strategic. As a company grows, there’s a necessary shift for all leaders—to be more strategic than tactical. You move from “get the right people in seats, and do it fast” to “recruit, retain and hire against a long-term growth plan.”

As for what that means for my own leadership, it’s about balance. I have to make sure I’m being thoughtful about scaling our now-global headcount—and at the same time making sure that I’m not losing touch with people’s personal experiences at Carta. The work shifts to be more strategic, but that doesn’t mean we can forget about the benefits of those early-on deep dives with our people.

HRE: How does an organization like Carta, which is undergoing such rapid growth, ensure employees stay connected to its culture?

Bailey: Carta wouldn’t be the company it is today without our culture and our values. These elements got us off the ground, kept us focused and helped us recruit and retain the best talent. It’s deeply important to me and the rest of our executive team that our people feel connected to that culture, no matter how much we grow. We want Carta to be a place where everyone can be the best versions of themselves.

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Staying connected to our culture means, first and foremost, staying connected with one another. We come together often as a company, through a weekly, companywide Show and Tell (where we showcase new projects) and a weekly town hall (an open forum with our CEO Henry Ward). Every quarter, we have a companywide hackathon, and the ideas from the hackathon have even resulted in new features for our products.

But it’s more than just meetings. Our values show up in our work—in the solutions we build for our customers, the events we host, the policy work we do. One of our primary values is ownership—acting like an owner. Everything we do is deeply connected to creating more equity owners in the world and helping people understand and benefit from that ownership.

See also: How TruGreen grew its talent strategy to meet a 500% increase in hiring demand

HRE: How has Carta evolved its approach to career development, particularly by leveraging coaching?

Bailey: Our perspective on career development is rooted in what we call “mountain jumping.” Most people focus so much on climbing one specific career mountain in their lifetimes, that they may not stop to explore other mountains accessible to them along the climb.

We want to give our people the chance to pause and ask themselves if there are other peaks they’d like to pursue. We even have a Slack channel called #open-role-market, where we highlight open roles available at Carta and encourage our own people to apply.

Our Cartan2Cartan program is one that I especially love; it’s our peer learning program that helps us make sure that all Cartans continue learning from one another. We’ve also used BetterUp for 1:1 coaching and on-demand specialists for our employees since 2020. Since using the BetterUp platform, Carta employees have seen a 36% increase in goal attainment; a 32% increase in stress management; a 25% increase in work/life balance; and a 25% increase in self-compassion. From navigating difficult conversations during times of economic uncertainty and social unrest to staying healthy throughout a pandemic, dedicated coaching has been a critical resource for Carta’s workforce.

And finally, we encourage micro-mentor relationships at Carta and we’re moving to a continuous feedback model, using a sophisticated tool to institutionalize some of the career growth activities and habits we’ve cultivated at Carta.

HRE: What has the response from employees been like to those strategic HR efforts?

Bailey: The response to all our coaching and development programs has been overwhelmingly positive. They see it as a signal that Carta is committed to investing in our people. In fact, people have enjoyed their experience with BetterUp so much that we’ve had requests to extend BetterUp coaching engagements beyond the end of the program.

Also see: Gifting to employees? Consider offering them your gratitude

HRE: In what other ways is Carta looking to strengthen its investment in employees and enhance retention?

Bailey: Retention is a North Star for our people team. But we want to enhance retention in a meaningful way. That starts by understanding the employee journey at Carta. Why do people work here? What makes them proud of the work they do? When do they feel most motivated?

We need to deeply understand what our people want and need from Carta in order to make sure they stay engaged with their work and, ultimately, stay at Carta. From there, we can create an experience with unique benefits, perks and practices that feel personal to Cartans.

We’re also removing friction in the Cartan experience so that they can focus on their work. That means shortening the onramp for new hires and making our people processes easy and clear to navigate.

HRE: What are the competencies you had to develop as a modern HR leader that, when you first got started in the profession, you may not have had?

Bailey: When I first started, I was focused almost exclusively on relationship-building and solving the problems that were right in front of me. As I continued in my career, I realized in order to be an effective HR leader in today’s ever-changing environment, I needed to develop additional competencies.

The three that proved most valuable were learning to work with data, building organizational influence and coaching my direct reports. Each of these competencies helped me plan strategically, and then gain buy-in from other leaders across the organization to execute against those plans.

HRE: Outside of work, what keeps you motivated?

Bailey: My kids are my biggest motivation. Being a mom to two young children has given me new perspectives, and I love experiencing life through their eyes.

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Jen Colletta
Jen Colletta is managing editor at HRE. She earned bachelor's and master's degrees in writing from La Salle University in Philadelphia and spent 10 years as a newspaper reporter and editor before joining HRE. She can be reached at [email protected].