Kelsey Bishop Of Candor On How To Use Digital Transformation To Take Your Company To The Next Level

An Interview With Cynthia Corsetti

Strong company culture even while remote. One of the biggest “costs” of remote work and leaning into the new digital world is the impact it can have on your culture. However, if you can really lean into technology and processes around recognition, feedback, 1-on-1 meetings, and asynchronous check-ins, I think your culture can be more intentional and even stronger than it was in person.

Digital transformation has become a crucial component for businesses striving to stay competitive and relevant in today’s rapidly evolving landscape. As technology continues to shape industries and redefine business models, companies must adapt and leverage digital tools and strategies to unlock new opportunities for growth and innovation. In this interview series, we aim to explore various aspects of digital transformation, including best practices, challenges, success stories, and expert insights. We are talking to thought leaders, industry experts, entrepreneurs, technology innovators, and executives who have firsthand experience in driving digital transformation initiatives within their organizations. As part of this series, we had the pleasure of interviewing Kelsey Bishop.

Kelsey is the Founder and CEO of Candor, the culture platform for modern teams. Kelsey leads a remote team of 10 and has raised $5M from Afore Capital, Contrary Capital, and others.

Thank you so much for joining us in this interview series. Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I was first exposed to the startup industry in college, when one of my classmates started a company called Campus Insights. I led Sales for Campus Insights for two years before we sold the business to Harvard. I was hooked on startups at that point — I loved the high impact, fast paced nature of the work. So, I decided to move out to San Francisco to work at a venture-backed startup.

I worked in early stage Growth and Operations for a few years across different industries and found that my experience would vary based on the company’s culture. In some teams, I thrived and in others, I didn’t. I realized that company culture has the biggest impact on my happiness at work.

With this realization, I started working on Candor. Today, we help hundreds of teams connect and engage their employees through our platform for shoutouts, check-ins, and feedback.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

I’ve made so many mistakes on my journey, but I think the biggest (though I’m not sure if it’s particularly funny) has been mishiring. I hired too quickly in the beginning of Candor and it led to some painful corrections to part ways with folks. After these first hires, we started doing something called a “mutual assessment” which is a work trial we do with folks before offering them a full time role.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful for who helped get you to where you are? Can you share a story?

So many! I’d have to say Felix Lau, who was the first person to join the Candor team. He took a huge bet on us — forgoing a salary and just taking equity — and he has spearheaded every iteration of Candor since day 1 as our designer.

It’s rare to work with someone who takes so much ownership and accountability of a product, but Felix has been able to do that for us. We’ve never lived in the same city, but find a way to meet up every couple months somewhere in the world.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

I re-read the Alchemist once a year and always get something new from it. My favorite concept from the book is that “the universe is conspiring to help you achieve what you want.”

I think this is the crux of building a startup and creating something new in the world. It feels like you’re pushing a ball uphill when you create something new, but when it’s something that should exist and that people want, the universe helps you find a way to make it happen.

Are you working on any new, exciting projects now? How do you think that might help people?

We’re working on a new feature for teammate celebrations, specifically, work anniversaries and birthdays. Candor currently helps teammates give each other shoutout and recognition for work, so our celebrations feature will be a natural extension of that. We believe that so many of the “small moments” are easy to get right with a little intentionality, which is what we’re helping teams with. Never forget a teammates’ birthday again!

Thank you for all that. Let’s now turn to the main focus of our discussion about Digital Transformation. Digital transformation can mean many things to many people, from your perspective, how do you define digital transformation in your industry?

Digital transformation is being able to build your company in a remote-first world. After the pandemic, we realized that not every team or every organization needs to be in person to be effective. Digital transformation is the method by which companies effectively make the transition to this new digital-first world.

Which companies can most benefit from a Digital Transformation?

Most companies will need to undergo a digital transformation if they want to attract young or international talent. Young talent, especially Gen Z and Millennials, expect that companies they work for can effectively work remotely, since they value flexibility in their work environment. Companies who want to recruit talented and less expensive international talent will also need to adapt to the new digital world to effectively work with teammates abroad.

Has integrating Digital Transformation been a challenging process for some companies? What are the challenges? How do you help resolve them?

Change is hard, especially for larger and more mature companies. Switching software can be complex and training managers to be effective while remote is tough.

That said, companies can lean into new software that encourages more asynchronous workflows, like Notion, Figma, and Candor. Companies can also consider hiring coaches for their managers who can help adopt new ways of working.

Based on your experience and success, what are “Five Ways a Company Can Use Digital Transformation To Take It To The Next Level”?

1 . Strong company culture even while remote. One of the biggest “costs” of remote work and leaning into the new digital world is the impact it can have on your culture. However, if you can really lean into technology and processes around recognition, feedback, 1-on-1 meetings, and asynchronous check-ins, I think your culture can be more intentional and even stronger than it was in person.

2 . Recruit international talent. Recruiting internationally can have massive benefits to companies — lower cost talent with the same (or higher) talent bar can be a game changer for companies. If you can figure out the right way to make your company natively-online, you’ll be able to more effectively work with talented engineers in India, Europe, or elsewhere. Our team at Candor has teammates across 7 different countries at the moment.

3 . Asynchronous communication for more productive employees. Migrating to a digital-first way of working doesn’t mean you have to spend all day on Zoom. In fact, employees can be even more productive if you adopt asynchronous ways of communicating, like on Slack, Notion, or Figma. Employees can feel free to work on their own schedule and have more time to do tasks than if they were sitting in meetings or getting distracted in an office.

4 . Cut costs by removing the need for an office. Companies don’t need massive offices with expensive leases in New York City or San Francisco. Consider reallocating the office budget back into R&D or into hiring more talent.

5 . Attract the next generation of leaders and employees. Gen Z and Millenials will expect a company to be digitally-savvy. The companies of tomorrow will be able to keep up with the demands of the next generations of employees. These generations look for companies that can provide flexibility and a more forward-thinking culture.

In your opinion, how can companies best create a “culture of innovation” in order to create new competitive advantages?

Creating a culture of innovation is all about fostering an environment where curiosity, experimentation, and constructive failure are embraced. Here are a few ideas:

  • Empowerment: Empower employees at all levels to share their ideas and take initiative. When people feel their contributions can make a difference, they’re more likely to innovate.
  • Safe to Fail: Establish a culture where failure is seen as a stepping stone to innovation. This means celebrating the learnings from failures, not just the successes.
  • Cross-Functional Collaboration: Break down silos between departments to encourage new perspectives and solutions that might not emerge within homogenous teams.

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

Winston Churchill said, “Success is not final, failure is not fatal: It is the courage to continue that counts.” Building Candor hasn’t been a straight line. There are always moments of doubt and failure, but embracing this mindset helped remember that it’s about the journey and not the destination.

How can our readers further follow your work?

By signing up for Candor at or following me on LinkedIn.

Thank you so much for sharing these important insights. We wish you continued success and good health!

About the Interviewer: Cynthia Corsetti is an esteemed executive coach with over two decades in corporate leadership and 11 years in executive coaching. Author of the upcoming book, “Dark Drivers,” she guides high-performing professionals and Fortune 500 firms to recognize and manage underlying influences affecting their leadership. Beyond individual coaching, Cynthia offers a 6-month executive transition program and partners with organizations to nurture the next wave of leadership excellence.