Chris Powell - CEO of Talmetrix: Red Pill Moments, Going from Corporate to Startup, and Channel Partnerships

So, you know, I was in that space where I had to decide, "Do I want to stay in the familiar corporate world, or do I take the leap into entrepreneurship?" And let me tell you, it was not a straight path. It was more like taking one step forward, two steps back, feeling like, "Am I really ready for this?" And what really pushed me was, at some point, I realized that I had done so much in the corporate world that I wasn’t really growing anymore. It was comfortable, but not fulfilling.

Callan Harrington 05:35
I’m curious about this because, you know, you had a long career in the corporate world, and I mean very much corporate—you had companies like Deloitte and ING on your resume, and you worked your way up to leading human resources at Scripps Networks. Did you always know you wanted to do something entrepreneurial, but you kept getting those next big opportunities, or was the goal originally to go as high as you could up the corporate ladder?

Chris Powell 06:32
That's a great question. You know, when I look back, I think it was a mix of both. While I was matriculating through corporate America, I was also intrigued by entrepreneurship. My first real entrepreneurial venture was actually with my brother and his wife. They asked me to help them start a real estate development firm in Chicago. So, I was still working my corporate job but side-hustling with them on the venture. I loved the freedom of entrepreneurship—the idea that my direct efforts were impacting the business. But, at the same time, there was the comfort of the corporate gig: nice salary, benefits, stability, the whole nine yards.

But what I learned from that experience with my brother and his wife was that while I enjoyed building something from the ground up, the vision wasn’t mine. It was theirs. And that made me realize that if I was going to do this, I wanted to be building something I was truly passionate about.

Callan Harrington 08:25
So, you got a taste of entrepreneurship but decided to return to the corporate world to keep climbing. What was the moment that pushed you to take that final leap into full-time entrepreneurship?

Chris Powell 08:49
Yeah, after that venture with my brother, I made the conscious decision to go back to corporate and see how far I could climb. But, in the back of my mind, I was always saving for that "one day" when I could make the leap for good. I wanted to save enough capital to take a bigger swing, to go all in without worrying about stability for a while.

But then, about four years into it, I hit another decision point. I was being recruited for some major HR jobs with Fortune 200 companies, including big-name sports organizations. At the same time, I was also talking to this early-stage HR tech company, Talmetrix, which had caught my attention because it aligned more with my passion for data and employee insights. I found myself sitting in interviews for these corporate roles, thinking, “Do I really want to keep climbing this ladder?” I realized I was hearing the same corporate talk—what I call "Charlie Brown conversations"—womp, womp, womp—and it wasn’t exciting me anymore. That’s when I knew it was time to take the leap.

Callan Harrington 09:05
I can imagine that must have been a tough decision, especially since you'd worked your way up to leading HR for these massive companies. Did you have moments where you thought, “Maybe I should just stick with this?”

Chris Powell 09:05
Absolutely! It wasn’t easy, especially when I had job offers in front of me that would have been a “nice life.” But what I realized was that I wasn’t excited about those opportunities. And when you're not excited, you’re not going to be fully engaged. That’s when the entrepreneurial bug really bit me. It was about impact. I wanted to be somewhere I could see the direct results of my work, where my efforts were tied to real, tangible outcomes.

Callan Harrington 10:33
That’s really insightful. So, when you did make the leap to Talmetrix, were there any moments in the early days where you thought, "What did I get myself into?"

Chris Powell 10:52
(Laughs) Oh, on day two, I had one of those moments! We were trying to set me up on the company’s email platform, and back then, Google Workspace was just starting to gain traction. I’m sitting there as the former head of HR from a major corporation, and I couldn’t even get my email set up! I was like, “Okay, there’s no one to call but me. I guess I’m the IT guy now.” It was a humbling moment, but it was also a reality check.

There were many moments like that early on where I had to remind myself, “You’re in startup mode now, Chris. Roll up your sleeves.” It took me about five years to fully detox from the corporate mindset. I had to relearn how to engage and operate in a lean, scrappy environment.

Callan Harrington 11:40
That’s fascinating. What were some of those key things you had to unlearn coming from a corporate environment?

Chris Powell 11:43
One of the first things was understanding that even though I was delegating tasks, I still had to be accountable in a very hands-on way. In corporate, you delegate, and you trust that there’s a whole team to support the execution. In a startup, the team is you and a few other people. Even if I delegated something, I couldn’t just step away. I had to be right there, checking in, rolling up my sleeves, and helping out.

Another big shift was the realization that there wasn’t always enough money for everything. In corporate, there’s usually a cushion. You’re working with big budgets, and if something goes over, it’s not the end of the world. But in a startup, when it’s time to run payroll and you realize the money isn’t there, that’s a different level of stress. It really forces you to be resourceful and scrappy.

Callan Harrington 13:19
Were there ever moments when you thought, “Maybe I should go back to the corporate world?”

Chris Powell 13:30
Oh, for sure! About four years into it, I seriously considered going back. We were trying to hit that growth curve that everyone talks about, and things weren’t moving as quickly as I had hoped. I had friends who were still in the corporate world, living nice lives—traveling, no big worries about payroll or cash flow. It was tempting, especially when you're grinding day in and day out and not seeing immediate results.

I even took an interview with a company. It was a great position, a senior HR business partner role for one of their divisions. But halfway through the interview process, I realized, “I can’t go back. This isn’t me anymore.” That was the turning point where I fully committed to entrepreneurship. I knew that I could bring my whole self to the work I was doing in a way that I never could in corporate. That realization made all the difference.

Callan Harrington 14:12
I love that. It’s really powerful, especially because it’s such a personal realization. You had to step back and say, “This isn’t just about the job or the money—it’s about being able to fully express myself in the work I do.” What was the impact of that turning point for you? Did it change how you approached your business?

Chris Powell 14:15
It absolutely did. After that interview, I had this moment of clarity. I realized that my highest and best use was in entrepreneurship, specifically in the HR tech and employee insights space, where I could create real value not just for myself but for the clients and teams I worked with. I also recognized that the work I was doing at Talmetrix had the potential to make a much bigger impact than I could ever make in a singular corporate role. That was a big shift in mindset for me.

The other defining moment came during COVID. The pandemic was a huge test for all of us, personally and professionally, and navigating that as a leader was challenging. We had to make tough decisions, including cutting some positions, which was emotionally hard because I’m incredibly loyal to my team. But it reminded me that leadership isn’t just about making the logical decisions; it’s about leading with heart, especially in tough times. That was another reminder that I was in the right place because I had the opportunity to lead with empathy while making strategic decisions that would sustain the business.

Callan Harrington 15:09
COVID was such a pivotal time for a lot of businesses. How did it specifically impact Talmetrix, and what were the lessons you took from that experience?

Chris Powell 15:19
COVID definitely shifted the way businesses thought about their workforce, especially around remote work, well-being, and employee engagement. For us at Talmetrix, it was an eye-opener. Our revenue took a hit, but we still had enough business coming in to sustain us. However, like many companies, we had to make cuts, which was tough. But in making those decisions, I had to remind myself of our core mission—to humanize data and further workplace well-being. That mission became even more relevant during the pandemic, as organizations struggled to understand and support their employees in an entirely new context.

As a leader, I had to learn how to navigate those emotional challenges while also staying focused on the long-term goals of the business. It was a reminder that people matter—how you treat them in both the good and the tough times matters. And the pandemic pushed me to find ways to keep the business sustainable while staying true to our mission.

Callan Harrington 16:07
That’s a great insight, especially around the human side of business. One thing I’ve noticed is that people who’ve had corporate experience often bring a unique perspective to startups, especially when it comes to scaling. Did your corporate experience help prepare you for moments like that, where tough decisions had to be made?

Chris Powell 16:23
Definitely. Coming from the corporate world, I was used to working with large budgets and making big decisions, especially in HR. When you’re managing people, budgets, and operations at scale, you develop a certain level of preparedness. But even with that experience, I wasn’t fully resourced to handle the early challenges of startup life.

In the corporate world, I was managing an operating budget of about $130-$140 million a year. But when you’re in a startup, you're not dealing with those kinds of numbers. You have to make things work with much smaller resources. So, yes, my corporate experience helped me understand the processes, but I had to adapt those lessons for a leaner environment. That’s the unlearning I had to do—realizing that not everything from a big company applies to a small, growing business. You have to scale ideas appropriately for where your business is at in its growth journey.

Callan Harrington 17:23
That’s really insightful, especially the part about scaling ideas for the size of the company. You mentioned earlier that you had to unlearn some things from corporate. What were some of the specific examples of those lessons?

Chris Powell 17:33
One of the biggest lessons I had to unlearn was how to delegate in a small organization. In corporate, you can delegate tasks to a team and trust that everything will get done because you have the resources. But in a startup, delegation still requires accountability. Even when you delegate, you’re still very much involved because the team is so small. You have to learn how to balance hands-on work with leadership.

Another example is around process complexity. In big organizations, you have more complex systems and processes because you're managing large teams, multiple departments, and sometimes even global operations. But in a startup, if you try to apply those same complex processes, you’ll choke the organization. You need to streamline and simplify while still keeping things efficient. For example, sales methodologies like MEDDIC are great for large enterprises, but they have to be adjusted for smaller companies so that you don’t overwhelm the system with unnecessary complexity.

Callan Harrington 18:15
That makes a lot of sense. Knowing when to scale down complex processes and focus on what matters most is key. You’ve mentioned that you help organizations with employee data and insights. How do you keep a pulse on what’s happening both inside and outside of organizations?

Chris Powell 18:24
We’re fortunate to work with a diverse range of organizations across different industries, both in the U.S. and globally, which gives us a great learning environment. We actively listen to our clients to understand what’s going on with their workforce and use that data to help them make informed decisions. Our platform allows us to gather employee feedback, but we also look at external factors to see how they might be influencing workplace behaviors.

I’m also a voracious reader. I consume a lot of content to stay on top of trends, whether it’s from business journals, research papers, or industry reports. One of the biggest changes we’ve seen is the compression of time when it comes to trends. Things that used to take years to reach other parts of the world are now happening almost instantaneously. So we have to stay agile, constantly learning and adjusting our approach based on the data we’re seeing. Finding the signal in the noise has become more challenging, but it’s also more important than ever.

Callan Harrington 19:33
Finding the signal in the noise can definitely be tough. How do you approach that with your clients? How do you help them filter out the noise and focus on what matters?

Chris Powell 19:43
It’s all about measuring what matters. The first step is always clarifying the organization’s mission or objectives. What do they need to achieve, and what data will help them get there? Once we’re clear on that, we set up various beacons to collect the data—whether that’s employee surveys, customer feedback, operational data, or other key metrics. The idea is to get a holistic view of the organization, not just rely on one source of data.

A lot of companies limit themselves by only collecting data from a single point, which can lead to blind spots. By collecting data from multiple sources—employee feedback, operational performance, customer satisfaction, etc.—we can create a more complete picture of what’s really happening. It’s like putting all the pieces of a puzzle together.

One example was when we worked with a hotel management company. We combined employee survey data with guest satisfaction scores, revenue performance, and even time and attendance data. By looking at all those data points together, we could see correlations that we wouldn’t have noticed if we’d only looked at employee feedback alone. That’s the power of having multiple beacons in place.

Callan Harrington 21:06
That’s such a smart approach, especially when you’re validating what employees are telling you with other data points. Did you start as a pure software company and evolve into a hybrid of software and services?

Chris Powell 21:21
We started as more of a pure software company, but over time we evolved into a hybrid of software and services. What we realized was that we were losing the race on software features and benefits alone. There are always new competitors coming into the space with the latest technology. But what kept our clients loyal was the fact that we weren’t just providing software—we were a strategic partner. We helped them interpret the data and apply it to their business in a meaningful way. So now, we’ve shifted to being more service with tech, rather than tech with light service. That’s been a big part of our success.

Callan Harrington 22:00
That’s really interesting because so many companies, especially in software, push for automation and self-service to increase margins. But what you’ve found is that adding services has actually been a big advantage. What impact has that shift had on your business?

Chris Powell 22:15
The shift to adding services has been a game-changer for us, especially when it comes to client retention and growth. The truth is, especially for mid-market and larger enterprise clients, they’re not just looking for software that spits out data—they want a partner who can help them make sense of that data and apply it to real-world challenges.

What we found is that offering services—whether that’s data interpretation, consulting, or helping to build a strategy around employee insights—has allowed us to deepen our relationships with clients. It makes us stickier because we’re providing value beyond the software itself. And that value-add is something that can’t be easily replicated by competitors who are purely focused on features and automation.

We’ve seen this especially with our larger clients. When you’re dealing with an organization that has thousands of employees, they often have internal teams that handle HR and data analytics, but they still come to us for our expertise and the strategic insights we can offer. That’s something you can’t replace with just software.

Callan Harrington 23:15
That makes a lot of sense. And I think a lot of software companies are starting to realize that you can improve client success and retention by offering more tailored services. Speaking of retention, you mentioned earlier about channel partnerships. How have those partnerships played a role in your growth?

Chris Powell 23:30
Channel partnerships have been crucial for us. In fact, I would say they’ve been one of the biggest unlocks in our growth. When you’re a smaller company, partnerships can extend your reach and give you access to new clients that you might not have been able to engage on your own. What’s been really powerful for us is partnering with boutique consulting firms and other service providers that don’t have the same measurement and insights capabilities that we offer.

These partnerships are often collaborative. The consulting firms are in there, working closely with boards and C-suite leaders to shape strategy, and we come in to provide the data and insights that inform that strategy. It’s a win-win because we get to work on really interesting projects, and at the same time, we’re expanding our market reach.

One of the things we’ve also realized is that these partnerships have allowed us to innovate. When we’re working on bespoke projects with partners, we learn a lot. We experiment with new measurement models or new approaches, and some of that innovation trickles down into our broader offerings, especially for the mid-market clients who may not have the resources to do that kind of innovation on their own. So, the partnerships have been instrumental not only for growth but also for driving innovation within our company.

Callan Harrington 24:43
I love that. Channel partnerships can be tricky, though. What advice would you give to companies that are looking to maximize their partnerships? How do you make sure those relationships work well?

Chris Powell 24:54
You’re absolutely right—partnerships can be tricky, and they definitely take work to get right. I always tell people that partnerships are like dating. It’s not about swiping left or right and hoping for the best—it’s about finding partners that align with your values and philosophy.

For us, it’s critical that our partners share a similar belief in the importance of people and the human side of business. If we’re working with a partner that’s purely focused on profit and efficiency without regard for people, that’s not going to be a good fit for us. We look for partners who are philosophically aligned with us in terms of being human-centric and believing in the potential of individuals within organizations.

The other thing is that communication is key. We make sure that we’re constantly in sync with our partners, whether it’s through regular check-ins, shared goals, or even joint planning sessions. The more you communicate, the easier it is to stay aligned and ensure that both sides are getting what they need from the partnership.

Lastly, it’s important to be flexible. Every partnership is different, and you have to be willing to adapt depending on the needs of the partner. Sometimes that means playing a bigger role in certain projects, and other times it means stepping back. Being flexible and open to adjusting your approach is key to making partnerships work in the long run.

Callan Harrington 26:00
That’s such great advice, especially about the philosophical alignment. It sounds like you’ve built something really special at Talmetrix over the past decade. What’s next for you? What are you looking forward to in the future?

Chris Powell 26:15
For me, the goal now is to continue creating and contributing, but with a little more balance. I’ve been with Talmetrix for over 10 years, and it’s been an amazing journey. But I also want to make sure that I’m finding time for other passions in life. I have this goal I call the “three by three by nine” plan, which is about working three days a week, three weeks a month, nine months a year. That way, I can still contribute and stay involved in the business world, but also have time to learn new things and give back to the community.

For example, I’ve always wanted to learn to play the piano, so that’s something I’m going to focus on. I also want to spend more time doing community work, whether that’s mentoring young entrepreneurs or contributing to causes that I’m passionate about. So, it’s about striking that balance—continuing to contribute in the business world, but also making space for personal growth and giving back.

Callan Harrington 27:04
I love that plan! It’s so important to find that balance, especially after you’ve spent years building something. Last question for you, Chris: If you could go back and have a conversation with your younger self, what advice would you give?

Chris Powell 27:20
I would tell my younger self to take the blue pill more often! (Laughs) Seriously though, I’d say, “Take more risks. You’re going to be okay. In fact, you’re going to be more than okay—you’re going to be great.” It took me a while to realize that it’s the moments when you take the biggest leaps that lead to the most growth, both personally and professionally. So, I’d encourage my younger self to lean into the uncertainty and trust that it will all work out in the end.

Callan Harrington 27:50
I couldn’t agree more with that! Taking those risks early can lead to so many great opportunities. Chris, thank you so much for this conversation. I really enjoyed it.

Chris Powell 28:00
Same here, Callan. Thank you for having me. It was a great discussion.

Callan Harrington 28:05
Absolutely! And to our listeners, I hope you enjoyed this conversation with Chris Powell. If you want to learn more about Chris, you can find him on LinkedIn, and we’ll also include links in the show notes. If you liked this episode, feel free to connect with me on LinkedIn as well, and if you really want to support the show, a review on Apple Podcasts or Spotify is always appreciated. Thanks for listening, and we’ll see you next week!

Chris Powell 28:20
Thanks again, Callan! Looking forward to seeing how this conversation resonates with your listeners. It’s always a pleasure sharing these experiences, and I hope some of the lessons I’ve learned can help others on their own entrepreneurial journey.

Callan Harrington 28:30
I’m sure it will, Chris. The insights you shared, especially about navigating the leap from corporate life to entrepreneurship and the importance of building meaningful partnerships, are invaluable. And I think a lot of our listeners will appreciate hearing about how you’ve managed to blend technology with a people-first approach—that’s something that’s becoming more important in today’s business landscape.

Chris Powell 28:45
Absolutely. People are at the core of every business, and the more we can do to keep that focus, the more successful we’ll be. Whether you’re building software or providing services, it all comes down to how you treat your team, your clients, and the people around you.

Callan Harrington 28:55
Well said. Well, I won’t take any more of your time, Chris. It’s been a real pleasure, and I’m sure we’ll be keeping in touch as you continue your journey with Talmetrix—and maybe when you’re down to your "three by three by nine" plan, we’ll have you back on the show to hear how it’s going!

Chris Powell 29:10
(Laughs) I’d love that, Callan. I’ll let you know how the piano lessons are going, too!

Callan Harrington 29:15
Perfect! Thanks again, Chris. Take care.

Chris Powell 29:18
You too!

Callan Harrington 29:20
And to all of you listening, thanks for tuning in to this episode of That Worked. Be sure to check out the show notes to connect with Chris and to learn more about Talmetrix. And, as always, if you enjoyed the episode, drop us a review on Apple Podcasts or Spotify—it really helps the show. Thanks for listening, and we’ll catch you next week!