Founder & Executive: On Collaboration & Passing a Mission-Driven Company to New Leadership

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Jessica Tien

Content Marketing Manager, Foothold Technology

Nov 18, 2021

Radicle Health acquires mission critical human services software companies. These companies are often founder owned and operated, so providing flexibility for founders is a core part of Radicle’s strategy.

Different founders care about different things, so a one size fits all approach doesn’t typically work. When selling their business, some founders are seeking retirement, while some are not. Some founders are looking to shift their personal role in the business, while some want to keep doing what they’re doing.

In any of these situations, Radicle will supplement the founder’s leadership team with an executive from ASG’s (Radicle’s capital partner) Executive in Residence program.  This person’s specific role will depend on the unique circumstances of the business, as well as the founder’s short-term and long-term objectives. But in all cases, their primary goal will be to leverage their fresh perspective to help the business grow and to help the team.  

Foothold is a great case study for this model in action.

Marlowe Greenberg (Founder of Foothold Technology) and Tyler Hoffman (CEO of Foothold Technology and former member of ASG’s Executive in Residence program) talk candidly about their relationship, collaborating effectively, and the hard work of passing a mission-driven company over from its founder to new leadership. 

When you were thinking about selling the company, why did you feel most comfortable working with Radicle compared to other firms that were interested? 

Marlowe Greenberg (Founder): Most of the investors talked a lot about the things they do and why they were great. But Radicle was different — they had recently bought another behavioral health software company and they were trying to figure this industry out. I really liked that level of humility — which was totally unusual, in my experience, especially relative to other investing firms. 

Tyler, you moved through a couple of different roles at Foothold before taking on the CEO position. How did this gradual transition into the CEO role work out? 

Tyler Hoffman (CEO): What the gradual transition gave me was time. And I needed that time to build people’s trust. In a company like this one — very mission-driven, with a strong culture and many long-tenured employees — anyone coming in on the heels of an acquisition is going to find it challenging to build trust. 

I needed time to demonstrate to people that I was acting in their best interests. That wasn’t going to happen overnight. I needed time to prove myself, but also to show that I wasn’t going to have all the answers right away. 

Marlowe: We talked about this all the time. There was authenticity in the fact that he didn’t know very much about the industry but was so open to learning. You can’t teach that kind of humility. 

How did you manage to make decisions together, especially if you didn’t always agree on the way forward? 

Tyler: Marlowe played a huge part in this. He needed to be comfortable sitting on the sidelines of conversations he used to lead, because if he didn’t, I wouldn’t have been able to find my voice as a leader. It takes a special person to do that. I always felt like Marlowe’s primary goal was to set me and Foothold up for success, even if it was hard for him at times.

As far as decision-making goes, we were often on the same page about the “what.” We were not always on the same page on the “how.” We have very different styles — like, polar opposite. 

But what played to our advantage was, again, operating from a place of humility and open communication. We speak very directly with each other, especially when we disagree. That ability to speak honestly with each other — especially about the hard stuff — is key. 

Marlowe: In the end, it’s just a dance — you ultimately decide, what is the right answer, regardless of who it came from? You need to compromise. 

As the founder, what has this partnership allowed you to take off your plate? What have you been able to focus more of your energy on?

Marlowe: I no longer need to spend time pursuing accounts receivable and managing all the government, tax, and regulatory issues that come with owning a business. Also, team management and customer relations has been taken off my plate. 

Now, I spend most of my time being strategic and forward-looking: thinking about long-term strategy, finding opportunities for product development across the Radicle portfolio, and looking for other cutting-edge companies to partner with. 

How did you hand off day-to-day responsibilities from founder to incoming CEO? 

Tyler: My original directive was to jump in and help out the business and team however I could, in collaboration with Marlowe. Over the next 12-18 months, I took on more responsibility and Marlowe pulled out of the areas that he was less interested in. We both naturally gravitated towards the areas that aligned with the business’s needs. 

In terms of the actual process, it looked different for different buckets of transition items, but generally it followed some version of the following process: at first, I would be in the background and Marlowe would lead. Then, Marlowe would lead and I would support. Then, I would lead and Marlowe would support. Eventually, I would do it without Marlowe, but he’d be available to support if I ever needed him. This phased approach worked well, for the most part. 

Then there’s a slightly more nuanced point about how Marlowe was showing up, though, even if he was in the background. Sometimes, just his presence in a room (or in a Zoom) would interfere with my ability to act as the CEO. Naturally, many people still saw him as the leader of the company, and that sometimes made it hard for me to lead effectively. So in certain situations, I’d ask Marlowe to sit it out, even if it felt weird for him not to be involved. We would have candid conversations about that, and over time we figured out which conversations it made sense for Marlowe to be included in, and which ones did not.

How has your collaboration style evolved over time? 

Tyler: We have very difficult working styles. But at this point, I’m not trying to make Marlowe a replica of me, and vice versa. I do everything I can to honor Marlowe’s working style and he does the same for me. 

Marlowe: To add on to that, we’ve stopped trying to change each other. But we do take what’s good about each of our working styles and we encourage each other to do those things. We’ve continued to support and coach each other — about deadlines, communication style, those kinds of things. 

What advice do you have for other founders and executives that are partnering with founders? 

Marlowe: Ego is not going to help you. Being able to admit when you’re wrong and being able to hear honest feedback about your business — these are crucial.

Tyler: Naively, coming into this, I thought I just had to be “nice” to Marlowe to win him over. It’s so much more than that, though. It’s much more about being authentic. 

With all the founders I’ve worked with (not just Marlowe), just being myself – the good, the bad, and the ugly – was the best recipe for success. Focusing on showing up as yourself will make everything else a lot easier, particularly when you need to navigate complicated situations with no straightforward answers. 

As a founder, what is the best thing to come out of this transition?

Marlowe: The business has really benefited from the rigor that Radicle has brought here, without losing the aspects that made it such a great place to work. There is much more rationale and process in our decision making as a company. 

On a personal level, there was a lot of freedom coming out of it. Now, there’s more space and flexibility in thinking about what I want to do and spend my time on. There’s time to think about the big questions, such as: what markets should we focus on, what features could we build that would transform how our customers work, and who should we partner with to develop that functionality? 

What advice would you give to other founders who may be looking for a partner? 

Marlowe: Do your due diligence on potential acquisition partners, and take it seriously. Once you hand over ownership, the business isn’t yours anymore. Sounds obvious, but founders don’t always think through the reality of this concept fully. 

But most importantly, you must find a partner you trust to treat your employees like humans, and your customers like gold.

Let’s help the organizations our communities depend on.

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