The following interview is a conversation we had with David Wald, President of Aclaimant, on our podcast Category Visionaries. You can view the full episode here: $30 Million Raised to Build the Future of Active Risk Management

David Wald
Thanks for having me, Brett. 

Brett
Not a problem. I’d love to begin with some big news that I just read on LinkedIn yesterday. So talk to us about the big news that came out.

David Wald
Yes, we have been super fortunate to be in a position to bring in just an incredible talent to our organization. So Kathy Burns, we announced yesterday as our new CEO, with me continuing on as president and Co-Founder, and she was one of the pioneers of the space that we’re in. We’re in a category called Remus. So I spent probably four years trying to recruit her to our organization, three years with her as a board member in the last year with her as the executive chairperson. And we kind of woke up this year and realized that I think there’s a whole lot more she could do in the organization. So we sat down, worked well together, and were fortunate to convince her to come on board full time as our new CEO, effective yesterday, actually.

David Wald
So the news is fresh off the presses, and I think we have a very bright outlook for this year with her at the helm. 

Brett
A lot of founders I know and a lot of founders I speak with are either doing something similar or they’ve done something similar. I’ve seen a lot of them move into the president role. I’ve also been seeing a lot of them move into the chief product officer role to really focus more on product. So I’d love to just learn a little bit more about what you learned from this transition and what you’ve learned from this journey and experience so far. 

David Wald
Oh, yeah. Well, it’s been an atypical experience based on how I would have drawn it up if you had asked me ten years ago when we started, like, when do you think you’re going to not be CEO anymore? And I would have been like, yeah, right but I think, and we have some really good board members and some really good ambassadors who’ve been super supportive that it kind of just like, lay it out. And we’re like, you know, hey, I know you’re not thinking about this, but you have an incredible talent here. And I think what’s really interesting, I think as a Co-Founder of a company, is to step back and really ask the right question, which is, with the talent you have around the table, how do you make the highest likelihood for you guys to be successful? 

David Wald
And so that’s what we did. And I think here it’s still hard to find really good talent. And if you check your ego, you can kind of step back objectively and be like, my goal with this business is to grow it. How do I help protect my employees, our customers, our investors? And when you kind of put that lens out, it became pretty clear for us that this was a move that we could make that would help everybody, myself included, with the only kind of thing having to do is just, again, just, you got to check the ego to look at objectively and figure out what the right move is. And last thing I’ll add here is, I probably wouldn’t have done this for anybody.

David Wald
I know part of the VC playbook is, you know, new CEO’s can always kind of push things forward faster. But I think for me, I and the other co-founders wouldn’t really trust our organization, anybody’s hands. We had a really fortuitous experience with cathy in that we got to know her for years. The board member, she kind of worked with us basically about half time last year as executive chairperson. And I think in that experience, we really got to feel comfortable and recognize just how incredible she was, which made everything so much easier than, I think, trying this to do. A hard switch of like, all right, Damon’s here today, Cathy’s coming. Boom. 

David Wald
So I think those are kind of some of the insights and the behind the scenes that kind of helped us get comfortable and realize this was absolutely incredible move for us to make for everybody. 

Brett
On the topic of ego, it takes me back to a conversation I had probably two weeks ago. I was on a hike with a friend who’s a Founder of a pretty large tech company, and hes one of those folks whos stepping into a product role. And as were having the conversation, kind of listing it out, and he was really bummed out, really depressed about the transition and everything he was telling me, though, sounded positive. Hes like, yeah, I dont like being the CEO role. I want to focus on product, went down the list, and then basically what it came to, all that was left is what you said. It was just the ego of letting go of that title. What was that like for you? And internally, what was that dialogue like? 

Brett
How, how did you let go of your ego and make that decision? I do think that’s like one of the biggest roadblocks from founders making this choice. 

David Wald
Yeah, absolutely. I think the knee jerk reaction is always the wrong one. It might eventually be the right one, but my experience is always, you got to sleep on things. My first reaction when someone was like, hey, you should think about not being the CEO anymore was, but I’m the CEO, that’s what I do, that’s who I am. So I think what we started to realize was there’s ways that I can help the organization. It sounds similar to what your friend was going through that dont necessarily require me to be the CEO today. And so as I thought about leverage, I think for me, one of the biggest learnings in the brightest company for the past ten years is trying to figure out how you can get more leverage out of everything.

David Wald
I realized that where I think I can add a ton of value here actually becomes easier as president. And Kathy can come in and really help us to push things forward. And candidly, the other thing ive always known about Kathy was, I think, imagine she built the company that we run right now in a prior life to about almost 100 million in revenue. So I know that she’s incredibly talented, but I didn’t fully really step back to think about what it would mean to have her at home in terms of doors that would open perspective. And so I think it started to kind of step back even from like knee jerk reaction to thinking about even both how I can contribute here. It actually becomes a lot easier working with her, and also she’s great.

David Wald
So when I think about, like, is the risk here that I lose power or is like the real opportunity here that I can find a great partner to work with who will both help me grow and also help our company grow, I think it became a lot easier. But it’s always hard because you’re so used to having to prove everyone wrong as a startup Founder that I think getting out of that mindset as you start to get to scale, really, I think becomes one of those interesting maturation curves everyone goes through.

Brett
I think that’s super helpful and valuable for founders to hear that. Like I said, there’s just a lot of founders who are dealing with this right now. Something else you mentioned there is. This wasn’t really part of the ten year plan. Let’s go back ten years and let’s talk about the early date company. And let’s talk about the founding story.

David Wald
Yes, the good old days. So our founding story always cracks me up. There’s three co-founders, myself, our CTO, Joel Friedman, and Michael Schultz, who at this point in time as a board member, and our Founder. Michael is actually my father in law, but at the time we started this business, he wasn’t. So, Mike, story goes, as a 35 year insurance veteran, he has been part of agencies and carriers and tpa’s and all the things that make the world go around in the insurance space. And a long time ago, when I was just dating his daughter, who’s now my wife, he approached me with this idea for an app and basically said to me, hey, I was at VC at the time. I had this idea for an app. You should help me build it.

David Wald
And of course, my reaction was, oh, my God, what could possibly go right with me starting work to work with my girlfriend’s father? He is incredibly persuasive, incredibly insightful, but it’s the one of the most fun business partners I’ve ever had the chance to work with. But he wore me down. Eventually, we jumped into this thing, and lo and behold, something silly. Like six months into working this, we had a chance to pitch three huge companies. Kelly Services, CNA and the Navy. And out of nowhere, nights and weekend project. For six months. All three companies said, this is great. Let’s get it in procurement. And, like, that’s the real minute that a claimant was born. It just kind of. He saw the opportunity. We jumped on knowing nothing about insurance or risk management technology, and it’s been a whirlwind ever since.

Brett
What was that early go to market strategy. Like, what were you guys focused on? And then, how have you seen that evolve? 

David Wald
Yeah, it’s a great question. I think, trying to look back over the past ten years, I think the one thing that we probably didn’t fully appreciate starting is early companies are all go to market. Product is helpful, and the product can help there. But in my opinion, you got to find a way to actually move the product, especially in this environment. If you don’t have sales, you’re dead unless you’re an AI company and you managed to convince people otherwise. But the interesting thing for us, so early on, we focused very narrowly. Our thought was were going to just find staffing firms and insurance agencies that like our product, or we’re just going to kind of call them. So our early days were really working through networks, working through referrals and even kind of going down. 

David Wald
I still remember in our office we kind of pulled out one of the yellow pages, right. And just let’s get all the healthcare companies that do staffing in Chicago and let’s go ahead and call them all and see if someone will use it. So it was really outbound focused, very referral based. As we grew over time, our go to markets obviously become much more sophisticated. And if you think we started in 2014, even the go to market tools have become so much more sophisticated in the last decade that right now we run a very data driven inbound referral and channel strategy on our go to market thats very driven using targeting and tech tools. I think if you think about our space, so we’re in group of software called risk management information systems. 

David Wald
It’s really about companies who are trying to find ways to be safer, trying to find ways to help manage and mitigate and optimize insurance costs and claims. So there’s some very clear signals you can imagine of a company that’s trying to do things to be safer, either things that went wrong or things they’re proactively trying to do to be right. And so we’ve been able to harness a lot of those signals and really create a very targeted, very efficient strategy for being able to track these people down and then get them into funnel and manage the show. What we get this show is brought. 

Brett
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Brett
How would you define the marketing philosophy? 

David Wald
Yeah, so I think as a company, our tagline is really to help companies become better risks and protect what matters most. And so part of the embedded culture of a claimant is really around helping companies to choose to better and to choose to help and make the organizations a better places to work. So from marketing perspective, a lot of what we’re doing here is really focused around thought leadership, but helping companies that want to get better in this respect, that want to be safer, that want to manage us, work tightly to understand that they have an option here to change the way they do things and to really start to lean into making this a competency in their organization. So in marketing, what that translates to is really kind of a combination of thought leadership and empowerment.

David Wald
I mean, kind of really helping companies to buy into this process and philosophy. It’s always easy to say, oh, I’m not going to fix safety right now, but eventually it always blows up in someone’s face at some point in time. So to get out of that mindset, you can’t beat people into being safer. You really have to have them understand that they have a choice and they can choose to better. And that’s been the core part of our marketing philosophy.

Brett
How do you define thought leadership and how do you think about thought leadership?

David Wald
Yeah, I think it’s overused candidly, but I think for us it’s really about how do you help your ideal customer profile, or how do you help your champions understand something that will help them do their job better or will challenge them to think differently. So I think for me, it’s really about helping people to think about. All right, what are my biggest burning questions of this company and risk management? It can be simple things like understanding how laws are changing and how that’s going to affect my ability to do my job, understanding what other companies are doing. We started doing a lot more work with our customers and case studies and helping people to see that there’s other ways to do a thing and people are finding better results. 

David Wald
So for me, thought leadership really is about not even trying to sit out there and beat your chest and say, look at how smart we are. But I think it’s a lot more around helping people to understand how we can help and how you can help them get their toughest questions answered in a way that kind of lines up with the value you’re trying to drive. 

Brett
When it comes to your market category. I know you mentioned it’s remiss there. What was like when you first started out? Was that already a defined category or did you really help define that and evolve that category? 

David Wald
Although I would love to take credit for it to buy in the rim as category, it’s been established since about 2000 or so. The way to think about Rimus without going too far into a history lesson is big companies. Back in early two thousands had so many insurance claims that as they started to move their insurance in house, they needed assistance to help manage it. So early remiss was really a claims system for a large company to act like an insurance carrier. If you’re going to way oversimplify it, over time, that’s been the predominant driving motion of remiss, is really to help support large enterprise organizations. Our claim to fame really is that we believe that large organizations have put systems and tooling in place. They have their sophisticated programs. 

David Wald
But a number of these middle market organizations, the companies that are up and coming, are now starting to encounter their own wave of things that make their businesses risky, expensive, and challenging. The past five years alone. Pick your poison. COVID, supply chain, severe weather, political instability, you name it, rising amounts of people working, remote wages going up. All these things make it a lot more difficult and potentially risky to run businesses. And this is now affecting not just people like your Walmarts, Coca Colas and Amazons, the world, but also your 100 person almond farmer or your 75 person construction firm. 

David Wald
So what weve been trying to take the approach on the remiss category is finding a way to democratize the remiss function, software, the platform, and really facilitate the next hundred or 200,000 organizations that want to find ways to use Remis to become better and safer and kind of helping to facilitate that transition. So that’s kind of been our approach at define the category, but trying to reimagine it for the modern world.

Brett
What about messaging and positioning? How have you seen that evolve? 

David Wald
Yeah, so similar. I think when we first started off, we had a very narrow worldview. I think it’s probably for the benefit. When we kind of think about us early on, we’re like, all right, we’re going to service staffing companies with Rivas. And I think as we began to grow, we started to realize that it’s not just one kind of company that has risk and claims. I mean, the reality is every business, as soon as you hire your first employee, as soon as you ship your first bit of product, is introducing risk in their world. That’s why insurance exists. And so for us, I think over time, we’re just kind of very narrow. Like, we’re just for staffing, we’re just for construction. 

David Wald
To understanding that we’re really positioned as kind of the remiss for the middle market, or the company that wants to have a mindset like the middle market that wants to act small and move fast has really been, I think, what we’ve managed to really start to narrow in on as our kind of key messaging and positioning, just so we can. 

Brett
Understand the scale that you’re operating at. Are there any numbers that you can share? 

David Wald
Yeah. So today we have about 40 employees we work with about 10,000 organizations across the United States and North America, and they range from small mom and pop businesses to some larger companies being able to share like Caesars Entertainment and tele services and Carvana, as well as large insurance companies like Safety national and Holmes Murphy. So we’ve managed to kind of find our way into some of the arts and minds and leaders in kind of our spaces and then kind of into a number of organizations that are much smaller, that still need help and be safer and better. 

Brett
As I mentioned there in the intro, you’ve raised over 30 million to date. What do you see you’ve learned about fundraising throughout this journey? 

David Wald
Still many things, especially in the past few years, its probably easiest for me to break it down into eras completely unintended, though. I want Super bowl, and that kind of got in my head. So I think early on we actually, I think strung together 18 months, were raising $20,000 at a time we first got started, kind of really learned that fundraising is a grind and that you got to like be creative and never ever send your laurels when you’re running a business that doesn’t make money. And thats what software businesses and BC businesses tend to be. In our seed, were an insure tech before it was really a category. 

David Wald
And so really understanding from a seed fund, you got to find typically the needle in the haystack that understands your space in your team and really can let you chase down your dream versus trying to shift what you’re doing to fit the vc you’re going after. And then for D, as you start to hit scale, it starts to become a different kind of relationship you’ll have with those team members that they’re there to kind of help you grow in scale. And so for me, I found the most value, not always in chasing the highest dollar term sheet, but in trying to find the best partner who can both be a critical and constructive member of the team who doesn’t just say yes, you’re great, and then also is there to support you. 

David Wald
We found one of the most important things for us was finding somebody who has been through good times and been through bad times and not just the newest money on the block. Because in our worldview, things don’t always good or go well. And when they don’t, you want someone who’s not going to freak out and try and fire the company or fire sale. And I think, thank God, because the world’s been weird for the past 14 or 18 months for startups. And I think we’ve seen a lot of people who have been in less fortunate spots than us that think having a really good, supportive group of investors that not only has been there financially for us, but also help us talk through tough decisions and figure out new approaches and get to where we’re going today has been kind of key. 

David Wald
So many different things in many different stages, but I think hopefully all helpful for somebody. 

Brett
Lets imagine that you’re talking with a Founder and they say they want to go after a similar space, not in a way that competes with you, but they want to sell to a similar buying group. What would be the number one piece of advice that you’d have to give them? 

 

David Wald
Yeah, I think its in our specific space. I think its something that you have to go in with a lot of humility and a lot of understanding. So we live in a world that is highly regulated, that is full of expert practitioners who know their stuff. And even for us, were blown up for years. So we’d walk in, we would say things and they would look at us. You’d use the word claims or work comprom and you get a sideways lesson. Then the reality is these are people who are managing risk, and the first thing they see with you is, oh, my God, this is risky. This guy doesn’t even know the words that I’m saying. So I think the biggest thing for us in this space is really, it’s about half of your homework. You have to be an expert. 

David Wald
You have to be able to speak and meet people on their level and probably even bigger than us. For all companies, understanding the customer, be able to speak their language and be able to understand what they’re saying with their specific words. And vocabulary is so critical for even getting in the door in our space. And probably the first thing anyone has to do if they want to compete insure tech, risk, tech rimus or any category is similar. 

Brett
Final question for you. Let’s zoom out into the future. So maybe three to five years from today, what’s this big picture vision that’s.

David Wald
Going to be built? I am so excited about where the remiss space is headed, and im so excited about where were positioned in a way that I haven’t felt in probably a couple of years, not because they weren’t doing well, but because its been weird. I think with the team we’ve put in place. And Cathy, I think, was just one of the phenomenal chips that have fallen for us in the past, probably even nine months. But I think for us, we really want to kind of catalyze the next 100,000 companies that want to get into Remis, and so I believe we can establish ourselves as the preferred choice of the middle market buyer who wants to become safer and wants to kind of help manage risk of their organization. 

David Wald
So our goal is to help find ways to really make this kind of software accessible and to help organizations across verticals in North America really look to us as the trusted choice in the space. Amazing. Love the vision. 

Brett
All right, David, we’re up on time, so we’re going to have to wrap here before we do. If there’s any founders listening in that want to follow on with your journey, where should they go? 

David Wald
Easiest way to look at our website, www.aclaimant.com blog, news and webinars are there, and if not, you can always just follow my LinkedIn feed. Just check me on LinkedIn. David Wald should be easy enough. Love it. 

Brett
David, thanks so much for taking the time. 

David Wald
Thanks, Brett.

Brett
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Brett
On the next episode.