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Host Callan Harrington dives into the strategies, decisions, and lessons that have shaped the careers of top marketing and growth leaders in the insurance industry. From bold moves to costly mistakes, each episode uncovers real-world insights that listeners can apply to accelerate growth in their own businesses.
Chris [0:00:00]: Before you even really get into the process, are you engaging with the right people around the right things.
Chris [0:00:05]: So before you even start that?
Chris [0:00:07]: Those are the two questions.
Chris [0:00:08]: And are they the right people, do they own the P&L?
Chris [0:00:12]: You could talk about where in an organization is the right person?
Chris [0:00:16]: It's less about what the title is and more about what they own.
Chris [0:00:20]: It's about does that person own the P&L.
Chris [0:00:23]: Do they have the responsibility for that and kind part two of the matrix?
Chris [0:00:27]: Does that individual who we are working with, who is our champion?
Chris [0:00:31]: Do they have a mandate beyond the operating plan.
Callan [0:00:37]: Welcome to The Insurance Growth Lab, who we go deep on the growth campaigns and strategies driving real results in the insurance industry.
Callan [0:00:45]: Callan Harrington founder Flashgrowth and in each episode, I sit down with marketing and growth leaders from carriers sure tech and top to break down one specific initiative, whether it's how they marketed a product, scale a channel or solve a specific growth challenge.
Callan [0:01:02]: It's no fluff, just tactical insights you can apply in your own company.
Callan [0:01:07]: Today, I'm joined by Chris Kessler.
Callan [0:01:14]: Chris is the chief product and platform officer at Bold Penguin, and I've been fortunate enough to work with Chris directly, and I have always been extremely impressed with how he approaches process building and leadership.
Callan [0:01:28]: In this episode, Chris talks about his time and strategy consulting before joining Bold Penguin, and it is clear how that background impacts how he operates today.
Callan [0:01:40]: One of the areas that I think it shows up the most is in solution, and that is where we focused our time for the deep dive.
Callan [0:01:49]: In short, solution is the part of sales where you work with the client to create the best solution together.
Callan [0:01:57]: That said, it is so much more than that simple definition.
Callan [0:02:02]: I think solution is one of the most slept on pieces of enterprise sales, and I'd go as far as say that I don't think you can win million dollar deals without an extremely strong solution process.
Callan [0:02:16]: The first time Chris actually walked me through his process for solution I was blown away and had no idea how detailed he really got in that.
Callan [0:02:27]: And he didn't disappoint on today's episode either.
Callan [0:02:30]: After hearing him talk us through it, it's easy to see why Bold Penguin has been so successful at consistently landing household names as enterprise clients.
Callan [0:02:40]: So with that, I'm gonna stop talking and let's get to the show.
Callan [0:02:45]: Chris, I'm excited Have on, man.
Callan [0:02:54]: You've been on the list for a long time.
Callan [0:02:56]: And obviously, we did all the founders and then I mean, I can tell you once I move to the insurance side I was, like, this is a brainer.
Callan [0:03:05]: Like, you got appreciate it then.
Chris [0:03:07]: I feel like I've made it now.
Callan [0:03:08]: This is a stage case.
Callan [0:03:09]: A lot know.
Callan [0:03:10]: I know.
Callan [0:03:11]: Refer this as, like, This is things think...
Callan [0:03:14]: Like, this is turned around after.
Callan [0:03:16]: This this is it.
Callan [0:03:17]: So how do y'all, five thousand different areas that we can take this.
Callan [0:03:21]: And I know we'll talk about the intro, but moved straight up the ranks.
Callan [0:03:25]: And super happy that she got the c level chief product officer.
Callan [0:03:29]: I'll just put it on the record very well deserved.
Chris [0:03:33]: I appreciate it.
Callan [0:03:34]: Now, a part that I'd love to kinda kick this off and tell us about Tulsa Globe.
Chris [0:03:41]: I could do that.
Chris [0:03:41]: I could do that.
Chris [0:03:42]: Well, in Tulsa Oklahoma was my, how did you end up in insurance story.
Chris [0:03:46]: They've been bad.
Chris [0:03:48]: Right?
Chris [0:03:48]: Because even nobody I mean, maybe did that one guy that started risk management college and did insurance all the way through.
Chris [0:03:55]: That was the one guy.
Chris [0:03:56]: Everybody else fell new insurance.
Callan [0:03:57]: And I've never in the business for...
Callan [0:03:59]: And I've been doing it for fifteen years.
Chris [0:04:01]: Yeah.
Callan [0:04:02]: I've never met that guy actually.
Callan [0:04:03]: I've never met the guy.
Callan [0:04:04]: He's out there.
Callan [0:04:05]: I think.
Callan [0:04:05]: I heard.
Callan [0:04:06]: I believe that I
Chris [0:04:07]: heard he's out.
Callan [0:04:08]: I believe it.
Chris [0:04:09]: I believe he exist.
Chris [0:04:09]: So as everybody has their own...
Chris [0:04:11]: Their own way that they fell in, my story revolve ground, Tulsa, Oklahoma and getting stuck there on a Valentine's day weekend.
Chris [0:04:19]: I was working, I doing strategy consulting at K g, working on a big deal with a strategic buyer, looking at acquiring a company, and we're doing deep diligence on the the industry, the market, key trends, operational levers, really on picking the deal for them and driving diligence.
Chris [0:04:37]: So kinda round the clock work, ton of fun, working with executives on both sides of the deal, working my ass off twenty four seven flight, late Thursday night.
Chris [0:04:48]: Last flight, my wife and I were in Chicago at the time.
Chris [0:04:50]: Last flight out of Tulsa Oklahoma.
Chris [0:04:53]: I think it was the thirteenth.
Chris [0:04:55]: So going back to Chicago, and my wife and I had a...
Chris [0:04:59]: Something planned all afternoon, and then we're gonna get a big dinner.
Chris [0:05:02]: We were gonna go see a show.
Chris [0:05:04]: It was...
Chris [0:05:05]: And this
Callan [0:05:06]: was all booked, it was.
Callan [0:05:07]: It was
Chris [0:05:08]: I knew it was to the nice, and I...
Chris [0:05:09]: Because I've been working my ass off.
Chris [0:05:11]: She was, like, we need this.
Chris [0:05:12]: We were just gonna kinda carve out Do a little bit of a station thing, enjoy the city because you've been gone.
Chris [0:05:19]: So get the airport, run through Tsa.
Chris [0:05:21]: Get there.
Chris [0:05:23]: And, you know, as I'm getting that, I'm getting text.
Chris [0:05:26]: Your gate moved, your gate moved, your gate mode.
Chris [0:05:28]: I'm like, oh, boy I've seen this move And turn off, get to the gate.
Chris [0:05:32]: It's delayed.
Chris [0:05:33]: So instead of, I think it was like an eight fifteen flight.
Chris [0:05:36]: Now it's eight forty five.
Chris [0:05:38]: And now it's nine and the gate switch is in Tulsa Oklahoma.
Chris [0:05:41]: I mean they're all, like, two gates.
Chris [0:05:42]: So I were just going back and forth between the two gates.
Chris [0:05:44]: But there was that gate switching, finally about ten forty five.
Chris [0:05:49]: They called it.
Chris [0:05:50]: And they're like, nope.
Chris [0:05:51]: Not yet now.
Chris [0:05:51]: Well, Tulsa, Oklahoma is not, handled for anybody.
Callan [0:05:56]: You can just drive.
Chris [0:05:57]: No.
Chris [0:05:57]: From...
Chris [0:05:57]: No.
Chris [0:05:58]: And you can't drive it.
Chris [0:05:59]: Yeah.
Chris [0:05:59]: Drive.
Chris [0:05:59]: It's not, like, maybe being an Indy or Detroit or something run out to hertz and get a car.
Chris [0:06:04]: So, no.
Chris [0:06:05]: That's off the table.
Chris [0:06:06]: So, stuck in Tulsa Oklahoma, starting to look at options, and there are no options and they are all.
Chris [0:06:11]: So I'm there Friday, and I'm there Saturday, and I flew home Sunday morning.
Chris [0:06:17]: And then I flew back Sunday night.
Chris [0:06:20]: So I did a day trip to Chicago, back home after getting stuck in Tulsa Oklahoma for the weekend.
Chris [0:06:27]: Most the aftermath So the aftermath was I ended up in insurance.
Chris [0:06:32]: That was a bit of the straw that broke the Camel back.
Chris [0:06:38]: And it was collective.
Chris [0:06:39]: I mean, I I didn't wanna be in tulsa go over the weekend can note no offense.
Callan [0:06:43]: Yeah.
Callan [0:06:43]: Yeah
Chris [0:06:43]: Yeah.
Chris [0:06:43]: Beautiful wonderful city.
Callan [0:06:44]: Yeah.
Callan [0:06:44]: Absolutely.
Chris [0:06:45]: But some really cool spots, but did not wanna be there over the valentine's day weekend.
Chris [0:06:49]: And so that was the beginning of starting to think about what's the next move in my career, which ended up taking it to nationwide in their office of corporate strategy and taking that strategy, experience nationwide, which was how I fell into insurance?
Callan [0:07:05]: Man.
Callan [0:07:05]: That's a pretty good one.
Callan [0:07:07]: I've told mine on the the show a few times.
Callan [0:07:09]: It was literally...
Callan [0:07:10]: I was going into my junior year in college.
Chris [0:07:13]: K.
Callan [0:07:13]: And my best friend brandon and who you knew.
Callan [0:07:15]: Yeah.
Callan [0:07:15]: Yeah.
Callan [0:07:15]: I was interviewing at Northwestern mutual.
Callan [0:07:18]: Yep.
Callan [0:07:18]: And I was the only phone number that he had memorized when they asked who else would be good at doing this.
Callan [0:07:25]: And so I remember picking it up.
Callan [0:07:27]: Like, on my flip phone, had no idea who was.
Callan [0:07:30]: Yep.
Callan [0:07:31]: Obviously, hung over from the night before.
Callan [0:07:32]: Is all like a Friday and I pick off.
Callan [0:07:35]: I was like, yeah.
Callan [0:07:36]: I think I answer, like, y.
Callan [0:07:38]: Yeah.
Callan [0:07:39]: That sounds right.
Callan [0:07:40]: This is Northwestern mutual.
Callan [0:07:42]: Yeah Yeah.
Callan [0:07:42]: We're interested in, like, an internship of, obviously, I had nothing lined up.
Callan [0:07:45]: Yeah.
Callan [0:07:46]: Yeah.
Callan [0:07:46]: Yeah.
Callan [0:07:46]: Rate.
Callan [0:07:47]: So that's probably one of the best ones I for
Chris [0:07:50]: that that's how I fell in told look oklahoma over Valentine's Day.
Callan [0:07:53]: And we'd worked together for one.
Callan [0:07:54]: Yeah and I didn't realize just how much.
Callan [0:07:57]: I knew you did some strategy stuff.
Callan [0:07:58]: I knew you did some pee stuff.
Callan [0:07:59]: Mh.
Callan [0:08:00]: I didn't realize just how much strategy work that you did.
Callan [0:08:04]: I mean, I kinda curious if it wasn't for...
Callan [0:08:07]: Because the grueling schedule.
Callan [0:08:08]: Strategy solve it was
Chris [0:08:11]: it was.
Chris [0:08:11]: Yep.
Callan [0:08:12]: If it wasn't for that, would you continue to do that?
Chris [0:08:15]: You know, it's a good question.
Chris [0:08:16]: I love the pace of it and as you climb up in a firm, you're both delivering and selling.
Chris [0:08:21]: Yeah.
Chris [0:08:22]: Right?
Chris [0:08:22]: And more and more delivering and selling and more selling than delivering.
Chris [0:08:25]: Yep.
Chris [0:08:25]: And I was on that trajectory and I loved it, But the pace of doing that, And then an aspect of selling service work only, really wanted to get into selling more product work.
Callan [0:08:38]: Mh.
Chris [0:08:38]: And maybe product service bundled and round out some experience in my career with those capabilities versus the service.
Chris [0:08:46]: Because when you show up with service work, it can kinda be anything.
Callan [0:08:49]: And you
Chris [0:08:49]: can make you can make it up to be anything let's solve your problem, where, you know, when you move into more of a tech company.
Chris [0:08:55]: I mean, it's solving the problem, but you have a different set of tools.
Chris [0:08:58]: Yeah.
Chris [0:08:59]: And a different level of constraints and how you solve that problem.
Chris [0:09:03]: And so you have to be a little bit more creative.
Chris [0:09:04]: So I to challenge myself more in that.
Chris [0:09:06]: But I did love it.
Chris [0:09:07]: I love the pace.
Chris [0:09:08]: I've got to work on some really cool deals worked on the R automotive.
Chris [0:09:13]: Their first financing, tran, and which is a pretty big deal So got to work on that.
Chris [0:09:18]: On behalf of the investors gonna rebuild the business plan.
Chris [0:09:21]: And and did some really, really cool work, but between the pace and the balance between pace and life, and then expanding my career ended up shifting out.
Chris [0:09:30]: So probably wouldn't I thought about going back at different times, but I I really found that sweet spot in insurance and technology and bringing that strategic lens to that.
Callan [0:09:40]: What was to change a pace like when you went from that to nationwide?
Callan [0:09:45]: And I think this is not a knock on big company
Chris [0:09:48]: not at all.
Chris [0:09:48]: Is a
Callan [0:09:49]: big company.
Callan [0:09:49]: Yeah.
Callan [0:09:49]: And Yep for it's just a different pace.
Callan [0:09:52]: It's much more of a quality of light.
Callan [0:09:54]: And that not saves it's not hard and obviously, in certain positions, you're gonna be grinding faster.
Callan [0:09:58]: But what was that change like for you.
Callan [0:10:00]: Yeah.
Chris [0:10:00]: I was waking up and saying, well, I'm only working fifty hours a week or sixty hours a week.
Chris [0:10:04]: Right?
Chris [0:10:04]: And on the bubbles when you're doing strategic planning and it's a little more but I mean, I traveled to des moines like twice over the course of the year.
Chris [0:10:11]: You know?
Chris [0:10:12]: It wasn't every week, Tulsa to the West Coast, you know, back to New York.
Chris [0:10:17]: Right?
Chris [0:10:18]: So and the pace was different.
Chris [0:10:19]: You know, you have one client, one customer in the in the office of corporate strategy at Nationwide.
Chris [0:10:24]: So the pace was, you know, I always joke that, you know, I was red lining after nationwide after about ninety days.
Chris [0:10:30]: I was healthy.
Chris [0:10:31]: I was eating right.
Chris [0:10:32]: I was sleeping great.
Chris [0:10:33]: And it was just more...
Chris [0:10:35]: Well, the work was challenging.
Chris [0:10:36]: I worked some phenomenal people who I stay in contact with to this day, good friends, challenging work, really really sharp people moving a massive organization forward.
Chris [0:10:47]: It was kind of single threaded.
Chris [0:10:49]: It made it a lot more manageable from a schedule and travel standpoint than being all over with another client and their problem and their need and their delivery is the most important thing, and then you get on the phone thirty minutes later it's a whole another client.
Chris [0:11:03]: So it's just...
Chris [0:11:03]: It was more of that single thread that I think made it a lot more manageable and quality of life significantly improved.
Chris [0:11:10]: Yeah.
Chris [0:11:11]: During my time at nationwide.
Callan [0:11:13]: I'm laughing because any service business, everything is, like, due yesterday.
Chris [0:11:17]: That's right.
Callan [0:11:17]: And everything's is an emergency It.
Callan [0:11:19]: It doesn't matter what time it is Now I'm a total gun for punishment.
Callan [0:11:22]: That's why I went back to.
Chris [0:11:25]: Now I'm preaching in the choir.
Callan [0:11:26]: Yeah.
Callan [0:11:26]: I get exactly what you were saying.
Chris [0:11:28]: And there is a thrill.
Chris [0:11:29]: Right.
Chris [0:11:29]: I mean, there's that thrill of that delivery.
Chris [0:11:31]: There's the thrill of the sale from when you're in that.
Chris [0:11:33]: Oh, for services space net.
Chris [0:11:35]: More of a competitive person love and miss in a lot of ways.
Chris [0:11:39]: Yeah.
Chris [0:11:39]: But I get enough of that through, you know, especially over the last six and a half years with Bald Penguin and how we have matured and how we have gone to market being able to put all that together has actually been really cool sweet spot.
Callan [0:11:53]: I wanna come back to that.
Callan [0:11:54]: Before, I wanna get into the weeds, and and the beauty is you already kinda talked about it a little bit.
Callan [0:11:59]: He talked about pairing those services with the product, which for anybody else, like, Salesforce has done this for years.
Callan [0:12:05]: And the dirty little secret was enterprise Saas was part of its Saas, or what services.
Callan [0:12:11]: And now that's all becoming more normalized as we kinda come into this next phase, but one of the big things I wanna talk about.
Callan [0:12:18]: I really wanna get the weeds on this is you specifically are one of the best...
Callan [0:12:24]: I'd...
Callan [0:12:24]: Actually, I won't even say one of the best.
Callan [0:12:25]: You were the best I've ever worked with in solution in c creating the deal with the actual customer.
Callan [0:12:34]: I don't think I've ever seen anybody doing it.
Callan [0:12:36]: And I'll say we talked about this before.
Callan [0:12:38]: Yeah.
Callan [0:12:38]: The first time that you walked one of our clients through your process.
Callan [0:12:41]: I was like, Whoa.
Callan [0:12:44]: I was blown away.
Callan [0:12:46]: Like, I actually didn't realize
Chris [0:12:48]: It's good on paper.
Callan [0:12:49]: Whoa, I I didn't realize just how intentional every single step was.
Callan [0:12:54]: Yeah.
Callan [0:12:55]: And prospecting gets talked about all the time.
Callan [0:12:57]: Right.
Callan [0:12:58]: Yep.
Callan [0:12:58]: And it's an easy one to talk about.
Callan [0:12:59]: If you don't yeah client coming into the door, it's really tough.
Callan [0:13:02]: Cross a up, upsell gets talked about a lot.
Callan [0:13:04]: Yeah.
Callan [0:13:05]: Yeah.
Callan [0:13:05]: But this piece of the new business sale.
Callan [0:13:08]: I don't think you're getting million dollar deals without it.
Chris [0:13:11]: Person.
Chris [0:13:11]: Absolutely.
Chris [0:13:11]: Yeah.
Chris [0:13:12]: Anything large.
Chris [0:13:12]: Large, anything innovative, anything where there's c creation, anything where there's risk.
Callan [0:13:18]: Mh.
Chris [0:13:19]: Anything that doesn't fit the mold is not a I...
Chris [0:13:21]: I show up by demo and I slide the contract across the table.
Callan [0:13:25]: Right.
Callan [0:13:25]: Especially in insurance,
Chris [0:13:27]: That's right.
Callan [0:13:28]: With insurance, carrier specifically.
Callan [0:13:29]: That's right.
Callan [0:13:30]: Who have the biggest needs and because they're the biggest businesses.
Callan [0:13:32]: Not to the other business are important, but they're the biggest in this world.
Callan [0:13:35]: Let's go through that process.
Chris [0:13:38]: Yeah.
Callan [0:13:38]: The deal comes across What does that look like
Chris [0:13:41]: for your.
Callan [0:13:41]: And if you've got an actual example we can go through great.
Callan [0:13:43]: You don't have to mention the names or anything like that, but, like, what does that look like?
Chris [0:13:47]: There are a number of deals that kinda rhyme.
Chris [0:13:49]: Right?
Chris [0:13:50]: Yeah.
Chris [0:13:50]: And throughout this process.
Chris [0:13:51]: So maybe just aggregating the process a little bit together, but you could fill in any any logo or any name and it would rhyme in one way or another with with the process.
Chris [0:14:02]: When I look at the process, I think about that starting spot, Before you even really get into the process, are you engaging with the right people around the right things.
Chris [0:14:11]: So before you even start that, those are the two questions.
Chris [0:14:15]: And are they the right people, do they own the P&L?
Chris [0:14:18]: You know, you could talk about where in an organization is the right person.
Chris [0:14:22]: It's less about what the title is and more about what they own.
Chris [0:14:26]: Yeah.
Chris [0:14:27]: And not only just owning the P&L, I think when I look at it, when I'm engaging with our business development and our sales team as they're bringing these deals in.
Chris [0:14:34]: It's not even so much about, again, that title, it's about...
Chris [0:14:39]: Does that person owned the P&L, Do they have the responsibility for that.
Chris [0:14:42]: And kind part two of the matrix.
Chris [0:14:45]: Does that individual who we are working with, who is our champion, who we are going to, do they own...
Chris [0:14:52]: And do they have a mandate beyond the operating plan.
Chris [0:14:55]: Yeah.
Chris [0:14:55]: So operating plans one year.
Chris [0:14:57]: Right?
Chris [0:14:57]: So they might be a P&L owner but they're managing the P&L.
Chris [0:15:01]: They're not owning it long term.
Chris [0:15:03]: And so those are really the two pieces.
Chris [0:15:05]: There...
Chris [0:15:05]: Those are the two criteria that I look at as it we're engaging early in a deal to say, are we engaging at the right place.
Chris [0:15:12]: Do the right person.
Callan [0:15:14]: What when do you say we.
Callan [0:15:14]: So like, the solutions team?
Chris [0:15:16]: That's that's right Well.
Chris [0:15:17]: So a lot of times, you know, deals are coming through a number of different ways.
Chris [0:15:20]: Right?
Chris [0:15:21]: It could be kind of from more in the marketing and it could be from our sales folks, bringing deals in and saying, okay, How do we push this forward?
Callan [0:15:29]: Yeah.
Chris [0:15:29]: It's an opportunity?
Chris [0:15:30]: It's a lead.
Chris [0:15:31]: What do we do with it?
Callan [0:15:32]: Yep.
Chris [0:15:33]: So the first gating item is, are we in at the right spot?
Callan [0:15:38]: I don't wanna focus too much on title.
Callan [0:15:39]: Typically in the insurance world.
Callan [0:15:40]: You gotta go high.
Chris [0:15:41]: Pretty high.
Callan [0:15:42]: Not necessarily c level.
Callan [0:15:43]: Vps at big companies have a lot of time.
Callan [0:15:46]: Where, I guess, that's my opinion.
Callan [0:15:48]: Do they have to be c level in your.
Chris [0:15:51]: They don't have to be.
Chris [0:15:51]: And that's why I say it's more of P&L ownership, one.
Callan [0:15:55]: Yeah.
Chris [0:15:55]: Two, mandate and authority beyond the operating plan.
Callan [0:15:59]: Okay.
Callan [0:15:59]: What's that mean?
Chris [0:16:00]: So operating plan, meaning, one year.
Chris [0:16:03]: Mh.
Chris [0:16:03]: Management.
Chris [0:16:04]: So more strategic.
Chris [0:16:05]: Do they have the strategic authority to make decisions longer term.
Chris [0:16:10]: Okay.
Chris [0:16:11]: If that individual might own the P&L, but it's puts and takes around the P&L?
Chris [0:16:15]: Yeah.
Chris [0:16:15]: To make sure it comes in within some variance of budget.
Chris [0:16:18]: That's great.
Chris [0:16:20]: But if they're not thinking more strategically an out.
Chris [0:16:23]: Or they don't have the authority or the mandate to do so.
Chris [0:16:27]: If we're talking about a bigger deal.
Chris [0:16:29]: You have to be thinking strategic, you have to be thinking a little bit longer term and outside of just one year performance.
Callan [0:16:37]: Is that a requirement on the sales team.
Callan [0:16:39]: That those have to be there before, you'll do one of these engagement.
Callan [0:16:43]: Absolutely.
Chris [0:16:45]: Otherwise, if those criteria are not meant.
Chris [0:16:47]: I've learned this through the scars.
Chris [0:16:49]: You get involved you put a ton of time in.
Chris [0:16:51]: You build a pretty good rapport, you build a great business case, you solve the problem, you lay out the road map.
Chris [0:16:59]: Yep.
Chris [0:16:59]: On what you're gonna deliver, and that person doesn't have the decision right.
Chris [0:17:03]: They don't own the P&L, and they don't own the long term strategic mandate to execute.
Chris [0:17:08]: Yep.
Chris [0:17:08]: And so then what you end up doing is facilitating towards somebody that's probably gonna say no or have a higher probability as they move up the channel that someone will say now.
Callan [0:17:21]: Yep.
Callan [0:17:21]: Yep.
Callan [0:17:21]: Now I think that makes total sense.
Chris [0:17:23]: And it's just too much investment to do it right.
Chris [0:17:25]: Now there are there are variations and there, you know, there's still solution based selling that can go on and should go on kind of in it every way.
Chris [0:17:34]: But to really bring all the forces of, you know, more of a a strategic approach being thoughtful driving towards solutions and putting the full effort, there really has to be those criteria in play with who we're engaging.
Callan [0:17:50]: Yep.
Callan [0:17:50]: Alright.
Callan [0:17:50]: Those things are in play.
Callan [0:17:52]: Yeah.
Callan [0:17:52]: Comes next.
Chris [0:17:53]: What comes next is and we're talking about the right things.
Callan [0:17:57]: Yeah.
Chris [0:17:57]: So not talking about that operating budget.
Chris [0:17:59]: Right?
Chris [0:18:00]: If, again, if we're selling a big deal.
Chris [0:18:01]: If we're working on a very big deal, we've gotta be making sure that we're now having a strategic conversation.
Chris [0:18:08]: So we're not going in and that individual who now meets that criteria is not thinking we're coming into outsource five percent of the team, and they're just looking at just getting, you know, an extra two percent of margin and one small aspect Yep.
Chris [0:18:23]: Of their P&L.
Callan [0:18:24]: Yep.
Chris [0:18:24]: We have to be talking about something important and something big if we get involved like that.
Chris [0:18:29]: So that's the other piece that I bring...
Chris [0:18:31]: I would want our team to bring to the table before engaging.
Chris [0:18:34]: Okay.
Chris [0:18:35]: And so once those are in place, then it's sitting down and having that first conversation that's really a strategic conversation.
Chris [0:18:43]: It's a strategy session on in worsen over the phone, win in person.
Chris [0:18:48]: In person without question.
Callan [0:18:50]: Okay?
Callan [0:18:50]: So this is something I'm glad to hear you said.
Callan [0:18:52]: Because no question.
Callan [0:18:53]: I harp on this all the time.
Chris [0:18:55]: Yep.
Callan [0:18:55]: And it's, like, to the point now, where I just feel like, I'm like the old man harp on all of the young people.
Callan [0:19:00]: Like, I like I finally I got to that point.
Callan [0:19:02]: It still matter so much
Chris [0:19:04]: without question without question.
Chris [0:19:06]: You cannot do it.
Chris [0:19:07]: You cannot do it virtually.
Chris [0:19:09]: Especially that first session?
Callan [0:19:11]: What's the first session look like?
Chris [0:19:13]: So the first session looks like a little bit of a our understanding of your challenges long term?
Callan [0:19:20]: Mh.
Chris [0:19:21]: What's ground on that.
Chris [0:19:22]: What are you trying to solve long term and why are we here to be helpful in that?
Chris [0:19:27]: Why do you think?
Chris [0:19:28]: And then it's kind of a whiteboard session on understanding an un picking current state problem.
Chris [0:19:35]: Literal whiteboard.
Chris [0:19:36]: Literal whiteboard.
Chris [0:19:37]: I travel with whiteboard.
Callan [0:19:40]: Do you really?
Chris [0:19:41]: Some little ones.
Chris [0:19:41]: Yep.
Callan [0:19:42]: I had.
Callan [0:19:42]: Didn't know.
Callan [0:19:43]: Because typically, I I know just case.
Chris [0:19:46]: Just in case Like, you know, we can do some stuff on the side.
Chris [0:19:47]: Yeah.
Chris [0:19:48]: Mandatory.
Chris [0:19:48]: When we're setting up these sessions and we're working with the supporting folks and the administrative staff, we need a room where there are whiteboard or whiteboard can be brought in.
Callan [0:19:59]: Okay.
Callan [0:19:59]: What goes on the whiteboard?
Chris [0:20:00]: So what goes on the whiteboard is not that sexy.
Chris [0:20:02]: It's building out current state process.
Chris [0:20:04]: And as we do that, highlighting the areas of challenge.
Callan [0:20:10]: Mh.
Chris [0:20:10]: And typically, as you're doing that, it's a very rich converse.
Chris [0:20:12]: It ends up being a very rich conversation because our understanding of the problem, where you wanna go?
Chris [0:20:17]: Where are we today?
Chris [0:20:19]: Yeah.
Chris [0:20:19]: Right.
Chris [0:20:20]: And that's where you ground.
Chris [0:20:21]: Where are we today and building out that process, building out that data flow, understanding the operating model, workflows and processes and supporting technology of the business today, and we go full stack on that.
Callan [0:20:37]: So who's in that room at this at this stage.
Chris [0:20:39]: So decision maker that we talked who is that person that owns that longer term strategic view with near term P&L management, their direct reports.
Chris [0:20:51]: The people who have the answers?
Chris [0:20:54]: The worst case scenario in those meetings is you have that person, and they bring a few people, and it's a bunch of Oh follow all up on that.
Callan [0:21:03]: Seek getting whiteboard anything whiteboard because nobody be nuts.
Callan [0:21:05]: Yeah.
Chris [0:21:05]: So it might be a very, you know, I'll say junior person.
Chris [0:21:08]: Yeah.
Chris [0:21:09]: But that's not a junior person.
Chris [0:21:10]: The subject matter expert.
Chris [0:21:11]: Yep.
Chris [0:21:12]: In that process.
Callan [0:21:13]: They know the skeletons are there.
Chris [0:21:15]: That's exactly.
Chris [0:21:15]: That's right.
Chris [0:21:16]: So, you know, as we think about that, often wanna have different representations.
Chris [0:21:20]: Right?
Chris [0:21:20]: So, you know, maybe it's the workflow or the process representation.
Chris [0:21:23]: The data representation, the tech representation, the sales or go to market representation.
Chris [0:21:28]: So you wanna have representation from across the business at that meeting?
Chris [0:21:32]: Because it is a strategic representation.
Callan [0:21:34]: So in your world, would that be...
Callan [0:21:36]: I'm gonna say random title here.
Callan [0:21:37]: Yeah.
Callan [0:21:38]: Head of commercial lines, and then the commercial lines team below that.
Chris [0:21:42]: Yep.
Chris [0:21:42]: Okay.
Chris [0:21:42]: Often that would be, and then it would be often individual contributors or managers or again, people that can speak directly to how it actually works.
Chris [0:21:54]: Yeah.
Chris [0:21:54]: And the bigger the organization, the bigger that gap and who...
Chris [0:21:57]: The people that actually know how it works.
Chris [0:22:00]: Mh.
Chris [0:22:00]: Is.
Chris [0:22:00]: Yep.
Chris [0:22:01]: So it's a little bit of a mix.
Chris [0:22:03]: And so going into that, yes, You want main decision maker we talked about, key lieutenant and then subject matter experts.
Callan [0:22:10]: Okay.
Callan [0:22:10]: Alright.
Callan [0:22:10]: So you're starting to whiteboard board.
Callan [0:22:12]: And I heard you say is, like, here's what's current state?
Chris [0:22:14]: That's right.
Callan [0:22:15]: So you just how what you go through first?
Callan [0:22:16]: Is I go through the current state first.
Chris [0:22:18]: And sometimes it's a little painstaking.
Chris [0:22:19]: Just did this recently in q one of this year with a very, very top five player in the insurance distribution space, and it was pretty cool.
Chris [0:22:29]: At the end of that first session, it was the Ceo.
Chris [0:22:32]: Yeah.
Chris [0:22:33]: Who was our decision maker.
Callan [0:22:34]: The end
Chris [0:22:34]: of that session, he's like, I know more about my business than I ever did.
Chris [0:22:37]: He's like, and actually, the questions you're asking and how you're...
Chris [0:22:41]: We're moving through this.
Chris [0:22:43]: I think you might know just as much as anybody else in this room today as well.
Chris [0:22:47]: So how much of that
Callan [0:22:49]: comes from the consulting days?
Chris [0:22:51]: Massively, massively, because it's a strategic conversation says you're here, you wanna go here and here's the problem from getting from a to b.
Chris [0:22:58]: Mh.
Chris [0:22:58]: Let's talk about a.
Chris [0:23:00]: And as we're talking about a, again, it ends up being a pretty rich multi dimensional discussion.
Chris [0:23:05]: And again, if you have the right folks in that room.
Chris [0:23:07]: Because as you're laying out literally kind of boxes and arrows and swim lanes and stakeholders, as we're painting that picture, so much of the challenge and so much of the opportunity just emerges.
Callan [0:23:21]: Yep.
Callan [0:23:21]: This kinda comes up just comes
Chris [0:23:24]: super organically.
Chris [0:23:24]: And if you walk out of that meeting without knowing, how that business could progress and how they could go from a to b, probably we're asleep.
Chris [0:23:33]: Yeah.
Chris [0:23:34]: If you do it.
Chris [0:23:35]: Right?
Chris [0:23:35]: Yeah.
Chris [0:23:35]: And really pull that out.
Chris [0:23:37]: So that meeting is really key to buy everybody around that current state process.
Callan [0:23:43]: Okay.
Callan [0:23:43]: So you got current state process.
Callan [0:23:44]: You're building out...
Callan [0:23:46]: Is the next piece to start build out It's like, okay.
Callan [0:23:48]: What's ideal?
Callan [0:23:49]: What's that ideal state?
Callan [0:23:50]: Where do we wanna go?
Callan [0:23:51]: What does that look like?
Chris [0:23:52]: Yeah.
Chris [0:23:52]: So then we take that back and we say, give us a a week or two weeks?
Chris [0:23:57]: Yeah.
Chris [0:23:57]: And we turn that into a deliverable, a document.
Chris [0:24:01]: Mh.
Chris [0:24:02]: That in great detail covers all of the pieces that we put on the board plus.
Chris [0:24:08]: Right?
Chris [0:24:08]: Because they we may have...
Chris [0:24:09]: We may punt on a certain area and say, okay, hey.
Chris [0:24:12]: You've already done some work digging through that, mapping that out once Just send that to us.
Chris [0:24:16]: And then we build all that together.
Chris [0:24:18]: We put all that together with the goal that we have a document and the same example from q one.
Chris [0:24:23]: I think it was like a it's like a fifty sixty page document.
Callan [0:24:26]: Did you charge for?
Chris [0:24:28]: We typically do.
Chris [0:24:28]: Yeah yeah.
Chris [0:24:29]: Yeah.
Chris [0:24:29]: Even in our current state with being a tech company, doing that discovery, again, we're putting a lot effort into that, and there's a lot of value just at the end of that discovery process.
Callan [0:24:39]: I was just how much of this would be different at, I mean, you were at, you know, what is big for?
Callan [0:24:43]: Like, how much was
Chris [0:24:44]: not not wildly.
Chris [0:24:44]: Not wildly.
Chris [0:24:45]: Interesting.
Chris [0:24:46]: The difference is, at the end of that, you know, from a strategy standpoint, a lot of times it's this really pretty dac on, like, here's what the different options that you could take.
Chris [0:24:54]: Yeah.
Chris [0:24:55]: You to execute towards your vision.
Callan [0:24:58]: Yeah.
Chris [0:24:58]: Now being a tech company at the end of that, here's our road roadmap our shared roadmap to solving your challenges and helping you realize your aspirations.
Callan [0:25:09]: Yeah.
Callan [0:25:09]: So you can actually implement on right.
Callan [0:25:11]: You can execute on my should say.
Callan [0:25:12]: So What is something like that cost?
Callan [0:25:15]: I how you even come up with
Chris [0:25:16]: this price.
Chris [0:25:17]: So it it depends on the scope Break?
Callan [0:25:20]: Because a
Chris [0:25:20]: lot of times you're going in and it's a little bit more defined.
Chris [0:25:22]: One of the most important things from a strategic standpoint is, you know, our distribution strategy, and aligning the right resources, capabilities and technology Mh.
Chris [0:25:34]: To expand distribution.
Chris [0:25:35]: It could be how do we improve our operations?
Chris [0:25:38]: Could be different areas of scope.
Chris [0:25:41]: Yeah.
Chris [0:25:41]: And that would be generally how we would think about sizing that up?
Callan [0:25:45]: Mh.
Chris [0:25:46]: We also think about what's the opportunity on the back end of that?
Chris [0:25:49]: Yeah.
Chris [0:25:49]: Which you know, you kinda get a lot of our lot of our partners get, you know, a little bit of discounted consulting because there is an opportunity for us to work together back end and we take that into account.
Chris [0:26:00]: But, yes, it's a consulting engagement in a lot of ways, and we put a lot of effort behind it and try to drive a lot of value just in that discovery and solution development process.
Chris [0:26:10]: So, you know, it's hard to say exactly what that is, but it could be seventy five k to a million dollars.
Callan [0:26:17]: Yeah.
Callan [0:26:17]: So it's a real line item.
Callan [0:26:19]: Like, this is a real.
Callan [0:26:20]: Yeah.
Chris [0:26:20]: Yeah.
Chris [0:26:20]: And it goes back to the commitment of that individual?
Chris [0:26:24]: Is they're thinking about doing something big doing something innovative.
Chris [0:26:27]: Why are we even there in the first place?
Chris [0:26:28]: Yeah.
Chris [0:26:29]: And if you're like, why I want you to show up and do ninety days of a ton of work?
Chris [0:26:33]: And I'm I'm not gonna pay you for it?
Chris [0:26:35]: Are they serious?
Callan [0:26:36]: No.
Callan [0:26:36]: No.
Callan [0:26:37]: I hear you on that.
Callan [0:26:38]: I one hundred percent hear you.
Callan [0:26:39]: Yeah.
Callan [0:26:40]: It's like, when you give away an assessment for for free.
Callan [0:26:42]: It's...
Callan [0:26:42]: How long?
Callan [0:26:43]: How good that assessment gonna be?
Callan [0:26:44]: How much you really gonna put towards a free assessment or whatever it might
Chris [0:26:49]: be
Callan [0:26:49]: because you almost like, for that to even make sense, unless it's, you know, sometimes they'll do it for, like, you know, those unicorn scenarios Right...
Callan [0:26:57]: But you're not gonna probably put your best effort.
Callan [0:26:58]: And that's probably gonna be very temp digitized on what you're doing.
Callan [0:27:01]: Okay.
Callan [0:27:02]: So You are delivering this shared road map.
Callan [0:27:04]: One of the things that I've heard you talked about before, and I thought I've never heard describe like that.
Callan [0:27:08]: When we talk about this road map you're delivering.
Callan [0:27:11]: How much of this is core product.
Callan [0:27:13]: How much of this is services how much of this is future road map?
Callan [0:27:16]: What does that look like?
Chris [0:27:17]: Yeah.
Chris [0:27:17]: Yeah.
Chris [0:27:18]: So services piece outside, you know, core map, eighty twenty.
Chris [0:27:23]: You know?
Chris [0:27:23]: I mean, it's an overused ratio.
Callan [0:27:25]: But you want eighty percent of that should to be on to be core product.
Chris [0:27:29]: Right?
Chris [0:27:29]: So After we've done the current state and we come back with the current state, there's a session where we all align that.
Chris [0:27:34]: This is the current state, and these are the opportunities that we see.
Chris [0:27:38]: Mh.
Callan [0:27:39]: And so
Chris [0:27:39]: we'll all align you know, we'll line up all those opportunities.
Chris [0:27:42]: And then we'll start to typically use a kind of a value effort matrix on all those opportunities that we're starting to see.
Chris [0:27:49]: And then over the next, the next session we'll be dialing in those opportunities and collaborating on that value because we'll we'll take a first pass and we'll map that out on a matrix and it'll look cool and, you know, we'll I have all the the scoring behind that.
Chris [0:28:03]: But to really move that forward into really be crisp on that.
Chris [0:28:07]: That's gotta be collaborative because they know their business.
Chris [0:28:09]: Right?
Chris [0:28:09]: They know.
Chris [0:28:10]: You know, whoever, who our partner knows what might be more challenging, what might have more efforts to get done and or what might unlock more value.
Chris [0:28:19]: Right.
Chris [0:28:19]: And so that's kind of that next session that says, okay.
Chris [0:28:21]: We have our current state we know the big rocks of opportunity.
Chris [0:28:25]: And then as we're doing that, we're building the future state vision to solve for a lot of those.
Chris [0:28:31]: And as we're doing that, we are thinking about those swim lanes and those key pieces of activity and lining those up against our set of solutions.
Chris [0:28:41]: Yep.
Chris [0:28:41]: And that's where that magic can kinda happen to say, okay, At the end of that, here's that eighty percent that falls in our core thing, Here's ten percent that's gonna be just for you.
Chris [0:28:53]: And here's ten percent that's actually...
Chris [0:28:55]: That actually aligns with our road roadmap.
Chris [0:28:56]: And now that you are one more vote for that thing.
Chris [0:28:59]: We've heard that from three other partners.
Chris [0:29:00]: We're accelerating our road roadmap to meet that.
Callan [0:29:04]: And that ten percent just for you.
Callan [0:29:05]: That's the services.
Callan [0:29:06]: That Like...
Chris [0:29:07]: Well, also so the whole thing could be services.
Chris [0:29:08]: Mh.
Chris [0:29:09]: That ten percent is it could be custom built.
Chris [0:29:11]: That whole the full implementation all the set of solutions or the solution.
Chris [0:29:16]: Could be services could be done by us could be done by a partner could be done jointly could be done internally.
Chris [0:29:22]: There are a number of different ways that will handle the services piece.
Chris [0:29:25]: The services often go more heavily into that ten percent because it is net new.
Chris [0:29:30]: Yeah.
Chris [0:29:30]: From
Callan [0:29:31]: it is custom.
Callan [0:29:31]: We're highly configured.
Callan [0:29:33]: Probably not very repeatable.
Chris [0:29:35]: Not very repeatable.
Chris [0:29:36]: So that component is often carved out, but the services can be bigger and broader than that for the entire.
Chris [0:29:42]: Gotcha.
Callan [0:29:44]: I'm curious how often do they go through this process?
Callan [0:29:47]: And then go somebody else.
Chris [0:29:50]: It's happened.
Callan [0:29:53]: We just probably like you started charging for it.
Chris [0:29:56]: That's right.
Chris [0:29:56]: Yeah.
Chris [0:29:57]: Bingo.
Chris [0:29:57]: I Yep.
Callan [0:29:59]: Yep.
Callan [0:29:59]: You nailed it.
Callan [0:29:59]: Yeah.
Chris [0:30:01]: Yeah.
Chris [0:30:01]: Kinda felt like a jump the first time around that happened.
Chris [0:30:03]: But, yeah.
Callan [0:30:04]: Which makes
Chris [0:30:05]: ones?
Chris [0:30:05]: Yeah.
Chris [0:30:05]: Doubt doubt.
Chris [0:30:05]: And the reality is, you know, partners that we've worked with even the ones that take that path.
Chris [0:30:10]: You know, I have been great partners often come back
Callan [0:30:13]: around.
Chris [0:30:13]: Yeah.
Chris [0:30:13]: And have been very appreciative.
Chris [0:30:15]: But, yes, That is part of the reason we charge.
Chris [0:30:17]: And typically, again, because of that buy and the amount of buy in that gets built and the amount of trust that gets built throughout that process.
Chris [0:30:27]: Sure.
Chris [0:30:28]: We've got a pretty good hit rate.
Chris [0:30:29]: Yeah.
Chris [0:30:30]: Got a pretty good hit rate.
Callan [0:30:32]: I mean, it's gotta gotta assume it's kinda hard not to.
Callan [0:30:34]: I mean, joe I'm only be, like, if that's valuable but that has to be valuable.
Callan [0:30:37]: Yep.
Callan [0:30:38]: Like, that has to be rock solid, and they have to know, like, what you just said.
Callan [0:30:42]: Like, okay.
Callan [0:30:42]: We do trust that you know our business, probably even better than waiting.
Callan [0:30:46]: Mh.
Callan [0:30:46]: Or at least as good as we do.
Callan [0:30:48]: So...
Callan [0:30:49]: Okay.
Callan [0:30:50]: This process gets completed.
Callan [0:30:52]: Yep.
Callan [0:30:53]: You deliver this, you deliver the full proposal now what.
Chris [0:30:58]: This where some of the challenge comes in because sometimes it's a timing thing.
Chris [0:31:01]: And this is where it's, like, okay.
Chris [0:31:03]: We've got a board meeting in a quarter.
Callan [0:31:05]: Mh.
Chris [0:31:06]: And so then the question is what can we get started today?
Chris [0:31:08]: And that's why that road map, there's some art in that road map.
Chris [0:31:11]: Mh.
Chris [0:31:12]: And some science.
Chris [0:31:13]: And that art looks at what is the cadence, what is the cycle of the business on a quarterly annual basis, where are they towards their funding cycle towards their budget planning?
Chris [0:31:24]: To be able to unlock the bigger pieces of this?
Chris [0:31:27]: And what can we pull forward today to get started?
Chris [0:31:30]: Because, as you know, I think you even said this to me This where I learned time kills all deals.
Chris [0:31:34]: Right?
Chris [0:31:34]: Percent.
Callan [0:31:35]: Dave, I gotta give Dave Credit.
Callan [0:31:36]: It was dave Dave G, who was at Bold Penguin is Cro of play on sports.
Callan [0:31:41]: Great guy who we both but that Dave.
Callan [0:31:43]: That gotta alright.
Callan [0:31:44]: We Go
Chris [0:31:45]: all the way back up the chain to to the God godfather.
Callan [0:31:48]: On that one.
Callan [0:31:48]: Firmly believe it.
Callan [0:31:49]: I'm man I see it all the time.
Callan [0:31:51]: You gotta gotta give the dave.
Chris [0:31:53]: Awesome.
Chris [0:31:53]: That is actually the biggest challenge out of the back of that is hey.
Chris [0:31:57]: This is cool.
Chris [0:31:57]: We wanna go.
Chris [0:31:58]: Let's go.
Chris [0:31:59]: Gosh shit.
Chris [0:32:00]: Our annual planning cycle kicks off in the second half of the year?
Chris [0:32:04]: We did this and we completed it in April?
Chris [0:32:06]: Guys, we don't have the budget to kick this off the today?
Chris [0:32:09]: This is gonna be a, you know, q one next year thing.
Callan [0:32:13]: Will you start working in delay payment?
Chris [0:32:15]: It depends who it is.
Chris [0:32:16]: It depends on what we're doing.
Chris [0:32:18]: It depends on our relationship because this process isn't necessarily just for a net new customer.
Chris [0:32:23]: Yeah.
Chris [0:32:23]: Right.
Chris [0:32:23]: We will go through this process ongoing with partners.
Callan [0:32:26]: Yep.
Chris [0:32:27]: As they're thinking about their road map.
Chris [0:32:29]: Their strategic road roadmap.
Chris [0:32:30]: What's important in how we can support them in achieving those aspirations.
Chris [0:32:34]: So the answer is it it depends, and there are ways to structure it.
Chris [0:32:38]: Right?
Chris [0:32:38]: I mean, there are different ways to structure it, especially as you think about longer term engagements and bigger solution sets towards a in a a big innovation play.
Callan [0:32:48]: How much does this help when you go into procurement.
Callan [0:32:50]: So for anybody.
Callan [0:32:51]: I mean, I'm think, if you listen to this show, you're probably familiar with procurement, with the bigger companies in the insurance space.
Chris [0:32:57]: Yeah.
Callan [0:32:58]: It's pretty intense and it lasts a long time.
Callan [0:33:00]: Yep.
Callan [0:33:00]: How much does this help?
Callan [0:33:02]: How does it help?
Chris [0:33:05]: Or not at all.
Chris [0:33:05]: I...
Chris [0:33:06]: You know what?
Chris [0:33:06]: I haven't really witnessed it helping dramatically at all.
Chris [0:33:09]: I mean, if procurement needs a business case
Callan [0:33:12]: Yes done.
Chris [0:33:13]: Then it's done.
Chris [0:33:14]: Exactly.
Chris [0:33:14]: And so in...
Chris [0:33:15]: From that regard, at all, it'll speed up the business case cycle for sure.
Chris [0:33:19]: Mh.
Chris [0:33:20]: And I've seen that because it's the slam dog.
Chris [0:33:22]: It's like, alright.
Chris [0:33:22]: Here's a hundred and fifty page deck that lays out all the value and lays out the road map and that can be helpful in that.
Chris [0:33:29]: But when you're talking about security review and you're talking about the financial review and you're talking about, all the procurement processes for an enterprise to work with us, whatever else might be.
Chris [0:33:44]: Sure.
Chris [0:33:44]: It is especially in the insurance space.
Chris [0:33:47]: Yeah insurance and financial services more broadly.
Chris [0:33:49]: Brutal.
Callan [0:33:50]: And if anyways, right?
Callan [0:33:51]: Like, it has to be.
Chris [0:33:52]: It does.
Chris [0:33:52]: No.
Chris [0:33:53]: They're doing the right things.
Chris [0:33:53]: I mean, you know,
Callan [0:33:55]: but it's brutal,
Chris [0:33:55]: but it's brutal It's long and it's brutal.
Callan [0:33:58]: Do you find that they will knowing that that procurement could take six months to a year that they'll once you have this they'll least kick off that process or will they still wait until you get to the other side, I've seen both ways, but I'm curious to get your take.
Chris [0:34:12]: What what we try to do is get procurement going as soon as possible.
Chris [0:34:15]: Mh?
Chris [0:34:15]: So even as we're doing this discovery work this, interesting.
Chris [0:34:19]: Start some of that process.
Callan [0:34:21]: Saying, you
Chris [0:34:22]: know, no harm no file.
Chris [0:34:23]: If at the end of this, we're not for you or we delay the reality is...
Chris [0:34:27]: Let's knock out that security assessment.
Chris [0:34:29]: Yeah.
Chris [0:34:29]: Do your financial review.
Chris [0:34:31]: Let's get some of those core pieces out of the way.
Chris [0:34:33]: Let's trade some template paper.
Chris [0:34:35]: Let's get an Msa in place, and then we can we can line up the orders under that Msa.
Chris [0:34:40]: Let's do some of those things to expedite that cycle.
Chris [0:34:43]: And that's on the net new side.
Chris [0:34:45]: Yeah.
Chris [0:34:45]: Working with current partners generally not as much a challenge.
Chris [0:34:49]: You know, there...
Callan [0:34:50]: What's you're globally procured getting the other one Actually.
Callan [0:34:52]: Easier.
Callan [0:34:52]: I mean, it's a lot of people don't realize is that you get all the time like, well, why do they just go with Accenture again?
Callan [0:34:58]: And this is nothing it's not not gonna...
Callan [0:34:59]: Accenture.
Callan [0:35:00]: Yeah.
Callan [0:35:00]: But it's, like, why do they go with Accenture against?
Callan [0:35:02]: Because I don't have to go with procurement.
Chris [0:35:04]: That's right.
Callan [0:35:04]: It's easy.
Callan [0:35:04]: You get...
Callan [0:35:05]: You cards there and you exactly.
Callan [0:35:07]: You get the next exhibit in place, you you scope it out then you go.
Chris [0:35:11]: Yep
Callan [0:35:11]: The...
Callan [0:35:11]: Once you get that first one, which I think is such an underrated point.
Callan [0:35:14]: It's just easier to go with you.
Callan [0:35:16]: Even if there's...
Callan [0:35:17]: And I'm not saying this the case with bull penguin.
Callan [0:35:19]: But even if there's a better product out there, do you really wanna go through that whole thing again.
Callan [0:35:24]: Yeah.
Chris [0:35:24]: It's a great question.
Chris [0:35:25]: Many many don't.
Chris [0:35:26]: Well, and in part just the timing.
Chris [0:35:28]: Right?
Chris [0:35:28]: I mean, if you have objectives that you have to meet, and the procurement cycle could take six, eight, twelve months.
Chris [0:35:35]: Yeah.
Chris [0:35:35]: I mean, that there's an opportunity cost.
Chris [0:35:38]: A hundred percent.
Chris [0:35:39]: But I think it's a really good point, You know, that even if a solution in front of you may not be your perfect solution.
Chris [0:35:47]: Yeah.
Chris [0:35:47]: If it's a ninety percent solution, but it's there.
Chris [0:35:50]: You know, What why would you not?
Chris [0:35:52]: Burton hand.
Callan [0:35:52]: Yeah.
Callan [0:35:52]: Exactly right.
Callan [0:35:53]: So I love that process.
Callan [0:35:55]: I rarely hear people talking about that process.
Callan [0:35:59]: And then, you, I was gonna...
Callan [0:36:00]: Yeah, I've already kinda talked about it, But when did you start to implement a lot of those skills from consulting at Bold Penguin?
Callan [0:36:06]: What stage was that when you start to do that?
Callan [0:36:08]: Was that Asap right away?
Callan [0:36:10]: Or did you kinda have to, like, test that, prove that out?
Callan [0:36:13]: Yeah.
Callan [0:36:14]: What did that look like?
Chris [0:36:15]: It didn't get formalized day one.
Chris [0:36:17]: Mh.
Chris [0:36:18]: Right?
Chris [0:36:18]: It was it was a little bit of building to the need.
Chris [0:36:21]: Right?
Chris [0:36:22]: And it was just applying two different paths together towards, you know, an outcome and and then flexing into being the solution provider with the strategic process.
Chris [0:36:36]: And so mel those together out.
Chris [0:36:38]: I'd say, you know, within very early on and and Bold Penguin is, you know, just has a tremendous history of working with some of the biggest and best governors learners in the insurance space.
Callan [0:36:48]: Or Dna from day one.
Chris [0:36:49]: The day one.
Chris [0:36:49]: So pretty quickly, you know, we had to do that.
Chris [0:36:52]: And the ability to do that and walk through that process and really articulate that process.
Chris [0:36:57]: Yeah.
Chris [0:36:58]: And guide customers and partners through that process became pretty important.
Chris [0:37:02]: So it got hardened pretty quick.
Callan [0:37:05]: Yeah.
Callan [0:37:05]: What was the turning point?
Callan [0:37:06]: For you, what was the turning portal?
Callan [0:37:08]: It's just like, okay.
Callan [0:37:09]: That really work.
Chris [0:37:11]: Yeah.
Chris [0:37:11]: Yeah.
Callan [0:37:12]: Was there a piece that you added?
Callan [0:37:13]: Was it the whiteboard session?
Callan [0:37:15]: Was the...
Callan [0:37:15]: What was that turning point where was like, okay.
Callan [0:37:18]: This is a big deal.
Callan [0:37:18]: Like, this needs to be standard.
Chris [0:37:20]: Yeah.
Chris [0:37:20]: It was a big partner.
Chris [0:37:21]: It was a very...
Chris [0:37:22]: It was one of our one of our big partners today?
Chris [0:37:25]: We went through this process as many early stage companies are our founders did a phenomenal job of engaging those early clients.
Callan [0:37:34]: Mh.
Chris [0:37:34]: And putting Bold Penguin on the map, and then bringing a team in and empowering that team to then scale.
Chris [0:37:40]: Yeah.
Chris [0:37:40]: And so was in that mode as I had just joined and selling a very, very big customer, the need to do that process to get them across the board since that one was on my back.
Chris [0:37:55]: And so to do that, but then, you know, engage with the founders around that, and learn, you know, from how they thought about the process and from their process and the crown moment was, you know, one of the founders was there, and he's like, I, you know, thought I'd come in I'd need to play the founder card and he's like, I fell asleep I was super bored.
Chris [0:38:13]: He was like, that was all...
Chris [0:38:16]: And his point was that was awesome.
Chris [0:38:17]: Yeah.
Chris [0:38:18]: I.
Chris [0:38:18]: We just finished one of the phases of the whiteboard boarding sessions and kinda more thinking future state.
Chris [0:38:23]: And what's cool.
Chris [0:38:24]: That partner goes back to five, six years ago, and we're...
Chris [0:38:30]: We've executed all phases when big phases multi year phases.
Callan [0:38:34]: Yeah.
Chris [0:38:35]: And we're now on, like, the next crunch of phases together.
Chris [0:38:38]: Yeah.
Chris [0:38:38]: That's kinda cool.
Callan [0:38:39]: That's amazing.
Callan [0:38:39]: Where do you guys go to celebrate?
Callan [0:38:40]: Tulsa Oklahoma?
Chris [0:38:44]: My wife went
Callan [0:38:45]: let year.
Callan [0:38:45]: I know.
Callan [0:38:46]: We know it's a beautiful city.
Callan [0:38:48]: But you're band.
Callan [0:38:49]: I was
Chris [0:38:51]: I I've never gone back.
Chris [0:38:52]: I'm not allowed.
Callan [0:38:53]: Not allowed.
Callan [0:38:53]: So you worked your way up to the ranks to sea level Bold Penguin.
Callan [0:39:00]: You know, curious for you, and I've got some thoughts on this as well, but You bull penguin we sold in less than five years.
Callan [0:39:07]: Yep.
Callan [0:39:08]: I still say we.
Callan [0:39:09]: But, like, we or are, but, like, absolutely...
Callan [0:39:11]: Bull penguins sold in less than five years.
Callan [0:39:13]: When did you...
Callan [0:39:14]: Or did you have a feeling like, okay.
Callan [0:39:17]: There's really something here.
Callan [0:39:18]: Like, this got a real shot.
Chris [0:39:20]: Yeah.
Chris [0:39:20]: You know, it's good question.
Chris [0:39:22]: Actually, really joining.
Chris [0:39:24]: Yeah.
Chris [0:39:25]: A good friend of mine who was an executive at nationwide.
Chris [0:39:28]: Mh.
Chris [0:39:29]: Was very early on with Bold Penguin, the Coo.
Callan [0:39:33]: Yep.
Chris [0:39:34]: At pulled Penguin.
Chris [0:39:34]: And after he joined, said, hey, let's go.
Chris [0:39:37]: Let's go grab a beer.
Chris [0:39:38]: Think there might be an opportunity for you here.
Chris [0:39:41]: You've done the kind of the consulting thing.
Chris [0:39:44]: You've done, You've played in kind of the private equity and early early stage company space, and you've checked the insurance box, the commercial insurance box.
Chris [0:39:52]: So why don't you come on board.
Chris [0:39:53]: And so before coming on board, I really did more of an in, like, an investor lens.
Callan [0:40:00]: Yeah.
Chris [0:40:00]: To the opportunity.
Chris [0:40:01]: I took more of an investor lens, the opportunity.
Chris [0:40:03]: And looking at where specifically small commercial insurance distribution was at that spot and the way that the founders, were looking to attack the market.
Chris [0:40:15]: We're looking at the market opportunity was pretty excited as Was like, alright.
Chris [0:40:20]: There's...
Chris [0:40:20]: This is a live one.
Chris [0:40:21]: This is one that would be really cool to join at each chapter throughout the course of Bull penguins history and, you know, been blessed to to be pretty early on, you know, and still there day, you know, it's just like, the next unlock.
Chris [0:40:34]: Yeah.
Chris [0:40:34]: Each step.
Callan [0:40:36]: Yeah.
Callan [0:40:36]: You know, it's funny.
Callan [0:40:37]: Because, obviously, I knew Ben pretty well.
Callan [0:40:40]: And we had worked together at the shipyard And and others, like, when I joined, I was, okay, Know what I'm gonna going.
Callan [0:40:46]: Know what Getting into.
Callan [0:40:47]: I know these two guys are enterprise at their core.
Callan [0:40:50]: They're very innovative, and they're not afraid to take big swings.
Callan [0:40:54]: Really big swings.
Callan [0:40:55]: And I've been on the side.
Callan [0:40:57]: Where we've missed some of those swings.
Callan [0:40:58]: And a big thing too for me was this was kinda rooted in the Dna of of Bold Penguin was I was going to start my own business at some point.
Chris [0:41:05]: Yep.
Callan [0:41:05]: And they were a hundred percent okay with that.
Callan [0:41:07]: Building on the side whatever that might be.
Callan [0:41:09]: And that was, I actually used that as a recruiting piece on my team to get more of those entrepreneurial minded people.
Callan [0:41:14]: But I do remember after I got in for a couple months.
Callan [0:41:18]: I was like, oh, Oh, this is this is for real.
Callan [0:41:22]: I.
Callan [0:41:23]: I just No.
Callan [0:41:25]: Yeah.
Callan [0:41:25]: Because we had raised a decent amount of money, but you see people raise money all time.
Callan [0:41:29]: Yeah.
Callan [0:41:29]: And a lot of people raised a lot of money all the time, and and that wasn't necessarily for real, but it just had that feeling of Okay.
Callan [0:41:36]: This is real.
Callan [0:41:36]: The revenue traction real.
Callan [0:41:38]: The deals that are bringing on are real and there's actual problems being solved.
Chris [0:41:43]: Yep.
Callan [0:41:43]: And my favorite thing about Bold Penguin by bar was was the people.
Callan [0:41:47]: I know that gets said all the time, but, like, That was still is, a smart group of people.
Callan [0:41:53]: It was a lot of fun.
Callan [0:41:54]: It was definitely obviously work hard player art atmosphere, but Yep.
Callan [0:41:57]: Nothing beat the people.
Chris [0:41:58]: Yeah.
Chris [0:41:58]: That early Dna was...
Callan [0:42:00]: Well, it was so much fun.
Chris [0:42:01]: Was cool.
Callan [0:42:02]: So much.
Callan [0:42:02]: I mean the office was crazy.
Callan [0:42:03]: Yeah.
Chris [0:42:04]: Absolutely.
Chris [0:42:04]: Yep.
Chris [0:42:05]: I mean, can't you you, you know, you can't recreate that lightning in a bottle.
Chris [0:42:09]: Right.
Chris [0:42:09]: Right.
Chris [0:42:10]: I mean, that chapter was cool.
Chris [0:42:11]: Yeah.
Chris [0:42:12]: That it was awesome.
Callan [0:42:13]: It was a ton of fun.
Callan [0:42:14]: Chris, last question I got.
Callan [0:42:15]: Yeah.
Callan [0:42:16]: If you can have a conversation with your younger self, age, totally up to you, what would that conversation be?
Callan [0:42:22]: What advice would you give them?
Chris [0:42:24]: You know, I...
Chris [0:42:26]: In some ways, I've had a fairly varied career, You know, when I go back, I was gonna go just started in finance and I was gonna stay in the finance track and do the finance thing and work that track, probably, you know, try to get into private equity through that pretty typical track.
Chris [0:42:42]: And now, that's what I was gonna do.
Chris [0:42:43]: Throughout my career, I've I've kinda run at the next interesting problem, Mh.
Chris [0:42:48]: Including, you know, joining bold bang.
Callan [0:42:51]: Absolutely.
Chris [0:42:52]: And through that, know, it's always been...
Chris [0:42:53]: Am I doing the right thing, am I progressing my career in the right way?
Chris [0:42:57]: Sometimes, you know, maybe taking a step back financially or taking a step back on paper.
Chris [0:43:03]: Yeah.
Chris [0:43:03]: From a career standpoint to run at that next problem or that next interesting opportunity, And I've done that a number of times, and I I think what I would say to my younger self wherever that might be in that arc of a career to this point would be, you know, just go after it.
Chris [0:43:18]: Don't worry.
Chris [0:43:19]: About the paper.
Chris [0:43:21]: Yeah.
Chris [0:43:22]: Around that opportunity.
Chris [0:43:25]: You know, if you're solving a problem and you're having fun and you're working with good people, and you're doing something cool and something big.
Chris [0:43:31]: Don't worry.
Chris [0:43:32]: Yeah, and work out.
Chris [0:43:34]: I think each one of those and even as ian between those as I was thinking about what that next move is.
Chris [0:43:38]: Spend a lot of time being being pretty thoughtful and deliberate on that.
Chris [0:43:42]: You know, as I look back good.
Chris [0:43:44]: But, you know, just run with it.
Chris [0:43:46]: That would be the advice I'd half.
Callan [0:43:49]: I mean, I think it's excellent advice, and I think one of the things it's hard.
Callan [0:43:53]: It's really hard as you get older to say, okay.
Callan [0:43:57]: Here's my market rate.
Callan [0:43:58]: And or I'm in this position, and I'm making really good money.
Callan [0:44:01]: But I don't love it to it's hard to make that decision.
Chris [0:44:06]: Yeah.
Callan [0:44:07]: But so often even though if it feels like a step back could be, like, could be two giant steps forward.
Callan [0:44:11]: Such what you're saying.
Callan [0:44:13]: Isn't it?
Chris [0:44:13]: That's exactly right.
Chris [0:44:14]: Yeah.
Chris [0:44:14]: It's exactly right.
Callan [0:44:15]: Yeah love it.
Callan [0:44:16]: Yep.
Callan [0:44:16]: Chris, this was awesome, man.
Callan [0:44:17]: I'm glad we can get you on here.
Chris [0:44:20]: Dude that made it.
Callan [0:44:21]: You you guys sent to your brother.
Callan [0:44:22]: Made it.
Callan [0:44:22]: Any money concerns you're, like, you'll never have it again.
Chris [0:44:26]: He so well.
Callan [0:44:27]: Good Awesome, brother.
Callan [0:44:28]: This is great.
Callan [0:44:29]: Appreciate it.
Callan [0:44:29]: I hope you enjoyed Chris and i's conversation, I could talk about solution.
Callan [0:44:41]: As under the radar as it is all day along.
Callan [0:44:43]: And I think it is critical to Land enterprise deals.
Callan [0:44:46]: If you wanna learn more about Chris, you could find him on Linkedin in the show notes.
Callan [0:44:51]: Also, if you like this episode, you could find me on Linkedin to let me know.
Callan [0:44:55]: And if you really wanna support the show, give us a follow on Youtube, give us a review an Apple podcast or spotify.
Callan [0:45:01]: Every time you do it, it is very much appreciated, and I thank you all for listening today, and I'll see you next week.