
Loading summary
A
The agile brand.
B
Welcome to the B2B Agility podcast, where we look at the factors that drive success in B2B marketing, with a focus on the people, processes, data, and platforms that make B2B brands stand out and thrive in a competitive marketplace. I'm your host, Greg Kilstrom, advising Fortune 1000 brands on martech, marketing operations and CX, bestselling author and speaker. Now let's get on to the show.
C
Many entrepreneurs dream of scaling a niche product, achieving market dominance, and ultimately securing a successful exit.
A
I'm going to just start that over again.
C
Many entrepreneurs dream of scaling a niche product, achieving market dominance, and ultimately securing a successful exit, but few actually make it happen. How do you take an idea from concept to acquisition? And what key lessons can other business leaders, including marketers, take from that journey? Joining me today is Chris Tulkov, general manager at docusketch, an automated estimation and documentation platform that helps homeowners rebuild after natural disasters. Before leading Docusketch, Chris founded Ask Amy, a platform that has successful. That was.
A
I think we'll have to do something in there as well. Anyway, I'm definitely not leading Docusketch. I still lead the product Amy, too. So I'm leadership at DocuScatch.
C
Okay. Director of Dr.
A
Sketch, too. And then while you're at it, I know there was one other thing. I read it says carpentry somewhere and it was actually carpet cleaner was my first job, so. Oh, okay. You see that word come up? I think it was in my bio. So if you carpet cleaner when you see that one.
C
Okay, perfect. So I'm just gonna say before joining docusketch, and then you can tell, you can talk about your role when I. After, I want to ask you to introduce yourself. So I'm just going to say, before joining DocuScatch, Chris founded Ask Amy, a platform that was successfully acquired. And then I'll mention the carpet cleaning and stuff.
A
Beauty.
C
Okay. Joining me today is Chris Tilkov, general manager at docusketch, an automated estimation and documentation platform that helps homeowners rebuild after natural disasters. Before joining docusketch, Chris founded Ask Amy, a platform that was successfully acquired. But his journey didn't start in tech. He began his career as a carpet cleaner before transitioning into the world of technology and entrepreneurship. Chris, welcome to the show.
A
Thank you for having me, Greg.
C
Yeah. Looking forward to talking about all this with you. Before we dive in, though, why don't you give us a little more background and how your journey from carpet cleaning to technology led you. Where you are today?
A
Sure, yeah. Somehow I'm started in this industry, restoration and insurance when I was 17 and I'm a millennial. I don't think you'll find too many millennials out there that stayed in the same industry so long. I was a flood technician at first and a carpet cleaner and so a flood tech would be somebody that comes to your house or business anytime, day and night when if you have a. I had a flood. So I learned a lot about building science and materials to demolition at the same time. Through my career I was often studying part time and what I was learning studying mirrored what I was doing in the field. So I studied architecture and engineering, I studied business and ultimately onto technology. I created some successful products for the companies that I worked for along the way, tied into ERP solutions and came up with sales reporting for one company that fundamentally changed the way they did business and moved on to build a national estimating platform for a franchise group. I, I eventually kind of really wanted to try something on my own. So that's when I stepped out and put my efforts into amy, which is an automated review platform reviewing insurance based estimates and you know, the long, short highs and lows, strikes and gutters on that journey as any entrepreneur has, but ended well. And I'm now part of Docusketch and Docusketch captures 360 images at the beginning of the the job for the insurance industry. We write the estimate and use my product to review those estimates. So very natural fit and no looking back and no regrets.
C
Yeah, love it, love it. So yeah, let's maybe, maybe take a, a, a step back and start, start towards the beginning here and you know, I want to talk about building and, and scaling the, this product with which you know, certainly fills an important niche there. So you know what inspired you to launch Ask Amy and, and how did you identify the, the market need?
A
Yeah, well, first off I, I kind of mentioned I had a couple successes for others and I, I really did want to try something on my own. I actually pitched the idea of Amy to one of my employers and it just wasn't for them. They weren't looking to get into the tech space. So. Fair enough. And I kind of assessed and realized that I was at a time in my life that I could take the risk. And so before what inspired you kind of sometimes have to do a self assessment if you are really trying going the bootstrap method like I did to really assess things. So I was single, no dependence. It was the time for me. This was the Only industry that I knew and I specialized in reviewing estimates. It's very time consuming to do that. You've got somebody on the restoration contractors kind of side of the negotiation doing it. You've got groups on the carrier side of the negotiation doing that. There are not enough people, there were not enough experts. And it was a terribly inefficient process. So that was the need. I was confident from my experience and having, becoming an expert, traveling, being a trainer, really knowing these systems inside and out that you, that I could design a system that could parse these out and, and help in the process. It was definitely a leap of faith. You couldn't test a small partial product here. You had to kind of build enough rules behind it so that it actually produced a result. But it was like I say, it was the time in my life to go out and, and really try to do so. I, I saw a pretty significant need to improve efficiencies across the industry.
C
Yeah. And so I mean in, in that stuff. Cause I, you know, there's, there's different kinds of founders. There's, you know, there's, there's the technical founders that are, you know, they're, they're writing code, but may not have as much of the hands on experience that you had. So in other words, you're, you're coming at this from like the market need was something that you experienced and the data, for lack of a better way of explaining it was, was firsthand knowledge. Right. Is that, did you have other data that was kind of guiding your, your decisions there as well?
A
Eventually, I mean that became helpful when the, the company grew, we were able to empirically show both time savings and value change in the estimate to make it both more compliant and more accurate. Um, for like the personal experience. Yeah, every single estimate is meticulously reviewed and there was very little automation out there. Um, it did quickly become data driven when you do have that empirical value coming. Like today for example, as part of docusketch, at the scale we're doing reviews, we're reviewing billions of dollars in estimates value. And each estimate on average there's big ones and small ones, but on average will move hundreds of dollars to add additional items in that are warranted work that somebody is really going to be doing in somebody's home or business. And it also will move hundreds of dollars in to reduce it for compliance overages or mistakes. So we're really bringing the two sides. I don't want to put them on as adversaries, but they're negotiating. We're really trying to get them to a reviewed and approved estimate quicker with improved cycle times through the use of our combined product, Amy and Docusketch.
C
Yeah, yeah. And so you know, this product obviously very valuable and time, time saving for this industry, but you know, it fills a niche and so, you know, it's not necessarily something, you know, consumers aren't going out looking for this. So you know, when you look at scaling a product like this and when you look at the competition in the space, you know, how do you, you know, what were some of the biggest challenges that you had and gaining traction and you know, what, what, you know, what methods organic growth, partnerships, paid marketing, you know, what, what methods were used to really scale it?
A
Yeah, I, I am the technic more on the technical side. So I spent a lot of time on product. It had to be right. And I believe that, yeah, you had to have enough rules in this thing to make it presentable to somebody and they had to be accurate. We're, we're helping people settle like we're commenting on an estimate to assist them to sell a claim. So it had to be right. And for sales, I really ended up leaning on my reputation in the very beginning. So the product was first kind of built on the shoulders of my reputation. I traveled a lot. I provided training for both restoration contractors and insurers. I was known for speaking at conferences, et cetera. And now for and a way the biggest users of Amy are actually Docusketch internally. So it's kind of like an internal customer is the acquirer. The value proposition that we've created together from initial documentation to estimating a review and has how that scale together we combining those products for a greater one for our common clients now has been a huge catalyst. We're doing, you know, many times over the volume that Amy was doing by itself.
C
Yeah, yeah. And so, you know, certainly there's, there's that the deep technical knowledge, you know, both technical from a code perspective, but also technical knowledge of what's needed for the, for the business to make a compelling product. You know, that's certainly a key part. What about branding and storytelling and, and some of those marketing things like how, how much of a role did that help as, as you were going to market and, and scaling, scaling.
A
Yeah. So yeah, the brand, like I kind of mentioned the brand at first at least stood on, on the shoulders of my reputation. But for storytelling maybe I can tell a, tell a story here. So how I ended up at Docusketch, a big part of it was through through somebody I knew. So I grew up in this industry, as we said. I eventually was leading an estimating department and a national franchise group estimating department. When problems with some of the estimates occurred. They kind of go uphill to a certain point to me. And Nelson Higgins, who is works at Docusketch now as well, was in the same position but on the carrier side. So he ran the review teams and. Great guy, but we had to figure things out together. So reputation being what it is, when things got to us, we always knew that we could look each other in the eye, get to the bottom of things. You know, somebody wasn't going to like it at the end of the day, usually me, because I was the contractor and they were paying the bills. But we, we'd come to like a amenable agreement on things and where these things can often be seen as adversarial at negotiating all the time with the same people. He was eventually who, who introduced me to Docusketch, his company. He eventually stepped out and was creating an estimating product that's now docusketch estimating. They acquired his company and I was introduced and made, you know, becoming part of the product at the very same time. So branding in this case was very much me. I was told by competitors in the industry that where, you know, they were coming up, that, you know, when we, when we say we're trying to figure out if, if they're looking at any other products, they'll hear my name as often as they'll hear the product. They'll say, oh, you're working with Tilcov versus oh, we're working with Amy. So it was very apparent that it was kind of one in the same. I was really transitioning a lot of my knowledge to a database is a lot of what the product was and learning more from all the experts around the industry and combining it. But yeah, reputation was huge for, for the brand in, in the. This particular case.
C
Yeah, yeah, yeah. And, you know, it sounds like, you know, and I've been through the, the acquisition process before as well. And, you know, there's, obviously there's opportunities that line up. So, you know, knowing the right people and your reputation, all those things are, are a key component of it. But there's also a mindset shift. You know, there are some people that have all those opportunities and they're like, no, I'm going to go it alone. And, and, and all that. You know what I mean? At what point did you like, kind of make that mindset shift and say, okay, this, you know an acquisition is the right move and you know, or, or was it always part of the strategy?
A
I'd say it was always a want of the strategy. I had some early investors earlier on and I learned a lot from that experience. I had to buy them out to own a hundred percent. Again it was just not the right fit. From best I could tell they wanted to use it for their own internal purposes. Then there were some tire kickers and I didn't really want Amy the product to end up with any one company just like the investors that were involved in beginning that used it for one purpose. So Amy's a very unbiased attempts to be unbiased down the middle helps settle quicker. Not going to add too much for a contractor, not going to take too much out for a carrier but just have like let's bring the industry resources together. So I didn't want it to land with a group that just wanted to use it for one purpose. So. So I knew that about the product that I wasn't going to sell out or I maybe one day I would have had to sell out but it certainly wasn't part of the plan. So I wanted the right bit. And when docusketch came along and I understood the I was aware of their product 360 image kind of the source of truth for a claim and documentation around that. And that's where Amy fits as well. We just want to get to the right number, be. Be truthful, honest, put it all right in front of everybody and help speed up the touch points on the claim, speed up the cycle time. I get to reviewed and approved quicker. So that was the right company at the right time. I mean it was quite by the time it was acquired it was quite profitable. I'd gone through the tough times which were very real and it was quite profitable. So I would have loved to have cruised along a few more years at the profitable time if that's the peak. I don't know. I don't know. You can never know what would happen if you kept on going the other way. You make the choice. And the last thing for the acquisition was the timing was right. I mean just like I said, the timing was right for me to go out and try to create a product and you know, I could maybe afford to fail and take that risk. The acquisition timing ended up being quite kind of stressfully just within a couple days of when my, my firstborn son was came into this world. So it created quite the hectic time. We tried to actually avoid that Scenario Docusketch was great in adjusting timelines to try to accommodate. But when Docusketch ran two weeks late and my child came two weeks early, it created, created some intense time. So quite the week there in the end. Yeah, yeah.
C
So what were, what were some of the, the lessons that you learned through that acquisition process that you might share with some other, other founders that are, you know, early. Early on, let's say.
A
Yeah, sure. What was very apparent and probably a lot of people would jump to really quickly was like, our books were well managed, no significant items to clear up there. Our pricing model was very simple and easy to understand. It made sense. We didn't have many options for our clients or exceptions, so we didn't have to sift through all sorts of scenarios. And I learned during that, like, how valuable licensing was as a model. So how much investors liked a licensing model. I didn't necessarily strategically do that purposely. It was the model I picked for, you know, it just made sense to me. And you know what, I guess it was attractive to me as a business owner and that makes sense how it would be for investors. I mean, in hindsight, to say that reliable recurring revenue is attractive to investors should be pretty obvious. Sure, sir, but how, how much that mattered was part of what drove a good valuation. Then lastly, like, knowing, knowing that the other founder out there was going through the same process as me, you know, it made the acquisition process quite, quite simple knowing that somebody in my very similar position to me was already ahead in the process. I trusted that person and we're already going to become part of docusketch. So we cleared hurdles pretty fast on a trust basis, which I don't think you should always be, be careful out there. And I certainly was careful, but I think I was able to move, move along a little bit for faster on that path with that knowledge.
C
Yeah, that's great. So, you know, obviously your, your knowledge and your experience is, is really deep and in your industry to broaden it out. You know, I see a lot of applications myself to, to other industries as well. But just curious, from, from your perspective, you know, what lessons would you share with marketers across other industries as far as your approach to growth and customer acquisition.
A
Other industries from a guy who's been in the same industry since he was 17. So I guess it remains to be seen for me what's been interesting. I've learned a lot after becoming part of Docusketch. It was a much bigger company. It's continued to grow and expand and serve our customer base and so I'm learning a lot from how bigger organizations operate and I was from more like bricks and mortar going to the job site boots on the ground type industry too. So pretty, pretty significant. Some days I might be saucer died at some of the knowledge and ideas that are going on around me. But, but how the Docusketch organizes, assesses, prototypes, reports and everything has been interesting to see and I know that my expertise contributes to Docusketch. We have so many boots on the ground type people from the past that really drive our product. So like we, we do rely on that. I think I've got, I think I'm going tangential to your original question but, but we push like we know that we have some of the best people in the industry that with from both the restoration contractor side, the insurance side and tech side now as well. Working with these people every single day has been just a great privilege and I'm learning so much for them. So sorry I don't have a big gem to share there but I'm learning a lot all the time from this change.
C
Well Chris, thanks so much for joining today. One last question before we wrap up. I like to ask everybody here, what do you do to stay agile in your role and how do you find a way to do it consistently?
A
Well, yeah, quick story. There is some of the clients that actually come to Amy. This will relate to how I stay agile, I promise. Come to Amy, come to Docusketch. They're actually like the technicians or the project managers. They just try our product. They don't go to the owner or the operations person per person. They see it, they see the value. And then after doing a few files understanding it, there are introduction to the company and similarly some of the biggest successes in my career have been not through asking but by just doing, you know, go out, try a product, develop a prototype. If you can hire somebody without asking, be careful out there too. Don't take these as what you should do right now, but basically always keep moving. And I hope that most of the your listeners are in positions where they can, especially if they're creatives. I hope they're in positions where they can get out there and try new things. And if you are creative and you can't, it might be worth looking for a position that allows you to do that thing. And for managers out there, foster an environment that encourages creativity and stay agile.
C
Yeah, love it. Well, again I'd like to thank Chris Tilkov, general manager at docusketch for joining the show. You can Learn more about Chris and Docusketch by following the links in the show notes.
B
Thanks again for listening to the B2B Agility podcast. If you enjoyed the show, please take a minute to subscribe and leave us a rating so that others can find the show more easily. You can access more episodes of the show at www.b2bagility.com. That's B2B agility.com while you're there, check out my series of best selling agile brand guides covering a wide variety of marketing technologies topics. Or you can search for Greg Kilstrom on Amazon. Until next time, stay focused and stay agile.
Episode #72: Concept to Acquisition with Chris Tilkov, DocuSketch
Date: December 2, 2025
Host: Greg Kihlström
Guest: Chris Tilkov (General Manager at DocuSketch; Creator of Ask Amy)
This episode explores the journey from entrepreneurial concept to successful acquisition, featuring Chris Tilkov’s transition from a hands-on technician in the restoration and insurance industry to a technology entrepreneur, with insights for B2B marketers and business leaders. The discussion covers the creation and growth of the Ask Amy platform, the challenges of scaling niche technology products, the importance of reputation and relationships, lessons learned in the acquisition process, and ongoing agility in the workplace.
Chris on Industry Loyalty:
"Somehow I started in this industry, restoration and insurance, when I was 17... I don't think you'll find too many millennials out there that stayed in the same industry so long." (02:47)
Identifying the Need:
"There were not enough people, there were not enough experts. And it was a terribly inefficient process. So that was the need." (05:16)
On Product Integrity:
"It had to be right. And for sales, I really ended up leaning on my reputation in the very beginning. So the product was first kind of built on the shoulders of my reputation." (08:36)
Brand and Reputation Connection:
"When we say we're trying to figure out if they're looking at any other products, they'll hear my name as often as they'll hear the product." (11:34)
Acquisition Timing:
"When Docusketch ran two weeks late and my child came two weeks early, it created some intense time. So quite the week there in the end." (14:47)
On Agility and Experimentation:
"Some of the biggest successes in my career have been not through asking but by just doing... Always keep moving." (19:12)
Chris’s tone is candid, approachable, and rooted in deep industry experience. His narrative balances technical insight with humility, emphasizing practical experimentation and the human side of scaling and selling a business.
This episode offers a personal, strategy-rich look at product development, growth, and acquisition in B2B technology. Chris Tilkov’s journey demonstrates how deep domain expertise, personal reputation, and a willingness to experiment can power innovation, while partnerships and acquisitions thrive on aligned values and trust. Marketers and business leaders across industries will find practical lessons in agility, relationship-building, and the importance of choosing the right moment—and partners—for growth and exit.