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Episode 403: Nick Ornitz & Shannon Kay Co-Founders of Topline Pro

Episode 403 of The VentureFizz Podcast features Nick Ornitz and Shannon Kay, Co-Founders of Topline Pro.

Make something people want is the motto behind Y Combinator.  It sounds simple, yet so many founders miss this fundamental requirement.

Topline Pro is a perfect case study in getting it right. They didn’t fall victim to early false positives; instead, they listened, experimented, and successfully pivoted to solve a true, massive problem for an underserved market.

Topline Pro is building AI that empowers local home service pros to grow and scale their businesses. They provide a critical platform to help with the marketing, sales, and operations of running a business in the trades, allowing these business owners to focus on their craft.

The company recently announced a $27M Series B funding round led by Northzone, with new participation from Tactile Ventures, and Industry Ventures, alongside continued support from existing investors Forerunner Ventures, Bonfire Ventures, TMV, Flybridge, and BBG Ventures.

In this interview, we dive into:

  • The inspirational backstory of Nick and Shannon and how they decided to build a company together after meeting at HBS.
  • Their initial concept called Dwelling, the “false positive” they experienced, and the strategic pivot.
  • Their time at Y Combinator and how early access to GPT opened their eyes to the potential of AI.
  • The value that Topline Pro is providing customers and the exciting opportunities ahead following their Series B.
  • Growth plans, hiring goals, and the culture they’re building at Topline Pro.
  • Advice for non-AI native companies that are starting to build out their own AI strategy.
  • And so much more!

Episode Sponsor: As a longtime champion of the local startup ecosystem, Silicon Valley Bank supports innovative companies with the solutions and financing they need through every stage of growth. With more than 1,500 bankers and relationship advisors, and $42B in loans as of Q2 2024 – SVB delivers the right people, service and resources to support your entire financial journey. Learn more at SVB.com.

Transcript

Keith Cline (00:01)
Greetings, I’m Keith Klein, the host of the Venture Fizz Podcast where I interview the most fascinating people in the tech scene. This is episode 403 and today’s guests are Nick Ornitz and Shannon Kay, co-founders of Topline Pro. Make something people want is the motto behind Y Combinator. It sounds so simple, yet so many founders miss this fundamental requirement. Topline Pro is a perfect case study in getting it right. They didn’t fall victim to early false positives. Instead, they listened, experimented, and successfully pivoted

to solve a true massive problem for an underserved market. Topline Pro is building AI that empowers local home service pros to grow and scale their businesses. They provide a critical platform to help with the marketing, sales and operations of running a business and the trades, allowing these business owners to focus on their craft. The company recently announced a $27 million Series B round of funding led by North Zone with participation from Tactile Ventures and Industry Ventures alongside continued support

from existing investors, Forerunner Ventures, Bonfire Ventures, TMV, Flybridge, and BBG Ventures. In this episode of our podcast, we cover lots of great topics, like the inspirational backstory of Nick and Shannon and how they decided to build a company together after meeting at HBS, their initial concept, which was called dwelling, the false positive they experienced, and the strategic pivot, their time at Y Combinator, and how early access to GPT opened their eyes to the potential of AI.

the value that Topline Pro is providing customers and the exciting opportunities ahead following their Series B, growth plans, hiring goals, and the culture that they’re building at Topline Pro, advice for non-AI native companies that are starting to build out their own AI strategy, and so much more. Okay, now a quick word from our podcast sponsor, Silicon Valley Bank.

All right, without further ado, here’s my interview with Nick and Shannon.

Keith Cline (02:34)
Nick and Shannon, thanks so much for joining us.

Nick Ornitz (02:37)
Of course, great to be here.

Shannon Kay (02:38)
Thank you. Great to be here.

Keith Cline (02:39)
excited to talk to the two of you. I’ve been following Topline Pro for a while now. It’s one of these companies that has just been, I think, we’ll probably get into this a little bit more detail, but like my brother-in-law, he’s a general contractor, small business owner. He is like, you when I think of what you guys do, super helpful, because I think my sister manages the books and does probably his quoting and I don’t even know what he does for marketing. Exactly, right? So.

Nick Ornitz (03:03)
Sounds very familiar.

Shannon Kay (03:04)
Yep.

Keith Cline (03:06)
I live the world that you guys are helping service. before we get

into that, I did want to talk about your Series B funding announcement, right? So when companies announce their funding, they want to make a splash. I think some are really incredible at doing that. Some maybe just missed the mark, but I thought your announcement, the video you guys did was amazing. So I just want to talk about like, what was your strategy around that Series B?

Nick Ornitz (03:33)
Appreciate the compliments. We’ll pass them on in large part to one of our team members,

Shannon Kay (03:34)
Yes.

Nick Ornitz (03:38)
who orchestrated a lot of it. ⁓ But one of our goals in the funding announcement was to help tell the story of these business owners that is oftentimes behind the scenes. And so we really wanted to bring that to life. And for us, we don’t sell to other big tech companies. And so the funding announcement wasn’t to try to get new customers. It was in big part to share the mission, share the story of the business owners we support.

one that creates visibility and two, hopefully, and it definitely did do this, bring talent to Topline Pro that wants to work on that mission. So that was our main goal with it.

Keith Cline (04:11)
side, how did you pull off the video? Because I thought the video was well produced.

Shannon Kay (04:15)
Yeah, our marketing lead, Maddie really crushed it to put it lightly. She did a great job. She found this, this awesome space to record in, found an amazing team to record, frankly, like put a, put a lot of effort into the, script and the practice and the, the end production and a lot of time to next point coordinating with our customers to be able to tell those stories. And, ⁓ she, she just crushed it and wasn’t afraid to sort of go above and beyond. And I think it really.

shows in the end product and in the end video.

Keith Cline (04:48)
Yeah, it was

well done and that’s a piece of content that obviously lives and breathes out there in multiple use cases, capacity. So, you know, it’s a lot of work, but I think in the long run, it definitely is, you know, pays off. So, yeah.

Nick Ornitz (05:00)
just to add a little bit of advice for other

folks that are considering, think that ⁓ there are some routes where folks go out and they spend a lot of money on a video like that. And we were able to pull it together on a pretty light budget. What we wanted to do is ⁓ make sure that our customers were highly featured in it. So we brought a lot of our customers to our office and then brought them to film the testimonials. And so we made sure it wasn’t just focused on how do the visuals in the video look the best possible, but

How do we bring to life the customer stories? And ⁓ I think we opted to reserve budget towards that and flying our customers in and all of that versus the highest end graphics. The video production team did a good job, but definitely recommend ⁓ that you can put together a great video like that on a relatively low budget compared to what some folks out there charge.

Keith Cline (05:50)
That’s great feedback because you can find budgets and video production across the full spectrum because they will charge you as much as they reasonably can. But you can do so much now for so much less. And like you said, like the it was very ⁓ high quality, the production you could tell. But you can do so much with so like the cameras and the graphics. And I mean, everything I think about what we do at VentureFizz is really low budget.

but I think it’s super high value as far as the content, but obviously the images and the graphics that you can do now, it’s really cool that way you can do. So, all right, let’s get in the background stories of the two of you. So Nick, where’d you grow up? What were you like as a child?

Nick Ornitz (06:35)
Yeah, I grew up in the Northeast. As a child, I was always into sports and competitive. So I think that plays out well in the startup world. ⁓ But I was ⁓ one of many siblings, I four siblings and three of them run or had run service-based SMBs over the course of life. And so ⁓ can touch more on that as we go. That was a big piece of the passion for what we’re doing at Topline Pro and getting to see that.

Shannon Kay (06:36)
I’m

Nick Ornitz (06:59)
I was the last sibling, I guess you could say, got to see the different journeys and we’re talking about video production. Two of them went into that world of photography and video production and so got to see others build their businesses over time. And I think that was inspiring for me to want to build a business in the future as well.

Keith Cline (07:19)
and a bakery in the mix too. So Eric, who is part of your company, was started a bakery at one point, right?

Shannon Kay (07:20)
Yeah.

Nick Ornitz (07:21)
That is true.

That is right. American Press Bakery. And I at one point was even in the kitchen making the stroopwafels. And then I had to sell them door to door in the local town, stopping by restaurants saying, hey, do you want to carry stroopwafels? I brought them to high school and I would walk around with a duffel bag full of cookies. So that was a great way to make friends.

Shannon Kay (07:31)
I’m

Keith Cline (07:45)
See, already on the path to entrepreneurial success. Just hearing that story alone, I would invest in your company. So, all right. So you went on to Cornell. You studied chemical and biomolecular engineering. So what laid you down that path?

Shannon Kay (07:50)
Hehehehehe

Nick Ornitz (07:59)
Yeah, so a little different than what we’re doing today, but I was in the chemical engineering world at the time, was really excited about the ⁓ space of ⁓ energy and trying to focus on renewables at the time. And so went into college for that, ended up loving the problem solving aspect of engineering. But I spent a summer in a lab and pretty quickly realized that spending all day in a lab was not going to be for me and missed the ⁓ collaboration, the human component of

the business side of the world. so from there went into the world of construction management, was on a job site with a bunch of contractors. And I joke around that at 18, they were probably managing me, trying to tell ⁓ steelworkers what to do, but it was fun nonetheless. And definitely learned the lesson of don’t wear brand new timberlands to a job site because it gives you away pretty quickly.

Shannon Kay (08:48)
you

Keith Cline (08:48)

Wait a second, you can’t wear those here, those are brand new. That makes sense. All right, Shannon, how about your background story?

Nick Ornitz (08:54)
Exactly.

Shannon Kay (08:57)
Yeah, I grew up in Gastonia, North Carolina. It’s a town just west of Charlotte, similar to Nick, played a lot of sports growing up, quite competitive. think a lot of that translates into the entrepreneurial world too. But also very much a builder and something that my parents really encouraged when I was younger, ⁓ my bed was lofted. So to close my bedroom door, I’d have to climb.

down the ladder to actually close it. And I convinced my parents to let me drill some holes into the wall and like build a pulley system so that I could then close the door without having to climb down, which is part lazy, part problem solving. But they, really encouraged like just being able to tinker and build. And I think that, that has certainly been a through line in kind of my, education career and certainly what we’re doing today at Topline Pro.

Keith Cline (09:34)
Nice.

Nick Ornitz (09:35)
Yeah

Keith Cline (09:51)
It’s very obvious for you why you went on to study industrial engineering at Clemson.

Shannon Kay (09:55)
Yes, very much so.

Yeah, absolutely loved like the problem solving component of industrial engineering. Like it is quintessential observe hypothesized test, react to that data and iterate. so kind of that continuous improvement mentality and that like, how do you really break down a problem into its root cause? How do you understand all the different pieces of a system has been

than very core to what we’re doing today as well.

Keith Cline (10:28)
So how did you get your career started out at Clemson?

Shannon Kay (10:30)
So I similarly spent a summer in a manufacturing plant, which I loved the like problem solving piece of it, missed maybe some of the office setting. And so I ended up going to Deloitte. I worked as a technology consultant there doing some systems engineering. it was played as a very small piece of a larger puzzle, trying to figure out how to integrate like 50 plus.

systems altogether and how do you transfer data and that exposure to data really piqued my interest in just analytics and data and what does that look like and I found my way to Wayfair as everyone does at some point in the Boston area I think with a ⁓ really cool job that was integrating business and technology and so we would

Keith Cline (11:15)
in Boston,

Shannon Kay (11:23)
take data and try to build models to answer questions like when, where, and how big should we open all our next warehouses? Yeah.

Keith Cline (11:31)
Got it. Okay,

back to you, Nick. So after college, how’d you get your career started?

Nick Ornitz (11:36)
Yeah. So I looked at a couple of paths. One was going ⁓ into the world of consulting at the time, and some others were going more into industry. And ⁓ I thought that consulting was a great way to jumpstart and seeing how other businesses operate. And so went down that world, ⁓ ended up focusing entirely for the most part on companies that sold into the trades. so companies like Home Depot and Bear and HVAC dealers and distributors. And so

A lot of that was centered on pricing and marketing and sales of those products to the home service industry. And just got to see, do you think about what to price, even a fire alarm in Home Depot all the way up to a full HVAC system. And ⁓ through that, a lot of the work was centered on actually talking to user studies for the end customer being the contractor. And so spent a few years getting exposure to the home service contracting businesses through that world.

loved ⁓ the combination of problem solving, but also exposure to new industries and companies over the course of the years I was at McKinsey, but definitely had the itch to build something. And so left there to go to business school with an aim at building a startup in the home service space.

Keith Cline (12:51)
So you had that idea in mind upon entering Harvard Business School.

Nick Ornitz (12:56)
The idea of building a startup in the space didn’t know exactly what it was going to be, but the premise of exactly, exactly. And figured that business school would be the perfect time to do that. Two years where you have the freedom to explore, also chance to meet incredible people. I was fortunate enough to meet Shannon and the space and time to do so.

Keith Cline (12:59)
Yeah, yeah, but still had that inclination. Yeah, wow.

Okay, so this is where the two of you met was at Harvard Business School and Chan and you were at HBS, but also getting a master’s in engineering sciences too. So it was a combo.

Shannon Kay (13:27)
Yes.

Yeah. So this was a new program when I went to school. It was a dual degree in engineering sciences and business administration, very much focused on starting tech ventures and everything from the product side, the data side, the engineering and just the general business side. And it was a wonderful, wonderful experience. And I was fortunate enough to meet Nick. We were in the same section of about a hundred students. So we really got to

know each other very quickly. One of the really great things about the case method is you get to learn how people think and problem solve. And so we just got to see that day in and day out. And then we became friends really quickly. We joked that we just needed to turn the magic on the intramural soccer field into a co-foundership. I think five and a half years in, we might be better co-founders than soccer players at this point. ⁓

Keith Cline (14:20)
Okay.

I’m

Shannon Kay (14:26)
But yeah, was, was, ⁓ went to school, very interested in entrepreneurship and was fortunate enough to connect with Nick and started having all these fun conversations about the opportunity and the home services space.

Keith Cline (14:38)
Interesting. Okay, so the two of you both had interest in building a company at some point. So that’s actually was in my brain wondering if that was the case. So, all right. So the two of you met some synergies. Hey, we work well together. At what point did you start kind of brainstorming ideas to actually build something?

Nick Ornitz (14:59)
Yeah, so it’s the end of the first semester of business school. So we were a couple of weeks out from winter break at the time, which is funny to think back to the concept of having a winter break in these semester ways of thinking about time. we went into that, ⁓ having talked about an idea that was called dwelling, ⁓ morphed into what was called dwelling. And you can share that story, but both went into break saying, hey, you know, we’re really excited about building this space.

We have an initial idea, but let’s spend a couple of weeks just reflecting, we ready to really dive into this? And we came back from that in January and kind hit the ground running from there. And shortly thereafter, COVID hit and everything went virtual at school. And so this was a moment where one of the big areas of business school is all the in-person time and events that you go to. And ⁓ now we were faced with the opportunity to take that time and put it into dwelling.

what later became Topline Pro. ⁓ And so we decided to double down on this concept and really work on it together.

Keith Cline (16:06)
Cool. Shannon, so what was dwelling?

Shannon Kay (16:09)
Yeah, so dwelling, called it tele-maintenance for your home. So it was ⁓ basically, it’s a virtual home services marketplace. So you have an issue with your shower, you can FaceTime a plumber and get some support instead of paying for the estimate fee. And then again, the site does it when maybe the fix was relatively easy. And so we started that like next set in January of 2020. And so ⁓ come March, it was ⁓ a very desired service with

COVID hitting of people preferring not to have, preferring to minimize the number of people that were coming into their homes. And so it was, think the kind of looking back on it now, chat GPT does a lot of that where you can take a picture of the shower and say, hey, what’s wrong? Can you give me advice to it? I think we eventually, yeah, it’s shockingly good at it. Yeah, YouTube as well.

Keith Cline (16:58)
You can? Is that something you can actually do? I didn’t know that. I’m always on YouTube, like.

Nick Ornitz (17:00)
Yeah, yeah, it’s pretty cool.

Keith Cline (17:06)
Wow, okay.

Wow.

Shannon Kay (17:08)
Yeah,

so I think we didn’t know what form that would take at the time, but I think we started to feel that maybe this wasn’t a full business in and of itself and that there might be larger pain points for home service professionals that we would want to dig into further.

Keith Cline (17:25)
But it is a concept that I’ve heard many entrepreneurs try to solve. And it must be just really hard to go, you be the middleman between the consumer and these professionals. Because I just think about, yeah, I could go to ChatGPT, I could go to YouTube, and I usually like see if I can dabble because I’m not technically inclined to fix things. It’s going to be a bigger mess. I’ll like the plumbing stuff is usually pretty intuitive. So I’ll go to YouTube, figure it out.

But if I had a home service pro that was on FaceTime or whatever app with me and said, do this and do this, I can follow instruction pretty well. But it just seems like it’s one of these ideas that have been tried and tried, but just never really became that moment of the next great company type of thing. ⁓ you pivoted. So what did you do next?

Nick Ornitz (18:21)
Yeah, so that feedback resonates a lot. kept hearing all these positive, like homeowners were like, this is such a pain point. I know I always go to YouTube. I can’t figure it out. So we for several months heard this really positive feedback. Like if you did an NPS score of our ⁓ early, ⁓ early users of dwelling, it was really positive. ⁓ What we came to find though, is that the ⁓ business owner at the end of the day wanted full-time jobs. And Shannon and I had actually used some of the marketplaces to try to get virtual appointments.

⁓ And so we bought leads from these marketplaces and then tried to convert them into ⁓ virtual visits. And we found that we were spending a lot of money quickly without actual quality jobs coming through. And so when we started speaking to more of the plumbers and appliance techs that were on our platform, the same thing ran true, which is I want a way to grow my business. I’m tired of trying to buy leads that don’t necessarily convert. ⁓ Yeah, tools aren’t really built for me. They’re built for the bigger businesses out there.

And so we stepped back and we said, well, let’s try to solve that problem. And the way we’re going to solve it, we ⁓ transitioned and pivoted dwelling into what was then called pro phone. So that was our second name. ends at Topline Pro. ⁓ And around that time, we got into Y Combinator and that was a kickstart for us to double down on this idea of pivoting. And the concept of pro phone was we were going to help the pro no longer be a marketplace. We were going to help them convert.

homeowners that were reaching out and into full-time jobs. And the biggest problem there was they don’t answer their phone because they’re busy in the field. And so we were going to help them with the communication side of the business. Yet to get their attention, we were going to build a website for them to say, hey, we can build your website and we can help with your phone and communications and we can share more. But we learned which of those was, was gravitating over time.

Keith Cline (20:12)
Right, because the contractors are generally in the field and they still use their phone all the time to manage their business. So that makes sense. what was, Shana, what was the thought of Y Combinator? Because ⁓ how is the application process, the interview process getting in?

Nick Ornitz (20:19)
Yes.

Shannon Kay (20:30)
Yeah,

absolutely. For us, it was a great experience. We actually applied twice. So we applied once early, early on with Dwelling. Did not get an interview, ended up not getting in. honestly, even just the fact of having to fill out the application process, it’s kind of a business model document in and of itself. Like it really forces you to, you can’t gloss over questions. You got to like dig into it and make sure you have an answer you believe in there.

⁓ so it was a really, really helpful exercise for us. applied, ⁓ again, for the, next batch, which was probably four to six months later. And I think we were able to show some of the traction and progress and maybe scrappiness of those early days. And we’re fortunate enough to get a, ⁓ an interview. very quick interviews. It’s 10 minutes. So it’s, and I think, I think they ask on average 20 questions. It’s very fast paced. So, ⁓ so, ⁓

Keith Cline (21:20)
10 minutes, wow.

lightning around.

Shannon Kay (21:28)
Yeah, exactly. But also a fun experience just to, know, how quickly can you, you really do need to reflect on everything about your business. And so we were fortunate enough to get in. It’s a three month process and it’s very focused and you’re really running at 110 % for those three months. You set a big goal and you really go all out on trying to achieve it. And I think that

level of ⁓ ambition and honestly discipline that it really encourages was wonderful for us to go through early on and definitely has shaped a lot of how we operate even today.

Keith Cline (22:10)
What were the key takeaways from your experience through the program?

Shannon Kay (22:14)
Yeah, the big one, they, ⁓ there’s a screensaver for Google Chrome. So it’s kind of intense. has like, it counts to the thousandths of seconds, I believe down to demo day. And so you’re really just seeing like how valuable every single moment is. It’s, should, I should say this is definitely optional. ⁓ but was, was great for like, was great just to see like how, how much every minute is, is counting. ⁓ yes.

Keith Cline (22:30)
Wow, I didn’t know that, okay.

Yeah, it creates a sense of urgency. You’re

like, oh, we got whatever weeks left. But all of a you’re like, wait, we only have that many weeks left.

Nick Ornitz (22:49)
Yeah.

Shannon Kay (22:49)
Exactly. ⁓ And then the other big piece I’ll share is the kind of networking side of things. Not necessarily capital and networking, but you go through it with a bunch of other startups. And so we would have small group conversations and it was just ⁓ a great way to get to know other founders at various stages, some earlier than us, some at our stage, some a little bit later, but just have that community because obviously

startups are lot of ups and downs and ⁓ it’s helpful just to know that other people are going through those ups and downs as well. And you can learn a lot from having ⁓ that network of other founders and the partners at YC as well.

Keith Cline (23:32)
Okay, so we get to Topline Pro. So what’s the conclusion that gets you to that, hey, we’re really onto something now with this company?

Nick Ornitz (23:43)
Yeah, so we went through Wacommer, this was winter of 2021, and while we were going through it, we got access to GPT, and this was before the world knew of chat, and we said, okay, the contractor has this pain point of discoverability, so the website was resonating, our website product that we used to get their attention was resonating, and they do have this problem of conversion with the phone products, but there were some challenges in driving adoption of that before you have the former, for example.

A lot of these business owners have their phone number already on the side of their truck. And so getting them to change that is quite hard. And so we combined those two and we said, they like the website product. They want the solution of the phone product, but it’s hard to get adoption. And we have this new technology, GPT. Let’s combine those insights into one learning. And that was doubling down on the top of funnel problem first. And so we use GPT to convert the website product into a done for you tool.

was no longer a DIY solution. It wasn’t an agency. was fully automated that aspect of the business and that knee interaction. And so we said, okay, what else can we do that’s automated to drive growth for the business? And that led to all of the firms and marketing. So your social media, all the things that you might hire a marketer to do. And I think at the time we appreciated it, how impactful GPT was, but we didn’t realize the scale that AI was going to grow into today.

And so we really were just focused on chipping away at the contractors problems, the pros problems with this new technology. And then when we saw the chat come out and all the other adoption, was like, wow, we’ve been using this new technology, but we’ve been focused on the customer problems from day one.

Keith Cline (25:26)
Yeah, because if you’re a small business owner, yeah, you could cobble this all together on your own. Maybe go to one of the website building sites or you could hire an agency, which they’ll be more than happy to charge you tens of thousands of dollars to still only spend a lot of time giving them what they need to create something that you’re like, well, this isn’t doing what I thought it was going to do. Maybe I’ve had experience doing that. And then, yeah, and then they do the all the SEO. Go ahead.

Shannon Kay (25:27)
them.

Nick Ornitz (25:41)
Yes.

You’re not alone. You’re not alone.

Shannon Kay (25:49)
A lot ⁓ of engineers

on our team at some point were building early days, know, decade, two decades ago, building some form of online presence for service professionals. So it’s a very common problem people have been trying to solve for a long time that AI really is changing the equation on being able to solve that problem at scale.

Keith Cline (26:16)
Yeah, and then there’s not promises, but beliefs that they’re gonna handle all the SEO and the content and all these things. And it’s gonna be like, okay, I’m just gonna pay this agency to do everything. It doesn’t work out that way at all. It’s still incredible amount of time that I would have to allocate on my team. And it wasn’t always what I thought it was gonna be. Because you just think it’s gonna be like that silver bullet and it’s like, everything’s done. But no, it took.

a lot of work. the more I learned about Topline Pro and how you’re combining everything with latest tech stack, AI, and just the ability to plug and play and not have to worry about building and cobbling or working with an agency, was just like, this company’s amazing.

Nick Ornitz (26:58)
Amazing. Yeah, we really, you know, that insight that there’s this information asymmetry and between growth products and then the small business owner and that it’s not really clear what’s being done for you. And so one of the ways, one of the challenges for that historically is just the cost of doing all of those things manually and then communicating them. And so to us, AI was

Shannon Kay (26:59)
Thank you.

Nick Ornitz (27:23)
the solution to like a really real problem for these business owners and that gap of now we can provide all of those services and products ⁓ at a lower cost and make it really transparent on what is happening. And so it really was the right technology with the right problem. And we were fortunate enough to be playing in that space at the right time.

Keith Cline (28:14)
All right, so how did you even get it started though? Like, is building out this type of platform isn’t easy? You you talked about your backgrounds. It’s not like the two of you are technical folks per se. So how did you even get started to build out this platform?

Shannon Kay (28:29)
Yeah, a lot of it was bit by bit. I’ll share a dwelling story. We, we found out we were going to be featured in a article, ⁓ dwelling along with a couple of other companies. And we had a very, very basic, mostly Google form driven product at that point. And we used a software called bubble at the time. So a low code software. Yeah. To build version one of our platform in 10 days. And that was in.

Keith Cline (28:51)
Yes, I know, Bubble, yep.

Shannon Kay (28:59)

  1. So now the lovable replete, like the amount of, you know, do it yourself platforms, it’s really wild what you can do with it. But early on, we just, really took this approach of building a lot pretty quickly. So we kind of asked ourselves, if you were to hire a marketer to your team, if we were trying to market a landscaping business, what are sort of the key activities that we would want to do?

⁓ first one is have a website. So, ⁓ okay, let’s build out and kind of automate that process. Next up is social media, having a strong online presence on other platforms. So we built out, ⁓ we use AI to write written social media posts. Now that’s evolved into other mediums. ⁓ so graphics, videos even, and then, ⁓ reputation management is a big one. So how do you collect.

and show off five-star reviews, build trust with clients that are looking at your business. so we, and I think that was true in 2021 and 2022 when we were building this and even more true today is how quickly you’re able to build new features and new offerings, use that to learn and then double down on what’s working and deepen those offerings over time. So that was really the approach we.

took early on, I’d say even today is part of the approach we’re taking in the way we’re building the business in the company.

Keith Cline (30:33)
And how is the marketing side handled, like the content, the SEO? The world of search is changing so rapidly. I’m experiencing it with VentureFizz. ⁓ know, obviously you can just type in a company now and Google’s going to give you some top line results. That is what they’re looking for. So it’s a better user experience, but doesn’t send them the VentureFizz to click on anything on my site. So how is that affecting your world with your customers?

Nick Ornitz (31:00)
Yeah, so we really purposely over the last year plus have been focused on how do we not only help with the marketing for the business, but how do we also help with the sales and operations of the business. at the end of the day, we want a home service professional, whether it’s a landscaper, painter, a roofer to focus on their trade. So the work that they do best in the field is also what they most of the times enjoy doing and feel like they have a team that’s supporting them on each of those areas of their business so that they can

not get home at 8 p.m. and have to deal with, whether it’s the marketing or the sales, getting back to a customer or op sending a quote. And we really want that experience to be end to end. And at the end of the day, the businesses will be more likely to succeed if we can do that and they’ll have better lives because they don’t have to spend time on each of these areas that they don’t enjoy as much. what we did is we focused on building up product across those other areas and how that plays into your question about how is search changing and how does that impact it is.

It’s not only how do we drive discoverability for the business, but also how do we help with converting those customers into from a quote to a job. And so we’ve been focused on that full stack offering. So you can come in the door to Topline Pro and not have a web presence today, and we can help with your discoverability. You can also come in the door and already have some web presence and we can help you with the conversion. And so being able to serve more of the market, no matter where you are on that journey is really important to us.

In terms of search, are seeing the landscape change. have one of our customers, Aidan, was in our office recently and he was saying, hey, I just had a homeowner book me by finding me on GPT. And they searched for a landscaper near me on chat. So we are really focused on how do we focus on everyone’s calling it GEO today. So how do we focus on factors that are influencing GEO the same way that we focused on trying to help businesses be discovered through SEO in the past?

Shannon Kay (32:38)
Mm-hmm.

Keith Cline (32:53)
Now reputation management, you highlighted, which is so important.

consumers like to see reviews, they like to see hopefully very high reviews in terms of the number of stars. So, but I would think that’s tricky for the business owners to get those reviews because maybe people had a great experience and they have full intentions of leaving one they just forget or they just like, ⁓ you know, so how do you help your service pros get those almighty reviews?

Shannon Kay (33:24)
Yeah, ⁓ we have a few different ways we do it, kind of to that exact point. So one, they could send out a request, know, hey, loved working at your house as a small business owner. really helps me to, you know, have your feedback and your review. If you feel inclined, you can click here and do it. But we’ve also really recognized the value of doing it in person. So a lot of business owners are like, yeah, right when I finish the job, I would love to.

be able to have that opportunity. so we have a QR code that pros can share and a homeowner could quickly scan and access and then actually review cards like a physical card that they can will basically upload their view link to and then they can share and take some directly to their their Google business profile to be able to leave those wonderful five star reviews. So yeah, it’s it’s providing a lot of different mediums and then it’s

Also, I think asking for reviews can feel a little unnatural at times. so it’s talk, it’s also sort of talking with business owners about the benefits of leaving reviews and having reviews. And that helps with discoverability. And I think when they, when you frame it that way, it, it’s, ⁓ it’s more, Hey, help me invest in my business than, ⁓ you know, just give me say, say nice words about me. And so those are some of the different tactics we’ve taken with it on the actual.

product side, several different mediums, but also on how to think about the benefits of review and benefits of reputation management.

Keith Cline (34:59)
Let’s talk about Topline Pro today. So what’s the scale of your business in terms of number of customers or whatever you can share and then your funding history because we started out the video talking about your Series B. So, you know, the different times you raised.

Nick Ornitz (35:15)
Yeah, so it’s been a fun growth journey for us over the last few years. ⁓ Today we serve several thousand home service companies, so it’s tens of thousands of actual pros in the broader network with their ⁓ teams. Within that, when we announced the Series B, we made it public around the amount of job value that has been booked through Topline Pro, which is at the time over 655 million of job value.

that’s flowing through the pros that we support and we’re ⁓ glad that numbers is growing quickly since. We are really right now focused on covering more of the landscape of how we can support these businesses. So not just, ⁓ of course, growing the number of businesses we support, but also moving beyond just marketing into sales and into ops of the impact we’re having. so

With that, we expect the job value to increase not just because of the number of pros on the platform, but also the success of the pros that are using Topline Pro today.

Keith Cline (36:14)
I mean, it just seems like such an obvious, right? Like the ROI, if you’re helping drive that much contract value revenue, right, for the service pros, ⁓ that’s an easy ROI and that’s a stickiness factor for you guys. And then the more they’re using you, obviously more value they get, but there’s still that stickiness where they have you as ⁓ their operations, right, for marketing, sales, and web presence. So it’s a…

When you went to raise capital, especially for your series B, it seems like it’s obvious, but obviously raising capital is never easy. So what were some of the conversations like for your B round?

Nick Ornitz (36:54)
Yeah, I think the journey of raising capital over time, of course, it shifts from the seed. just a vision and a belief. And by the time you get to your B, there’s real metrics and real data in the business. And so ⁓ one piece that helped us in that process was the fundamentals of the business were really strong. And we’ve been focused ⁓ not just in the years where everyone started saying, how do you focus on efficiency? That’s been true since day one is making sure that we’re not taking $1 and turning it into 50 cents.

building a foundational business that has strong economics and has real customer impact. And so that was one angle. think the second piece of it is there is this massive market of home service companies that has not been served historically. You have 2.6 million home service companies in the U.S. About 200,000 fall in the market size or the business size that someone like Service Titan would serve. And then about 2.4 million are these long tail businesses that had been really hard to build for. So you have

Keith Cline (37:50)
Wow.

Nick Ornitz (37:52)
marketplaces that have tried to solve for it, you have the agencies that try to solve for it. And now there’s a true why now moment with AI that enables us to not only build product that ⁓ serves them well and delivers value, but also allows us to reach them. And so it was this combination of strong metrics that show our ability to execute as a team, but combine that with this market opportunity where tech is changing the landscape. And I think you’ve seen that in other businesses over time.

where tech has evolved, whether it was mobile, back then enabled platforms like Uber to be built, to now when we look at AI, the largest market that we believe it’s going to change the game on is fragmented long tail markets, whether it’s in the trades or other small businesses.

Keith Cline (38:40)
Now in terms of the team, Shannon, so you have operations split between Boston and New York City. So what is that, you know, the different teams in each location, size of your team overall, and then plans for growth and hiring?

Shannon Kay (38:54)
Yeah, we actually, uh, tomorrow, uh, we’ll hit a hundred employee count. So, um, yeah, we’re about, we’re about 30 people here in Boston, uh, 70, about 70 based in New York and growing. and so, yeah, we’ve, we’ve certainly, we’ve invested from early on in a in-person culture. Uh, and so we’re, we’re in person, um, the majority of the week in both offices and have found even from the

Keith Cline (39:00)
Wow, that’s awesome.

Shannon Kay (39:24)
very early days, just the fun and energy that that creates, ⁓ and sort of the fast paced problem solving of turning around in your chair and being able to ask a question and get getting right into whatever that problem is. So yeah, so we’re, we’re split between Boston, New York and definitely growing in both offices across pretty much all functions right now as well.

Keith Cline (39:50)
Fantastic. like, because what is your go-to-market strategy? Like, how do you reach out? Like, how do you get your customers?

Nick Ornitz (39:57)
Yeah, so a variety of channels, but we from the day one knew that our customers really valued being able to talk to someone. And that has historically been a challenge in the SMB space is how can you ⁓ do an outbound motion at a low price point product? ⁓ And what we’ve been focused on is building tools internally that enable that to be possible. And so how do we help provide ⁓ real customer service to small businesses where they can talk to an account manager anytime? How can they?

talk to a salesperson if they have questions about the product when they’re thinking about signing up. And so to do that, we have to automate aspects of those jobs that would otherwise take up a ton of time and prevent them from serving our customer as well. So we are predominantly outbound team. We do have a really, really strong referral rate, which is something we’re proud of, a good sign of ⁓ fit there. And then we go to in-person events. So later this week, some of our team will be going to the Equip Expo and a few other trade shows as well.

Keith Cline (40:55)
Okay. What type of culture are you looking to build at the company?

Shannon Kay (41:00)
Yeah, we, ⁓ we like to describe our culture in our core values. So, a couple to highlight here, one, no bullshit. So we talked about some of the information asymmetry early on. That’s very core to us that we’re building, ⁓ product in a company of real value that is changing the lives of home service professionals. We’re doing that in a way with strong unit economics, ⁓ that we’re going to be able to have like.

the maximum impact that we possibly can. so No BS is very core to what we’re building. Another one I’ll highlight is one team, one dream. So very, very collaborative culture at Topline Pro. Being laser focused on what’s the goal that we’re working towards, which is empowering home service entrepreneurs to get more done. And then last one I’ll…

kind of highlight there is a boom. And so we celebrate wins big and small for us and for our customers professionally and personally. And so we have a channel in Slack called the boom channel. When we onboard a new customer, we’ll celebrate adding someone to the top line pro team, but also like personal wins for our customers that they book a large job or they’re opening their

adding a new crew team and personal with our team as well. You know, we’ve had a couple of team members get engaged this summer and being able to celebrate those. so again, that kind of entrepreneurship and building a company being a journey, we want to make sure we’re celebrating all the successes, big and small.

Keith Cline (42:48)
Yeah, it’s a lot of work. You gotta celebrate those successes. Okay.

Nick Ornitz (42:52)
Our VP of data was part of the HubSpot early team and he likes to talk about how the energy on the floor is similar to the energy in the early days there where ⁓ part of that boom channel is every time that there’s a new customer brought on board. We have theme songs that play in the office and ⁓ celebrate it. So there’s ⁓ a little bit of chaos with a little bit of focus, which is great.

Keith Cline (43:17)
definitely getting a lot of HubSpot vibes from your company. So I hope it’s the same outcome. All right, so one of the things that I discovered while preparing for this interview, listening to other podcasts was very much a, it seems so obvious, but I don’t know if all entrepreneurs do this. And it’s the obvious of talking to your customers to identify problems and solutions. And you guys evolve the business multiple times.

Nick Ornitz (43:22)
Ha

Shannon Kay (43:22)
That’s

big compliment. Thank you.

Keith Cline (43:46)
What advice would you give to entrepreneurs around that customer conversation discovery piece?

Nick Ornitz (43:52)
Well, I see as the tagline build something people want and that is really simple and sometimes it can be like easy to gloss over it. But I think you get a lot of ⁓ tech businesses where they build things that they want ⁓ or their idea of what their end customer wants. so I think number one advice is be brutally honest about the feedback you’re getting from your customers. We learned that some of the hard way with dwelling, we thought, well, they’re saying this is a real problem and they’re happy with it. But then when we asked them to pay

$10 a month, they won’t do it. And so be really honest about what your customer is telling you both directly and indirectly and make that part of the company’s culture. Today we’re using AI to help us convert all of the calls and emails that are happening between our customer and our team ⁓ to distill both product insights, operational insights, and there’s so much you can learn from those transcripts that

even as you’re scaling, don’t want to lose touch of touch base with.

Shannon Kay (44:56)
I was just going to add early on in, in YC and Nick and I, think we built a wait list of maybe 500 users. Nick, you can keep me honest on that. So we called hundreds and hundreds, probably thousands of, know, when you convert who’s being added to the wait list. And so that was a lot of our like YC and early days experience was just talking to as many customers as possible. Another YC axiom is.

write code and talk to users. so, ⁓ I’d say that that’s very core as well as just making the customer as central to what you’re doing. The really believe if you do that, other things will follow. You’ll be able to build the strong business. You’ll have, ⁓ have other successes. your laser focus on how do you help solve problems for the customer?

Keith Cline (45:46)
probably going to butcher this analogy, but it complements what we’re talking about here in terms of contractors. But I held a product management event last week and one of the panelists said, you know, a contractor, like if they’re building something, they may want like a hole in the wall. it’s the drill is the tool to make the hole, but they don’t want the drill. They want the hole in the wall. It just so happens that the drill is the thing that makes it happen. So build something that people want. Absolutely. Absolutely.

Companies are stressing out about AI if they’re not native. So they’re thinking through our strategy, how are we going to add some type of AI component and maybe it’s a fit, maybe it’s a not. So what advice would you have for companies that are trying to figure out their AI strategy that maybe aren’t AI native?

Shannon Kay (46:34)
I think the big piece for us is experimenting as much as possible. So really trying to create a culture of experimentation. It’s Nick and I saying here’s this new AI tool. Let’s try it. It’s how do we empower all 100 of our team members to have that mentality and how do we create a space? think our, ⁓ a lot of our teams, but certainly our engineering team is very quick to try something for a month, see what sticks, see what doesn’t stick.

oftentimes come back to it a few months later. Things are, the AI ecosystem is changing so quickly that it feels really difficult for any one person to be perfectly up to date with everything. But it does feel manageable to spread that out across a team as much as possible. And so I think that’s been probably one main piece of advice is just how do you bring the entire company into.

built maybe embodying that strategy and then experimenting on what’s working right now, what’s not, being quick to try things out, but also being open to coming back to them at later points in time.

Keith Cline (47:45)
Make sense? All right, some rapid fire questions. ⁓ Nick, I’ll let you go first. Three apps you can’t live without can’t be email, calendar, or Slack.

Nick Ornitz (47:54)
I will Topline Pro has to be the first one. Amazing. I mean, it’s cliche, but I use chat and some forms or fashion every single day. Another app that had been using is fixer for helping with email drafting, email replies. Most of 90 % of our day to day is in Slack and ⁓ 99.9 % of the companies is within Slack, but all external is still email. And so balancing time saved on that. ⁓

Keith Cline (47:56)
Hahaha, of course.

Nick Ornitz (48:24)
is critical. And then on the personal life side, I’m a whoop user. So another Boston company, but ⁓ do enjoy the stats, the good, the bad that it tells you.

Keith Cline (48:36)
I won’t go there but I was gonna ask you your real age or whatever the status that you can, but you don’t have to answer. How about you Shannon?

Shannon Kay (48:40)
Yeah, yeah.

Nick Ornitz (48:40)
I got some gray hair, so we’re good.

Shannon Kay (48:47)
I’ll echo chat, use it all the time. This is a really practical app, but Todoist I use for my to-do list and I’ve built a little integration in Slack so I can add an emoji, which creates a Todoist entry using Zapier. So that’s really key to just make sure no balls are getting dropped. And then

Keith Cline (48:57)
Okay, yep.

Hmm, cool.

Shannon Kay (49:09)
Within the within Topline Pro, we recently switched over to Hex ⁓ and have been using it’s a analytics BI tool. They have a feature called Hex Notebook Agent. And it’s an agent that’ll help you get started and go deep on different analyses. And we found that has like really enhanced the really enhanced capabilities within the operations team.

across the entire company as well. Engineers, product managers, able to now get answers to business questions faster than ever before. So big hex fan. ⁓ That’s a more recent one last couple of months.

Keith Cline (49:52)
Very cool, yeah, there’s some different ones there. How about a good podcast book recommendation for entrepreneurs?

Nick Ornitz (50:00)
I’m going be simple, but how I built this, I love how I built this and all the stories that you hear there. think one of the cool parts of it are that it’s not just B2B SaaS companies that are on there, but how do you get insights and learnings from ⁓ other types of businesses? And then this is a classic book, but as a…

leadership team we over the past year read and have done some workshops on five dysfunctions of a team and how do you pull some insights from that out and how we’re operating. So I think that’s a great book.

Keith Cline (50:32)
Yeah, if it wasn’t for Guy Raza, I don’t know if I would have this podcast. Cause I was like, I think I was painting my basement and I was just burning through all his episodes. And I was just like, I should just do this for venture, like, like, like tech entrepreneurs. And anyway, seven, eight years later now, ⁓ how are you Shannon?

Shannon Kay (50:48)
Yeah, I’ll add one for the really early days, ⁓ Why Startups Fail by Tom Eisenman. ⁓ And so it goes through some common anti-patterns of the early days. One that I think we experienced the false start with dwelling where we got some early positive feedback early on and maybe hung on to the idea a little bit longer than we would have otherwise. And then more recently, I read Scaling People by Claire Hughes Johnson. And it’s a just very

practical approach to scaling businesses. And so I’ve really enjoyed pulling some frameworks from there.

Keith Cline (51:24)
Cool. All right, outside of work, what do you like to do for fun?

Shannon Kay (51:29)
I love to be outside as much as possible. So running, swimming, biking in the summer, skiing in the winter. So great being in the Boston area, so close to some Northeast mountains. And then more of my creative outlet. I love taking photos. I have my grandfather’s old film camera. So just going on a long walk around the city and taking some pictures, probably only about.

20 % that actually turn out. So I’m working on increasing that percentage, but it’s really fun. And I’ve actually started using chat to give me feedback on the photos of like almost a photography coach. So those are some sort of my workout and creative outlets there.

Keith Cline (52:16)
Very cool. How about you, Nick?

Nick Ornitz (52:18)
⁓ First and foremost, probably taking care of dog, Caro. She’s one of our team mascots and she comes into the office a good bit, she’s a little shiba inu, which is great. And then I don’t know if this is your like quarter life crisis, but started doing some triathlons this year, third life crisis, ⁓ one of those. So trying to, yeah, also like Shannon loved doing things outdoors. So hiking, skiing, ⁓ running, like that.

Keith Cline (52:34)
⁓ nice.

So you’re training for the Iron Man. Cool. All right, Nick and Shannon, thank you so much for taking the time to walk us through your background stories, obviously all the great work that you and the team are up to at Topline Pro and wishing you all great, great success.

Shannon Kay (52:46)
Hehehehehe

Nick Ornitz (53:00)
Amazing. Thanks so much for having us.

Shannon Kay (53:02)
Thank you. Thanks for having us. Bye Keith.

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