Ep 20 - Ross Keating - Co-Founder of Overpath

0:01 Hi, welcome to the Founders and Funding podcast. I'm your host, Philip Smith. On the podcast, I'll be interviewing founders, investors, startup advisors on how to fund the journey of your startup and some tips and advice they have for you along the way. This podcast is sponsored by Perfect Technologies and Laden. Enjoy the episode. Ross, welcome to the Founders and Funding podcast. Thanks. For having me, Philip. Well, it's my pleasure to have you. Just to start us off just for the listeners. You've got a very nice background of New York there. I do. I'm based in Dublin, but I'm in New York for the week. My wife is over here on work rotation at work at the moment. So over here for the week and then back again in a few weeks time.

0:47 It's a nice opportunity for me as well to meet some of our design partners and to meet some VCs that view tours are around later this year. Fantastic. I thought it was a green screen. And then, you know, I was, I was astonished to see you really, really are there in New York at the moment. So that's great. Yeah, for sure. And the sun is shining. It wasn't over the weekend, so good opportunity to look at the skyline. Absolutely. To start us off, Ross, tell me a bit about your company and your role. Yeah, sure. So I am the Co founder of Overpath. So in Overpath we are building AI agents for every member of a revenue team. We're building in a new category which we're calling revenue execution.

1:32 And what Overpack does is it connects if you're a Rep and Overpack connects to all of the channels in which you work. So that's your e-mail, your calendar, your call recording, your, your CRM. And we build this context layer on which the agents can live. So that means the agents can do some productivity tasks like move your deals along in the CRM or write your follow up e-mail or help you prepare for a call. But they can also then give you performance feedback. So that could be in advance of a call, it could be after a call. And they are not just reactive, but they are also proactive. So it means because they understand dynamically the data on which you're or you're working, they can proactively intervene in a deal or they can proactively guide you through the the work that you're doing. What were, what were we?

2:24 The behaviour in the market that we're looking to capture is essentially every Rep is doing at the moment. And that's working with foundational models like Claude and Chachi, BT and and Gemini, which are fantastic models as we all know, but they are not purpose built for sales and you know bring some challenges with them when you go to integrate them at an enterprise level within sales organizations. Fantastic. I really like that because it's, it's, it's, it's fantastic and innovation and you know, it's, it's captured that kind of the, the, the AI flow and and innovation that's happening. But because our eye driven, I think that's really attractive to companies is that it's it's driving that bottom line, which is that what they're really trying to achieve from all the different tools that they're using sounds like it's cutting through the noise and actually getting them to where they want to be.

3:14 Yeah, I think that's a really important point. You know, the go to market tech stack that built over the last 1520 years, it's obviously a very mature tech stack, but it requires reps to context switch between tools, right? So I log into my CRM and then maybe I go to my revenue intelligence tool or maybe I go to my sales automation tool. Maybe I've got a data provider. And at the same time, we're doing a lot of my work in e-mail or in Slack or over the phone or in person. So the idea with Overpass is that we create this AI layer where I can continue to work wherever I choose to work, right? So at the moment we, I do my own work now in, in Slack, right? And our, our first agent, Molly is live in Slack.

3:57 So I do all of my sales activities now, pre call, post call, deal management, planning my week from from from within that environment. Fantastic. And what does an average day look like right now? An average day right now is, is scrappy and can change a lot given exactly where we are. So we raised money back in December. So we have been building a team and building a product and starting to build distribution since January. So we're, you know, 3 1/2 four months into that. So my my focus at the moment kind of encompasses a number of of things. One of those things is, you know, using the product.

4:40 So we have a couple of design partners using it and we're using it internally ourselves. And a lot of what I do is about creating fast feedback loops so that we can get the product not only to a point where it is usable, but where it is driving value. And then secondly, we are thinking about distribution very early, right. So we started a video first content strategy back in January. The 1st hire, that first hire in the commercial side that we brought in Michael Paul, who you know is a is a content creator. He's a, he's a video editor, which is probably not a typical way that a an early stage start up goes to market. But it's really, you know, thinking hard about the fact that technology is getting easier and easier to build. We know that we're building in a very crowded space. So we really believe that, you know, building distribution and building brand earlier than typical for a start of our size is is more important than than ever. So it's a lot of content creation and then it's a lot of outreach, you know, starting to build our go to market flywheel, starting to engage with new design partners and you know, starting to think about how we scale our commercial org. Fantastic.

5:57 Yeah. Well, look, I think you're thinking about it and, and doing it the right way. I think a lot of companies they, they don't really ever get that kind of, we call it kind of creation, but we're just trying to speak to people in a in a, in a way that they understand that that's engaging and that solves their problems and speaks to the solution. So I think to get that right, I think everything else will flow from there really well. And how has the company funded its journey to date? So we did proceeds fundraise back in December. So it was a VC LED round. So it was led by Elkstone with participation from Sure Valley 11 Angel. So we raised 1.6 or just over 1.6.

6:38 So it gives us about 18 months runway, 1820 months runway. And you know, it's really designed for us to build a team, to build a prototype to take the product to market to, to get to revenue with a view towards a seed or or Series A, you know, at some point early mid next year. Fantastic. And what is the best way to fund a startup strength in your opinion? You know, I think there's a there's a danger of, you know, falling into a glamour trap here, right? As you know, it's the it's the VC funded startups that get the the the PR in the business. Post big headlines, yeah.

7:21 Exactly. But really I think the, the best way to, to fund the startup is dependent on the kind of business that you're building. And you know what that business model looks like. I mean, for example, I have another business, the Lenox Academy, which is a, a services business. It's a, it's a training business running for about 3 years. And you know, that's a very lean operation. It doesn't have engineering costs, it doesn't have nobody marketing costs at the moment. Uh, you know, we, we run it, we run a very lean, lean structure there. So, uh, that was one which, you know, has we've been able to run as a profitable business from the start. It didn't, didn't need capital. Umm, and then on the over part side, obviously, you know, there's a, there's a few few elements to this, but one is that because we're, we're building a team fast, we've got R&D costs, we've got infrastructure costs and we are building this business with the goal of an exponential outcome, right, which aligns with venture capital expectations.

8:24 So it made sense for us to go out and to do, you know, a relatively large precede round. There's, there's probably a, there's a happy medium in the middle there, right, which startups take as well, which is to do a private round early and to go out and really test the market. So I think the best way to fund the startup aligns with what your, your goals are for the business and what the business model needs. And another mistake that startups fall fall into is going out to market to raise money without a real understanding of what they need the money for or without the understanding of how much they need and, and why they need it. And you know, it's a big, big red flag to to AVC or to any experienced Angel investor as well. Yeah, I've had a few of those conversations with, with founders who, you know, they're very eager to get VC funding or do a proceed, but they kind of jump in between what, how much they should actually, uh, raise or, or the rationale for it. I think it's, you've got really, I think valuable and unique experience there to have both bootstrapping business and to have, you know, raised, uh, funding. So I think it's, uh, it's, it's, it's a good journey to have both experiences, but like there are pros and cons to, to, to both. I think bootstrapping can be fantastic if if you can do it. But I think sometimes, like with overpath, this speed is important because I think with a lot of these companies, AI is moving so fast that if you took the time to bootstrap, you might not have years to just grind away at that. You do need that that speed to

9:54 capture the market before it moves on. You're spot on there. A big parts of the message when we went out to raise was about speed of execution. It was a reason we didn't do an Angel around early and went straight down to the VC route because, you know, we're building in a, in a category that is a new category, but it's one that's forming very quickly and there's, you know, competitors emerging all the time. So this is about how do we build product fast? How do we get to market fast? How do we build brand fast? How do we get a create usage and, and get a user base quickly? So the speed of execution is, is definitely a big factor here, which also was a, as you say, you know, it was a, it was a key reason to go about fundraising, to go back to looking for, to for venture funding.

10:45 Yeah, yeah, 100%. It's, it's just, it's just every time I talk to a set up now, there is just that before things are moving fast, but things move at a whole new speed now with AI that there really isn't that much. There's a lot more uncertainty about the future now or like what's going to be where is AI going to be in a year and how our companies then operate or create new startups and how fast will it move. So I think the safest bet now and before before maybe it seemed risky to to raise money, move fasting that action now is probably the the safest journey to go uncertainty and to look at the founding team then a bit as well. Ross, I suppose this is again one of those kind of a you know, broad strong questions.

11:25 But what? What are the best skills new founders should possess? Yeah so firstly I'm I'm lucky to have a fantastic Co founder German O'Connor uh who has built and exited 2 software businesses already. So he built box ever and skill Co as well. So a part of us coming together as a team, I suppose, was how do we combine or how do we create complementary skill sets, you know, that we believe would be successful for for this business. And so obviously he has the experience of scaling and organizations, gaining a technology organization and going through that deep trajectory that a venture backed company requires.

12:11 And he's also got a technical background, so he's that he's able to to fulfill that. The technical conversation with the product team and the product conversation with the product team. Yeah, which I wouldn't have been able to do, right. And then on my side, I suppose having spent the last three years building Lennox, you know, spent a lot of time with sales leaders and sales reps understanding what the market dynamics look like, what the skills are that are required in order to be a successful Rep, or what the mechanics are in order to roll out methodology across the sales organization. So I suppose there's a domain knowledge there. And I think maybe as technology gets easier to build that domain, understanding of what the problems that your user is experiencing is more important than that than ever. And similarly, I think as technology gets easier to build, already mentioned this, but distribution is more important than ever, right?

13:14 So obviously I've, I've spent a lot of time in building Linux, but I've also spent a lot of time posting content on LinkedIn. There's a smaller audience there now. So there's a nice combination there hopefully between myself and Dermot where he's got that, you know, kind of deep technical products understanding. He's also done a, you know, he's done multiple commercial roles and CEO roles as well, right? So he has a commercial understanding too. And then on my side, there's the there's the domain understanding and maybe that the focus on distribution. I think that's a great partnership to have. I think it's always the case you can have that or you know, the Kill funding team have all those scales. But I think if you can, I think it complements each other extremely well.

13:57 If you can, if you can have that and and to look then back at the investment piece, how can companies attract investors effectively? Yeah, I mean, look, I, I think there's a few pieces in this. We we probably went about it a slightly unconventional route. And so, you know, we went about a fundraise before we incorporated a business or before we really had a product German to spend time building a, a prototype. We certainly didn't have any users. I, I don't recommend that route. You know, we were in a, we were in a strong position given maybe those complementary skill sets or complementary backgrounds that I've described there. So I think the best way that you can go about attracting investment is to, you know, have a very strong point of view on the world that you're that you're building for. So you have a very strong thesis on what your industry or your domain is going to look like in three, 5-10 years time to begin building for that.

15:01 And then really to get traction right, I think, you know, you need proof points, you need users actively using your products, you need customer conversations. The biggest mistake that you can make is, you know, building something in your head or building something from the ideas in your head and not going to get into the, to the hands of, of users, right? That's something that we've tried to do very early, even kind of post fundraisers. How do we get something into the hands of users when it's really scrappy and has lots of hold on? It doesn't work well, right. You know, there's a famous quote out there that if you're not embarrassed by your first product release, then you ship too late. And you know that that's, it's a, it's a painful thing to do, to sit in front of your users and to, to, to hear very tough feedback about products that had bugs in them or features that didn't exist yet.

15:56 But it's a necessary 1. And I think for most startups, you should do that before you go out looking for, for money, or at least before you go out looking for meaningful amounts of money in order to, to, to, to scale. But then also the other thing is that at a very early stage, really what what investors are investing in are, are the founders, right? Yeah, there's only so much, there's only so much information that you can get about a very, very early stage. There's only so much due diligence that you can do right, because it's, it's a very short lifespan the organizations had. So really you're looking for the, for the expertise of the founders. You're looking for the vision of the founders. You're looking for their ability to execute, their ability to hire talent as well, right? Access to, to, to talent.

16:43 And so I think, you know, having that thought process around what your founding team looks like is, is key, right? If you can get a, a Co founder with a complementary skill set, I would encourage you to do that. I don't think I would ever build a business solo again. But even if you can't get that Co founder thinking about what is the profile of your founding team, your founding engineering team, your founding commercial team and showing that you have the ability to you know, to to to acquire that that that talent in the in the business. Yeah, absolutely. Well, look, I think particularly for your for yourselves in Dermot, I think for investors, it's, there's, there's a lot of good rationale for why you would be great founders to invest in because you've had success, such a success already.

17:26 But I think yes, certainly for first time founders that do face that struggle of why should I invest in you as a person? So I think trying to build that credibility throughout your career is something that that might be needed before we finish. Ross, if you had one key piece of advice to share on funding to start up, what would it be? So, but maybe we've touched on some of this, but you know, it's about having firstly, having a, a clear objective on what you're trying to achieve in terms of the size, why you need it, what's like what that is going to do for you, you know, over, over the next period of, of time. So, so planning exactly what you need and finding the right mechanism to fund your startup is, is really important.

18:07 And then I think the best piece of advice that I got was to run your fundraising process like a sales process, right? So to run it like a Sprint. So when you decide that you're going out to market and you know, you've built your data room and you've built your deck and you've built your financial model that you then meet as many investors that fit the profile of investor that will fund your startup in a short a time as as possible. You, you do that for a whole bunch of reasons. One, you know, you can create competitive dynamics between investors 2, you, you sharpen your, your pitch very fast. You get very fast feedback on, you know, whether this is a, a thesis that is, is landing with investors, but also, you know, you, you maximize, you maximize your own time efficiency, right? Like the worst thing that you can do is to go through an elongated fundraising process where you're trying to build a business and then going back and fundraising, going back to build a business, right?

19:09 It's just, it's fundraising is a, is a, is a, you know, it's an all-encompassing thing. So I think for anyone out there that that that's listening and is thinking about raising money, build your thesis, get the right materials together, get the right team together, and then meet as many investors as you can in a, in a shorter time span as you can. Fantastic advice. Ross, thanks so much for going on the podcast. It was really great speaking to you. Not at all. Thanks for having. Me a pleasure Ross. Best of luck with Overpath and I'll be watching you on LinkedIn to see more. Thanks, Philip. Hi, thanks for listening to this week's episode of the Founders and Funding podcast. If you'd like to be a guest or have a guest suggestion, please get in touch.

19:52 Thank you.