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The Role of Venture Studio in Building a successful StartUp with Egan Montgomery of High Alpha

Want to grow fast in your career? Then work with the smartest people that you can find.


Today, we have Egan Montgomery, the Director of Go-To-Market at High Alpha, a venture studio based in Indianapolis. High Alpha helps B2B SaaS startup founders and companies launch and scale through their unique venture studio model.


Egan's passion for helping others and his intentional actions led him to succeed in his career and become a startup leader. 


In this episode, Egan talks about the role of venture studios in helping startup companies launch and scale. He touches on the common problems of startup founders and companies, how to find product market fit, and how startups can take advantage to move fast and expect more in their business.

Episode Highlights:

02:36   Interesting story of how Egan came to and stayed in Indiana

06:38 Egan's early career growth at DemandJump

09:13 The difference between working in a startup and a large established company 

12:05 How Egan works with a venture studio like High Alpha

19:13 The willingness to absorb, learn and work with new ideas

21:52 How High Alpha supports startup founders to be successful

25:40 High Alpha's approach to product market fit identification

34:07 What are the criteria for identifying the ideal customer profile

40:29 How startup executives can be more involved in the investor side of the business

45:27 The growth of Egan as a leader after working with startups

Grayson Faircloth:  20:48  

And are there specific resources or people that you learned from that you want to kind of call out.

Egan Montgomery:  20:55  

My favorite substack right now is Lenny's newsletter, he writes about going to market and product. His background is a lot of things. But I think probably most known for Airbnb, and now this newsletter, but it covers a really broad set of topics. And I think it's just a fantastic resource for anyone that's going to market a product.

Grayson Faircloth:  21:15  

Yeah, I've been subscribed to as well. He's the marketplace guide. Correct.

Egan Montgomery:  21:19  

He talks about everything. He talks about the marketplace. He talks about b2c apps, he talks about b2b, he talks about all the different types of go to market. So that's why I like it. He has a lot of range. And he sees a lot of patterns, and really just does a lot of work sort of for you. Yeah. And he's a great writer, and he gets great guests and all that. So that'd be a good one. A good one to start with.

Grayson Faircloth:  21:45  

Yeah, no, definitely plus one on that statement, one of the hop back into the high alpha studio model, I was interested. So high alpha, you guys have seen so many more startups and launched so many more startups than any individual founder could ever do, like in their lifetime reasonably. So is the idea with like the whole venture studio model, because of the fact that you've seen so much more of like what works and what doesn't work, that startup will have a higher success rate than a traditional startup, or what are like the key things that you would say like a venture studio, like high alpha is able to help with the, like a typical startup wouldn't have access to,

Egan Montgomery:  22:27  

I think the yes, the reps or the at bats are a huge component of how high alpha helps a founder, go faster and reach their fullest potential to reach the company's fullest potential. And that's, you know, inclusive of all of the 35 plus companies that we've launched, we also have a capital portfolio. 

I couldn't even tell you how many companies are there, but the capital team has made a lot of investments outside of the studio. And then, you know, the the history of the four founding partners, and they've been involved in so many companies, the exact target and others, you know, that sort of all culminate in this really kind of, I think, awesome amount of learning and pattern recognition, you know, but it's also, like I said, like bodies, like just having people around you who can help you think through all of these really hard, complicated problems. 

And then, you know, I'll also say the things that are repeatable, and there are, you know, I'm talking out of both sides of my mouth a little bit, because I just said, like, every company is different. But there are, you know, some amount of things with every company that are the same. And I think that's more true in some of the functions at high alpha, like finance, and HR, you know, like, we know how to set up a bank account, we know how to do all the legal stuff that's associated with starting a company, we've got great playbooks for writing employee handbook, and, you know, all of that kind of stuff, you know, is relatively repeatable, but even across design, marketing, go to market and product market fit, there are things that we can we can do and repeat that help people go faster. There's this sort of thing from the military where, you know, sometimes the military is criticized, they do so much drilling, and there's so much process, they get criticized for not being creative. 

But what the military would tell you is that they drill all of the stuff that is the same every time so that when those situations present themselves, that stuff is just automatic. And so you have brain bandwidth to be creative with the rest of it. That's how I think about the value of high alpha, like, there's more white space where you can be creative and think about the things that there's no way you can productize but you're dedicating more of your energy there. And that's, I think, really, really powerful for an entrepreneur.

Grayson Faircloth:  24:49  

Yeah, I particularly love that example. I'd never heard about an army specific example. But the power of being able to know a particular process or or something well enough, you can break it, essentially, you can see now, okay, I know the baseline, like I know, like my flow of the sales conversation well enough that you can now do those experiments. And you can say, Okay, we've got this baseline on if we just follow the standard process, it should succeed at, you know, this percentage rate, let's start doing some crazy stuff. 

And that's what high alpha than just startups in general, in my opinion, are all about. Is that experimentation? Like, how can you take that process? You gotta have it in there in the first place. But then once you have it, yeah, so I love that you mentioned that. You also talked about product market fit. And that's something that's super interesting to me. I'm interested in how you guys define like product market fit for your studio? Companies like and how do you approach things like, do we have product market fit? Yeah, I'm sure it may vary, but I'd love to hear your perspective on that.

Egan Montgomery:  25:54  

Yeah, so the product market fit function at high alpha is, believe it or not relatively new, of course, we've been focusing on Product Market Fit related things for the full duration of the company, but having bodies here who are thinking about that every single day, that's a relatively new thing. And they're spending a lot of time thinking about how we define product market fit? You know, but there's a couple of things that I think have emerged. 

One is we ask all of our companies to self report, on a scale of one to five, do you have product market fit. And we ask that every single week, a lot of people that you talk to about product market fit, who have been around software for a long time will say that it to a large degree, it is just a feeling you feel the market start to, you know, when you first start the company, you're pushing, like you are like a bull, just trying to get your company your name out there trying to get customers. 

And at some point, when you start to have product market fit, that kind of power dynamic reverses the market and is now pulling you into it. And so there are ways that you can measure that pull, inbound leads, word of mouth, referral, type traction. So those are things that that we look for, of course, product usage metrics, our daily active user da use, or monthly active user ma use, are those increasing at a high rate are people logging in, what percentage of users from a single company are logging in, all of that, you know, again, can change a little bit based on the type of company. And then I think, you know, one of the biggest things is when revenue starts to sort of grow at a high rate, and it's smooth, right? It's not the kind of lumpiness that's so persistent in early stage software, but it starts to really smooth out. 

And like a lot of times when you see an ARR chart for a successful company, a billion dollar plus company, it'll look like this perfect, like, up into the right hockey stick thing. But they're omitting the beginning phases of that where it's a total jagged line, when that jagged line starts to go away, and it starts to smooth out, I think that's another sign that product market fit. But, you know, I think the honest answer is that there's not a perfect definition. I mean, there really isn't, some of it is the feeling some of it is watching some of those metrics and, and trying to be smart. But yeah, and it can change over time to a product that a market is embracing, can fall out of favor due to competitive changes, or regulatory changes, or just changes in tastes and preferences. So it is an always on sort of thing of trying to make sure that you do truly have product market fit.

Grayson Faircloth:  28:47  

And would you say product market fit for a high alpha studio company is more of like, not necessarily like a vanity metric in terms of like, nothing happens from it? Do you use it as a trigger? Like, oh, you've hit four out of five on product market fit? We didn't just start a fundraising type of thing? Or is it more of just like, let's keep a pulse on everything that's happening within all of our companies? Like how do you guys actually act on that? I would say

Egan Montgomery:  29:11  

it's more the latter. For the time being, it's more of a pulse. It's more of helping to understand, you know, who might need a little more support and resources from a product standpoint, versus who's maybe in a better position with what they've built. But ultimately, I think we want to be able to start to predict when a company is going to self-report product market fit because there are other metrics that we're tracking on a weekly basis. 

And we're trying to see like, does attainment of a revenue goal? Is that an accurate predictor of product market fit? Or is a product usage goal, a leading indicator of product market fit or is talking to a lot of customers and people in market, a predictor of product market fit or is it some combination of all three of those things that are something completely different that I haven't even Haven't even brought up?

Grayson Faircloth:  30:01  

Yeah, you guys have access to quite a vast amount of data. I'm just realizing this. Yeah, you guys could do some really cool things. They're switching themes a little bit. So you're using or you're using that product market fit to kind of get a pulse check. What are some of the other things that you're doing to post checks with your founders? And like, what are the problems that are common that people are coming to you with? In your post checks?

Egan Montgomery:  30:25  

Yep. So we asked for a Northstar metric. And then pacing against that metric. We asked for product market fit that the scale product market fit. And then we also ask about morale, which is really cool. 

And I think super important, because, you know, startups are so hard, they are so hard. And energy founder and founding team energy is so important, because not every day, not every week is going to be rosy. So those are some of the big things that we track.

Grayson Faircloth:  30:59  

And then when you see like the pacing is maybe slowing down versus a previous week, that would be like the time where you would kind of step in? And like what I guess getting to the second half of the question around the common problems, like are there common problems? Or are the problems pretty, like specific to the actual organization itself? Like I'm sure sales is probably a common problem, but like, what are like the sub problems to that?

Egan Montgomery:  31:28  

Do you think there are definitely common problems, many of them related to sales, go to market product, recruiting, you know, I think one of the big things I bucket under just like the cold start problem, like the first day that I meet a CEO, we have zero product, zero revenue, zero customers, no pilot commits, like you have nothing other than like an idea, and the resources of high alpha and the founder and their brain. 

So, you know, how do you go from that to a company that has traction in the market? Or does the product market fit? And there's a lot of things that need to happen in order for that to occur. But, you know, like, one, one common thing to maybe be more specific is like, credibility and social proof. Like how do you convince the first customer to sign up when you don't have a referenceable customer on your roster, when you don't have a case study or any sort of proof point that the thing that you're doing works? 

You know, I think founders selling there's all kinds of interesting problems that come up around that, like, oftentimes, you know, the founder hasn't been in a sales capacity before ever, like they've got superpowers in some other area. And so, but they're out talking to Home Depot, and Marriott, and Hilton, and it's like, some of the most complex selling environments that you could possibly drop someone into. 

So how do you overcome that just the sheer like building of assets, like, really quickly, we need to arm them with a website and a really great first call deck and sales, collateral, and ROI calculators and, you know, all that kind of stuff. And then the whole time the target is moving, because we're learning more about our target market. And we're learning more about what we need to build. And then you need to go back and update things. So there's probably like too many to even go into on this podcast. But those are a couple that definitely come up a lot


Grayson Faircloth:  33:36  

Something I'm interested in, well, is the definition of that like, initial, like, ideal customer, like how do you so I know how alpha, when you're creating the ideas, you have some sort of like, ideal customer defined in that case? 

Like, what are the things that you're like? Is it around job titles, I'd assume it was around companies, I was like, what are the things that you're looking at when you're creating like that initial ICP? And then how are you kind of like tweaking that and developing it as time goes on?

Egan Montgomery:  34:07  

Yeah, I always say that the specific way that they're defined has to be based on criteria that you can go to a database, or an ad network and plug those criteria in and actually because otherwise, it's not usable, like people talk about behavioral ICP characteristics. Well, that works if you have heavy content, motion and a bunch of like, buyer intent tools installed and and even then I would question like, how much can you really get into a behavioral characteristic until you're in the selling process, of course, and then it's a little different. 

So I think that it's important to simplify it down to something that is targetable. So that is things like industry, revenue, headcount, growth rate technologies that I used all of that kind of stuff. Now we do at every stage of having an idea for a business have some sort of perspective on what the ICT is, and we're always wrong or changes. And, you know, I think the important thing is, you have to have it defined, you have to have an ICP defined, because you need to be able to either validate or invalidate, whether it is right, that's a mistake that I see a lot of people make is, they don't have any definition around ICP, or it's so broad, or there's so many different target markets that they're going after, that they never actually get, like red or green on is this my ICP? So being wrong is actually like an awesome thing. 

Because you know that's not someone that you should be selling to, and you can redefine the ICP and go out and do it again. The other comments I'd make on ICP, the, the most successful companies that I work with, have really niched down their ICP, so they've gotten really, really tight on who they're selling to, and what specific problems they solve for that buyer. Because, you know, I talked about credibility when we were talking about problems. Well, one way to kind of beef up credibility is with really specific and strong positioning, you can only do that if you have a tight definition around ICP, and it makes a whole bunch of things a whole lot easier like running marketing campaigns and building sales playbooks, and all that kind of stuff. 

But I love the question, because I think there's these opposing forces in startups where like, you want this idea to be really big, and you want a huge addressable market, and you think that your investors are only going to invest in the business, if there's a huge amount of people that you can sell to. And to some degree, that's probably true, you need it to be a big and compelling market. 

But the messaging and or what you believe, as the long term does not have to be what you message on your sort of public facing material or website or whatever you can get as specific as you want, when you're talking to a customer and still tell a big story, you know, to an investor to employees to get them excited to join or whatever. But a sure way to not succeed is to be way too broad with the target market.

Grayson Faircloth:  37:26  

And I'm curious, so when you get that specific, are there some fun characteristics that you will use? Like if a company has to have a persona, is this a good fit? Is it pretty standard? Or I'm interested if they're just any fun, like attributes that have gone into ICPs? At high alpha, that maybe you're not like a standard job title, stuff like that?

Egan Montgomery:  37:49  

Man, that's a good question, grace, and I can't think of anything, oftentimes, I'm advocating for the boring stuff, because that's the stuff that's searchable. I mean, the one thing we use a lot that I think is pretty common is like roles, specific roles that exist at the company. And sometimes those can be fun. Like, if you're, if you're looking for early adopters, in a certain market, like usually we find it's a positive signal if the company has someone in charge of innovation, or someone in charge of emerging technologies or something like that. So that's one that is maybe a little a little different than just job title and industry. 

The other thing I really like, I really like Technographics, like, what technologies are they using? We use Zoom info, which has pretty good data on that. But I know there's a lot of tools that you can use to zoom in on that. That allows you to get much more specific in your messaging like “Hey, I know you're on greenhouse or I know you're on HubSpot”. So yeah, maybe those two out?

Grayson Faircloth:  38:48  

Yeah, no, definitely a fan of the technology indicator. So right here, I'm interested, there's something new that I'm seeing less it's not involved in like the sales intelligence platforms, but it's more of like, you know, even books meeting, pre meeting, I want to learn a little bit about Egan. Have you seen much about the like, it's almost like personalities and behavioral, like there's a software that I can tell you, if I'm selling to Egan, I need to, you know, cut the small talk. He just wants to get into it. Have you done anything around ICPs? Or do you have any founders or anything playing around with that?

Egan Montgomery:  39:24  

I have seen it. I haven't done too much experimentation with it yet, although I probably should, because that's a really interesting and compelling idea. And I could see, I could see it being helpful, just around sales effectiveness and kind of mirroring and making sure that you're addressing the person in a style that is conducive to them actually buying something. Short answer is no, but I probably should be.

Grayson Faircloth:  39:51  

I think it's super cool. So let me know if you find anything about that. I just picture this world where it's like, yeah, I mean, you can almost have an AI selling based on your specific like, how you like to buy very a lot of cool stuff around that. But yeah, cool. Good to know that it's also new to you as well. 

We talked about this a little bit earlier, but I wanted to bring it up again. One of the goals of this podcast is to help develop current and future startup executives. And so I'm interested, like your opinion, interacting with a lot of startup executives that like the top top tier, what does an effective startup executive need to know about just like the interactions with the venture capital side of the business? 

Like what are the things that you're having to educate founders on early stage startup founders that maybe they don't know about, you know, the venture capital side of the business? Or maybe they're like a VP of marketing, but want to grow into a CMO where they have to maybe be involved more in like the investor side of the business?

Egan Montgomery:  40:54  

Yeah, it's a good question, Grayson, I think, you know, one of the things that comes to mind is that a really great investor is going like, genuinely wants to be helpful, like they genuinely want to help the company succeed, and provide resources and provide help and guidance. And one thing that I see sometimes is not necessarily in our portfolio, but I've been around the software industry a lot. You know, I think sometimes founders can try and be overly guarded. Or they can try and, you know, do too much like positive, optimistic storytelling. 

And of course, it's good to bring positive energy, and it's good to highlight wins, and all of that kind of stuff. But you can't make progress as a seed stage company, or as any stage company, if you're not being honest about what's not going well, where do we need help? And no matter how good of a founder you are, how good of a company you are, there's tons of stuff that is not going well. So I think that's really important to keep in mind, just like a really great seed investor is going to do everything in their power to be helpful.

Grayson Faircloth:  42:03  

And what typically might a seed investor? Like, what should you go to your investor to help with? It may look a little different for studio companies, because they can almost come to you for anything at this point. But like a typical non-studio company, what types of things do you think a seed investor would be best to help with in the first place?

Egan Montgomery:  42:22  

I would say, any sort of knowledge sharing from other companies in that investor's portfolio, they have a lot of pattern recognition going on. And so I think it's always okay to ask, what are you seeing with your other companies around sales win rates right now? Or who's having success with fundraising? So I think that's an area that they can help. Always intros, whether that be sales intros, recruiting intros or interests to other investors. I think that's another area that an investor can be helpful. 

And then I would say like, most good investors will always connect you with another company in their portfolio, like a peer, another founder, or, “Hey, my director of marketing is thinking through a new”, kind of pipeline generation channel, can you connect them with a Director of Marketing at another company, who's doing something similar? So, I'd say community intros and just kind of general pattern recognition across the portfolio.

Grayson Faircloth:  43:25  

Okay. Yeah, I love that. And on the metric side of like, investor updates, that kind of stuff. I know, you're more on the studio side. But have you seen and maybe heard from your founders that there's specific metrics that you know, investors are wanting to see or not see, are kind of what talk through that a little bit.

Egan Montgomery:  43:45  

I'll keep it to an early stage, but most investors will be looking for, I think, a working MVP, with some signs of repeat use or retention. So our customers are logging in using the product and getting value out of it? And what are the metrics associated with that? They're looking for traction in the market. 

So oftentimes, that'll be pipeline and revenue Arr, or in a product lead motion, it might be free trial starts and MRR and then and then I think they're looking for, you know, maybe some of the non metric or less business performance stuff, like is it a big market? Can a founder tell a great story? What does the founding team look like? As you get later, you know, I think the metrics get more specific, and those are I think, pretty well published and I'm probably not even the best person to talk about them but you know, think about now you have customers who have who have or should be being renewed and being up sold to so what is gross churn look like? What does net churn look like? 

What's net revenue retention and IRR on download? On. But I think in the early days, like there's some beauty and really focusing on like, do I have a product that people are using? Am I able to sell that product? And do I have a big vision for this company? And can it be really big?

Grayson Faircloth:  45:14  

Yeah, I think that it's probably better than having 10 million different metrics that you check on. So I want to end off with one last real question, and maybe a couple fun questions if we have time. But I'm interested in looking back, and this is kind of a fun one, to start it off, he literally started off as an intern, and then went into more of that, like, individual contributor role. And then now go to the market leader role, like, what do you think has life changed about like, knowledge wise, like, mindset wise, just like anything that you think that you wish, the earlier version of Egan would have known or stuff like that?

Egan Montgomery:  45:53  

Oh, man, I mean, that is certainly the thing that has changed, like, I am so much more experienced than I was, and I look back, you know, even three and a half years ago, when I was leading marketing, and sometimes I cringe at like, all of the stuff that I didn't know. And I know that you know, me in three years is gonna look back at me now and cringe again. But like, at the same time, that just means that you're getting better and that you're focused on learning and improving. So while it's kind of hard to think back on those times, and you wish that you had known more at the time, you know, the very positive side of that is like, that's, that's what growth is, you know, you didn't ask me this, but since the nature of the podcast is kind of the startup executive, and people kind of aspiring to be in those roles. 

You know, I think that that is like optimizing your career for some kind of learning and just maxing out experience. It's all in the some of the stuff we've hit on a lot today, but like, always be learning to run towards fire, say yes to stuff like, nothing is going to be more helpful than those things. You know, startups are beautiful, because they're merit based, you know, for the most part, of course, there's politics and whatnot, in a startup, like any organization, but much more so than a big corporate monolith, it is based on what you know, it is based on how effective you are. 

And if you are getting better, you will be successful. And I think, you know, one other thing on that note is like, one thing I'm kind of proud of, about how I've sort of made decisions in my career is, I've never made decisions based on money, or based on title, the number one most important thing to me, was to work with the smartest people that I could find. And like, when I started that demand jump, I was reporting to the CEO who had sold like, eight companies. I mean, how could you get better experience than that, and I reported to CROs, a former Walmart CMO, and personally would lead North American sales for exact targets. 

And then I came to high often, like a huge reason I made that decision was because I wanted to work with... Drew and I wanted to work with the people that worked with Drew. And when I came to high alpha, like I took the title cut, I took a pay cut. And I'm like, you know, I'm proud of that. Because that just stuff kind of works itself out in the long run. If you're optimizing for, you know, money that might feel like a lot of money at the time, or you're optimizing for a little better title at the expense of working with great people and getting kind of outsized experiences relative to your peers. You're making a mistake.

Grayson Faircloth:  48:39  

Yeah, I love that. I think let's end it there. I think that was great. Is there anything you want to plug the LinkedIn book coming out soon, anything like that?

Egan Montgomery:  48:48  

Not no books in the works. Right now. I'm probably most active on LinkedIn. You can just search my name Egon Montgomery. There aren't too many Egan's in the world. And then on Twitter as well. It's just @eganmontgomery.

Grayson Faircloth:  49:00  

Cool. Well, this was awesome. Really appreciate you joining.

Egan Montgomery:  49:04  

Thanks, Grayson. This is really fun.

Grayson Faircloth:  0:05  

In this episode, I want you to think, what can you learn from someone who's helped launch dozens of tech startups. So today our guest is Egan Montgomery, Director of go to market at high alpha, which is a venture studio venture fund, based here in Indianapolis, Egan's originally from Chicago found himself in Indy, after graduating. And he's actually the youngest guest we've had on the podcast so far. 

So extra impressive, just given how crucial of a role he is in high alpha. In this episode, we're going to touch on a couple different things. First one being finding product market fit as an early stage startup. So it's something that I'm sure plenty of people in the startup space have either dealt with or will deal with in the future. We'll talk about what a venture studio actually does. What is the role of a venture studio in the whole startup space? And then Egan is particularly good at thinking about how you can advance your career quickly and effectively. 

So Egan was always very intentional with his actions in terms of how can I help out? And how can I grow myself in my career as a result of helping out. So if you're interested in any of that, stick around, I think this is going to be another great episode. And looking forward to diving into it. I'm here with Egan, welcome. How's it going, Man?

Egan Montgomery:  1:21  

It's going great, Grayson, glad to be here. Glad to talk. I'm always down to talk to startups. So this will be a lot of fun.

Grayson Faircloth:  1:27  

Yeah, and this will be interesting. So the people who have joined previously have been like, either kind of running a startup, like co-founder or like an early stage company. So it'll be interesting to get like the more VC perspective, I know you work with a lot of the early stage companies. It'll be even more interesting to get that VC studio model. We'll dive into that. But yeah, I'm particularly excited for that perspective. I think it's gonna be a lot different than a lot of the other people who have been on the podcast so far.

Egan Montgomery:  1:56  

Yeah, I feel that it's unique. Being on this side of the fence, I should say, I myself am not technically an investor. I do sort of absorb, you know, some of that just by osmosis. And just by being at a place, like high alpha. So glad to share some of that perspective. But I do still, you know, identify as an operator. I mean, I spend most of my day rolling my sleeves up in the weeds with brand new startups kind of across industries. So hopefully, I can share a little bit on both sides of the fence.

Grayson Faircloth:  2:28  

Yeah, no, that'd be awesome. But let's, let's take a step back. Let's talk about just the general background. What brought you to Indy? What kept you here?

Egan Montgomery:  2:36  

What brought me to Indy was college. I'm a Butler Bulldog. And as soon as I got here, I pretty much never looked back. I grew up in Chicago, but I fell in love with Indy almost immediately and was fortunate to get a full time job here right after school and stuck around. The specific story that I've how I got here is kind of interesting. So I, like 100%, was going to go to a big 10 school. I applied to like seven schools, and I think six of them were big 10 schools and one of them was Butler and Butler was the last one that I even applied to when my mom and I were driving from Purdue to Indiana. And we drove past the big sign on i 65. For Butler and for Hinkle Fieldhouse. I was a basketball guy growing up I played in in high school. And I was like we have to see Henkel like, we can't just drive right past it. So we whip off the highway, and we pull up to Butler's campus and we park on the opposite side of campus from Henkel to Indianapolis, people will probably be able to visualize what I'm talking about. But we walked across campus, and I just instantly knew that it's where I wanted to go. And it was so different from all the other places that I was looking, but then ended up working out.

Grayson Faircloth:  3:56  

That's awesome. It's probably one of the first times in history that we've been able to tie a billboard back to the actual conversion as well. So that's awesome.

Egan Montgomery:  4:04  

Yeah, there you go. I should call the butler marketing department and let them know just that.

Grayson Faircloth:  4:09  

Yeah, I'm sure they'd love that, actually. And so that very first position, you graduated college, you actually did an internship, right, that ended up turning into the full time role. Is that the case?

Egan Montgomery:  4:20  

That's right. Yeah. One of the things that was unique about Butler is they required you to do two internships. You couldn't graduate unless you did two internships. And I did one summer going into my senior year, I guess. And it was at a big healthcare company. 

It was, frankly a relatively prestigious internship for Butler students and I think Indianapolis students in general and I worked really hard to network my way in there and get the internship and amazing company doing really awesome things for the world, but it just like clearly wasn't a fit for me that kind of corporate behemoth style of work. And so I went out looking for basically the complete opposite of that experience. 

And for me that was what ended up being a precedent marketing technology company called demand jump. And I had a friend who worked there and ended up as a, I think we call it a content marketing intern. But I mean, it was just anything and everything that needed to be done.

Grayson Faircloth:  5:24  

You started on the startup, How soon did you like recognize a difference from that first internship in terms of just like energy, I'm assuming just like day to day like happiness,

Egan Montgomery:  5:34  

first day, I mean, within minutes of being there, I just felt like it was a better fit. For me the pace, you know, was immediately faster like onboarding, for example. I mean, my onboarding at this company was like, five minutes. And it was like with the CEO, and then it was like, Okay, here's a list of projects, go get your hands dirty. And within, you know, probably a day, maybe two days, I was writing blogs for the business, I had, you know, admin access to the social media accounts, I was learning Google Analytics, like, just the breadth of work that I was exposed to, really quickly, like, just immediately gave me a different feel.

Grayson Faircloth:  6:14  

And so you're new to the startup? How did you actually like to develop into this startup? Because and I guess, let's talk about like, demand jumped a little bit before that, like, what was the overarching idea of the company first? And then how did you fit in coming in? And then how did that kind of expand over time?

Egan Montgomery:  6:31  

Yeah, so the company has since made some changes, since I've left, so I can only really speak to the time that I was there. But when we started, the initial idea was around marketing attribution. So there's been a lot of companies that have tried to solve attribution, I think some of them are more successful than others. But demand, Trump's angle at the time was, we had a really sophisticated kind of data science, and that sort of underpinned our platform. And the job was to basically track the path the purchase of a customer.

 So there's this really cool concept that you know, marketers always think in terms of funnels, but the way that a customer actually navigates to you to a purchase decision is much more like a spiderweb. There's all these different sorts of intertwined paths that people take. And if you analyze all of that data, you find that there are specific nodes that are really, really important, you know, many, a large percentage of your customers will kind of hit this source of traffic. And that could be any number of things, a website, a blog, search, keyword, whatever. And then if you could help companies sort of organize all of those different touchpoints in the most efficient way that you could ultimately increase your sales, reduce and spend any number of good things. 

So that was the initial idea. And my role, like I said, started, you know, mostly in content, but getting to work on a lot of different stuff. And this was a new concept. I mean, this whole idea of spider webs and the type of data science that we had applied to the platform were very new. So there were all types of fun, content, marketing, and storytelling challenges that we needed to overcome. And that was really the bulk of my work for the first, I'd say probably, probably two years. And over time, I just, you know, kept raising my hand to take on new projects, and, you know, worked hard and all that all that kind of good stuff. And over time had taken over, inbound, you know, brand marketing, product marketing to some degree outbound. And you know, next thing you know, you wake up one morning, and you're in charge of marketing.

Grayson Faircloth:  8:45  

Yeah, talk about that a little bit. Because yes, you can say you wake up one moment, but like actually raising your hand, what does that actually entail for someone who maybe he's in a similar situation, where there may be a content marketing specialist? Is there a role, which is probably what you were when you first got started? Like, so what do you mean by raising your hand and what like, what the conversations with your manager look like to get you from, you know, content marketing specialist all the way up to Director of Marketing.

Egan Montgomery:  9:13  

Yeah, well, for one thing, I think it's about breaking down any guardrails or any perception of what you think your role is. So contrary to the very first company that was a large telescopic organization, I had, like, three jobs there, and those were like the only three things I was responsible for. And going outside of that Lane was not only I mean, it would potentially aggravate people because you are stepping on their toes. Sure, working at a startup is so different. I mean, you need people who are willing to say yes, who are willing to lend an extra hand in an area that may be so far removed from their actual job description. And I think those are the people that ultimately succeed. 

So what I mean by raising my hand like my mom No, there was just like, run towards fires, like if there was a problem, be the person who was willing to jump in and fix it don't be overly guarding of your time. I mean, of course, you need to work life balance needs to be able to unplug, but don't get hung up in the normal, you know, sort of definitions of roles and responsibilities just run towards fires, because you're all, you're all chasing the same thing at the end of the day. And I think there's a really clear sort of delineation between the people in the early stage who are willing to do that, and like doing that and get energy from running towards fires, and the people who really just want to, you know, try and stay in their lane. And just one thing I'm interested

Grayson Faircloth:  10:37  

on just like that point, and we'll get to like how you're so involved in all these different companies at the same time. But have you seen both types of personas be successful in startups? Or is it clearly that if the team is not willing to do a bunch of different things, it's likely going to fail?

Egan Montgomery:  10:55  

Yeah, I think early days, I really try to stay away from kind of black and white declarative statements. But this is one thing that I think is true, you know, 98 99% of the time, like the run towards fires, people, if you can stick with that sort of metaphor, Are always the people who are successful in early stage software companies. 

Now, at some point that changes at some point, the company gets big enough for the problems to get specific enough that you do need to bring in more specialists. And I think that can vary depending on the type of company that you're building. And, you know, the funding that you have, and all of that kind of good stuff. But pre series A, I would say at least like you want the people who are just willing to run to the thing that's most important.

Grayson Faircloth:  11:45  

Yeah, I figured that would be kind of where you went with it. But I wanted to see what that one or 2% might be. Let's skip ahead a little bit. So you became director of marketing. And then you got involved with this company called high alpha, which is like where you're currently at? Could you give a little background on what is high alpha? How did you got involved with them in the first place?

Egan Montgomery:  12:05  

Yeah, so high alpha is a venture studio, we're based in Indianapolis, and a venture studio, I think the simplest way to think about it is a startup studio, and a venture fund smashed together in one entity. And so what that means is we're coming up with and validating ideas, we're launching those ideas as companies. And then there's capital that we can inject into those businesses. And the whole idea is to go faster to help entrepreneurs go faster and farther, because they're all of the studio resources like me, you know, my function is go to market. So I help with sales and marketing. We have brand marketing, product design, brand, design, HR, finance, product market fit all kinds of different resources that an early stage company would need plus capital. So a founder, Ken arrived on day one and was surrounded with so many more resources than then you would get if you were just out doing this doing this thing on your own.

Grayson Faircloth:  13:12  

Then how did you find that Ohio alphas were well known in the area, but how did you actually get involved with them? Yeah,

Egan Montgomery:  13:20  

I had heard of them, of course, and had been to many of their events. But I got connected with Drew, who at the time, was the Director of Marketing at high alpha. He's now the CEO of a high alpha company called holder. And Drew and I just got to talking and really hit it off. And he had a role open on his team on his marketing team. And one thing led to another and we were working together.

Grayson Faircloth:  13:48  

So you joined a high office team under marketing originally, correct?

Egan Montgomery:  13:52  

Yeah, I was a marketing manager. When I started here three years ago, it was the

Grayson Faircloth:  13:55  

idea that you were focused on the studio companies at that time, or were you focused on high alphas like internal merchanting?

Egan Montgomery:  14:02  

Yeah, good question. I was focused on the studio companies, that's where I've always focused the majority of my time. And part of why it was, I think, a good fit. I had just spent four, almost five years in the trenches with an early stage software company. And, you know, I remember like in my application, and in the interview, I talked a lot about empathy, which I think is so important at this stage, because no matter how you slice and dice at startups it is really, really hard. And I thought that I could bring sort of a sense of empathy because I just lived it, you know, to the job and so yeah, I spent most of my time both then and now with studio companies.

Grayson Faircloth:  14:46  

Take me through that journey from you know, marketing manager to becoming director of go to market when did high alpha start thinking about maybe go to market as a more holistic, like department or or like focus, versus like, we have marketing, we have sales, it seems obvious. Now a lot of companies are starting to think about it. But how did you guys think about it? Like a couple years ago?

Egan Montgomery:  15:11  

Yeah, high alpha, I think has always been just second to none at brand design, marketing, communications, PR, you know, a lot of those types of functions that often live under under marketing, I have always said that I'm like a salesperson traffic and marketers body. And a lot of that is because of the people who I reported to and the culture at demand jump, which was very performance driven, very performance oriented, and very sales driven. So I had to learn to think as much if not more like a salesperson than a marketer. 

And so when I showed up at high alpha, there was a lot of great stuff that we were doing in that area, but I wanted to do more of it, because I felt like it was important. And one of the amazing things about high alpha is it's such an experimental culture, we're always getting better, we always want to get better. And so when I kind of raised my hand and said, Hey, I think we could, you know, maybe be doing more in demand gen or more in sales enablement and support or more in ops. It was like no questions asked, go build a 90 day experiment. And let's and let's do it. 

So we actually did do that. I basically wrote a revised kind of 90 day launch playbook that had integrated some of the things that I was really good at and that I thought were important. What was wrong with you? Do you remember, love to home in your shed was a while ago, I mean, it's a lot of what turned into the current form of go to market. So the main pillars were demand gen, and our pipeline generation, sales enablement, sales support, and then sales and marketing operations. And then another bucket that we just called, like, experiments, which was kind of a catch all for just being able to move fast and break stuff and make mistakes. It's since evolved, I think, and gotten more robust from that original, those original playbooks. But that was really the core of it.

Grayson Faircloth:  17:14  

And so let's talk about the current state, how would you describe what you're spending like an average day on? What would you kind of say you're doing on an average day?

Egan Montgomery:  17:25  

I mean, I think about myself and our team as the kind of go to for anything founder led sales. So our job is to ride, you know, shotgun with a founder, through the very challenging founder led selling process. And so, you know, like I said, all those core pillars still exist, but it's very oriented around how do we go and get the first 10 customers? The Beauty and the curse of my role? Does that look different for every single company? You know, it looks very different based on your macro, go to market motion, are you product lead? Are you a sales lead? Are you a marketplace? 

Those are going to be totally different, but it can also change based on are you selling up market? Are you selling mid market? Are you selling SMB? What type of product? Are you selling? Do you have security compliance? Risk? Is your platform well built out? Or is it still, you know, there is still a lot of work to do on the product side? I guess the point is, they can really change. 

And I think the key is to be agile, and to be experimental, like I mentioned earlier, and just to always be learning, you know, there are certainly patterns that we can pull on. And there's playbooks and frameworks that are relatively consistent, you know, from company to company, but it's really about just constantly learning, observing, and trying stuff until something works.

Grayson Faircloth:  18:53  

And you talked about a lot of things that maybe I would consider, like a typical director of marketer, or like the persona that you were in at the time might not know about, like product lead growth, like all these different things, it depends on all these different other things. How did you go from a heavy marketing background? Like, how did you learn about there's different motions for an enterprise based sale versus a, like an SMB based server, which is like a product led growth sale with no kind of formal, like actual sales, leadership training and stuff like that?

Egan Montgomery:  19:29  

Yeah. I mean, I think at first, it was a lot of reading. It was a lot of listening to podcasts. It was a lot of finding people in the software community who did live within those go to markets, or were selling a similar product to a similar buyer. It's just being willing, I think, to open up your eyes and be receptive to new ideas and to being taught because I can't run the demand junk playbook at every high Alpha Company. I can't run the dimension playbook at most high alpha companies. 

So You've really just got to be open to sort of absorbing and learning. But the other thing is just like working here, I mean, I have an advantage that I, to keep my job, I need to learn those things. And we are launching companies that have different markets and things like that. So you start to just pick things up, you know, really quickly. I mean, I've been here for three years, I feel like I've been here for 25 years. And I mean that in a good way. 

I have a team member who's been here for a year, and I can see just the growth in him because he's been exposed to so many different companies and ideas. So I think it's a combo of those two things like really being willing to do the research, and then also putting yourself in positions where you're kind of forced to learn you don't really have a choice.

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