Scale with Strive Podcast
Welcome to the Scale with Strive podcast - the place where you come to listen to some of the worlds most influential leaders in the SaaS industry!
Scale with Strive Podcast
'A GenAI Case Study: Waldo' with Dan Monahan
Welcome to the Scale with Strive podcast, the place where you come to listen to some of the world’s most influential leaders of the SaaS industry. 🚀
Our host is John Hitchen and on today’s episode, we are excited to welcome Dan Monahan, Head of Sales at Waldo!
Dan has a rich background in Sales and Leadership within the SaaS Space, beginning his career at ZeroTurnaround (which was later acquired by Perforce), before joining Forestry.io, leading a large Sales and Sales Engineering team.
Moving on to Snyk, he helped grow the revenue from $30M ARR to $300M ARR - and now he is at the very early stages of Waldo, an AI company focused on research and strategy.
Today, we focus in on the Gen AI space and the company Dan has recently joined, Waldo. We explore the factors he considered before making his move, what the product does and delve into the competitive space of Gen AI.
Some of our key takeaways from the conversation were:
💡 The factors to consider when considering joining an early-stage company
💡 Exploring Waldo’s AI research platform and its GTM Strategy
💡 Why sticking to your ICP, even in a busy market, is key
Let’s Dive in!
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Connect with Dan here - https://www.linkedin.com/in/danieljohnmonahan/
Connect with John here - https://www.linkedin.com/in/johnhitchen/
Learn more about Strive here - https://scalewithstrive.com/
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0:00 Introduction to Dan
3:16 Why Dan Joined Waldo
7:33 Waldo's AI Research Platform Explained
11:20 Go-to-Market Strategy and Future Vision
21:09 Building Teams for AI Startups
24:35 Closing Thoughts
Welcome to the Scale with Stride podcast, the place where you come to listen to some of the world's most influential leaders of the SaaS industry.
Speaker 2:I'm excited to welcome today's guest, Dan Monaghan. Dan has a rich background in sales and leadership within SaaS growth, having over six years stint at Xero Turnaround, a Bain Capital portfolio company which was later acquired by Perforce. He then joined his first bowl start company, Forestryio, leading a very large sales and sales engineering team. Dan then moved on to his second bowl start company, Sneak, a very world famous company, where he helped grow the revenue from 30 million ARR to 300 million ARR the revenue from 30 million ARR to 300 million ARR After taking a step back into a regional sales manager role when he joined, he then earned two promotions in 44 years, ultimately becoming the director of sales for Central and West. Now Dan is at the very early stages of Waldo, an AI company focused on research and strategy. Dan, I'm excited to have you today. How are you? I'm doing well, John. How are you? Oh good, Thank you, Living the dream.
Speaker 1:So do you want to give us a little introduction yourself, just for our viewers? Yeah, yeah, for sure. So first off, thank you for having me. So yeah, to your point. I originally started my career at a Series, a Bain Capital Venture startup. But even before that I thought I wanted to get into finance. So I went to Northeastern, I got a finance degree. I would say the beauty of that, you know, you get to do co-ops and internships, you find out what you don't want to do. And you know I realized that finance wasn't for me and really wanted to get into the early stage startup game game focusing on enterprise software. So yeah, to your point. I spent six years at zero turnaround, got acquired by perforce. Then I was the head of sales for two and a half years at another small series, a seed company, forestry, and that's what the last four years at sneak and most recently now I'm at waldofyi nice.
Speaker 2:Well, I can see why justin at waldo wanted you. You've definitely got early stage experience and well known in bold start, so, no, it's great to have you today. And obviously, gen ai is just such a huge topic of conversation at the moment. I think you guys have got a really interesting product. So topic of conversation at the moment. I think you guys have got a really interesting product, so let's start off here for our viewers. Then Most of them probably won't know who Waldo are because you're so early. So do you want to give us a little overview of the company and what you guys do?
Speaker 1:Yeah, yeah. So we are an AI platform that is going to allow marketers, brand strategists, researchers get the insights and strategy they need on any company, product space, competition, to really just get smart quickly and not only find the research you need, but generate insights and strategy to have a good point of view on who your customer is or who you're going to be pitching for new business as well.
Speaker 2:Amazing, sounds, really exciting, and that's not quite the area you've worked in at Snyk in the DevSecOps space. So I guess that leads me into my first question for you why did you join Waldo? Because that's such a huge jump left field, right?
Speaker 1:you know, jump left field right. Yeah, so you know my background has been in cybersecurity, devops, tooling, web content management. But for me, I'm pretty technology agnostic. I'm not married to hey. I spent four years at Snyk. I had a great run there. Let me go to the next cybersecurity company.
Speaker 1:Like, I think there is value when you have a lot of domain expertise in a certain vertical or market, to just like parlay that into the next role. But for me it really comes down to I found the right founder and I found a company that has awesome product market fit. So for me, like at the seed stage or series A, it's kind of like those two criteria are like 1A and 1B. So you can be successful with a company that has product market fit but maybe it's not the founder you want to work for. But on the flip side, you can't be a head of sales. In my opinion, pre product market fit fit. You can be like the head of strategic research, um, but like waldo had those two things. You know I really loved uh justin. Obviously I talked to him for several months before I joined and just seeing the traction and the market opportunity uh really made it a no-brainer for me to join.
Speaker 2:Nice, I've just come back from RSA Security actually over in San Fran and I spoke to a ton of investors and they say the same two things. They almost say like the people are more important than the product, right, but obviously it's the two that they look for when they look at these new GNI areas. So like that's really interesting to see that echoed. And you know said you spoke to justin for a couple of months. Uh, I guess justin, uh, previous founding partner at boldstar, you know his company called wonder, which we all know. I mean, what was it about justin then that you you thought you want, you want your next project to be with him yeah.
Speaker 1:So you know, first off, he's a great guy. I think that that helps a lot, especially when you're coming in as the head of sales, Like I realized early on in my career when I was the head of sales at a previous company that the founder has been thinking about this, working on it and selling it years before you join most likely. So just that level of expectation and pressure when you come in and deliver is really high, versus maybe going to like a series D or E company where it's like, hey, you know, you got one or two quarters to ramp. So for Justin, it's like you know I like him as a person but outside of that he's very product focused. So you know he is like boots on the ground talking to customers. So he is boots on the ground talking to customers. No-transcript, you know he's not out there just building Waldo kind of like in a room by himself with his engineering team, not talking to customers, like he's talking to them every week, getting feedback, talking to partners.
Speaker 1:So from the product perspective, I have a lot of trust that not only is he going to build what we need today, but you know, for a hockey analogy, he's skating to where the puck is going in the future as well and you know know he helped start bold, start ventures, so from like a fundraising perspective, he's obviously on very solid footing. So for me it's like product ability to fundraise. And also, you know, he gives me the autonomy to build the sales process that I think is going to be the most successful for waldo and obviously we work really closely designing that together and making sure that I'm keeping him in the loop on what I'm doing. But it's really giving me the autonomy to build and I'm going to focus on this area and you're going to hammer away at product and ideally those two things are going to meet and we're going to have an awesome company.
Speaker 2:Amazing. Sounds like a great guy to be partnered with, particularly as GenAI becomes more popular. This guy's a second-time founder, very knowledgeable at raising money, as you mentioned, and sounds like a good guy to work with. So I guess let's talk about Waldo a little bit today. I think the viewers want to know a little bit more about Waldo and yourself. So, ai, research and strategy what does that mean, and how big is this market space already? Just so we can comprehend it?
Speaker 1:Yeah. So I mean, the market is large. So where we are starting is really in the advertising space, and that's also what attracted me to Waldo. It's not, hey, we're going to be a strategy insight research platform for everybody in the world, like, I think, ideally you get there, but I think at this stage of a company you need to be super focused and narrow and, like, know your ICP. So the market is very large. So there's obviously you know the big, you know advertising holding companies, all the networks and agencies under them, but then there's also internal brand and marketing teams at large companies as well. If you think of a consumer packaged good company, not only are they researching and trying to get insights into their current products and portfolio, but also what the competition is doing as well.
Speaker 2:Amazing, really, really interesting. So let's kind of talk about the products a little bit. So the AI you know I've seen AI added onto businesses solutions, but it sounds like you guys are a true Gen I product. You know, if I'm an agency or a brand and I'm doing my internal analysis like help me understand how give me an overview of the product slightly. Yeah, yeah, so you know, and maybe I'll take a step back that internal analysis like help me understand how give me an overview.
Speaker 1:the product slightly, yeah, yeah. So you know and maybe I'll take a step back that, uh, waldo came out of justin's previous company, ask wonder, which was an on-demand research platform. So you know they had thousands of freelance researchers working for Ask Wonder to consolidate research and information to deliver to McKinsey or one of these management consulting companies, and so they built technology to really supercharge those freelancers and came to the realization of okay, we built all this internal tooling to make these people very good at their job. This can also be applicable outside of what we're doing, and so it got spun out into a separate company, which is now Waldo. But really, what makes us different from a deep research in OpenAI or some of these other more like horizontal AI platforms that are doing, you know, an awesome job? And not only the foundational models, but a lot of separate verticals as well?
Speaker 1:As you know, today we're really focused on providing strategy and insights to agencies, internal branding teams, marketing teams, so we have a whole 60 plus pre-built workflows that you don't need to prompt. That'll run you through the steps you need to get the insights. You need to be smart for your customer, to give them a new idea, to send it to your creative team. So not only are we looking at all of the open web, but also social media data, third party paid sources. You can customize it to pull in your own proprietary data. You can customize the workflows so it works how you normally do internally, but it's just going to automate a lot of the tasks. So I think everybody in business today is trying to do more with less and like how do you leverage AI to up-level your team? That's why people are coming to Waldo. It's pre-built, you can customize it and you can get a lot of value from day one.
Speaker 2:Amazing. That sounds really exciting and I guess it leads on quite nicely because I think AI is new. Right, we did the digital transformation era over the last 10, whatever many years. I feel like we're now going into the AI transformation area where that level of trust is coming into business. So I guess, how have your customers so far reacted to it?
Speaker 1:Yeah, so overall very positive. Again, I think at this stage of the company you need to be hyper-focused on your ICP, and so right now it's pretty much all inbound, and when somebody who's our non-ICP comes in, we try to learn from them to see like hey, can we push into this market at some point? But we're pretty tight on how we qualify and move people through the sales funnel. But overarching it's like hey, this is going to add a lot of value.
Speaker 1:We get a ton of feedback saying have you thought about this data source? How could you plug it into here? How could I feed some data from a third party library or partner into this to make it even better? And so that's really what we're focused on. It's like more integrations, making it easier for customers to customize it even better, and so that's really what we're focused on. It's like more integrations, making it easier for customers to customize it themselves and really just trying to understand where the market is moving and making sure that we either build that functionality or partner with the right companies to cover off some of those use cases.
Speaker 2:Amazing, so it sounds like it's being received quite well. The adaptation of Gen AI and I think you know what was really interesting there and I don't know how you feel as a salesperson, but you're so linear on your ICP right? Someone new comes in and you have to say no to them as a salesperson.
Speaker 2:I know that hurts to turn away potential deals, but that strategy of really like leaning in towards it, getting a really good reputation and brand on yourself and then starting to expand, is gonna be super, super helpful. So I guess the vision for waldo all right, let's give me all the good stuff yeah, yeah, and maybe just back to your previous point.
Speaker 1:It is very tempting, like you know, a Walmart or a Target or whoever like comes in and maybe today they're not the core ICP. You need to be really disciplined to not go down the rabbit hole with them if it's not the right fit today. I think in a lot of the cases those types of companies it is the right fit today but ultimately it's just you're guarding your team's time as a small company and you can use those conversations to learn and understand what you need to build for the future. But ultimately it's just you're going to win more if you're focused on your ICP at a seed or early stage Series A company.
Speaker 2:Yeah, yeah, no, I totally agree. I totally agree. It's definitely the right strategy to have and it's one that will help you accelerate faster to become the leader in those areas. So, um, so you've started within sort of the agency space, internal brand agency space as well, I guess. How do you, how have you come into the business and help shape that vision and what the go-to-market strategy of? Have you and Justin collaborated and decided on it and is that path rolling now?
Speaker 1:Yeah, yeah. So I think at an early stage company there's going to be a lot of founder-led sales to begin with. The founder will bring in a handful of reps before they hire a head of sales, which happened at Waldo. So how we're looking at segmentation is it's really hard for a sales rep to take a call with a 100-person company and then also try to sell to Meta later in the day. So it's definitely possible but it's a tough motion. So really we're looking at okay, what are our big, more kind of like enterprise strategic accounts. Let's align the right reps to those and have some level of segmentation where there's an SMB mid-market team that cover X number of employees and below and we have an enterprise strategic team that understands those customers, the sales cycle, the internal politics, to get deals done there. So we're starting to scale out those two teams right now like SMB plus strategic and enterprise.
Speaker 2:Amazing and I think what was quite staggering is you mentioned everything's inbound at the moment. So a salesperson's dream. But ultimately that means capitalizing on everything and getting ready for the transition of it not always coming in inbound. So looking to build out SMB and enterprise. I guess for you you've adapted to both sales cycles with the clients. Do you foresee this product always having that level of inbound capacity or do you think you know this is going to become a sales-led enterprise motion one day?
Speaker 1:Yeah. So I mean I am hedging my bets and starting the outbound motion, even with a ton of inbound demand right now. I think what I don't want to do is get caught flat-footed and for whatever reason that dries up or you know, we have a downturn in one month on, like inbound demo requests or free signups I want to have all the infrastructure and cadences and pretty much playbook to run outbound before we even need to do it.
Speaker 2:Nice. I have a saying which I say to my team all the time, and it's only the paranoid survive in sales and I think to have that ability to be like it's the dream day today, but it won't always will be, so I'll build the infrastructure for it.
Speaker 1:it's just an amazing and there's a lot of, obviously, technology. You know specific for that. Today, like when I started as an str, it's like you show up, you know you have your computer, you have salesforce, you have a phone and you're gonna go on linkedin or know whatever lead lists and add people call them. Now, like a lot of this stuff again, you need that sales overlay on it to call and follow up and be personalized. But a lot of like the consolidation of core ICPs contacts. You know you still need the point of the view of the customer but a lot of it of the heavy lifting initially can be done through automation.
Speaker 2:Yeah, certainly can, and I think that's how the modern sales team within SaaS is being built. And I was watching another podcast this morning, funnily enough, through Venture Guides, and they talk about how you really need to understand your ICP and be customer-centric, so understanding the person in the business and their pain points all the time. So it sounds like you're getting ready for this go-to-market strategy evolving, so maybe I'll ask the hypothetical questions which you haven't internally, but, like three to five years time, is there a kind of a vision or a mindset where you think this could be?
Speaker 1:Yeah, so I mean three to five years in AI is an eternity.
Speaker 1:I mean maybe three to five months, but no, I think, listen, we want to build an awesome business with a great go-to market team.
Speaker 1:I think and I realized that I didn't answer your earlier question about like where's Waldo going in the future. I think today it's very much a like whole perspective in terms of like you're going to go to Waldo, you're going to add a brand, you're going to run your workflows, get the insights and strategy you need. We want to move to more like you know, essentially a push model where you're going to go and you're going to add your brand. And like we're going to know what you want to accomplish and what you need to find out and we are going to send that to you daily, weekly, monthly. So a lot of like the research you know, which is all has citation and you can trust it and you can filter sources is pushed to you with not only a kind of like the foundational understanding of what you're trying to learn about, but also some like creative ideas what you're trying to learn about, but also some like creative ideas, strategy points that you can use as a, as a jumping off point with your customers and prospects.
Speaker 2:Amazing, amazing, I think. I think you know that education piece is great and I think that's where people buy in. It's so much like the challenger sale right, telling them what they don't know and what they are missing out. So I think, what, what I'd be interested? You know, you've obviously spoken with justin and you're very much more within the landscape of genii how do you see genii, genii evolving? You just mentioned then it's hard to look past three to five months because it's such a new field. I mean, it's an exciting time. Everyone's kind of investing in ai and I call it that AI transformation period. So what kind of needs that? What's going to happen in the next couple of years?
Speaker 1:Yeah, I mean, if I were to guess and I think Justin would be a much better person to answer this question I'm very much listen. I try to understand the product, but how do I optimize the go-to market process to be sustainable in three to five years? But I think no matter what industry or vertical or who you're selling to, you need to be ready to compete with the big foundational models OpenAI, gemini, perplexity, cloud, whoever it may be. They are most likely going to try to own the entire stack and verticalize their products and I can see you know, once the foundational models are built like they push into hey, we want to have a marketing specific workflow or product. Also, we want to have a coding assistant, etc. Etc. So I could see them getting more specific, along with keeping their foundational models applicable for you know, the masses as well amazing.
Speaker 2:Well, it's going to be a great journey for you, for sure, um, so a couple of extra bits which I thought were worth mentioning. This podcast is focused on waldo, but I also want to focus on yourself into waldo, and we talked about why you joined. But you know you've got quite a unique career in the sense you've worked at early stage vendors, you've gone through huge amounts of growth and now I believe you're going to do it, and this is your baby. Now, what are the major lessons you've learned in your journey of around building businesses and teams that you want to apply into Waldo?
Speaker 1:Yeah. So I think maybe initially I'm somewhat of a glutton for startup punishment, so maybe that's why I joined a, a C company again. But I think you know a lot of it comes down to finding the right people and being able to recruit. And you know, I know there's a lens of hey, if you're a seed or series A company, like don't go get somebody who works at a huge company or organization. I'm just trying to find somebody who is motivated, smart, you know, hungry, driven, wants to win. You know I am open to hiring folks that have like non-traditional backgrounds as well. I think what I've learned, uh, at least from like a hiring and go-to market perspective is like, don't limit your options. In my opinion initially, like definitely vet your candidates, find the right people. But you know I've had success in the past hiring somebody from a total different industry that never worked in cyber security, and they were super successful just because they were willing to put in the work to learn and win.
Speaker 2:Amazing. I think that's definitely important and I appreciate the type of profile you want to recruit to build a team like that young, hungry, driven, motivated. What advice are you giving to those people who may join your team or you've created in the past around Gen AI? Because you know, gen AI ai, I think, initially was brought out and it was for the very technical people initially and then it's become more simplified and you know, before you know it, you can be on twitter on your phone on the train home or car journey. You can understand a little bit more of the language and speak the language. So what advice are you giving out to people who you would recruit? I have recruited around selling Gen AI now.
Speaker 1:Yeah, I think it's just you need to be comfortable with uncertainty and an ever-changing landscape. You need to be flexible on how you go to market in terms of your pricing and your packaging and your positioning, because, again, there's big heavyweights in these markets and when they make moves, hopefully you're in front of it and you need to adjust. But I think, specifically in the early stage startup world, it's really just like you gotta be comfortable, being uncomfortable and like that is just kind of like foundationally what you need to do to be successful.
Speaker 2:Amazing. Well, dan, I think you know you've got a very talented founder. I think you're very talented yourself and your journey, what you've achieved. So this company should do nothing but great things. I've really enjoyed speaking with you today. I think a couple of key takeaways for me. You know you chose an early stage company because of the founder and products, and I think that's something we should echo for our audience maybe other heads of sales, bpcrs, who are looking to join a gen I company, like what separates them, what makes a good company? Um, I think as well, like, particularly, what stuck with me is just, in this busy market, sticking to an ICP, no matter how hard it is to say no to sales, and I know that as well. So, look, I've you know I've really enjoyed speaking with you and, yeah, I look forward to seeing the growth.
Speaker 1:Yeah, thanks a lot, John. If I can have one final plug for Waldo Please. If you fit that criteria of smart, hungry, driven and are comfortable working at an early stage company, please add me on LinkedIn. I would love to talk to you. We're going to be hiring a bunch this year.
Speaker 2:Amazing. We'll put your LinkedIn profile in the podcast so everyone can see it and hopefully get some good traction.
Speaker 1:All right, Thanks a lot, John. Thanks for listening. I hope you enjoyed today's episode. Don't forget to subscribe. I hope you enjoyed today's episode. Don't forget to subscribe and if you want more information about the podcast, head over to our website. Scale with Stride.
