Jeremy Clarke CEO of Quin: Digital Human Assistant That Gets Work Done for Sales Reps #sales #ai

Jeremy, good to see you, buddy. Appreciate you joining. As a way of getting started, tell us a little bit more about your story and a little bit more on your journey.

Yeah, absolutely. Appreciate you having me. Yeah, journey started many years ago. Started building software products, actually just websites when I was in high school, and kind of throughout college continued to experiment and Got myself into building more web development, like platforms for clients, and then kind of ventured off into kind of my own startups and eventually landed a consulting gig at a company called Formstack, where while I was there, kind of ran into a problem that people were having, that they wanted to take this data that we're collecting through these online forms And they wanted to put it into the traditional kind of documents, you know, hard paper documents that they were using, whether it was an insurance company or whatever it may be. They already had their workflows and systems set up that were dependent on this paper. And so what I did was I built, you know, a templating system that allowed them to kind of take those documents, set up a template, and then every time they got a new form submission from their website, whether it was, you know, a new client signing up or an order or something coming in, you could automatically take that data, populate a document, and then you could send it out via email, you could save it in Box, you could send it out for signature with DocuSign. And so really what we did was created this kind of document automation platform. And so that was— I launched that in 2011 and then grew that by myself until 2016. Late 2016 is when I hired a first employee. First and only, actually. And then we did an exit in 2018. At the time, we were $5 million in revenue, just 2 employees, just me and one other. And so it kind of sold to private equity, which coincidentally, we ended up getting merged back with Formstack, where I started in the very beginning. So we were back together and kind of building this larger kind of data document kind of platform. And then I stayed on for a couple years after acquisition and then exited the company in 2020, where I took some time off and I did— I started racing, I surfed a lot, I, you know, and took a lot of time off. But what I really found was I'm a builder. I like to build and tinker, and I see problems, I like to try and solve them. And so I found myself kind of itching to get back into it and building little random side projects. And I decided, I think that I want to build something again, but I'm not sure if I want to go through the grind of the startup world like I did back in the day. It was always working vacations. It was endless sleepless nights if I was working on a new feature. I wasn't sure if I wanted to go through that again. So I decided to bring on a couple other people and kind of found this venture studio, Plainsight Ventures. And what our thesis was, our kind of goal with that is we'd have a couple different approaches. Like one, we would work on projects and ideas that we came up with. Another one would be we would partner with industry kind of experts or leaders. So someone that's been in a specific industry has this domain knowledge, they have a really good idea, but they don't have the technical expertise to kind of take that to market. And so the thought was we can kind of combine our forces and help them bring that to market. So we launched that in 2022, late 2022, I think, maybe '23. And our first product that we worked on was an end-of-life planning tool. So the ability to kind of have a central place to keep track of different bank accounts that you have and your will and any trusts and your advanced directives and all these different things that are important to have available to your family if something were to happen to you. But what we found is people really grasped onto the idea. They're like, yeah, I need that. But I'm not gonna die today, I'll just do that tomorrow. And so it was like one of those things, they just keep kicking down the— kicking the can down the road. And so we kind of put that one to the back burner and started working on this new idea called Quin. The original thesis of Quin was, can we help relationship-driven professionals build better relationships? And our kind of foothold in that market or idea was, can we help gather personal details about clients, whether it's their kids' names, vacations that are going on, like their favorite food, favorite, you know, interests, hobbies, and then periodically kind of provide the professional like, hey, you haven't talked to, you know, John in a while, you should reach out and ask how Susie and John, Susie's doing with her dance recital, or next meeting that you have with them. I'm looking for to meet with John, like, hey, where should we meet? And it knows, oh, John is a really, really big Italian guy. He loves Italian food. So you should try and find a restaurant for Italian. And so it was kind of a way to help kind of stay top of mind and in unique and interesting ways. And That's kind of when we started to experiment with AI and kind of being able to take all this unstructured data that we were collecting on these people and be able to kind of pick out bits and pieces, go search the web for interesting news articles that might be related to them or whatever it may be. What we found with the first version of Quin was it was It was adding more. Like, it was something that these people and these professionals wanted to do, but they weren't doing it already. And so Quinn was actually just giving them a longer to-do list of like, hey, here are the, you know, the 5, 10 people that you should reach out to today. And so they had to go and actually do work. And again, like, they're already very busy. And so it was hard to kind of get them to Kind of take that extra step and go send a bunch of emails and follow up and do these things. And so kind of working with the users that we had with Quinn, we kind of figured out that they really liked the ability to— like, we built the ability to text Quinn. So Quinn has its own phone number. You can text with Quinn and just like little notes about somebody, and it'll like squirrel it away in its memory. And so what we decided was kind of really lean in on that kind of like human assistant aspect of like, oh, you can just send a quick note and it'll like kind of do things for you. And so what we did is we integrated with their calendar, their CRM, project management, email, and we've kind of reformatted Quinn to be this digital human assistant that can actually get work done for you. So rather than saying like, hey, Here's a list of all the things you need to do today. It's actually going out and helping you get those things done. So every morning when you wake up, Gwynn will send you like a daily brief, like, hey, here are the meetings you have today. Here's the details about them. Here's about what you talked about last time. It'll also draft emails for you. So it monitors your inbox and will go out and find, you know, if whoever's emailing you is asking questions, it'll try to go find the answers. It'll use context that it can find from other emails that you've sent. It can go search the CRM for context. And so you could wake up every morning or throughout your day, Quinault has already drafted replies to emails as they come in. It can take notes, so it can join meetings just like this Zoom call and take notes. And then afterwards, it'll save the note in the CRM. It'll create any follow-up tasks that you need to do. It'll draft a follow-up email, like all kind of just done for you automatically. So our big kind of focus is really what can we automate and kind of get things done for the person that's using Quin.

Love it, man. Appreciate you sharing all that. And I definitely want to dive deeper into Quin because I'm a user, as you know as well, and I have a few questions from the sales side. But real quick, just from the founder point of view, I think for the audience, you know, I typically have founders, I have sales leaders, I have sales reps, but a lot of people They think entrepreneurship is sexy and they want to get into it, all that type of stuff. But I see being a founder sometimes as like the ultimate sales role because you have to do so much. You have to help with the revenue, you have to do the product side, etc. But what's your thoughts on like the product-led growth versus getting a sales team? I know you've probably been around both sides of it, but how do you see that? And then do you think the founder role is kind of like a sales role sometimes?

Yeah, absolutely. I think, you know, as a founder, you're constantly selling, whether you realize it or not, you're constantly selling. I mean, my early days of WebMerge, you know, the first 5 or 6 years I was by myself. So if anything needed to get done, it was me. So if it was jumping on demo calls, if it was whatever, it was me. And so, you know, a lot of— I had to wear a lot of different hats in that stage. And also, you know, from your question on the product-led growth is it also kind of becomes in a small team, small founder, especially like a technical founder like me, the product-led growth is the easiest path forward for, you know, for me, what we did with WebMerge was, you know, I had a good idea of what the core functionality needed to be. But the very first version of Quinn or for WebMerge was very basic. It was a WYSIWYG editor that allowed you to just set up a template. You could output a PDF and you could email it to yourself. Like, that was, like, that was the first version that was launched. And soon after that, we launched, you know, the Word documents, PDF, like fillable PDFs. And then you could have all these different integrations for delivery. And so it just kind of expanded from there. But all that was based on customer feedback. And so I didn't have time to kind of be proactive in like, oh, okay, here's our roadmap for the next 6 months. Here's what we're going to build. I didn't have time for that. It was support tickets. What were people asking for? That's what I built. And I did that for 5 years. I never in For WebMerge, never had a roadmap, never ever just did any planning. It was kind of, you know, I had a general idea, but it was mostly just woke up that day and was like, okay, what are people asking for today? And I tried to get it done that day, like just like really quickly iterate and build. And so it was very like, it's almost customer-led growth, but it was kind of very driven on that. And then at one point, you know, kind of how we transitioned into the, you know, my first hire, which was partnerships and sales. And the reason I did kind of make that hire was I was just being pulled in too many different directions. And to continue the growth of the business, it needed a person to go to conferences, to, you know, be on demos as much, and someone who gets energized by that. I'm kind of a more behind the scenes person, so that stuff doesn't energize me. And, and so that's when it was kind of like, okay, it's, it's time to kind of make that leap and bring someone on who again gets energized by being the face of the business.

Makes a ton of sense. I appreciate you sharing that. And real quick, cause you just, you mentioned that word energy and, um, I think you might've posted about this recently too, but I talk about it quite a bit as well. But from my standpoint, cause I am a solopreneur doing consulting, I want to make the majority of my week on revenue-generating and energy-lifting activities, right? So if I can have 80 to 90% of my week on things that are moving the needle, whether it's meetings or momentum with deals or energy things like working out or spending time with family or my dog, things that I enjoy doing, I really try to be relentless with that. Definitely not perfect, but do you look at that the same way? Like, you know, how do you— move the needle on the business side and then do things that really fill you personally?

Yeah, absolutely. I think it's, you know, you go through ebbs and flows, especially again when you're— it's just you and you have to do everything. Like, there's, there's no choice at the end of the day. Like, if something needs to get done, you got to do it whether it energizes you or not. Um, but it is a good— it also causes a, you know, emotional of emotional roller coaster. Like some weeks you're just like really excited to go get stuff done. And then other weeks you're kind of like, yeah, I'm just not feeling it this week. I'm gonna go. And a lot of times, honestly, back in the day, it was, if I ever felt like that, I would just go like, okay, just like take an hour, go surf. Like just go, just force yourself to go do something else rather than just like sit in front of the computer and bang your head against the wall on something that just is You're just not feeling up for it in the moment. So I think that's also healthy to just kind of be cognizant of that and be able to kind of realize that you you just need to take a break. So I think it's very important.

So true. You have to force yourself to take breaks. I mean, you're probably similar personalities to a lot that are very ambitious and can probably do a high workload, but eventually. The workhorse gets tired and you're going to burn out or you're going to have some ups and downs. So you have to force yourself to take breaks or have some type of accountability check to do that. And I'm not the best at it myself, but living in Florida or living in California helps because you have good weather and you can go do active stuff. And I always come up with the best ideas when I'm walking, when I have no phone with me and I'm just chilling. That's when you come up with the best ideas. So I want to dive into the problem that Quinn solves. But before that, one last thing on the the venture capital side? Because I know you have a studio and then you've obviously sold a company in the past. There's a lot of debate on LinkedIn and other areas of do you go bootstrapped or do you get VC money? I know you wrote a book about some of this, but there's a lot of context that goes into it and perspectives. But what, what are your overall thoughts on that bootstrap versus VC money? Anything that really stands out in today's market, which could be different from 5 years ago? Yeah.

I mean, I go back and forth. Yeah. I mean, I wrote a book, Bootstrapped to Millions. So my story has always been bootstrapped. I've always been a big believer in kind of doing it your own way. And really, that's transparently, I just didn't want a boss. The whole reason I wanted to build my own business was my own freedom. And the moment you raise money, You now have responsibility to other people. And so it just wasn't ever for me, even as I grew. I could have hired people for WebMerge much sooner. I could have hired more people, but I didn't want to manage people. I didn't like it. I just wanted a business that I could run by myself as long as possible with little responsibility. That was kind of my MO. And now I think You know, being going through that experience and then going through kind of trying it again through these different startups, I do realize I had a very unique situation. I think, you know, a lot of to have, you know, millions in ARR with just one employee and like, that's a very rare thing.

Like a unicorn right there.

Yeah. And so I can see the other side of VC now that I'm with Quinn and the venture studio. It's self-funded by me. And so we've not kind of gone out and raised any outside capital, mainly for the same kind of reason. Like, I've contemplated kind of going out and we've seen a lot of good momentum from Quinn. And so I think VCs can offer fuel to the fire as well as You can find good strategics. And I think that's where my mind kind of wanders a bit with the VC conversation is like, could we bring in a strategic pool of investors for Quinn that can kind of help kickstart it to the next level? That's where I wouldn't raise money for the sake of just needing money to go fund and hire people. I think that's where people get in trouble is you You're like, okay, I need to grow. I need to hire a bunch of people. That's where I'm not sold on hiring quickly. I think a lot of mistakes that happen when people go out and raise a $5 million round, they go out and hire too quickly before they actually have the systems in place. I think for founder-led sales is huge. You are gonna be the best salesman for the product in the early days and I think a big mistake that founders make is like, okay, I need a VP of sales. I need to hire someone that just knows how to go sell this product. And you might get lucky, but a lot of times that first VP of sales is just a giant waste of money. Like, you don't have a system set up. You really haven't figured out how to sell the product yet. You're not quite sure. You've just kind of gotten— you were good at selling the product because you knew everything about it. The salesperson They're not gonna know the ins and outs of the product as much as you do. And so a lot of those hires are just, they're not, they don't perform well. And then you hire a bunch of people and they do this amount of work and then are like, oh, we have more to do. Okay, we need to go hire more people. And then you end up like, you just keep hiring and hiring and hiring when you're not really sure what they're doing. Like everybody's has 20% output of what they actually could be doing. If you just told them, no, you have to do that work, they'll figure out how to do it. But if you're just going to hire more people when they say we need more people, you end up with a giant business when 100 employees, when you could actually probably get it done with 10. I'm a firm believer in just people way overhire in It becomes a, becomes a problem.

Yeah, a lot, a lot of great points there. And I haven't seen it as in depth as you, but I definitely have seen the overhiring. Really, those VP of sales could be great, but they, they get kind of thrown into the wolves and they're set up to fail. That's why the timeframe is usually brutal. Like they survive 11 months or whatever it is. And there's a lot of factors that go into it, but yeah, I tend to agree with what you're saying, but it's good to be open to both sides of it and things change are definitely changing fast.

So.

Everyone's position is a little bit different. Let's bounce to Quinn, and I want to talk about the AI landscape and how it affects sales. So as far as how I see the problem that Quinn solves is, for me, I'll give you an example. Especially my first 10 years of the career of my career, it was all about being that workhorse, just getting stuff done, work working crazy amount of hours, and of course that helped me get to a certain point. But what happens when that person gets tired? What happens when they're later in their career and they can't maybe maintain it, or they have a family? And I was never the best at delegating, or I just always thought I could do it best myself type thing. So a lot of salespeople are probably like that. But the last few years, I started dabbling in virtual assistants. When I have my own business, it's way more personal, personal because you want to be successful. So I did virtual assistants. I tried some other stuff, real people, and got a little bit of traction, but nothing too crazy. But ultimately, if you're sales, rep or a leader or anyone that's a working professional, as you put it, there's a lot of admin stuff, a lot of monotonous things that really just drag you down. And they're definitely not things that you typically enjoy to do. So whether it be meeting prep, updating the CRM, we could probably have a whole podcast on CRMs and why people don't use them. The meeting follow-up, some of the calendar jousting, like all that stuff can take like 10 or 12 hours a week at least, maybe more. And what I realized is like, if I can outsource that, maybe it's not 100% level of Dustin, but it's 85%, which is still pretty good. That's a huge time savings for me to focus on what I'm good at, getting meetings booked, keeping momentum with deals. And that's how I've been using Quin personally. And I see that's how it can help sales professionals no matter really what the industry is. But do you agree with that? Or can you explain more, just some of the stuff I touched on?

I mean, at the end of the day, the whole world has shifted in the last, I mean, even 5 years. But you think about the work that you do, when you describe yourself, okay, I'm a salesman. Okay. But you actually look at your day and describe what you do throughout the day. A lot of it is I answer a bunch of emails. I do a bunch of research on a lot of different people. I do You actually only spend like maybe 10% of your time on what your actual job role is. A lot of the other stuff you spend most of your time on is just not what you signed up for. And like, you know, it's, you know, we see a lot of across a lot of different industries, financial advisors, insurance, like all those are like relationship-driven professionals. And but yet they spend most of their time behind a computer doing computer work, which is not like the opposite. Like their job is in front of people with meetings, helping, advising, like all these different things. And so that's where Quinn can really step in and help of, you know, it's not gonna do, you know, again, it's not gonna do 100% of the work for you. Like there are, you know, human in the loop kind of things, but it can sit there and draft emails for you. So you don't have to think, you don't have to like, you just open the email, you can read it, you can skim it, you can Make sure it's correct, hit send. You don't have to like, okay, I gotta go log into my CRM, go look up their details, go, you know, wherever else other tools you're using. Quinn already has access to all those things and it can easily go find what you're looking for. The other thing is Quinn can do a lot of custom workflows and automations. So, you know, if you have something that you're doing on a daily, weekly, monthly basis that you kind of have to remind yourself For me, I have reminders on my phone to like on Wednesday night, take out the trash, put the trash on the street so that trash— when trash comes Thursday morning. So I have a lot of these reminders that are built in because I'll forget. It's just one of those things, even though I do it once a week, I'm going to forget. And so there's a lot of things in people's kind of work that is, okay, I need to check For clients that are coming up on their 65th birthday because I need to prepare them for different events that are gonna happen, retirement, Medicare, whatever it may be. But you're not constantly thinking every month, okay, let me go check for clients that are turning 65. But with Quinn, you can actually just set up a workflow like, hey, send me a list of all the people turning 65 this month and actually draft an email to them. with all the details about what we need to talk about. And like, you never have to remember it again. Quinn will just take care of it. And then you wake up one day and it's just a draft is sitting in your folder. And like, that's the power of Quinn, is it just takes that mental kind of workload off your plate to where you don't even have to like think about it anymore. It just kind of— it just— Quinn does it for you. It's there for you and you go.

Yeah, it's great points. I mean, the busywork thing, I called it the busywork trap. A lot of times salespeople, it feels good to do some of that. It feels like you're making progress. It feels like you're getting stuff done. But the reality is, especially if you're more commission focused, that's not helping you probably close a deal or get the next step. But it feels good mentally. So I think there is something there, a barrier, but that brings us to another point about the AI and the future of the salespeople. And then, yeah, those custom workflows, I almost look at it as like a AI agents for me, but I don't have to figure out how to do the technical side and all this stuff.

Exactly.

And vibe coding, which I don't want to do. So it's, it's almost like having all these dozens of agents that I can customize based off what I have going on. And that could be personal or professional. I use it for both and really prioritizing my week. I think that's where Quinn helps me a ton. So, but that busywork trap is key. And that leads me to my next question is really just this intersection of AI and sales. Like, what does the future sales rep look like? Whether people like it or not, I think the folks that are just skating by, just doing the busy work and they're comfortable and they have a big brand behind them. Eventually with what's going on right now with companies, I mean, they're seeing through that. So I think in the past you could get away with that and probably get by. But now these next few years, if you're just doing the busy work, resting on the brand's laurels, kind of being an order taker, it might be tough to be successful in sales. But what do you think? Like, how will AI disrupt That working professional, the salesperson.

Yeah, I think you're right. I think the underperformers or the people who are just skating by are gonna have a hard time because AI is expensive. It's not back in the heyday of SaaS and what with WebMerge and all these things, like it wasn't super expensive and it wasn't super expensive to run. Like I remember we had $5 million in revenue and maybe like $2,000 a month in technology costs. Like it was just insane, almost pure profit.

Crazy.

With AI, it's completely different. With AI, it's, you hope for a 30% margin. Like, and that's like because the technology to run it behind the scenes is so expensive that like it's, you know, my Google bill is massive because that's just what I run on. And so anyways, So the pricing is gonna be more expensive than hiring software, but it's more accurate, but it's still way cheaper than hiring a human. So if you can have the AI do just as good a job as the people who are kind of just like skating by and just order taking, like the companies have no need for that. They need people. AI can't go out and take clients to dinner, do like build actual real relationships. Like that's gonna be how sales professionals win in the new market is You need to go back to how it was 20 years ago where you went and you flew and you visited customers. You took 'em out to dinner, you took 'em to ball games. You actually built real valuable relationships versus just now people try to do the least. I wanna do the least amount of work and get the most amount of pay out of it. Like, so just, they're just leaning on automations, like Spray and pray automations of like, just, I wanna hire a software to send out 500 emails a day and I hope I get a couple demos a day and it's just like a numbers game. That doesn't work in the long run. It's people are, both AI is now doing that, but what that's also causing is the people on the other side of those calls are just completely ignoring.

Right.

My phone is completely blown up with random spam calls. I just block every single one of them. I like emails. I built a tool to basically block all spam. And so I just immediately junk, junk. Like it doesn't even like cross my brain. And I think people are also like also the same way. Like we used to use LinkedIn a bunch for outreach years ago and it was awesome. Today, people are just, for the most part, you still get some people that still respond well, but for the most part, people are, or it's just too much. And so I think that's where you're just gonna have to go back to what people aren't doing and like, so you can stand out and win on the sales side.

Yeah, definitely. I mean, that's a whole nother conversation. It's from a buyer's point of view, what is AI doing to the market? Because there's a lot of bad habits out there. Uh, the, the numbers game, the email cadences. At one point, there's always good intention behind stuff, but eventually it, it turns into something different. And, uh, like Salesloft, that stuff was working back in the early 2010s, maybe mid-2010s. And then now everyone caught on, then it just turned into this cadence game and a numbers game, which if you have a really transactional sale, that can work. But if it's more complex, it's more relationship driven, it's just not gonna work very well in my opinion. And, but the problem, the downside of AI is now it's making that 1,000 times faster. So now you can do even more spam emails, all this different stuff. And then people like yourself or the buyer, they have no idea what's good, bad, and different, nor do they even want to talk to a person. So they just completely shut off. So it makes getting meetings extremely hard. That's a whole nother convo for sure. But yeah, I think you're right. It's, it's, if you're really good at sales, you're really good at that relationship side, figure out a way to make, have AI help you be your assistant in some form or fashion. So that it frees you up more to do what you're good at. And, and there's always gonna be a need for that, at least in the next couple decades, of those people that can get things and have the relationships, all that type of stuff. And yeah, otherwise you're, you're probably gonna get left behind at some point. Might not happen in the next couple years, but eventually it probably will happen. So great stuff, man. We went a lot of different areas. One last question, then we'll let you go here, is just if you could go back and give yourself some advice. 10, 15 years ago, as you've been navigating all this stuff, what would you go back and tell yourself that might resonate with the audience?

Yeah, I mean, I think, as I said, I think at the time with WebMerge, I didn't realize the unicorn kind of situation that I had. I have no regrets there. I think ultimately I had a great business, great outcome. I think the feedback that I would give is just, it's starting up the venture studio. I was like, oh, we'll just rinse and repeat. Find this niche, find a niche product, take it to market and just kind of exploit that niche. And it's been really hard to find that similar success. And so I think that's where the biggest thing is, it's hard. Nothing changed, but just kind of reiterate, being a founder is hard. Being an entrepreneur is hard. It is catching lightning in a bottle. But it just takes— I think through investing and everything that I've seen, I think the people that win, there's one, there's a spout of luck for sure. Just right place, right time is huge. But the other piece is just perseverance. I think the people that push through and answer answer that additional email, make that additional phone call that day, build that additional feature. Like those people that are always looking to do one more thing each day, those are the people that win because the other people are just like, nah, I'll do it tomorrow. And everything just gets kicked down the can. And that's, those are the founders and startups that have a hard time kind of getting to success because you have to be able to push through the hard parts.

Well said. It's, uh, it's definitely not easy. You've obviously had a ton of success, but it's great to hear that perspective, and I'm sure very useful. It's, it's, uh, not always as glamorous as it seems, and there's gonna be a lot of ups and downs, and you got to be able to battle through that and, and have real— a lot of passion for whatever your, your product or service is. If you're not passionate about it, I feel like you're going to burn out at some point and not get past But yeah, this has been great. Well, if— well, maybe you don't want people to get ahold of you based off what we talked about, but if people do want to get in touch with Quinn or you, what's the best way to reach out?

Just find me on LinkedIn. Yeah, LinkedIn's the easiest way to reach out. I'm pretty active. Other than that, you can just find me on Quinn as well. Heyquinn.io.