Omer Khan [00:00:09]:
Welcome to another episode of the SaaS podcast. I'm your host, Omer Khan and this is a show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch and grow your SaaS business. In this episode, I took to Jen Knight, the co founder and CTO of Agentsync, a company modernizing how insurance companies handle agent licensing, compliance and onboarding. In 2018, Jen was working at Dropbox while her co founder and now husband Niji was at Zenefits.
Omer Khan [00:00:41]:
There he saw firsthand how insurance companies were struggling to keep their agents licensed and compliant, and no one seemed to have figured out a good solution. Niji became so convinced there was an opportunity that he quit his job to work on the idea from their kitchen, while Jen kept a day job at Dropbox and spent her evenings and weekends building the product. As tech outsiders trying to break into the insurance industry, they got a lot of pushback. People kept telling them that this wasn't a real problem that they were trying to solve.
Omer Khan [00:01:08]:
After months of building the product and talking to potential customers, they finally landed their first customer who paid $5,000 a year for their solution. But everything changed after a product demo when insurance professionals started listing all the ways AgentSync could make their lives easier. Their excitement showed the co founders that they were onto something big. In late 2019, the couple took a huge leap of faith when they found out Jen was pregnant.
Omer Khan [00:01:34]:
She quit her job at Dropbox and they decided to move to Denver where they'd both work on Agent Sync full time without any funding lined up. The timing seemed terrible and the pandemic just hit months later. But instead of failing, they ended up thriving. They raised their seed round and grew to 35 employees by the end of 2020, then to over 100 people the following year. Today, Agent Sync is valued as a unicorn. Brings in eight figures in ARR, serves over 250 customers and has more than 200 employees.
Omer Khan [00:02:05]:
In this episode, you'll learn how Jen and Niji, as complete outsiders, successfully won over a conservative industry. Why rethinking their product messaging led to breakthrough sales conversations and rapid growth. What content marketing strategies they used to build trust in a highly skeptical market. We talk about how bringing industry veterans onto their team early significantly accelerated their growth trajectory and how they managed to balance building a high growth startup while navigating some major life changes. So I hope you enjoy it. All right, Jen, welcome to the show.
Jenn Knight [00:02:39]:
Thank you for having me.
Omer Khan [00:02:40]:
My pleasure. Do you have a favorite quote? Something that inspires or motivates you that you can share with us.
Jenn Knight [00:02:45]:
I didn't have one, but it made me think. One of my favorite books of all time is Alice in Wonderland and there's a great quote in it by the dodo of all people, which is why the best way to explain it is to do it. And I love that one. For me that is often the case, especially in the industry I'm in. It's very hard to explain some of our things. If we just do them and can model them, we get on our way. So I decided to pick on that one today.
Omer Khan [00:03:11]:
Love it, love it. Oh, I love Alison. One point. Great book. Okay, so tell us about Agentsync. What does the product do, who's it for and what's the main problem you're helping to solve?
Jenn Knight [00:03:22]:
Yeah, so we're a company, we are focused on the US insurance market and we have a product that is infrastructure that supports agents getting access to products by supporting agencies and carriers onboarding those agents into the ecosystem. So niche, you know, you might not know all the nuances of that, but I always like to say we all have experienced purchasing of insurance. It is probably not a surprise to anyone that to get to the point where you can sell someone insurance is a generally paper intensive process with a lot of moving pieces.
Jenn Knight [00:03:55]:
It's a regulated process in the United States. So every insurance agent needs to be licensed for the type of insurance that they're providing us as consumers. And our software helps streamline that part of the onboarding process for agents so they can get access to products so they can sell those products to us. Our customers are agencies, carriers. So carriers produce the products, agencies recruit the agents to sell those products.
Jenn Knight [00:04:19]:
There's a bunch of other folks in the insurance space, MGAs, MGA's, IMOs, FMOs, we also support those and we're really focused on that journey of getting an agent ready to sell and then nurturing them through that process and then ultimately in some cases helping them get off boarded and making that all a data driven and technology backed process for our customer base.
Omer Khan [00:04:40]:
Great. So when you say agent, does that mean like the, the all state guy down the road from me could be using agent Sync to kind of sell insurance products?
Jenn Knight [00:04:50]:
Yeah. So the Allstate guy down the road from you, it's a, as a great example. So yeah, that's the agent that I mean. And they would be working with a team on their side, an administration team to help them. Allstate's interesting example because they are captive or exclusive agents versus independent agents, which is a whole other part. But in effect, when they wanted get into Allstate and come in, someone at Allstate looked at that agent's licenses and said, okay, great, you're registered to sell property and casualty in the state of Colorado.
Jenn Knight [00:05:20]:
Great, let me get you access to this set of products. And then ultimately they come to us and say, here's what I can provide to you. Some folks have experienced with independent agents and that's when you might say, I'm going to go shop my home insurance policy. I'm going to go talk to an agent. That person goes out and says, talks about your home and then comes back with multiple quotes. That individual has had to actually go through an onboarding process with every single carrier that they give you a quote for.
Jenn Knight [00:05:46]:
And that's establishing that relationship. And then those relationships ultimately get reported to the state department of insurance. So many of these transactions are, you know, five person transaction. There's you as the buyer, there's the agent you're talking to, there's the agency they work with, there's the carrier who's created the product, and there's the state regulators who manage the licenses for the agents in partnership with the agents to make sure there's someone who should be selling.
Jenn Knight [00:06:09]:
And then the carriers also report to those state regulators to tell them that the agent is allowed to sell that product.
Omer Khan [00:06:15]:
It sounds really simple.
Jenn Knight [00:06:16]:
It's super simple.
Omer Khan [00:06:19]:
Where are you in terms of revenue, customers, size of team?
Jenn Knight [00:06:23]:
Yeah, so we're eight figures in revenue. We are a touch over 250 customers and a touch over 200 employees.
Omer Khan [00:06:33]:
Okay. So I want to start by like where the idea came from. And you must have an extensive background in the insurance industry, right, when you started this thing?
Jenn Knight [00:06:46]:
Yeah, not at all. So I actually co founded this company with my now husband and so he's a CEO. I'm the CTO and we met together at LinkedIn. So he was working in sales operations and I was working in sales systems there. We both went off into our journeys in Silicon Valley and his next stop was at a company called Zenefits.
Jenn Knight [00:07:09]:
And while he was there he went in into a sales operations role and they ended up having challenges with departments of insurance salespeople at Zenefits, because there's a platform if folks are familiar with rippling or gusto or other trinet things like that. Zenefits was one of the first platforms there to give you the software to run your business, but also to have someone who could sell you health policies for, for your business. Right. So if You're a new business starting out.
Jenn Knight [00:07:39]:
Which meant that every seller at Denifits was both a SaaS software seller and an insurance agent. And Niji got exposed to some of the challenges of what happens when your agents don't get licensed fast enough. And so he went from being in sales operations to being the director of licensing compliance and spent 18 to 24 months working with the departments of insurance to do a lot of remediation work with them. After there were some challenges there and saw the problem. I was across the kitchen table from him.
Jenn Knight [00:08:14]:
I was at Dropbox at the time having a much more fun time potentially and hearing about this. And at the end of it, we thought there was a product to be built to really help with that specific problem statement and move it from a manual process to something that could be introspected with technology and also help folks scale more effectively. So that was where the idea came from. It came from a hands on experience that my co founder had.
Omer Khan [00:08:38]:
Great. And so for the first year or so it was just the two of you and you were running this business out of your kitchen. You were the only developer in the business and you just happened to have a full time job as well. So you were doing this evenings and weekends. Like just how did that go about? Like when he says, okay, I see this opportunity, you know, we've got these great jobs, I'm going to kind of jump off and do this thing.
Omer Khan [00:09:11]:
And by the way, can you spend all your spare time kind of building the product? Like how did that conversation go? And what was, what did you see there that got both of you excited about the opportunity?
Jenn Knight [00:09:24]:
Yeah, it's a great question. I do think there is a bit about founding that is the definition of insanity. Because we saw this problem, he had lived it and we had built systems together in the past. So we knew we really liked building things together. So the pitch was less about what we were solving for and more about let's go work together again on something. And so that, you know, that's fun. And I was at the point in my career where I loved what I was doing.
Jenn Knight [00:09:51]:
I'd done it at a couple places I knew I could continue to do it. But we were lucky enough to be in a position where like, let's try it, you know, worst case scenario. And I think it is a, I don't know, I think a blessing of the tech industry is that if you try to start a company and it doesn't work out, that isn't a black mark on your resume. That's a. You did an experiment. You know, companies get started and failed. Like, what did you learn?
Jenn Knight [00:10:14]:
How are you going to bring it to your next role? So we thought, hey, let's take a. Take a shot at that. And we really. Yeah, I really wanted to. To build it together. And that was kind of the. That was kind of the pitch. Then I learned all the edges of insurance, and now I'm like, you know, deep down, deep down that. That rabbit hole. But for us as well, like, we. We didn't. We wanted to make sure that we could continue to have the life that we wanted to have. So I took.
Jenn Knight [00:10:43]:
Took both jobs and he did. I think what is actually the harder thing, which is, was alone. I don't know how single founders do it. It's a very lonely business. So we made the decision. He said, is it ready for you to go? And he went. And then he took the challenge of waking up every morning in our kitchen and figuring out, okay, what am I gonna do today?
Jenn Knight [00:11:03]:
And then he would do all these things, and I would come home and say, okay, here's everything I learned and here's what we need to do in the product and how far can we get so we could demo it? But I have a very distinct memory. What got me really excited and what was like, okay, we're really gonna do this is we had a very, very basic version of the product. And he was on a call with how we'll be our buying Persona.
Jenn Knight [00:11:24]:
And these two women who are licensing admins, this organization, you could just hear them get excited. They were like, well, if I had that, I could do this, I could do this other thing. My team wouldn't have to spend their time doing this monotonous manual data entry. And if they didn't have to do that, they could just start listing all of the things they would do with their time back. And this was when the product was so, so basic, so that both of us had this moment of like, okay, like, let's go.
Jenn Knight [00:11:48]:
Let's go do this thing. Niji did get told explicitly when he started. Someone said, this is a terrible idea. This isn't a problem anyone needs to be solved. But he was convinced otherwise. And then hearing that excitement was really where, like, great. Like, this makes a difference to these people and how they do their job with just this very basic feature set. Like, we can definitely do more here.
Omer Khan [00:12:10]:
So I'm curious, like, what you describe when we started this conversation was like, sounds like a hugely complex product or platform, right? And how did you figure out what that simple version was going to be. So you said, you know, Niji was spending the days like just basically learning and talking to people. You obviously had experience as well in terms of working with this space. But there's always a challenge for every founder in terms of this problem is huge, the solution is probably huge. And how do I figure out what to build first?
Omer Khan [00:12:51]:
That's really people are going to care about versus they're going to say, oh, is that it?
Jenn Knight [00:12:55]:
Yeah, you know, it's a great question. I think for us, we had a little bit of a interesting journey in here because one, we had Niji's experience, which was great, and two, when we started, we had no idea that the problem we were solving was as big as the problem we were solving. And so it made it. Now looking back on it, and after I, you asked me, I had experience in insurance, I had none, I had zero.
Jenn Knight [00:13:20]:
So I came in with no notion of how hard this could be and from an engineering perspective started solving it how I'd been taught, you know, in my past of just engineering principles. Okay, here's the data set, here's the SOAP API and the xml, and here's how I would think about presenting that product and engineering mindset to a, to, to someone with the technology that I understand, which in the insurance space is relatively modern, modern tech.
Jenn Knight [00:13:47]:
And so what we actually learned pretty quickly was that the, what was common for our customers is they actually hadn't seen the data presented that way. They hadn't had this opportunity to really like look at what they were doing. And I also didn't get over worried about whether I was solving anything because I only knew what was right, right in, right in front of me. So Niji and I, when we started, we were like, we're going to build a product for compl for agencies.
Jenn Knight [00:14:12]:
And then we ended up working with the National Insurance Producer Registry, which is a, which is the main body that brings all the licenses together and then provide that programmatically as a reseller. And what we learned pretty quickly is that based on the foundation we built, we could actually solve a larger set of problems. But it was kind of just one. It was really just one little piece at a time.
Jenn Knight [00:14:31]:
Now one of the things I look back on, you know, is I was so far in it, just doing it one little piece at a time that by the time we started bringing in other people, there was a lot to learn, but it was really going out and saying, okay, we solved it for this piece. And then listening to customers and they're like, okay, we actually need this next thing. And then we could innovate on that. And Niji then tested in a market with someone else who was a slight, slightly adjacent.
Jenn Knight [00:14:54]:
So there was not an agency, but they were a little bit adjacent. And they're like, oh, yeah, we still have that problem. And then we got over to the carrier and we're like, yeah, we have that problem from a different lens. So for us, it was, it was more of we knew, we knew what he had struggled with at Zenefits and what we wanted to solve there. And then we just started rounding it out from there. But it did have some advantage at the early days of not having to worry about the whole picture.
Jenn Knight [00:15:21]:
Then we hit a point where we realized we really needed insurance expertise. And our first hire, who's been with us since the start, she now just passed her 40th year in the insurance industry and she is incredibly, incredibly knowledgeable. We needed that as our first hire because we did hit the wall with our customers. But then she and I could partner together to do exactly what you're talking about, which was, is this something relevant? Is this a distraction? How do we fit it in? Where does it fit for our vision?
Jenn Knight [00:15:49]:
And even sometimes I just explain to me what that person is saying, okay, I think I'm going to solve it this way is my solve, the right solve. And she could help me cross validate that. So I think it's a struggle for everyone. But the biggest thing for us was just rapid, rapid iteration in the start and then also not trying to get too far out ahead and just making sure that we were solving for what we knew and what we were hearing. And then we found a few new use cases.
Jenn Knight [00:16:15]:
And then the key was just keeping focus.
Omer Khan [00:16:18]:
How long were you building the product and how long did it take to get that first customer?
Jenn Knight [00:16:24]:
Yeah, so we built our first, and our main product is built on the Salesforce platform. And some of that's from my background. And it had some pickups in the sense of there's a lot of things you get, I guess, out of the box in that platform. Reporting, dashboarding, permissioning, security, ui, very kind of quick ways to iterate. And so the biggest challenge for us was integrating with our data provider. And that was just a.
Jenn Knight [00:16:57]:
Just a big lift given the kind of infrastructure that they have and how that worked at the platform we were working on. We had been building it to roughly. Six or eight months before we had our first, first customer. Niji had done a version of it, kind of an internal prototype while he was at Zenefits. So we kind of knew the contours of it. So if we. We always like to include that of, like, it was built quickly because it had been thought about for two years before it was built.
Jenn Knight [00:17:29]:
You know, we didn't go from having this idea and then trying to build it that quickly. It was like, we talked about it and thought it over, but it was. Once we did decide to do the build, we knew the contours of it, and so the build was fairly quick to that first customer who wanted very limited functionality. After that, the next customer was like, that's great. To your point, that's great, but I need X. And then we got into that fun chase of, okay, we're gonna build X. Should we build X?
Jenn Knight [00:17:55]:
Is that the right thing? Is that taking us the right direction or the wrong direction? But our. Yeah, our build to first customer was under a year.
Omer Khan [00:18:01]:
And what was that first customer paying?
Jenn Knight [00:18:04]:
$5,000? Very little.
Omer Khan [00:18:07]:
A month or a year?
Jenn Knight [00:18:08]:
I think they paid us $5,000 for the year. We had such a small product. We were like, great, Someone's gonna try it out. We're like, okay, up. I'll have to go back. And. Yeah, I think that was their. I think that was their. That was their contract. But it was, you know, for us, we have a. We have a model where we were pricing per agent that they were onboarding. And we also were like. We knew that the product was very, very small. You know, small. Solving a small use case for them.
Jenn Knight [00:18:39]:
So that was really, for us, a. We want to learn a bunch of things from you. The next customer was not that small. Uh, and we learned, you know, the other thing we thought about very quickly after that was, how much does this need to cost for it to be worth it for us? Um, and then, you know, there's like that and what features that needs to be there to. To actually command that value. But we started very small.
Omer Khan [00:19:02]:
That's great. I think a lot of founders would be happy if they could get a hundred bucks a month for that first customer. Right. So five. 5,000 is pretty good. Um, how long did it take to get to that first, you know, these. The elusive first 10 customers?
Jenn Knight [00:19:14]:
Then after that, the first 10, it probably took us. Just shy of another year. So it was 2020. We were, you know, 2020 was an interesting year all around. So, you know, had its highs and slows and. And business went through a lot of changes. You know, insurance space was also interesting. There were a lot of folks who had never allowed people to work from home. And so we, when Covid hit and March hit a lot of it, teams actually had to pivot all of their time and resources purely to helping their teams work remotely.
Jenn Knight [00:19:53]:
So we had a few deals pause and a few things happen there. And then of course after that there was a lot of okay, now we have more appetite to think about how we might serve our internal customers, our internal teams in a different way. But yeah, it was pretty, pretty quick clip after that once we figured out we had a few key features. So we were bringing data in great, but like not super interesting because what you actually want to do is action that data.
Jenn Knight [00:20:20]:
And so in the first year we built the ability to action that data so to go get a license from the Department of Insurance, to go appoint someone with the Department of Insurance. And that started to get us into that full cycle.
Jenn Knight [00:20:31]:
And once we could do that full cycle solution, demoing that and really showing that I could, where we could solve the full problem was such a need in the industry for a lot of folks too in the insurtech side who were coming around at that time, historically, compliance, because it was a bit of a black box. We do the rules inside, a lot of the rules inside of our product.
Jenn Knight [00:20:51]:
So they could use it to actually get a quick start of saying, hey, I have this really smart member of my team who also hasn't worked in insurance, but I need them to be the licensing person. And we could say, hey, we have a product that fits for that. So we were.
Jenn Knight [00:21:02]:
The timing was really good for us for when we came to market what was happening in the insurtech space where folks were building new MGAs or new models for delivering insurance and they wanted to rapidly grow that we were a really good fit for that.
Omer Khan [00:21:15]:
So I think it's great that you identified a specific small, all the kind of the MVP stuff that we sort of talk about. How did people react to these two tech people from Silicon Valley coming in and telling these people in the insurance industry, many who, as you were telling me earlier, end up spending most of their lives once they get in there. And it's a pretty conservative industry. What was the reaction when you started selling the product?
Jenn Knight [00:21:52]:
So the first thing that was true is that being new in this space is not an advantage to you. It's a new technology. Young new providers are not always an advantage. There is community of what is known and known to solve the problem. And then there's an assumption about, you know, are you, do you actually know how to solve my problem? If you haven't Come from this environment. I think one thing, Niji did exceptionally well because he had seen it. So one we did leverage, you know, as we. As we first went into market.
Jenn Knight [00:22:26]:
The novelty of Niji being at Zenefits, everyone in the insurance industry knew about Zenefits. Everybody in the insurance industry knew about what had gone wrong, and they were talking about it. And so he had the advantage of actually coming in and saying, like, I worked at Zenefits. And sometimes he's like, people would take my call because they just wanted to, like, hear about, like, what it was like to be there, right? And then that was like kind of an entry point to start talking about and showcasing experience versus technology. So there was like, that.
Jenn Knight [00:22:55]:
That piece of it. The other thing that I'd say he did exceptionally well is just listening.
Omer Khan [00:23:02]:
We.
Jenn Knight [00:23:03]:
You get the call, and it was really about, okay, we're going to talk about this product. But it's, you know, it wasn't a hard pitch. It was like, does this work? Can you talk to me about it? Would this be interesting to you? How do you think about that? And so that was starting to just get connections in the space. As I mentioned, our first hire was someone who could come onto the calls and confidently speak their language. And we learned that very quickly. You know, there's so many terms in insurance.
Jenn Knight [00:23:30]:
Sometimes those terms mean the same thing. I lovingly talk about this like a producer and an agent. Agent, same thing. But they can also sometimes be an individual and sometimes they can be a firm. And if you're me and you've never talked to someone in the insurance space and they're describing a problem to you, and you're like, are you talking about a person? Are you talking about a company? Or like, you know what, like, one of you talks about as an agent and the other talks about as a producer.
Jenn Knight [00:23:52]:
It took me a couple years to really get all of that straight. And so we hired that expertise in just to have someone who could come in and kind of support that, especially when we got into those, you know, more complex conversations. But in the early days, it was really figuring out creative ways to get on the call. And then once on the call, listening. And then part of what I would come home to is, okay, I heard this. Like, we think it's relevant. Could we model.
Jenn Knight [00:24:17]:
Could we model it or quickly prototype it into the product? Salesforce was helpful for that because there are a lot of ways we could rapidly do that. And so then the next time he got on a call with someone of that or he'd call them back and be like, okay, you know, does this represent it? But we didn't do a lot of super hard selling at that point. It was really more, how do you start to build that relationship and then build context?
Omer Khan [00:24:36]:
How is Nietzsche finding these people and getting time with them? You know, I imagine that, you know, kind of just sending cold emails probably wasn't, you know, the best way to do this.
Jenn Knight [00:24:52]:
It wasn't the best way. So some of it was relationships that he'd previously had through Zenefits, relationships that have been established there. He attended in his role industry conferences and had made connections with folks there as well. And so. And then because of some of the folks he worked with at Denavids, they also had connections. So at the very, very beginning, it was a lot of, you know, how do I get a few at bats talking to people and really lean on that?
Jenn Knight [00:25:21]:
And then, you know, they're willing to introduce me and this person's willing to have the conversation through that introduction. And then also because we're not going to talk about the technology to start, but we're going to just talk about being in the space and what it was like to be at Zenefits and what did he learn? And so that was kind of where we got that initial ball rolling. But it was, it was a, you know, it's a hard.
Jenn Knight [00:25:38]:
It was a hard space to come into for what we were solving, especially because a lot of people were like, this isn't really a problem. So that was also part of what we had to learn, was it's not going to be helpful for us to come in and tell you that we perceive a thing that you think is not a problem is a problem. It was more like, how do we then help you think about that in a different way? How do we think about that process for your organization in a different lens?
Jenn Knight [00:26:02]:
Or how do we show you something that allows you to think about that in a different lens? We are often displacing very manual processes or things that are homegrown that don't always have great data visibility. And so folks were like, it's not a problem. And we're like, but can you answer these questions about it? Or like, if you had a tool like this where you could answer these questions about it, would that be interesting to you?
Jenn Knight [00:26:25]:
And that opened up a lot more dialogue versus saying, you know, we learned very quickly no one there fear around compliance. I mean, no one wants to do fear selling. But that did not work at all, right? We're like, yes, things happen and regulators get involved, but that's not why you're doing this. Right. You do have to meet the compliance. But creating efficiency there is really about the agent experience and getting someone access to product and getting them ready to sell. That's a business. That's about business efficiency. That's about revenue.
Jenn Knight [00:26:57]:
That's about better operating margins and better efficiency. And so once we could figure out how to kind of tilt that conversation, it got more interesting too, for us, because then people were telling us all sorts of things. They're like, oh, if I could do that, I could do this. And then you got really good product ideas from our customers.
Omer Khan [00:27:13]:
So was it that you were talking about the wrong problem initially, or was it because you were talking about the right problem in the wrong way?
Jenn Knight [00:27:21]:
I think we were talking about the right problem in the wrong way. We were talking about it. We were talking about it to start from the compliance lens. But the problem there is is really about what does it take to get someone onboarded into your organization and ultimately outselling. And so it does come down, because it is a regulated industry, to aspects of it come down to these steps that involve this team. So it was the right problem to be talking about.
Jenn Knight [00:27:58]:
But the lens in the industry and the way we were talking about it to start, you know when you're like, oh, like, are you worried about how that's going? No, I'm not worried. Like, I have this team of five people, and like, we do the audits and everything's fine. So it was like, well, so then the question became more around, how do you think about a world where you want to grow your business or change your distribution strategy?
Jenn Knight [00:28:22]:
Can you react to it with that team the way they're operating today, or is there an opportunity to empower that team with technology that ultimately empowers your business to be able to react more flexibly? Right. And so it was really changing, like how we were talking about it and then what we were trying to unlock by solving that problem for them. And so that took a.
Jenn Knight [00:28:43]:
You know, it took a few at bats to figure that out and to really help frame it in the way that I think is more interesting for them and actually is like, solving the bigger problem.
Omer Khan [00:28:52]:
Yeah, yeah, I've seen that before. Where companies are sort of focused on the compliance thing, and there's been a sort of a fear sort of angle to it, which is the most obvious way to talk about it, like, all the consequences of if you're out of compliance. But the reality, I think, seems to be, which was your experience Here was that when you talk to people actually in the middle of all of that, yes, it's important to them, but it's not like they're losing sleep every night because they might be out of compliance tomorrow.
Omer Khan [00:29:27]:
And people, things are, things are going along and they feel like they've got things in place that seem okay. And yeah, it's such a nuance, but it's so important to understand. And you don't get. But what I think that the big takeaway here was when people are saying this is not a problem, you can either go down path a I think which is no, let's try to persuade them this is a problem or let's try to figure out.
Omer Khan [00:29:56]:
Let's just have genuine curiosity, let's ask questions and let's try to figure out what is important to them around this area. And I think it sounds like that's exactly what you were doing, which helped you to sort of figure out your messaging and where to focus and all that sort of stuff.
Jenn Knight [00:30:14]:
Yeah, and I think it was how did we, you know, I think from a philosophy perspective because operations and systems and the way we work together was really all designed about efficiency. Right? And efficiency and transparency. And how do you, you know, what Niji and I did in our past is like how do you make this the most effective workflow? And so we believed in principle that there would be business benefit from optimizing that.
Jenn Knight [00:30:41]:
And then to your point, you know, the, the first and most obvious one is well, we can do it from fear like you might secretly be out of compliance and you don't know it. But like they, that is actually not the case. Like it was actually more in a world where you could do that more quickly with higher visibility, what could you unlock? One of the knock on effects which is cool is you now have a crystal clear understanding of your state of compliance that is data driven.
Jenn Knight [00:31:13]:
But that wasn't the first point of value because there were other ways for them to achieve that in a way that met their needs. So that actually became more of a. This is core and it is something that you get. However, because you've made the decision to run this process this way you get all of these other benefits that allow you to impact other parts of your business. And one those are much. I think they're fun to solve. The compliance piece is a compliance piece point.
Jenn Knight [00:31:43]:
In fact, in the US every single state gets to decide their regulation. So it is its own very gnarly problem of like 50 states, D.C. guam, United U.S. virgin Islands, they all have their own version of things. And so that is a very interesting technical problem to solve, but what it actually unlocks is really a different kind of impact to the business. Right. So that was the learning for us pretty early on was like, to your point, I'm not going to try to convince you you have a problem.
Jenn Knight [00:32:15]:
Just going to try to help you see the opportunity if you approached that workflow in a different way.
Omer Khan [00:32:19]:
How long did you keep working full time on this until you said, okay, this is enough. I need to just jump in?
Jenn Knight [00:32:25]:
Yeah. So at the end of 2019, we felt like we had enough momentum. We still thought we were going to be quite small, but we felt like we had enough momentum for both of us to. Both of us to quit our jobs and that we were going to go fundraise in the. In the new year in 2020. So originally, our plan was that we were going to get through fundraising, and when we knew we were going to have a paycheck, we would. I would. I would leave.
Jenn Knight [00:32:56]:
And so based on that timing, I put in my resignation. I worked until May of 2020. We did not have a signed seed document at that point. So we had that really fun moment of, I think, many founder journeys and being an adult, we were like, great. We had found out we were pregnant. We had decided to move to Denver. We had a mortgage, and we didn't have a paycheck. And very shortly thereafter, we did get our seed and we got on with it. But there was a little bit of a moment.
Jenn Knight [00:33:29]:
You know, a lot of my friends when I was leaving, they're like, what are. What are you. What are you doing? You have, like, mat leave and all these other things. And I was like, I don't know, I'm just gonna go make this very smart choice. But, yeah, I made the decision. You know, we made the decision together both at that point to. To move the company to Denver. We made a decision in December of 2019, and also that that was going to be something we're going to take a crack at.
Omer Khan [00:33:56]:
What was the reason for moving to Denver?
Jenn Knight [00:33:58]:
So for us, you know, for what we did, and at that time, even still now, like, we wanted this to be true. We really wanted to have it verticalized. SaaS is a specialty game, and here in Denver, there is some talent in the insurance space, as well as access to talent in other areas here. We also wanted to be in a situation where we could have product and engineering and sales and support and that crew together in an office. So there was a.
Jenn Knight [00:34:28]:
There was the looking at talent out here and where we could find that mix of talent. And then personally we thought, well, let's take an adventure. I was born and raised in Northern California, as was Niji. And we were like, let's try like is Denver's a great city, super great for building businesses, super business friendly. And we had some folks who were, you know, I had actually never been here when we came and bought a house. But we had a lot of people who were like, it's a wonderful, wonderful place to be.
Jenn Knight [00:34:57]:
So we're like, let's take an adventure. Like let's, let's just go like full adventure mode. And so that's, that's, that's what brought us out here. We were very excited about who we could hire and you know, the kind of company we could build out here. It also brought us closer to our customers. Ultimately, insurance is not a west coast game. There are some carriers out there, but a lot of carriers are in the Midwest or in the northeast.
Omer Khan [00:35:22]:
So this, this little business that you were building in your kitchen, I think around that time you were pretty close to, if not already at the first million in ARR. Was this just the two of you or. I think maybe you told me earlier that maybe you'd borrow one, you know, your first hire. So that's great. But then to say, okay, I'm going to quit my job, we're going to have a baby, we're going to move to a different state, we don't have paychecks, we're hoping we get a seed round.
Omer Khan [00:36:01]:
It's about all of these life changing decisions all coming together at once. Oh, and by the way, we've got to keep the business going and finding customers, getting traction and all of that stuff. Was that a fun period of time?
Jenn Knight [00:36:12]:
It really was. I think it was actually for us kind of flipping it all on its head. I mean it's a little bit of our personality where we make, we think about things a while. We make principled decisions. When we make them, we just make them. And it was, yeah, it was, it was actually I look back on it very fondly, which maybe says a little bit about me and you know, maybe the founder mentality to some extent. It's always crazy. Like what isn't kind of crazy?
Jenn Knight [00:36:49]:
So for, for us helped us kind of hit this moment where like, okay, we're doing like, we're doing like we're all in. This is what we're doing. We. When we were coming out, closing our house, that was actually when we recruited our first proper Denver hire who led our customer success team, who's still with us now. And so that was employee. He was employee five. And we were like, here, we're going to do it. This is what we're going to do. But it was a lot of fun.
Jenn Knight [00:37:20]:
I think the early days, they're very, very hard. But when you're doing it with people that you really enjoy doing it with, every day is a little bit of its own adventure. And, yeah, we also landed in a great community in Denver, and that went a long way. And obviously, it was a bit of a crazy time with COVID but that also meant the neighborhood we moved into and the neighbors we gained here were such a close community. That was really awesome to come to.
Omer Khan [00:37:48]:
Let's talk a little bit about content, because you and I were talking earlier, and obviously this is a conservative industry. You said you've been running this business for about six, seven years, and you're still kind of seen as the new kids or the outsiders in some respect. And content became this play to build credibility. Tell me a little bit about why you decided to invest in content and what the. The strategy was and how it worked out.
Jenn Knight [00:38:24]:
So we realized pretty early on that it was going to be a challenge. Right? People, in terms of there are known players in the space. We are not one of them. And then because we don't come from insurance, we knew that there was going to be a bit of a hurdle of just people look you up, like, what's going on with that company? Do they actually know me? Do they know the problems that I have? Can they speak my language?
Jenn Knight [00:38:49]:
And so our first hire, Sandy, was the person who brought that internal, internally into the product and helped us think about that and came on some of the initial calls and really helped with that. But then we thought, okay, you know, there's one Sandy. And then we're also a brand out there. How do we start to bring that to life? So our first CEO, he actually invested a lot on the marketing side, really, in content creation with folks from the industry. And they were folks we hired who knew how to talk about different concepts.
Jenn Knight [00:39:16]:
And so we actually started creating, if you Google many terms in the insurance space, something from us will likely come up because we realized that we needed to show up as a knowledgeable source in this space in as many surface areas as we could. We're not always going to get a chance to talk to you. When we talk to you, it would be nice or ideal if you had some inkling of having come across us and that that was related to some piece of content that was relevant to your job.
Jenn Knight [00:39:47]:
And that meant that you knew that we knew what we were talking about in that space. And so we weren't just someone who was coming in and saying, this is a pure technology problem. So for us, the content was really designed. It was not about our technology, it was not about all that. It was about the space. What are the trends in the space, what are the insights. Also, just like it's confusing in insurance, it's confusing in insurance for people in insurance about all these topics where like, if our team is confused, probably everyone's confused.
Jenn Knight [00:40:18]:
Like, let's have a really great writer write a super concise and fun to read article about, like, what is an mgu. And that helps our team and then it helps us get out in the industry as a voice that is bringing light to these things and actually making it something that isn't a dry regulation or this other thing to read. It's like something I actually kind of want to read. And so that was a really, really big play of what we called agents Inc.
Jenn Knight [00:40:43]:
Everywhere in the context of it being relevant and valuable to the folks we ultimately were going to try to get on a call with.
Omer Khan [00:40:52]:
Right. So, so it sounds like the content was more about building credibility, authority. I think you mentioned like kind of having a voice. A lot of startups would look at content and say, okay, it's going to be an SEO thing and we're going to measure, you know, keywords and how much traffic we're driving and how we're ranking. Or it's going to be about lead gen and how each piece of content is converting into a lead.
Omer Khan [00:41:21]:
Was that something you guys were looking at or was it purely focused on, let's use this as a way to build authority and credibility. And if it's the latter, how do you measure that?
Jenn Knight [00:41:31]:
Yeah, so we did both, right? I mean we, like, we do all the SEO, all the keywords, all that. We look at how all these pieces perform. Some of them are gated too as well. So we could use them for, for lead gen. And that, you know, is a helpful, helpful muscle. I think on the, the, the piece that, you know, measuring the first piece is very, very hard. But I, I shared with you his anecdote. You know, we, we were like, we're going to be everywhere.
Jenn Knight [00:41:59]:
And then at some point someone came to us and was like, you guys are everywhere. And, and it became, you know, when we measured it more, you know, as our sales team was calling folks, they could come back in and say, like, this person had heard of us. Like, they had. You know, we could trace it to engaging with content or being at an event.
Jenn Knight [00:42:19]:
But it went from I'm spending the first portion of my call, like, trying to get you not to hang up on me and also explain this whole thing and you've never heard of me to like, 2% of the people I call have heard of us. 10% of the people I call have Heard of us. 30% of the people I call, like, everyone I call anecdotally, 90% of the people I call have heard of us in some capacity. And so that was more for us. That was our goal, was like, they've heard of us.
Jenn Knight [00:42:51]:
And having heard of us was both like, we're coming into the space, but also that we're coming into this space from a position of knowledge and being a knowledge partner and also technology, of course. But, like, that was how we kind of ultimately measured it internally was. You could. You could just hear. I mean, you could hear it on the floor, right? As I just went from having to always explain to I at least got that first pickup. And then that obviously has evolved over time. We've been around just. We turned six in October.
Jenn Knight [00:43:21]:
So now it's very common. But that. That was key at the beginning, just to create a presence.
Omer Khan [00:43:27]:
Okay, so going from the two of you working in the kitchen, 2018, getting to the point where you get your first 10 customers, the products there, and then you start to build some credibility. You're investing in content, more people are hearing about you, and then you raise the seed round, which is great. And then the business started to go pretty quickly after that in terms of hiring. Can you just talk about that? Like, how you went from, like, what was it, four or five people at the time?
Jenn Knight [00:43:57]:
So we went from four or five people. We were. I always forget to include myself. We were five at the beginning of, like, March of 2020. And then it was, you know, a few. And then we were probably about 35 to 40 by the end of the year. We raised our seed, we raised our Series A, and we did all of our raising, really. A lot of it consolidated between 20, 20, 20 and the end of 2021, and then a little bit after that. But we grew a ton. We grew.
Jenn Knight [00:44:33]:
That first stretch was, you know, that first year was getting to about 45 or 35 to 40 people. And then the next year, we grew quite a lot. I think we exited the year over a hundred. And, you know, that that was one of the biggest challenges, you know, I look back on, I think it is true in, in any environment of figuring out how to keep everyone together, figuring out how to keep knowledge shared out.
Jenn Knight [00:45:02]:
It was not, you know, we were just so used to being together and like, just we're talking to each other and, and I, I look back on it and I think about how quickly we did it, which was a challenge, and probably reconsider some of those decisions. And then also now, having gone through that phase, which I'd never gone through before in my career, there is a point 75 to 100. Everyone has their own number, and folks who've done this a few rounds, pick a place.
Jenn Knight [00:45:29]:
But where, if I were to back out from that, there's an investment in ensuring that everyone can be enabled to really participate in the company equally. That I think is very challenging.
Jenn Knight [00:45:43]:
You're so focused on the product and getting out into market and that kind of survival mode that, you know, it can be hard to be spending the time saying, like, okay, how are we always consistently bringing that back internally and really not relying just on relationships or people knowing that they just go to that one person, but thinking about how we're going to do that more systematically. You're never going to get it right.
Jenn Knight [00:46:02]:
But we grew, we grew very, very quickly, both in customer acquisition as well in team size, and it made for a bit of a wild ride.
Omer Khan [00:46:11]:
What kind of pains did it cause for the business?
Jenn Knight [00:46:16]:
Yeah, I think when I look back on it now, it created more silos than we'd anticipated or really understood the impact of. Everyone's moving towards the same thing, but when they're putting their heads down and really just thinking about it for their department, you end up getting skewed just naturally across the board. And so looking back on that, I would say that was probably the biggest challenge, was we all are on the surface marching the same direction, but we may be doing it slightly differently or not communicating effectively or.
Jenn Knight [00:46:52]:
The other piece that popped up that I think about a lot now is you have a very scrappy group of individuals and everyone wants to get it done. And so if something isn't working, someone is probably plugging that gap and really seeing that and then actually solving for the root cause of what isn't working can become really difficult. And as you're scaling up and there's so much of that going on, you'll have a handful of people who are really holding a lot of stuff together.
Jenn Knight [00:47:19]:
And on the surface it looks like everything's doing okay, but it's actually because this person's Just very passionate. They're like, I want this to work. And so I'm going to do like four people's jobs. And that doesn't actually help you get to that scale because you really need those four people to be, like, excelling at their job. And I really think that is the biggest challenge for us to start to unwind once we figured out, okay, we really have to, like, pull this all together.
Jenn Knight [00:47:41]:
And then we also have to look very in a disciplined way at how we are all operating. And if someone is reaching over to compensate, how do we build a system where we can get that back into balance? Because ultimately, to scale, everyone's got to be rowing the same direction and they also have to be accomplished in their own function and be delivering on all the things in that function.
Omer Khan [00:48:02]:
Yeah, I think that somebody sort of who's at the early stages, maybe trying to get to the first million in ARR, might kind of hear something like, oh, the hiring challenges of getting to 100 people. It's like, yeah, well, you've kind of made it right. It's like.
Omer Khan [00:48:21]:
And then there was something you just said earlier to me and you just said we were still in survival mode and we had to decide how much of our energy are we just going to put into making sure that we survive versus fixing all of these people issues as we're starting to grow. I think hopefully things are a little better now, now that you raised your Series B. And I think you got the unicorn valuation, which is awesome to see from kind of talking about where this business started.
Omer Khan [00:48:58]:
And remind me again, how big is the team now?
Jenn Knight [00:49:00]:
We're just over 200 people.
Omer Khan [00:49:02]:
Yeah. And I'm sure you've got a new set of challenges when you came.
Jenn Knight [00:49:04]:
It's always a journey. Every stage is its own journey.
Omer Khan [00:49:07]:
All right, well, we should wrap up. I want to get into the lightning round. I've got seven quick fire questions for you. Just try to answer them as quickly as you can.
Jenn Knight [00:49:15]:
Okay.
Omer Khan [00:49:16]:
What's one of the best pieces of business advice you've received for a startup?
Jenn Knight [00:49:21]:
The best bit of advice that we received from one of our early investors was to consistently send a monthly investor update that told them exactly what was going on. Things you were worried about, things that were going well, where the business stood. Every single month, religiously. Good, bad, ugly. To keep that relationship alive.
Omer Khan [00:49:39]:
What book would you recommend to our audience and why?
Jenn Knight [00:49:43]:
I'll go back to my first one. I love Alice in Wonderland, because we should all have a bit of imagination and maybe take a break from being serious about things and go enjoy drifting off into something.
Omer Khan [00:49:55]:
Great advice. What's one attribute or characteristic in your mind of a successful founder?
Jenn Knight [00:50:02]:
The biggest thing that I think about is you have to be flexible. It is never going to be exactly like you thought it was going to be. And if you spend a lot of time beating yourself up about it, it's not going to work. So just be flexible and forgive yourself.
Omer Khan [00:50:18]:
What's your favorite personal productivity tool or habit?
Jenn Knight [00:50:21]:
I should probably get one.
Omer Khan [00:50:25]:
You should. Especially everything you've got going on. What's a new or crazy business idea you'd love to pursue if you had the time?
Jenn Knight [00:50:31]:
Actually, it's not mine to pursue, but someone just came by my desk. We're in Colorado, so this is very appropriate. Everyone has a dog. They were telling my coworker that he needs to start a company called Trails and Tails and just take dogs on hikes all day. And I think that sounds like the greatest thing ever. Could you make it work? I don't know. But like, would it be really, really fun? Sure.
Omer Khan [00:50:52]:
Yeah. Love it. And finally, what's one of your most important passions outside of your work right now?
Jenn Knight [00:50:57]:
Trying to raise a good human. I have a four year old and also just enjoying. Enjoying her crazy presence. Four year olds are a ton of fun.
Omer Khan [00:51:07]:
Awesome. Thank you so much for joining me. It's been great to sort of unpack that story. Congratulations on everything that you guys have done in the last six, seven years. If people want to check out Agentsync, they can go to. I think it's AgentSync IO and if folks want to get in touch with you, what's the best way for them to do that?
Jenn Knight [00:51:27]:
You can drop me a note on LinkedIn. That is usually the easiest. I do respond to those.
Omer Khan [00:51:33]:
Okay, good. Jen, thank you so much and I wish you and the team the best of success.
Jenn Knight [00:51:39]:
Thank you so much for having me.
Omer Khan [00:51:40]:
My pleasure. Cheers.
