Lessons from Women-led Startups with Jenn Knight
Jenn Knight, co-founder and CTO of AgentSync has led her company to become the first insuretech unicorn by building tools and infrastructure that power the insurance industry. Jenn began her career at Linkedin as the company’s first Salesforce engineer and built out the Salesforce engineering and solutions architecture team. Nearly three years later, she joined Dropbox to build out financial systems, sales systems, and migrated the company’s ERP prior to its IPO. Before Jenn co-founded AgentSync with her husband Niranjan Sabharwal, she built the internal systems function at fintech leader Stripe.
On June 2nd, 2022, Jenn joined Advancing Women In Tech (AWIT) founder Nancy Wang for a fireside chat focused on Lessons from Women-led Startups at the Amazon Web Services (AWS) San Francisco Startup Loft. During the chat, Jenn shared her founder story, lessons she’s learned in creating demand and scaling product market fit, and how AgentSync has achieved zero-customer churn.
Nancy
How did you and Niranjan make the jump from industry to launching your own startup, and what inspired you to create AgentSync?
Jenn
Niranjan went to Zenefits, and at Zenefits, their sales folks were also brokers of benefits. They were selling with SaaS product, and then also benefits for the insurance portion of that. They got into a little bit of trouble with the regulators because they were not meeting their licensing needs. They had no consumer complaints, but they didn't actually follow all the rules of the road, and they scaled incredibly rapidly. So he joined in 2014, and they were 123 people. At its peak in early 2016, there were about 2000 people. And a lot of that was sales. They got in trouble. He moved into being the Director of Licensing Compliance under their General Counsel and spent about 18 months going state by state with a team from PwC, doing a bunch of remediation work and got to see the worst outcome that you can. They had a great outcome at the end in terms of paying out $10 million in fines, and that was a really good outcome. It really changed a lot about the company.
Then he was put back in sales operations. They said, "Make sure this doesn't happen again." He looked around and was like, "There are no tools to do that." So he and I had built systems together at LinkedIn, and we just started talking about what it looked like to build it together. That was where AgentSync was born. I spent my career doing business application building and design and got really excited about weird business application problems, and there just wasn't something serving the insurance industry in this way that was modern. So that was how we came across the idea over our dinner table in San Francisco.
Nancy
If you look back to your seed to Series A days, how did you pitch the company to your VCs?
Jenn
Well, we started pitching in March 2020. We bootstrapped the company, and we were able to figure out some of our product market fit and prove there was a business before we went out and had our first conversation through seed. I say that because when we first started talking to VCs, and we're like, "Hey, we think there's a big need in the insurance space." They're like, "Yeah, then what else? What are you going to do next in insurance?" It's a $1.3 trillion TAM, but it's not big enough. It's not cool enough. Not interesting enough. It was hard to understand what we were solving. What we decided to prioritize when we were pitching was we'd both been at companies that were growth-focused, so we put together a pitch that talked about what we were solving, why we thought it was interesting, how we were going to grow it, the space that we were going to go into, and really didn't go too much into what is the next thing. Then we looked for investors who were really excited about what we were solving, and that were operators themselves.
It wasn't easy. I mean, we were all doing it on Zoom because it was March 2020, and someone's going to roll their eyes and be skeptical. That's okay. We talked to a lot of people. And we waited until we found the right fit for that first batch because we wanted to make sure that we were going to be marching in the right direction with the right partner. But I don't know if I have any other words of wisdom other than, just buckle up for some skepticism. Not everyone's going to hop on board right away. It's going to take a little bit of work to find the right partner.
Nancy
On that note of skepticism, when you were asked the question, "Why insurtech?" To your point, it is a $1.3 trillion industry. It's really large. What differentiates AgentSync from other incumbents or other players?
Jenn
AgentSync is interesting because we are somewhat in the insurtech space. But we're not an insurtech the way that you would think about UI Hippo or Lemonade; folks who are changing the way that insurance products are built and insurance products are delivered. What we're doing is actually supporting insurtechs coming to market faster, and in a more efficient way because they all have the same obligations. Everyone in the insurance industry, is obligated to meet the regulatory compliance obligations that are put in by the states. Whether you're a carrier, an agency, whether you have been around for 100 years, you have been around for six months, that obligation exists. What we're focused on is infrastructure, not delivery of a new insurance product. And we're actually focused on helping companies be most efficient in their agent experience, bringing agents on, and understanding the opportunities with those agents. There are only maybe two or three other companies in the startup space that are focused on insurance infrastructure, not insurtech as a modification of how insurance is created and delivered.
Nancy
That's interesting. So obviously, you've hit upon a need in this industry because of some of the metrics I heard about agencies like zero customer churn and also 169% Net dollar retention, which is really high. That means once you land a customer, you're able to sell more to the client. Now, what advice do you have for the founders? How did you find your product market fit so quickly?
Jenn
For us, product market fit came fairly rapidly because Niranjan had seen the problem. We didn't invent a problem. We didn't take a small problem and make it bigger. He was like, this is a really big problem that was incredibly challenging to solve. If I had better tooling, I would solve it this way. Let's go build up better tooling and then go out to a few folks.
We were lucky. I had a few friendlies, and were like, "Hey, we were building this." There was a lot of skepticism, so we had to pivot pretty early on positioning. I think that's also something that Niranjan and I talk a lot about. There is a need for conviction but also a need for flexibility when you're founding. You don't want to be so flexible that you move away from your vision, but you do have to be able to respond to what people are telling you.
For us, there was this idea of regulatory compliance. You're afraid that you're not compliant. No one is afraid that they're not compliant. That was actually not a really effective way to talk to people about it. We found the companies were really interested in business efficiency and the experience of their agents. So the way we got to product market fit pretty quickly, as we said, "Okay, what does this look like if we adjust?" We started to add features that are focused on business efficiency. You being able to track this. Doing things more in bulk. Creating a better experience for your agents. Creating more self-serve, and that became the flywheel as we brought people on. So that was how we got to that point where we're like, "Okay, this is this makes sense."
Nancy
Did you find a difference in reception between customers who were new in the market understanding the importance of business efficiency as SaaS product versus maybe more of the mature players out there?
Jenn
What I've appreciated is that for us, it's not about the company and how long it's been around. It's about who is at the company. There have been insurtechs, who tell us that they don't care, it's not a problem, and they're not interested in investing in it at all. They usually come back after someone informs them it's a problem and they have to invest in it. Then we have some really forward-thinking folks in the incumbent insurance carrier that's been around for 50 years and have mainframe computers. Suddenly, you meet this person who's so excited because they have an idea of what they want to build. They can now see how we can enable that, and they're ready and willing to.
Nancy
Given your career and also journey as an engineer, leading application development teams, solutions, architecture teams, what skills do you find in your day-to-day as a co-founder now running a company you utilize most from that experience? Also, what new skills have you found that you needed to pick up along the way?
Jenn
I felt very lucky to have started my career in engineering. I don't have a CS background; that wasn't what I studied. I got lucky enough to get into the Salesforce ecosystem early on. One of the things that I feel very lucky about is when you're building these applications; you have to spend a lot of time thinking about the problem statement. It's right in front of you because there is someone on the sales operations team or in the finance team sitting literally across from you being like, "I have a problem. Can you help me fix it?" First, you have to understand what their problem is and the context of it. It's probably something you haven't heard about before. I was not a salesperson. I'd never done that before. At LinkedIn, I learned a ton about what it means to sell. Where is your process ineffective, and how is that a challenge? It was just a lot of good systems thinking. Before that, I'd done a little bit of work at Blue Wolf, which is a consulting company. That was a lot of pattern matching. For example, this is how businesses run, and this is how businesses are broken. That's actually what served me.
As a founder, so much of it is pattern matching systems, systems design in terms of people, and systems design in terms of technology. A lot of it is admitting what you don't know. The great thing about working across a whole bunch of different business teams is I often was in situations where I just didn't know anything. And I had to ask someone, "Now I own people systems. What does that mean? What are you worried about?" What a people team is worried about versus what a finance team is worried about are fundamentally different. They're all worried about moving their business forward, but they have very different concerns. So that was a really helpful skill in founding. Anyone who's in the process or considering it you're not going to know a lot. Figuring out how to bring it all together, where you want it to go, figuring out what isn't working, and then being comfortable letting other people run whole giant portions of it is kind of important. That's how I think from a skill perspective.
What served me most was bigger-level thinking. Obviously, the day-in-day-out when I was building the first version of the product, there were engineering skills that were important. But as the company grew up, it's more just how this company is designed and how you are making that work.
Nancy
What is your strategy around sourcing? I've found in my own diversity hiring journey that setting up a structure within the team to be able to support, train or coach lead board candidates has been beneficial.
Jenn
Yeah, we are growing our people team and thinking a lot about this. To your point, it's not enough to hire someone. How are you supporting them? How are you making sure that internally you have a culture that considers difference? That there are all different forms of that? And how are you making sure that you're not just reinforcing the assumptions about who people are and the life that they're living? It's a constant dialogue. It's not just, "Yay, I hired you." It's how am I supporting you through the journey and making this a really amazing experience in your career? That means everybody's learning. It's something we talk about. All of us are learning in this. I learn something new all the time about what someone's experience is like and then think about how we should modify an experience to better support them. I think it becomes quite intellectually fun when you start to open up to what does it mean for everyone who's going through whatever it is they're going through? Yes, it's totally easier if we all just look the same. It's easier if you have a modulus team. It's easier to get everything moving. It's also an echo chamber, and it sucks. Those are kind of the hard realities of things.
Nancy
Exactly, and to your point, the longer you wait, the more homogenous your team gets, and the harder it will be for someone to go on that path. One thing that you mentioned a while ago was, you know how it feels to be the only woman on a loop or being the only woman on the leadership team. So many women have been the only woman in the room, especially in tech. So in the infrastructure space, I can only imagine that it's even more so. Statistics show women make up just 14% of cloud jobs, and women are even more underrepresented in this space as founders. For example, a study by Workbench in 2021 showed that less than 2% of all enterprise software startups in the US have at least one female founder. So given that there are so few female founders in the infrastructure startup space, what can we as a society or a community do to make sure that we can encourage or foster more women to start companies in the infrastructure space?
Jenn
I wish I had a really compelling answer for you. I have a very young daughter and think about this a lot. There are things that I can do, or we can do today. Being out in the world and talking about what it's like to go through these experiences. I believe that there's an impact to that. Proving that you can build diverse teams so that you can be successful. That there is value in that.
I probably have the less optimistic view of it. It's not magically and dramatically going to get get better anytime soon. I think it'll take a couple generations of people putting in the work. That's women putting in the work, and also men who are supporting women. Men who, when they have an exit, decide to start a fund where they usually don't have 98% of their portfolio being male founders. We're not going to do it alone. This is a massive institutional challenge. The money is not centered with us, and the money is not on our side right now. And if we don't say that out loud, and start to think about how we can change that, it's not going to change. The opportunities that my daughter will have will be fundamentally different than those that are accessible to me. However, I don't know if that will actually shift that number in a meaningful way unless there's intentional conversation around it.
Nancy
So as a female founder in the infrastructure space, when you went into rooms with probably largely male VCs, when you were starting to pitch your idea around infrastructure around InsurTech, how did you work through some of the biases? Or what biases did you encounter first?
Jenn
Thank goodness for the pandemic. When we were a visionary seed, I was three and a half months pregnant and violently ill. We were literally pitching in our kitchen. And I was like, "I'm either going to faint, or I'm going to vomit." I just walked off the screen and puked in a corner, and walked back. Niranjan, bless his heart, remained straight-faced the whole time. Then I obviously got progressively more pregnant between our seed and our Series A. One of my favorite investor updates was in September, which was, "Here are all these great numbers. Also, next month, we're having a baby, and we're going to be gone for a minute." They were like, "Really?"
I didn't experience any very direct and blatant bias because I was a woman. But that period of time where everybody was pitching over Zoom was actually much better for women. I know of another woman founder who was pregnant while pitching, and no one got to know. We didn't have to deal with what would probably be a series of rejections based on the fact that we were going to disappear because, heaven forbid, we had a child.
But the thing I would say about all this, what I did appreciate is the advantage there is if you know people in the VC space or you have different connections. That inherently creates bias because who we were able to talk to and the kind of conversations we had, came directly from some of the relationships that Niranjan had cultivated over his time in different organizations. So, that was an interesting one that I was just observing and something that I'm kind of fascinated to see how it evolves.
There's still a lot of who do you know. Your access to certain capital is very much who you know. How do you know them? Well, you possibly know that you used to work at a company where you guys went and got drinks together, and that is just that bias working its way through.
Though I was saved from any very terrible direct biased experiences, we did get a few, "So you're married?" We don't have the same last name, so people didn't know. That was interesting. Many VCs didn't care. A few were like we don't do that, which blatantly doesn't make any sense. The biggest thing that I see is that it's still so very who's advocating for you silently in the background or detracting from you silently in the background. That's a lot to manage and has its own challenges to break.