Track 3: Leading the way: Women insurtech founders panel

Female representation in technology – particularly at the leadership level – is steadily increasing.  Insurtechs are leading the way, driving greater diversity and inclusivity within the workplace, and encouraging young female talent into the industry. 

Hear from a panel of women entrepreneurs who have successfully launched insurtechs what the keys to success are and what can be done to continue the movement. 

Key Takeaways:
  • Building your own unique value proposition.
  • Embracing disruption innovation
  • Creating the right culture for success
  • Fostering agility, leadership, and relationships
Transcript:

Margo Giles (00:10):

Yes,

Kate Stillwell (00:11):

Welcome to our round table session. Spread out into a giant room.

Hanna Wu (00:16):

I have a lot of space.

Margo Giles (00:19):

You want us to come up front? I will go sit. Yeah, come sit up front. Yeah, this is going to be weird. If not, wait for our volunteer coming from, she's literally going to be right here. Let us do it.

Kate Stillwell (00:34):

All right, thank you Janine.

Margo Giles (00:39):

Okay. My name is Margo Giles. I am the CEO of Iris Insurtech. And Iris is my third startup, but it is my first SaaS startup, so I am learning all about being a CEO on the software side. So I have lovely ladies with me today and I am going to let them give their intros and tell you a little bit about their companies and then we will jump into questions. Sounds good? Awesome.

Rachel Olney (01:04):

I can kick us off. So Rachel Olney, Founder, CEO of Geosite. It is a Geospatial Data Platform. The simplest way to think about it is really fancy Geospatial plumbing. So we work with all the Satellite Companies, Drone Companies, Aerial Companies, Geospatial AI companies, Climate Companies, you name it. Pull that all into a system, normalize deal with all the math, and then plug it into core policy admin systems and so that way people can use more data.

Kate Stillwell (01:33):

My name is Kate Stillwell. I founded Jumpstart, which is Parametric Earthquake Insurance for consumers who sold Jumpstart to Neptune Flood where I am continuing to lead the development of parametric policies and also Founder of Firebreak, which is Wildfire Mitigation and Wildfire Insurance powered by self-inspection data. So at some point maybe we will plug into Geosite.

Hanna Wu (02:02):

Hi, my name is Hanna, Founder and CEO of Amplify Life Insurance. We are a life, a digital life insurance platform, bringing life insurance savings, life insurance, retirement and life insurance investment plans to the digital space.

Margo Giles (02:19):

Awesome. Okay, so we are going to kick this off with my first question and my eyes are not as young as they once were. So this small can each of you can answer this one. So can you think of a decision crossroads or a point in your career where you chose disruption instead of the status quo? So was there a time in a meeting, was there a career change or a pivot that you did that really sets you on that sort of path to disruption?

Rachel Olney (02:44):

We do not have to always go in this order. No, I can.

Kate Stillwell (02:46):

You clearly have an answer.

Rachel Olney (02:47):

I have an answer. Okay. I was thinking about it this morning and there is lots of different moments. I think there is this fallacy that when you found a company, and I am sure you have experienced this too, where it is this epiphany moment where you are like, I am going to start this company. That was not the case for me. I dwelled on the industry problem that I wanted to solve for years before I started my company. And I call myself a reluctant entrepreneur. It is not my dream job. It is really not like I have to do this stuff all the time. I would much rather be be laying on a picnic blanket in the sun. It would be so much nicer. This is lovely too. I appreciate you all. But this problem just was like in my head all the time, how are people going to use all this data? And I could not stop thinking about it.

(03:34)

I was working on my PhD at Stanford and I was working as VP of product at another technology company and it was a startup. And I remember I was sitting in the office with the Founder, CEO of the company and I told him, I was like, I think I need to go start this company. This problem keeps popping up everywhere around me and I am going to do it. And I was really lucky in that moment and the panel before talked about mentorship to have somebody who was like, that is awesome, let us do it right? And so he was not reacting of how you could leave us? You have to stay in this job instead. It was just this resounding support of me going on this big adventure. And that was probably one of the pivotal moments. Yeah.

Kate Stillwell (04:18):

Kate, you got one? Sure. So at the beginning of Jumpstart we got no end of advice to start with a market that was a customer group that was a little more high net worth, just not to put too fine a point on it. And I had the latitude since we had not taken VC at the time to, and we did not have any other board members to say, you know what, we are going to stay true to our purpose, which was bringing this product to everyone who can afford it and really sticking to our guns about what our target market was at the expense of really high growth right away. But just recognizing that the noble purpose of insurance is to stimulate, to provide this financial buffer at a time of great need and shock and to help stimulate the recovery process, whether it is a small shock or a great shock. And the people who most need it are the people that we want to serve. So that was an intentional decision to disrupt the advice that we have been getting.

Hanna Wu (05:27):

Yes, happy to weigh in as well. I think I would say two times in my life where this has happened and both times ended in me starting a company. So similar to you, Margo, this is my first time in the venture backed technology startup life. And previous to that I started a financial planning agency, which kind of led me down this path. But before that I actually went along the route of pre-med but so very different. So I actually had gotten accepted into medical school and was on my way but was getting cold feet in that direction and felt that I was not sure if that was the life I for me. And so I took a year off and I actually ended up at a conference that was centered around financial planning and I said, hey, you know what? I am going to get my licenses and just try this out for a year.

(06:27)

And I ended up starting a Financial Planning Agency, decided not to go to med school and ended up helping clients set up these life insurance policies that were helping them invest in Private Equities and Hedge Funds through insurance dedicated funds through their life insurance policy. And just went down that route for a couple of years and thought to myself at some point about three years, four years down the line, how come everyday Americans do not know that you can leverage your life insurance policy for tax efficient wealth accumulation and how come this is not really available and accessible and common knowledge, whereas you have the high net worth and ultra high net worth corporations and banks using these types of policies to build in amass wealth and protect their assets. So then decided to start amplify much to the dismay of my husband and family. But yes, I think definitely to the point around sometimes you ca not get an idea out of your head and you just have to do it. And I think that was definitely the two moments. I hope that does not come back into my mind anytime soon.

Margo Giles (07:43):

I think I had a similar, I was in the agent broker space, so I had an agency in Florida and then through m and a had acquired about 15 agencies. And during that process, same thing, I needed this set of technology and I could not find it and it was really difficult to build and I would just lay awake at night. And the space that we are in Agency Management Systems or Policy Management Systems, they are big pieces of software. And so it is not like we decided to go and build a widget that was going to live in someone's browser. It was years of building massive software and then convincing a big company to go through a two year transformation to buy it. And the amount of just, I got the audacity, how dare you? Like no one is going to do this. But I could not get this problem out of my mind and I knew that I had the crew to solve it.

(08:35)

And we went out there and I, I am currently closing a raises right now, and so I have basically have gone through four months of just the worst speed dating experience of your life where you basically go to each and every investor and you sort of bear your soul, this is my baby, this is what I built. And then you just wait for to tell you that it is a terrible idea and then you find the ones that are really moved by the story and do that. But I think that for me was a big turning point. We were very financially secure with the agencies. They had been built up. There was no need for me to go and do this entirely disruption with my family was the same way, are you sure? And I was like, no, I am not sure at all, but please can we do it? So I think that is critical for women because I do not think enough women have the support to make that decision either at home or with their families because caregivers and their sole providers in some cases or financially if you are trying to get investment, we all know the sad statistics of female backed ventures. So I think it is important to find women like this. And I know that there were at least a handful on my journey that if I had not had them, I probably would not have been able to get here. So look for that.

(09:52)

But going back a little bit, some of you have spent time in the corporate structure, we are all entrepreneurs now. We are used to small business. But what can you say to some of the women that are maybe in that corporate structure and they do not have the freedom or they are dealing with the power sort of levels and how if you have done in the past, how have you navigated that earlier in your career versus now that we are a tenured Entrepreneurs?

Kate Stillwell (10:16):

Okay, I am going to go first this time. So the Insurtech is my second career, my first careers as a Structural Engineer. So I am still licensed as Structural Engineer. So designing buildings to be safe in earthquakes. And I will never forget my boss, not my first boss, but my second boss who is a very powerful charismatic person in the Engineering and Architectural Community. And there was a bit of a personality clash because I was super ambitious and when I got accepted to business school and asked the company to pay for it, and he said, oh yeah, we will pay $2,000 a year and for each year that you say yes, then you will have to owe two more years of service to the company. I am like,

Margo Giles (11:07):

I think that is Illegal.

Kate Stillwell (11:07):

So I mean we are professional colleagues now in committees and we have good respect for each other. He is retired. But I took it really personally and that was how I dealt with power struggles earlier in my career is like, God, he has this thing against me. And really honestly, it was not against me, it was just the business decision that was right. And maybe it had something to do with him actually. And just having the wisdom to realize, I mean my kids are now 12 and 14 and just this, it is a mantra for me. This is not about me, this is about them. And it took many years of therapy to me, me be able to get that in my head. But just being able to perceive other people's reactions are not so personal.

Margo Giles (11:57):

And do you guys have any

Rachel Olney (11:58):

Yeah, that is such a good one. I am like, yeah, the thing I was going to talk about. But yeah, realizing that oftentimes it is about other people. The one that I was going to add is when one thing I mentor, when I do have, especially folks who are still in college or debating grad school or debating a PhD or thinking about education, especially my education has nothing to do with what I do now. Absolutely nothing. Bachelor's, Master's, PhD, all Mechanical Engineering. And then for my PhD Dissertation, I did a curve ball and did organ theory because why not study a whole other body of literature that you have nothing to do with just for fun. And so I learned what it feels like to be an expert and know what I am talking about and I can very clearly tell when I know what I am talking about and when I need more information.

(12:53)

And what that gives you is this confidence to say when you are dealing with these power struggles, I know what I am talking about. This is what I am advising, you can take it or leave it and being very like sure of yourself. I think a lot of times part of it is cultural and all of that, but also once you dig in there and you are like, I am an expert. This happened on my team actually earlier this week. We went to the biggest Geospatial conference in the world and she is our Head of Partnerships and she sat my CTO and I down and she is, I think part of our strategy is wrong. And she walked through some ways that she wanted to change the way that we do partnerships, and at the end of it, she is like, I am sorry if I am being really rude or assertive or whatever. And I was like, stop, please. This is why you are in this role is to have your own perspective on these things. And if you agree with us all the time, why are you here? And so again, not everybody has the luxury of that person, but just knowing your stuff helps a lot.

Margo Giles (13:56):

Yeah, I think so. And that, I am going to flip a little bit into representation in when we are building products. I know that it big for a lot of us, so I have how does company culture and representation go hand in hand with being customer centric? What does it mean to represent not just gender but race and sex and in building products or building products for people of sort of non-white male, cisgender? So what does that mean for you guys? And is there anything, and is there initiative that you guys are taking inside the company to make sure you are customer centric,

Rachel Olney (14:34):

You want to go?

Hanna Wu (14:35):

Yeah, I mean, happy to share a little bit. I would say that for us, I mean I think we have chatted a little bit about this. It may wrap into the next questions, but one of the things that we found pretty interesting was that based off of the data around our customer set, we have a lot of male policy holders. A lot of it tends to be more men who own life insurance. However, what we found is that actually women are the ones who take that initial action, go through the walkthrough sometimes and put in their husband's information. And if we were to only look at that data, we would see that we would try to build products around men. We would build products and try to understand why men purchase life insurance. But in reality, the real customers for us, the real target consumers are actually sometimes often a wife or a spouse looking to purchase life insurance for the other person.

(15:48)

So actually I think for us really understanding what are the trigger points and who is the actual target customer? And for us, it actually happens oftentimes to be women and to build our platform and to build our marketing, to build our customer journey around why our actual target consumer is looking to purchase these policies and how we can actually help them solve that need and how we can create the messaging and the content and the customer journey that supports that. So I think that it definitely one of the interesting areas that we found in our business.

Margo Giles (16:26):

Well, it is also too, it is the insured that is not necessarily your customer. So your policy holder may not actually be your purchaser, and that it such a critical thing to, when you think about a data analytics, like you said, looking at a data set, you just glance at it and did some cursory analytics. You would say these products are all for men, but were 90% of them were purchased by women, so how do we navigate towards that female? Which is to me incredibly interesting, especially as we talk about data and what that means. Yeah. Did you want to

Rachel Olney (17:00):

Go ahead. I mean, part of the question was what are some practices internally? The only thing I was going to mention is really intentional hiring. So any of you that are in positions where you do have a say in hiring really or you can influence the people who are doing the hiring, really doing a constant education and training. The thing that I pair it to my team all the time is a lot of times bias just comes from under educating yourself on your biases, not doing the homework. And so we consistently do that inside of our company. So what are all the different biases that we might have on tons of different things, not just demographic but also education and region and all of these things. And then once you can see past those, you can have much better outcomes.

Margo Giles (17:48):

I think internally what we found too is that some of the criteria we had for hiring was bias without being biased. So I talk a lot about, I am hiring for an executive role and I put 15 years experience or has to have a master's or a PhD that immediately is eliminating people of color and women because we have not had the ability to hold executive roles for 15 years. So some of the things that you feel like are need are kind of status quo. Those things can be biased as well. And so going back and saying, we are going to be skills focused and not title focused and not education focused, but more do they have the heart and soft skills that we need.

Rachel Olney (18:29):

On that, we have a couple curve balls on our team, which I love. Yeah, it is absolutely my favorite. One of our absolute best Backend Engineers, Software Engineers. Her job before she came to our company was a Middle School Band Instructor. That was literally what she was before she came to our company, and

Kate Stillwell (18:49):

I thought that was only a job in the movies,

Rachel Olney (18:50):

It is a thing. She is like, oh my god, Tech pays so much better. I am like, yeah, than Middle School Band Teacher at a Public School for sure. Yeah. So we actually love career switchers because it takes a lot of courage to switch careers. And so we actually find people that do not have maybe even any of the experience in a new field. Sometimes they are the best because they are so driven to learn and they oftentimes do not maybe have the ego of somebody that it been it for 15 years and is very stuck in their ways and they just love what they are doing. There had to be some reason for them to take that risk.

Margo Giles (19:26):

So this is the same vein. So we have got a stat that says 400,000 employees are expected to retire in insurance in the next five years. What can we do for young women so that are coming out of college to entice them into insurance? And what can we do? What can we do not just in the hiring practice, but how do we get out there and get more women involved in our industry in general?

Kate Stillwell (19:53):

Well, I will chime in to answer that question and to tie it to some previous questions, which is like there is this perception of insurance in America and less so in the UK and other places, that it is a system to be gamed. How can I answer the questions in the way that is going to be best suited to me that I can game the system, that I can trick the insurers and abuse my information asymmetry to my advantage because I expect that the insurer is going to abuse whatever power they have to their advantage. And so that it a mindset that is very in the video game kind of mindset, and yet it really conflicts with this larger purpose of insurance, of providing this financial buffer and this easing of the uncertainty of not having the courage and knowing am I going to be able to take this risk or not?

(20:54)

Insurance actually empowers the risk taking and is a fundamental foundation of being able to have courage in one's life. And so how do we shift the script a little bit so that insurance starts becoming this thing that is more about what I want to continue to have some income, even if my spouse died, I want to prepare for the uncertainty and have that feeling of confidence as opposed to the, oh, there is this thing that I have to do and I would just want to crank the most out of it that I can. And so how do we create our companies in a way that really supports and reinforces that mindset of this is actually a supportive tool for our financial stability and our generational growth for being able to continue the trajectory, the economic and social growth that we have been having within our families. So I, I am kind of rambling here and I apologize for that, but I think that once we as founders rewrite the script of what insurance can be and what insurance is and communicate that to our customers in a way that it super transparent so that we ass Insurtechs in our messaging and our customer communications are really clear about what we are and what we are not, then those two things like how we operate internally, how we hire and also how we communicate to the customers becomes this upward spiral that elevates the whole industry.

Margo Giles (22:26):

Do you think women tend to lead with empathy and that maybe taking that veil off of I am getting insurance forced to and I am trying to get at the lowest price?

Kate Stillwell (22:34):

Yeah, I avoided going down that route, but absolutely that it under there also how we,

Margo Giles (22:40):

Do you think that having women in executive positions that tend to lead with empathy and have more of that customer sort of connection will assist in that? I hope so.

Hanna Wu (22:53):

Yeah, definitely. I would say it is interesting because it is almost both of those aspects can be solved, which is attracting more women into the industry, but also helping the industry grow into connect more with different customer segments. And both of those can be solved with more sort of representation in leadership. And also this is something that I myself and need to do more of as well, but I think it does take a little bit more effort from us who are already in the industry to really create events. I will say back in the day when I was running my own agency in the past, before I amplify, I would go to these conferences and I would be surrounded by the average age of a life insurance agent was in their fifties and they do not look like me. So I think it was very, for me, I saw it as an opportunity right in this space, which I still believe it absolutely is, right? It is an opportunity for us to step up and also relate more with people, both customers and also bringing different representation into the industry. But at the same time, I would say it does take more from us today to reach out and to build events together and to make it a more inclusive environment and to share more about what we are doing and how it can be different and how it can build a different future. So I think it does take more effort, but it is an opportunity.

Rachel Olney (24:43):

I love how authentic your love for insurance is. I just have to say that. Why use your time and talent for something you do not love? No abs. I completely agree. Do the thing you love, I will the like and inspiring others. Those are so important. The one last little thing I will add, and I will make it very brief is I do not know if I have inspired anybody to come into insurance. I do not think so yet. I have not been in the industry that long, but previously I worked in national security. My PhD was for the Department of Defense. I worked with a bunch of our special operations teams, all these things. I still go back to lecture at Stanford for space as a domain of warfare every year for the Technology and National Security course. My slides are fuchsia, they are beautiful. They are so pretty. They have this really nice, I love those slides so much.

(25:35)

My company colors are blue with a little bit of orange, very buttoned up, very helpful for marketing. But I am once a year I get to make a deck and I am going to make it how I want it. And I got to teach that class for six years while I was at Stanford and then now just guest lecturing. And I had so many women come up to me and be like, I went into national security because you were my instructor. And what I realized was there was space for me at the table. There was clearly space for you at the table and you were hyper girly. I will never stop being, it is who I am. I love it. And it is easier for me to just be myself than have to work hard at putting up some other front. And in the early days of a startup, and I am sure both of you guys have experienced this, especially as a woman, there is this moment where you are like, do I need to dress like a startup CEO?

(26:26)

I do not even backwards hat I do not even own. I mean, well, I have an old hoodie, I guess I could wear that one, but then I, yoga pants, do I wear jeans? I do not. it is so much more work than being like I am putting on my sundress and going to my meeting and not thinking about it. So I think being authentic also opens that door to a lot more people joining the industry. They see you and they are like, oh, okay, I can wear a bunch of jewelry and lipstick and I am not going to be, and I can still be taken seriously.

Margo Giles (26:57):

And we are coming to the end of time and I want to give everybody the opportunity to ask questions. So again, feel free and we are up here if you want to ask us anything. Okay, back.

Audience Member 1 (27:11):

Hi, so I am a American family and I am actually part of a post MBA, oh, sorry, General Management Leadership Development Program. So it is two years, three rotations, eight months each. And I just wanted to follow up on that question of getting young people into the industry, if any of your companies have a program like that or what is your viewpoint on those opportunities?

Margo Giles (27:37):

Yeah, so I lead, I am on the advisory board of Yukon's FinTech program, their brand new FinTech master's program. And we did a lot of outreach, especially on female side. And this year we had 50% women apply. Last year it was like 2%. And a lot of that was John Wilson who is in charge of that department, filling our advisory board with women. The advisory board was women, people of color, and therefore when we were out promoting and speaking, all of a sudden the people that wanted to join were also, they looked like us. And I think that that representation is key and giving people a voice, kind of like you said, being authentic and getting up and speaking. Again, this is not my favorite thing to do either, but I do feel sometimes there is a responsibility to be a loud voice in the room because if we do it, then people see it and they follow Internally.

(28:32)

At Iris, one of the things, we have initial initiative. So on our side we are dealing with brokers and wholesalers and the majority of customer service representatives, so entry level, 60% are women in that position nationwide. And so instead of going, again to my point about hiring, instead of going and looking for executives, we started going into that sort of secondary entry level. Maybe they are in an operations or an administrator role and teaching them how to go into software and doing that intentionally instead of saying, oh, we are just going to pick the best candidate off the top, putting in training and time into taking somebody that might have half of their skillset and putting them into the software program. So that it one of the things that we have done. We guys have any,

Rachel Olney (29:21):

Yeah, I mean at our stage, we are not that large of a company and we have tried doing internship programs or rotations and it is really hard at a super early stage because we just do not have the volume of people on our team to help support someone. So we had interns once and I felt so sorry. They were so neglected. And so now what we do is we spend a lot more time just volunteering our time for different programs. So to her point, also just serving on boards of those things or volunteer speaking at things, all that stuff. So I do a lot of stuff at universities.

Kate Stillwell (30:02):

Neptune has 45 employees, about more than half of which are on the customer support side. We get a lot of our customer support representatives from Disney Ambassadors. So our Neptune is based in St. Petersburg, Florida, and there is just a degree of enthusiasm and love for helping people that people who have worked for Disney as interns or for free will, they will bring that and perpetuate it through the rest of their life. The other thing is if you go to excuse me to Neptune's website, you will see that my counterparts on the management team, the other six guys are all white guys with crew cuts. So from an optics perspective, it just does, it gives a certain optics. What you do not see is that five out of the other five, the white guys with crew cuts are queer in some way or another and have a life experience that they have brought to the table that is very non-representative of the white guy with crew cut kind of mentality.

(31:11)

And so when we had a couple of new hires in New York and we brought them down to Florida for our company party, and the one woman is in her fifties, white woman in her fifties, another woman is a black woman in her forties. And they took me aside and they were like, how come all the guys are white guys, crew gods? It just makes me really weirded out. I said, do not judge a book by its cover. These guys understand the experience of being marginalized, just all the rest of us have been, and I will, it is not your responsibility to ask those questions, but I just want to assure you that they have this empathy for being on the outskirts of society. And then I took it back to the management's team. I was like, guys, photos, it is terrible. And they are like, oh my God, I never realized.

(32:04)

And I said, but all you guys understand the experience of women, black people. And they are like, we do. I was like, okay, you have to bring that to, and particularly to sales guy who oversees all the customer service guys. And he is like, oh yeah. And then he started some team building exercises and some discussion groups internally, and I did not yet had a feedback to the two employees in New York. It would be too weird for me to be like, Hey, is John Luke reaching out to you guys? But they are still with the company and they are still participating in all the events. So there is something to be said.

Margo Giles (32:38):

Now that leads me to one more question. What can our male, what can we do to help our male counterparts? At the end of the day, they are still the majority of leadership and executives and they might not understand or be comfortable navigating themselves any diversity and inclusion. So what do you guys think we can do to encourage them? Or are there any action items that we can do?

Kate Stillwell (33:01):

Yeah, so Jean-Luc asked me, what should I do?

Margo Giles (33:03):

Yeah, what do I do? Yeah,

Kate Stillwell (33:04):

I said, start the conversation. Say, listen, I am going to take the time today to share my experience of what it is like to be queer. And so he did one of these team meetings all about that. And then from there he started some other small group, just chat groups.

Margo Giles (33:23):

Yeah,

Rachel Olney (33:25):

I think so a couple, my CTO was on a panel recently and we are an all female executive team, which is totally bomb. I am telling you, it is so fun. But somebody on the panel said something that was sexist. It was like definitively sexist. I saw her and there was one other female panelist. They both just kind of looked shocked and did not know what to do with this comment. The totally went over the moderator's head. I was like, moderator, where are you? do not make me come up there and grab the mic myself. And later he is like, what comment? I was like, oh gosh, lot. But it was the sort of thing where it was not, it was borderline, right? Yeah. It was not overtly sexist. It is not like he was like, women are bad at math. It is never Sexism, Racism, Xenophobia. It is rarely that cut and dry and clean usually. And in this case, it was a comment about how when they have female mentees, they will, well, any of their mentees, they will coach them wear professional clothing and blah, blah, blah. And if you are a woman, do not wear a skirt too short, that it going to be distracting to men. And I was like,

Rachel Olney (34:45):

Oh, no, no, no, no, no, no, no. Not only are you telling women how to dress, you are also saying men's reactions are their fault for somebody. 27% of women in the United States have been physically sexually assaulted. And a lot of times what plays into that is the trope that the way that the women were dressing was a part of what caused that. And so even if it seems banal or a joke about like, oh yeah, do not wear short skirts, it plays into a much bigger problem. And so this goes back to the bias in education. And so the thing that I do, we do in our company very often, and I do anytime I meet other folks or give talks about this, is you have to educate yourself. That is the only way out of this problem because it is, all of us have bias. Humans are dumb dumbs. We rely on heuristics to get through our day. And some of those heuristics are harmful to others. And so you have to educate yourself. And so that it always my big one is like, go read a book. there is plenty of podcasts, or do it as an audio book.

Margo Giles (35:51):

And ask me. I won't be offended if you have a question, I am not going to take offense, but if you are trying to learn, then I will be there to help educate. Yeah, absolutely.

Hanna Wu (36:02):

Yes, definitely. I think one thing that I would add is there, sometimes there can be one thing that I have learned because I do not have a all female executive, although that would be awesome.

Panel Organizer Member (36:14):

It is amazing.

Hanna Wu (36:16):

But I think one thing that I have realized as a female executive is sometimes to recognize this is not just about male or female, but just in general to recognize a difference in leadership and how to manage the right expectations. I think one of the things is sometimes I would not say women, but I would definitely say before myself if I would always be concerned around how my executives view me, I guess. And sometimes you care too much in a sense. So I think just being able to draw those boundaries and being very clear about, okay, I recognize that I care about how my executives view me, but at the same time, making your expectations clear and making it clear around what you expect of others and how you operate in your leadership and how you operate both up and down and peer wise I think is really important aspect of being a stronger leader, whether you are a woman or otherwise. I think it is a really important aspect.

Margo Giles (37:30):

it is almost like training people how to interact with you. Yeah, this is what I accept. This is what I do not

Hanna Wu (37:36):

Accept. Exactly.

Margo Giles (37:37):

How are we doing on time? we are good? Yeah. All right, cool. Q and A more Q and A time. Yeah.

Panel Organizer Member (37:43):

Thank you. Thanks. Wow. Wow. You could just talk all afternoon and I would be okay with that. I promised you at the end we are going to ask all of our panelists to come back and answer questions. And so you are already conveniently seated right here. And Janina is here in the front as well. She was on our last panel, and I think that it in this massive crowd that we have, but really we can keep the conversation going or we can direct it in a way that it helpful to each of you. I know as a founder of a different type of business, there is so much to talk about, but I do not want to steer the conversation that way. We can talk about career journey, we can talk about asking for help, we can talk about adversity, we can talk about career change, about asking for what you want.

(38:27)

there is a million directions that we could go based on the wisdom that we have here. Or if you just want to share or reflect or say something in a seemingly recorded safe space, you are welcome to do that too. But I love these conversations. I think personally, I will just share to break the ice, I left my last traditional insurance role. I was an Agent Producer in a small Agency in Chicago. I was completely out of alignment. I was paid well. I was respected in my work. It was important work, but I just couldn't do it anymore. And a year later, I took a year off. I healed, I recovered. I did a lot of yoga, I took a lot of naps. I came back around and I started doing the work that I am doing now, which is consulting in a different way than you all are doing.

(39:15)

But the process that I went through was as much about my own journey as a woman as it was about being an Employee or a Small Business Owner or an Entrepreneur. And one of the things I used to do was go onto Eventbrite in Chicago and sign up for free events in the city that were hosted by organizations that had nothing to do with insurance. And one of was a tech founder panel of women, a lot like you all. And it was the first time that I allowed myself permission to say, my career does not have to look this way. It does not have to look the way that it is looked for the last 20 years and showing up in those unexpected places. And whether you are being a fly on the wall or you are raising your hand and asking a question can be a signal, can be a first step for all of us on this wild journey that we are on.

(40:05)

Because one of the things that I will reflect the generation that it coming into the business right now, I love. I love for a lot of reasons. tey are also really frustrating to throw a bunch of stereotypes and generalizations. They won't wait for 20 years to find their place. They won't wait to earn the next permission promotion in the next opportunity. And so they will leave and they will go to the place where they are culturally aligned and where their values align. And we need to solve that. And I think we are doing it as female founders in a sense, but as an industry, we need to answer that call. So lots of thoughts that I spewed right there, but happy to answer questions. We will bring you the mic, Megan's back there and can lend a hand as well if you have any questions or on your mind items. Yeah, what is your name? we are a small enough group if you do not mind, Janine. Thank you.

Janine (40:59):

Hi. First I want to say you guys, all of you are super impressive and being a part of a carrier and just listening to the courage that all of you had to take that step in your career is just, it is amazing. So my question is specifically for Kate, you were talking about really being transparent with customers, talking about the real reason that you have your products and giving them financial stability, and I am going to say building that emotional connection with them of the broader purpose of your company. So we have been trying to do that recently, but being part of a carrier, at the end of the day, it is all about bottom line. it is all about the KPIs, it is all about when we work a claim, how are we negotiating to bring our costs down and blah, blah, blah, blah, blah, blah. All of which seemingly cannot be in alignment with ultimately taking care of the customer and having that connection. So I do not know if any of you have kind of experienced that, but just I would love any perspective that you have on how do you maintain that focus on profitability but also be true to your word and really building the right relationships with your customers?

Kate Stillwell (42:24):

Yeah, I mean Jumpstart had, and Neptune also, but I will speak to Jumpstart first, is had the luxury of first starting from zero and second, having a product that is specifically parametric. So it is just very clear cut how much money and in what circumstances. And just almost by design it was counteracting people's preconceptions about what insurance is and how it felt. And so as I said, that was a luxury as the point to have a starting point. And so that it part of why I attribute being able to make the connection with our customers. So one example of how we were digital first, but the idea that we were going to acquire all of our customers digitally is reinforced bias about, because it means that our customers would end up being the people who buy things online who are white, young, and not all white, but young and affluent or at least some degree of affluence.

(43:32)

What we ended up doing and where actually a significant portion of our customers ended up coming from was from our outreach to in disaster preparedness Faires. So these are in-person community events. This was pre Covid and it is starting to come back since Covid, but mostly pre Covid. And we have this an earthquake simulator. It is a trailer that you pull behind a pickup truck and it is on hydraulic actuators. And then when you operate it, then it bounces the trailer back up and down and tilts its side to side, front to back. And so it makes people seem that bounces, people around the inside is fitted out a living room. And so we would take these two fleet week here in San Francisco where there is thousands of people who come by, and then we had a queue out the back to people who wanted to ride the earthquake simulator.

(44:16)

And so then we get an opportunity to talk to them. And then after this 7.0 earthquake, you would be getting a text within the next 24 hours saying you have $10,000 waiting for you. And they would be like, oh, wow. And people did not sign up on the spot, but the people who talked to us afterwards, for the most part, there were a handful of them, which are the emergency coordinators in their neighborhoods, the community emergency response train trainer. And so then once a year they get their neighbors together and they have a little picnic and a party and they talk about, okay, who has water and who has emergency generator, and how are we going to be prepared for the next wildfire, for the next earthquake, for the next flood? And so then when we followed up with our customers, which we do, we have a practice every time somebody signs up talking to them and well, if we can reach them, we end up reaching like 40% of them.

(45:03)

But many of them said, oh yeah, we found about out about you through Jessica and Oh yeah, I found out about you through Bob and Jessica and Bob. Those are their real names, were people that came and visited the earthquake simulator. And so having that trusted person be the source of how you find out about the insurance is really powerful, especially if that person, they do not have ulterior motivations because there is contamination about the motives and incentives of the insurance agents. And it is really hard to, and I know I am not really fully answering your question, but going back and saying, okay, how do we break the distrust? And there is so many points in the process of buying insurance that are full of distrust, the claims in particular, but also the buying process. And the reason that people say insurance is a scam is not because they really believe it is a scam, but because they think that every step along the way, there is some piece of negotiation with them and they have an imbalance of power.

(46:08)

So one of the other questions that we ask our customers and in addition to where did you find out about us is what do you like about us? What do you like about Jumpstart? And what we expected to find is it is affordable because one 10th the cost of regular insurance and it is affordable. But what we found is that the, there is no power imbalance. there is no arbitration. there is no big guy looking over my shoulder deciding what I am worth and whether or not I am telling the truth. Because if that it happening, then I am not going to tell the truth. I am going to lie. And so then it just creates this whole mess of distrust on both sides. And that it the number one thing that our customers found. We were like, oh my God, that really reinforced our whole mission to create this to transparent product that what you are going to get

Margo Giles (47:02):

Is that easier because the product is a lot more simplified. So as an agent, and I specialize in telecommunication construction, so it was very big risks. I mean, you need a PhD in law to go through a seven line of business policy that cost $2 million with a group of board members. So do you think there is anything that we can do to simplify that? To me, it always comes back to that confused mind says no, they do not understand necessarily what they are buying. You guys have the luxury of being very straightforward. you are buying earthquake insurance, but as a Florida homeowner, just a homeowner, my property insurance is. So the process of understanding what it does cover and what it does not and what scenarios, I am an agent and it is still creates that distrust. I mean, because you really do not understand even at the point of sale what it is you are actually covering. And I think that that it hard. And I think there is some AI that it coming, I think down the pike to help take some of that really confusing language. And I feel a lot of times if I am an agent, the carrier just kind of dumps it on us. they are like, here is the policy, go explain it to the insured. we are like, okay,

(48:11)

But it is always sneaking in an exclusion or there is some new thing that it coming in. Yeah. So do we educate somebody on a 78 page legal document that it really complicated.

Hanna Wu (48:21):

I mean definitely can not speak towards that side of the insurance policy, but it is definitely something that we deal with every day at Amplify because Life Insurance Savings and Investments Policies, it is like the client is putting in a greater amount than they would for term insurance for a much smaller coverage. And it is like, oh, you can use life insurance for your retirement. I mean, this is a lot of the times our customers are discovery customers and we have to bridge the education gap. And really what it is, it is very much to your point, not all incentives are aligned in the insurance value chain. And I think a lot of that is it causes this fracture between product design and what's actually what the customer actually wants. So you end up, the industry ends up building products that are centered around the distribution of agents, like both in terms of the economic incentive, which is the pricing of the policy, and also the product design and all the bells and whistles.

(49:24)

And you end up, the customer's actually even more confused and it is more expensive, and therefore you can not make it more transparent. So you are kind of in this loop of a black box that you end up building around yourself. So I would say on the carrier side, because we are kind of in between, we are kind of building out components of our own product. So we are on both sides of that. So it comes it for us, we really want to be able to understand, I think carriers should make an effort to understand consumer data, more consumer data, rather than just getting feedback from the distribution on what they should build. I would say that carriers should try to take more steps to understanding what consumers want to buy versus just what agents want to sell. And in addition to that, I also think that it has to come from the top.

(50:19)

I mean, we have worked with a lot of carriers throughout our time here at Amplify, and I think carriers, there is definitely certain carriers that have a predisposition to want to innovate from the top, whereas others, they want to continue status quo. And there is nothing wrong with that. But I think sometimes, you know, have this new generation that it coming up that may not want to be doing things status quo. So your status quo may not be in the same way of doing things for it. It is tough to think about things like 10, 20 years down the line when you have to make your dividends when you have to answer in the short term. But I do think that it has to come from the top in terms of understanding consumer data, working with Insurtechs, working with innovation. In order to make those changes.

Kate Stillwell (51:19):

I would say, I am going to go ahead, just steal the mic for a second. I am just going to say yes, the support has to come from the box. From a tactical point of view. One possible thing that I have seen work is for the top to say, you know what? Not create an innovation team, but really, and Lloyd's lab is a good example of this, create literally a sandbox where both sides are real, truly incentivized both sides internally within the company to and set a design challenge in the mindset of the ideal design challenges. For example, one design challenge might take the form of what if a policy was one page long? That is it, just one page, a whole policy, all the terms and conditions all in one page, and maybe a lot of definitions and stuff in the remaining 77 pages.

(52:10)

No seriously, in the UK, the proportion of people who buy insurance direct versus agents is flipped from the United States. So in the United States and Asia too. Now I know that. So a vast majority of people in Asia and the UK are, they understand it enough and they are motivated enough and they trust the system enough to buy it themselves. So that might be another design challenge. And so this group of people within the company, they have to have the support from management to have devote some of their time to it. What would it take to flip build trust? What would it take to have to have our carrier be synonymous with trust in the insurance industry?

Margo Giles (52:53):

So I spent about five years as an advocate for agents, for carriers, and on the carrier side, it just gets really dicey. So my question, I had a question that I was going to ask. I do not know if you guys read it, was the last question, which is where does data become bias and when is it data? So when we are building insurance products, there is like, there was the stat in Oregon that said 11% increase for women drivers. It made me think like, okay, is that a statistical bias or is that a stat that needs to be built the product? Is it a real tangible modifier for building an insurance product or is it bias? And I think when we were speaking with carriers about that, a lot of them said, well, the data is the data. Are we supposed to ignore statistical data because it does not align with a social gender norm? And I do not think that it as easy of a question to answer as we all want it to be, right? So I am totally open to see how that gets response from this group.

Rachel Olney (54:08):

Yeah, I am excited to hear your guys' points on this because you both design products. One thing I will say that goes a little bit to your question, a little bit to this question is we are a data platform. We deal with this question of how do you present the truth a lot? And early on, we made part of our codified values that we won't lie with data. And what that comes down to is, like you were saying, sometimes these statistics, sometimes the numbers there, sometimes you are not sure because there is a lot of bias and data and it is hard to actually nail all of it down. So how do you come up with the best version of the truth? And as you guys were talking about really having that relationship with the customer. For us, what it means is there are customers that we say no to and we walk away from.

(54:54)

We say, what you are trying to do with the kind of data we provide is not how this data works. And you are trying to assure yourself with some sort of data that you have come up with something, but you will be lying to yourself with the data. And so we will walk away from a deal if somebody is going to use the data in a way that we do not think is statistically or it is not well, or it is, a lot of times we deal with it, we are like, that it not how that sensor works. I am sorry, you can not do that with SAR satellites, or I am sorry, you can not do that from remote sensing data. I know that that company's marketing materials says you can, but you can not. And so we spend a lot of time just saying no and walking away when we know that the data is not giving people the answers that they need to act on. Yeah.

Panel Organizer Member (55:43):

Can I pop in for just a second? Sure. I just want, in the interest of time, because we are going right up to lunch, any question not related to what we are talking about, because we can keep going down this path, but I want to make sure that you have chance to ask questions. Anybody have anything else? You are still, she is up here if you want to pick her brain.

Margo Giles (56:05):

Come on, Janine.

Panel Organizer Member (56:07):

Anything else? Okay. Without, I would love, please. I don't know that it is hot, so give it a whirl.

Liz (56:19):

Okay. Definitely. When I finish out what you are talking about here, but if there is time, I would personally love just any advice from you women who have gone through ranks and made courageous decisions and went out on your own. But any advice and career journey or how to make that next step when it is not clear, when there might not be a path before you. So any advice on that I would appreciate.

Panel Organizer Member (56:48):

And what is your name? Liz. Liz. Thank you. Is that okay? Are we willing to go there or do we want to stay?

Rachel Olney (56:54):

It is, go ahead and take that. Did you guys want to add some stuff to bias and data and product creation?

Panel Organizer Member (56:59):

Let us go to advice and we can come back today. that it good advice. Okay. Okay. Thanks for being flexible.

Rachel Olney (57:04):

Do you guys want to start? I mean, so it is a very open-ended question, which I appreciate. I think one of the things you said right at the end of your question was making that leap or feeling like you are ready. You are never ready ever, ever, ever, ever. And I think there is this TikTok or maybe Instagram person and she always says, do it scared. Just do the thing even though you are scared. And I remember I was, the first ever time I realized I was starting a company, I was having coffee with a friend and I was like, I think I am starting a company. That was how I phrased it. The first time those words came out of my mouth was not like, hi, I am the founder, CEO of Geosite and I am super excited to be founding this world changing company. It was like, yeah, I think I am going to do this right?

(57:55)

And the hesitation came from, I have never done this before. I have no idea how this is going to go, but I was privileged to have resources to make that leap. And so either you have to find those resources or whatever, but my biggest piece of advice is you are never ready. So it goes back to if you are an expert at something and there is something that you have a competitive advantage. I started my company because I was like, there are maybe five people on the planet who know the combination of things that I know and have the combination of networks that I have who can solve this problem. From this perspective, the combination of org theory, what we solve is 50% a technology problem is 50% a bureaucracy problem. A lot of why carriers use our tech is because we solve a integration and procurement problem. They want to use a bunch of different data sets.

(58:48)

They do not want to have to deal with them all right? And so they work with us and we give them something more stable. And so the combo of org theory and engineering, the combo of understanding government, so search and Rescue in the United States is run on our platform now. It used to be run on an Excel spreadsheet, kid you not. So getting government funding to build out our platform was important. And so really doing the reflection of what are the things that I know and that I love maybe more than everybody else. And then feeling confident and being like, I am doing this because I am the right person for it, even if you are scared.

Margo Giles (59:26):

And I will second that. The finding the niche that was available to me in the agency as well. I knew a lot about this particular thing and I felt like I could speak to it intelligently and therefore I built a business niche business around that. And then jumping into the tech side, after six years being a tech consultant, now I had this incredible knowledge of operations on the agency side, and I knew how to translate that into software, which is incredibly, again, rare in our space. And the other thing that I would say that I stopped doing was asking permission. I stopped asking people permission to do things. I would just come to the meeting and I would put a website out or I would make a social post. And I stopped asking, is this okay? I do not know if that makes sense to you, but is this all right? Those things I had, and I instinctively want to make other people comfortable. it is part of my nature, but that was not hindering me in my progress. So I just stopped, stopped

Hanna Wu (01:00:22):

Asking very much. Along the same lines, I would say sometimes you have to be shameless. So I remember when, again, maybe Margo, you felt this way too, switching from the traditional side of the world over to the venture-backed technology side. And I remember going to my first investor meeting, I do not even understand the questions they were asking me. Yeah. I am like, what is that? Let me just pretend that I know what that word means. But I think you, and 10 times later, I am still learning new verbiage in every single meeting. So I would say two things. Like one, you are definitely going to have those instances of you are a stranger in this new world. But at the same time, I think what has been important for me is building that ecosystem of people who you can go to ask dumb questions like a phone a friend. And I think that has been really huge. After every meeting I would call someone and be like, okay, so what does this word mean? What are they asking? Or what should I have said? And you get a little bit better each time you fail. And I think the key is to fail really fast and know that that it a part of that process and it is actually, it is part of that growth. Yeah.

Kate Stillwell (01:02:00):

I will just repeat advice that I got at the beginning of the journey, which has really stayed with me as a mantra, which is, go with your strengths and do not try to really overcompensate. Do not try to be somebody who I am not and realize what my strength is this. And so these are the decisions that we are going to make.

Panel Organizer Member (01:02:18):

that it very true.

(01:02:21)

Love that I want to add. Woo. That was a lot. That was aggressive. I want to add one more to that. And that is this notion that not all the advice you get is right and it is not right for you. And at any point you are willing, you are able rather to say, thank you so much for your opinion. I am going to do it my way. And having that recognition that all of the people that have given us advice since we were we little women, little girls daydreaming about being princesses and all the things that were prescribed for us. it is not necessarily who we are today. And that it not how we are showing up in the world today. And whether it is starting a business reluctantly or with gumption either way, or just thinking about your next career move or changing something about your family dynamic, all of those things are risks.

(01:03:12)

And we all take them through our own process that is uniquely our own. And what works for Margot would not work for me. What works for Margo would not work for Rachel. And so you take all these little nuggets of gold and you listen to that gut, which we completely discount as women. I do not think I know there is something cooking there. And when it kicks in and you say, oh, nope, that does not feel right to me. Listen to that. And I think all of this is good to get the wheels turning and to get us thinking differently. And at the same time, I sound like a Oh, the places you will go at the end of the day, only you will know what is right for you. But we are going to leave it there. We have had such a rich hour and a half. I feel like we have been to the moon and back in all the conversations that we have had, but I do not know all of you personally. I feel like I have gotten to know you through this process. And Janine as well. All of us are fairly active on social media, so please do not be a stranger and connect with us. Were in your agendas and should not be that hard to find. And thanks to Nate and the dig in team for making this.