Episodes

Monday Oct 30, 2023
Monday Oct 30, 2023
Paul Monasterio co-founded Kalepa in 2018 with the mission to help commercial insurance underwriters bind business with confidence. Kalepa's AI-powered Copilot software enables underwriters to focus their time on the highest ROI opportunities and to quickly evaluate and optimally select risk.
Paul talks about finding the balance between underwriters saying yes to everything versus saying no to everything, to focus their time on selecting exactly the right opportunities that bring profitability and reduce claims risk. The first decision an underwriter has to make is where to use their time - so Copilot helps triage opportunities based on their attractiveness and alignment to the strategic book priorities.
Paul also discusses technology tools and changes applicable to commercial insurance, focusing on the right opportunities and understanding risk exposures in the right context. He sees that underwriters need to be better armed to address the complexity and nature of claims and new lines. He does not see a world in which there are fewer underwriters, or less work to do. instead, he sees winning carriers and MGAs as those who understand where to use technology to augment their underwriters' skills and not fall into the trap of thinking tech will drive personnel cost savings.
Kalepa is backed by IA Ventures, Inspired Capital, and leaders in technology and financial services. Kalepa was recognized as one of the most innovative insurtechs in the world as part of FinTech Global Insurtech 100 in 2022 and 2023, one of Benzinga's Best Insurtechs in 2021, and as a Cool Vendor by Gartner in 2020.
Prior to founding Kalepa, Paul was an executive at Facebook/Meta, Mastercard, and Applied Predictive Technologies, developing novel applications of data and technology to solve the most critical problems of Global 1000 firms in insurance, banking, and the public sector in the US, Europe, Asia, and Australia. Paul also founded Forg, a microfinance organization fostering micro-entrepreneurship in South East Asia. Paul graduated with a PhD in Nuclear Science and Engineering at MIT and holds Bachelors degrees with Highest Honors and Highest Distinction in Mathematics and Nuclear Engineering from the University of California, Berkeley.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Monday Oct 23, 2023
Monday Oct 23, 2023
Jeff Shi is founder of Insurtech Groups, connecting consumers with industry partners. by help consumers to better understand their policies in an effort to meet each of their unique needs.
Jeff talks about insurtech enhancing client experience vs. disruption. Insurtech Groups is consumer-facing technology that seeks to evolve the $100B insurance space across claims, service, billing and brokers.
Jeff foresees many more people joining from the insurance world and insurtechs becoming really good at making money from insurance rather than technology. Enhancing the client experience for the customer, carrier and agents is more important than 'aiming for the fence' with a new disruptive model.
Jeff describes how Insurtech Groups has stayed more conservative working with a fixed cost model rather than trying to scale too quickly on highly variable costs. The team builds revenue and growth into everything they do. He talks about the amazing leadership at innovative large carriers like Geico, Progressive and Liberty Mutual, and how he hires on those same principles.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Monday Oct 16, 2023
Monday Oct 16, 2023
Troy Stewart is President and COO of Brush Claims an insurtech that is streamlining the claims management process. Troy describes having started as a claims adjuster to now serving as President & COO of this successful business model, with his vision of tech driven, human-led claims.
In 2015, the company started building its own proprietary technology to remove bottlenecks, solving for escalations and time delays. By 2019 this traditional claims company had already fully transitioned from its legacy claims management system to its homegrown Hub applications, with a secure claims portal for policyholders, and a scoping application used by adjusters and contractors to pass information to the desk adjusters.
Troy recently spent eleven weeks at Lloyds of London's seventh innovation lab cohort, and brought back that knowledge to the US market, to refine its solution and create a consistent interface across carriers. It all starts with taking a holistic view across an entire process, and not cause disruption downstream. Technology can help bring more speed but the time savings of a new workflow may cause consumer pain and more calls to the call center.
Troy says that in a catastrophe situation, customers want to move quickly past the uncertainty after filing a claim and have certainty around what is coming next. Technology allows better communication and more options to correspond with claims teams and move the process forward more effectively, using a more data-driven indemnity methodology to make a determination.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Monday Oct 09, 2023
Monday Oct 09, 2023
Drew D’Alelio is a senior associate at Connecticut Innovations working on the Climate Tech Fund. He has a passion for combating climate change, innovative financing, and economic development. At CI Drew manages the entire investment cycle, from sourcing, due diligence, all the way through to portfolio management, and has invested in companies focused on insurtech, EV charging, circular economy, grid intelligence, and more. Drew holds a MPP and MBA from Yale and a bachelor’s degree from Northwestern.
CI’s $100 million climate fund launched in the summer of 2022 to catalyze Connecticut’s climate innovation economy, thanks to the support of Gov. Ned Lamont and CI CEO Matt McCooe. The fund plans to invest in 25-30 early-stage climate tech companies across a variety of sectors, including energy, mobility, circular economy, food and agriculture, insurtech, and more. Since last summer the Climate Fund team has been busy: adding nearly ten companies to the portfolio as well as launching Climate Haven, a New Haven based incubator to help the earlier stage Connecticut climate tech companies scale.
Portfolio companies include Bright Feeds, which is turning food waste into animal feed, AmpUp, which is an operating software for EV chargers, Budderfly, which works with corporations across the country to reduce their utility bills with energy efficiency upgrades, and Rethought Insurance, which is a leading flood insurance startup, protecting homeowners and businesses across the country from rapidly rising flood risk.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Monday Oct 02, 2023
Monday Oct 02, 2023
Did you know that over 1900 companies and 8000 agents are using Canopy Connect to increase conversion in insurance sales and verification?
Today we talk to Tolga Tezel, Founder & CEO at Canopy Connect, who was an early engineer at Dropbox. He helped build Nova Credit for US newcomers to obtain fair access to credit through their international data.
These experiences drove him to discover other areas where consumers have a difficult time getting value and convenience from their own data. From 2019 he began interviewing literally hundreds of insurance agencies and learned that getting accurate, comprehensive data from their prospects and customers was painfully difficult.
Tolga says that consumers want insurance to be personalized, seamless and easy, and they want basic control over their data, and carriers need better data to write better risks. Canopy Connect provides the technical infrastructure to do so.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Tuesday Sep 26, 2023
Tuesday Sep 26, 2023
Jamie Yoder is President of Sapiens North America, a leading global provider of software solutions and services for all sectors of insurance.
Jamie talks about the over-hype cycle of AI and ChatGPT, where companies tend to over-estimate the impacts in the short-term but grossly underestimate the impacts in the longer term. The technology has now caught up such that it can be applied to huge amounts of data and be practically applied to create insights and answers out of unstructured data.
He also talks through how Sapiens approaches IT and the business in an organization and gets past the initial excitement about the latest trends and into incorporating these new technologies to solve a sizable business opportunity. Sapiens removes existing impediments to implementation in an organization to produce a business result and capture the value of new technologies rather than prove an unrealistic business case.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Monday Sep 18, 2023
Monday Sep 18, 2023
Michael Hennessy founded Diathrive Health to helps patients and plans manage diabetes and its costs, with test strips that are 90% less expensive than market.
Diathrive seeks to reverse the traditional model and give patients better care and outcomes while reducing the cost. Michael heard early-on "To not go into healthcare because the insurance companies are ruining it." But he found his finance and VC background could be put to work for both healthcare plans and patients, filling the gap between preventative services and patients' everyday lives.
Diathrive performs an up-front claims analysis on an individual patient and guarantees a reduction in spend between $1,000-3,000 per person per year, putting 100% of its fees at-risk to achieve results that on average can save a carrier 70-80% per year. Michael says the science is in performing a complex claims analysis and applying the behavioural standards on diabetes to remove financial and administrative barriers for the individual at no-cost to them.
Diathrive works without prescription and without a wait time, and allows physicians to not work. in a fee-for-service model, providing more time to focus on providing direct care for patients. The company distributes over health plans as the diabetes solution, benefits management organizations, brokers-consultants and also direct to employers including municipal government.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Monday Sep 11, 2023
Monday Sep 11, 2023
Aaron Steffey and Chris Kolger are co-founders of Propeller Bonds, an insurtech managing general underwriter (MGU) equipped with a proprietary instant issue surety bond platform housing nearly 7,000 instant issue surety bonds.
Propeller is a tech company built to simplify, automate, and distribute surety bonds more efficiently for agents and carriers. Aaron manages the company’s strategy, fundraising, and growth efforts, and Chris oversees the Propeller's daily underwriting operations and technological advancements of the platform.
The company sold its first bond in 2020 and now has 3,500 agents signed up to the platform, signing thousands of bonds per month and responsible for fulfillment. Aaron describes how the company built in from the "ends" and have listened to and created new product variations for creative agents where needed.
Chris talks through why speciality surety bonds such as oil & gas or cannabis can be written at much better pricing with Propeller. The tech helps increase ROI for agents and brokers who often ignore surety but can include it as a piece of a viable business for themselves. Chris sees a future where the MGA model continues to reduce friction between broker and carrier.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Tuesday Sep 05, 2023
Tuesday Sep 05, 2023
Daniel McChesney, MD is the Founder and CEO of TripDoctor, pioneering digital health insurance and health care access for expats and nomads. As a world traveler and long-time expat, he saw an opportunity to improve the healthcare access issues of his fellow expats and nomads through better insurance products.
Expat insurance is a much larger market than travel insurance, a market of $25B where the rate of Americans moving abroad having tripled since the pandemic. TripDoctor is responding to that demand with an insurtech that makes expat healthcare simple, acting as a digital broker with access to the best plans and doctors for expats in their country-of-choice.
TripDoctor is a graduate of the Global Insurance Accelerator. The company's mission is to make expat healthcare simple, affordable, and accessible, and to improve the quality of life for expats. In the longer-term, the company will help drive down the cost of care by keeping people out of the emergency department and utilizing more telehealth and outpatient visits.
TripDoctor understands the local market policy standards and costs of care and expats situation, coupling them to products that make sense in that market, and connecting them with the best providers in that market.
Daniel describes a classic insurtech story of how the company pre-GIA would meet with carriers and ramp up meetings until they reached the predictable "no" person, either a threatened PnL owner or IT. And how the company realized through GIA they would write insurance themselves.
The company launched in Mexico, where expats are concentrated in five cities, building a network of physicians through neighborhoods where expats live. They work with local insurers to create products that are both attractive and accessible to expats.
In terms of growth markets, TripDoctor is seeing high demand for other types of insurance beyond healthcare, for example in commercial business lines, as well as life products that work outside the US and work with reputable carriers.
Daniel has +20 years of experience in early-stage MedTech, digital health and other healthcare ventures, Prior to TripDoctor, he co-founded DeciBio and helped to grow it into the industry standard for molecular testing and next-generation sequencing data analytics.
This episode was recorded live at Insurtech Insights New York 2023 in conjunction with InsurTech Association. Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.

Tuesday Aug 22, 2023
Tuesday Aug 22, 2023
Bobby Touran is CEO of Rainbow (www.userainbow.com), insurance that rewards businesses for putting safety first and evolves with small business’ ups and downs.
Bobby talks about how this latest company is transforming insurance into a positive, risk-preventing force for small businesses, starting with restaurants. Previously, Bobby was CEO of Pathpoint, a digital surplus lines brokerage focused on small commercial E&S business.
Rainbow is operating as an MGU formed at the end of 2022 focused more on small commercial insurance and delivering a customer-centric experience leveraging technology.
Rainbow is distributing through agents and focuses on continuous underwriting, specializing in a class of business and creating an "underwriting advantage". Last year's market headwinds helped the company focus on creating a differentiated value proposition and front-load building their insurance product, filing and experienced underwriting operators to immediately meet market capacity.
Bobby talks about how he's "fallen in love with the insurance industry," and reveals the journey of the company's rapid growth, from bringing on new coverage products and agency focused quoting features to expanding across the states.
Follow the Insurtech Leadership Podcast airing weekly hosted by Joshua R. Hollander. We give you up-close access and personal insights from the leaders of the fastest-growing #insurtechs and most innovative #insurance carriers and brokers.