The Insurtech Leadership Podcast

Focusing on the Life of the Underwriter and Making It Better via Technology (w/Adam Cherubini, CRO Send)

Adam Cherubini leads the partnerships and business development efforts of Send, a leading Insurtech productivity platform for managing new business, renewals and endorsements. Send is a rapidly growing InsurTech software company based in London and the United States with global reach. The company has developed an innovative connected workbench that enables re/insurers and MGAs to automate, streamline and optimize their underwriting operations. 

Their SaaS platform brings complex data out of silos into one solution, providing a consolidated view throughout the lifecycle. Its automation enables new and mature carriers to eliminate rekeying, improve predictability, and work smarter.

Adam has been in leadership roles at QuinStreet, Insweb, and Willis Corroon (now WTW). He has also led consulting projects at Voom Insurance, Kelly Klee, Notion, HYLA Mobile and Pie Insurance. He was a Co-Founder and CRO of Honeycomb, an innovative digital MGA disrupting traditional real estate insurance. 

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.

Why to Make the Jump from a Traditional Insurer to a High-Growth Insurtech (w/Max McClure, SVP Underwriting & Reinsurance at Steadily)

Max McClure is SVP Underwriting & Reinsurance at Steadily, having made the inspired jump from traditional insurers to a high-growth insurtech. Steadily is an insurtech that is bringing fast, affordable landlord insurance to rental property owners. 

Steadily focuses exclusively on US-landlords as a niche, which is overlooked by bigger insurers as "product 50/100".  It is a tech-forward solution, where all of the co-founders were landlords prior to founding the company. The CEO was able to exit his prior company and invest the proceeds into building a new style of insurance for landlords.

Max recognizes that bigger organizations would take months to do what Steadily can achieve in only a few weeks. For example, how legacy platforms understand concentrations of risk reactively, vs. Steadily being able to proactively create features around that to create better underwriting.

The issues in landlord insurance are the use of 1990's products without a digital interface. Steadily can underwrite in 10-minutes online versus having to email back and forth with an agent for weeks. From a profitability perspective, Steadily managing this as a niche enables them to dig in much deeper and tailor the offer than an insurance manager with 50 different products. 

Additionally, the regulatory environment ensures a supply of information that is sufficient for Steadily to add judgment, validate and extrapolate conclusions into creative solutions. As Steadily grows, it has begin adapting its steep upward trajectory and ensure it can accommodate high growth while maintaining outstanding profitability and customer experience.

Max talks about how they've found true product-market fit, where the brand and market are now established and landlords find them vs. having to do 'sales'. He also discusses the future of underwriting, claims and profitability, the flaws of specialist tech models and how understanding the underlying business is the most critical skill of all.

Max joined the Steadily team in early 2021 from TWFG where he was the Vice President of Claims and Underwriting. Previously, Max was the President of Atlas General Agency and a commercial lines underwriting supervisor with State Farm.

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.

Reinsurance on the Blockchain -- State-of-the-Art Report 2023 (w/Karn Saroya, CEO Re)

Karn Saroya is CEO of Re, an on-chain, fully collateralized reinsurer. Re is the world’s first blockchain-powered reinsurer is building a decentralized global reinsurance market. The protocol provides investors with access to a massive and uncorrelated asset class: insurance premiums.

Re as a protocol will back insurance programs that support the risks that people, businesses and governments take to build better lives, and navigate an uncertain future.

Karn’s first company, Stylekick, was acquired by Shopify in 2015. Over the next seven years he scaled Cover.com into a national insurance platform. Karn holds a Bachelor of Commerce from Queen’s University with Distinction and a Master of Finance from the Massachusetts Institute of Technology, where he attended as a Fulbright Scholar. He is also a Y Combinator fellow and alumnus.

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.

Lengthen Your Runway and Other Tips to Surviving a Down Market - (w/David Schapiro, Planck Co-Founder)

David Schapiro is Co-Founder at Planck AI based data analytics for insurance; Chairman of the Audit and Risk Committee at ManyPets - a provider of pet insurance in the UK, Sweden and US; a Director at Ahoy! Insurance - a recreational marine insurer; and advisor to Quantee - provider of AI-based dynamic insurance pricing; Herald - Digital infrastructure for commercial insurance; and Sayata - streamlining the quote-bind-issue process for commercial insurance brokers and carriers.

In today's episode, David talks about how to navigate the current markets, from an insurtech perspective and from an insurer's perspective.  He discusses how insurtechs can dig in to focus on business results and cut costs to extend their runway, buying themselves time for higher valuations to return or negotiating a down round with existing shareholders to protect their investment.  

He also contrasts that to the view of a large insurer, who have 80% retention, less than 100% combined ratio and have the wherewithal to be patient.  The insurers in particular now face decisions as to whether now is the time to partner up or run M&A with insurtechs, and help redefine how their culture will feel on the other side of this market inflection. 

A visionary and veteran CEO and Director with over 35 years’ experience with data analytics and Insurtech companies. David is well versed in leading and growing enterprise SaaS companies including Earnix and ClickSoftware (acquired by Salesforce $1.35B in 2019).

From 2006-2017 David was the CEO of Earnix, a provider of analytical SaaS for the Financial Services. David led Earnix from a small startup to becoming one of the leading analytical Insurtech players providing value to many of the top global financial institutions.

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.

Learning from Real Stories of Insurance Change (w/Bryan Falchuk, Founder Insurance Evolution Partners)

Bryan Falchuk is Founder of Insurance Evolution Partners, which advises carriers and their partners on how to navigate an evolving industry facing disruption and change. He is also the President & CEO of Insurance industry trade group, PLRB, that is dedicated to helping adjusters to make expert decisions on Property and Liability claims.

Bryan spent 20+ years in the insurance industry, including serving as Head of Claims for Hiscox USA and leading Growth for insurtech communications solution, Hi Marley. Bryan has also held leadership roles in corporate strategy, operations and distribution at carriers like Liberty Mutual and Beazley. He was a consultant in McKinsey & Company’s insurance practice and is on the advisory boards of several startups focused on the insurance industry.

Bryan is a best-selling author and public speaker, including several TEDx Talks. His best-selling book series, The Future of Insurance, shares case studies of legacy and startup carriers overcoming barriers to change.

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.

Breaking Down Barriers for Insurtechs: Why We Launched a Non-Profit Industry Association (w/Bob Sargent & Doug Ver Mulm, InsurTech Association)

Bob Sargent is President and Co-Founder with me of the Insurtech Association (ITA), a membership-based non-profit organization designed to support and represent all facets of the Insurtech ecosystem. Doug Ver Mulm is Volunteer Executive Director of the ITA.

In addition to his work with the ITA, Bob is also the CEO and Co-Founder of eSpecialty Insurance, a digital retail broker specializing in specialty lines insurance, and Doug is Co-Founder of a stealth startup serving the financial operations needs of the insurance industry - his second in Insurtech.

The InsurTech Association, launched in March 2023, carries the primary mission of supporting creators of technology. Open to any individual or organization with an interest in Insurtech, the founding board features a diverse group of founders who have successfully navigated the challenges of launching an Insurtech company. Four board members have experienced successful exits and continue to concentrate their efforts in the Insurtech space.

The ITA assists early-stage Insurtechs in navigating the inner workings of the insurance industry through various measures such as:

• Networking support
• Peer-to-peer dialogue
• Mentorship
• In-person and virtual educational events
• Community building
• General business acceleration

We encourage all followers of the Insurtech Leadership Podcast to join the ITA as members and to participate in upcoming events. For more information, please visit insurtechassociation.org/events. There are also sponsorship opportunities available for companies wishing to showcase their involvement in the industry to a startup audience, network with potential customers and partners, and expand their reach.

In addition to his roles at eSpecialty Insurance and the ITA, Bob is a strategic advisor to and an active investor in early-stage Insurtech companies.  Previously he founded, built, and sold a wholesale insurance broker and underwriting manager specializing in Professional Liability Insurance (E&O, D&O, EPL & Cyber Risk), and was a Board member and President of NAPSLO (predecessor to WSIA), the specialty insurance trade association.

Doug co-founded Stable Insurance, a commercial auto MGA focused on the rideshare and carshare space. He also spent over five years as a corporate counsel at Mercer, focusing on data security initiatives and IP issues. Before law school, Doug was a financial analyst at several investment firms in Chicago.

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.

Large Language: GPT4 Can Handle Insurance But Isn’t Ready for Core Processes Just Yet (w/Tom Wilde, CEO Indico)

Tom Wilde is CEO at Indico, an intelligent intake solution automating critical middle office workflows across insurance, banking, real estate and healthcare.

'Intelligent intake' at Indico means the starting point for insurers' most critical workflows including underwriting, claims and policy servicing. The common denominator is data culled from emails or other documents, taken from an unstructured format to feed core platforms and decision systems. 

The original digital transformation started with the new customer-facing mobile device, but transitioned through the back office then into the middle office of insurance where business-critical decisions take place. Tom describes actuaries as the original data scientists, taking data and turning them into decisions.  Their modern engines were designed to run on clean sets of data, but unfortunately the reality is that most data lives as unstructured and requires manual rework before it can be used.

Indico was early on understanding the impact of deep learning and large language models, and were the first to build a large language model that allows customers to customize their own machine learning models and solve unstructured data challenges. 

Tom feels strongly that generative AI (eg. GPT4) can easily handle the context of insurance, because the depth of context-understanding enabled by trillions of parameters can understand any context a human can. There are however three main problems to commercially scaling insurance use cases today using GPT4: it is extremely computationally expensive, insurers' data is still sensitive and proprietary, and GPT4 essentially makes up an answer (lies) when it doesn't know one.  Until these large language problems get solved, insurers will be held back from using generative AI in core processes. 

Prior to joining Indico, Tom was the Chief Product Officer at Cxense, a data management provider and founder of Ramp, an enterprise video content management company. Tom worked at Fast Search, Miva Systems, and Lycos. He has an MBA in Entrepreneurial Management from Wharton.

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.

We Turned Employee Safety & Compliance Into an Insurance Product (w/Jason Berkowitz, Founder ArrowUp)

Jason Berkowitz is currently CEO and Founder of ArrowUp, providing restaurant safety, compliance & leadership. ArrowUp helps restaurant owners reduce risk, satisfy compliance regulations and develop a culture of safety.

ArrowUp's Insurtech platform strengthens the relationship between the insured and insurer by utilizing tools to promote safe habits and capture data for enhanced underwriting, ultimately lowering risk and liability for insured restaurant owners.

He is addressing a market size of $16B in restaurant claim payouts annually, in a culture where lawsuits and union suits are commonplace. ArrowUp makes restaurants safer by providing leadership development, lowering turnover and building upon the culture within an organization to avoid unnecessary lawsuits. The results have been tremendous, with restaurants seeing 30-50% risk reduction based on OSHA standards for its customers.

Jason has opened over 50 restaurants, served as VP of Operations for Umami Burger, and COO and Partner for Tocaya Organica. 

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.

Rebuilding a 40-Year Old Company into a High-Growth Tech Platform for Agents (w/Jackson Cromer, President BondExchange)

Jackson Cromer is President of BondExchange, a leading national surety-focused wholesale insurance agency serving retail insurance agents for over 40 years. Since 2012 the wholesale MGA, based in Charlottesville, NC has been boosting its automation and tech capabilities as well as redesigning its end-to-end customer experience. The company is currently bringing in business financial data and personal asset verification via a new partnership with Finicity.

 

BondExchange's technology provides a one-stop-shop for agents to efficiently quote and issue bonds in all 50 states. The company is open architecture meaning it partners across multiple insurance companies and uses an easy process that is profitable for the agent. Underwriting has been fully automated via algorithmic processing of credit data, requirements on past-due amounts, the summary of liquid accounts. The company also uses a unique bond library documenting how a bond is filed, which forms must be used for reporting purposes, and with highly structured underwriting notes for example on specialty bond clauses.

 

Jackson describes how as trust in a relationship increases over time, premiums decrease. Therefore he is focused on customer service and adding value and capabilities in surety bonds on the platform. 

Jackson digs into how he is driving technology investment, organizational growth and building brand awareness via continuous agent communications in new and existing market segments.  He also addresses how the company is focused on its internship program to develop new talent into a specialist market such as surety bonds.

 

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.

 

Opening a Profitable Insurance Niche Market Means Finding Tribes (w/Blair Baldwin, CEO Boundless Rider)

Blair Baldwin is CEO of Boundless Rider, a specialty MGA focused on product innovation for the motorcycle, power-sports, and e-bike markets.

Tribes of riders form an underserved market niche that includes motorcycles, UTVs, snowmobiles and new forms of mobility.  Because these categories represent only 2-3% of an insurer's book, they have not introduced unique new customer personas of riders. Boundless created a new brand of customer experience, and added new features to the product. One example is an e-bikes optional endorsement linked to the Boundless mobile app that enables product discounts for usage. 

Blair says that the digital self-serve experience is outdated and cumbersome. They put in features that encourage safety for example requiring the use of a helmet in order to be covered.  His biggest surprise has been the collaboration with carriers to run this part of the business so that they can concentrate on larger lines of business. 

Prior to launching Boundless Rider, Blair was the Co-founder/CEO of Quilt, a venture-backed insurtech that was acquired by MassMutual, where he later ran a product innovation studio. Blair started his adventures in insurtech as the Chief Marketing Officer for Goji, an early insurtech pioneer that raised over $100M in venture capital funding. He is a graduate of Harvard College and Harvard Business School.

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.