Fintech Interview with Ascend’s Co-Founder & Co-CEO Praveen Chekuri

FTB News DeskNovember 15, 202222 min

The core of insurance products does not change owing to addressing customer issues on a wide scale. How can insurance companies ensure their customer reach?
Praveen Chekuri, Co-Founder & Co-CEO, Ascend

Praveen Chekuri is the Co-Founder and Co-Ceo at Ascend, the first modern insurance payments platform that provides automated, all-in-one financing, collections, and payables. The company is backed by Index Ventures, Distributed Ventures and their anchor limited partner NFP, HSCM, XYZ Ventures, First Round Capital, Susa Ventures, FirstMark Capital, Box Group, amongst others. Prior to starting Ascend, Praveen built a home maintenance startup called Sheltr, which provides homeowners with routine preventative maintenance service and diagnostics to offer data-driven proactive care to catch issues before they become costly repairs. The company became the first acquisition made by insurtech unicorn Hippo because of its intuitive and technological approach to building an insurance product that went beyond the customer interaction. Praveen started his technology career at Instacart, leading the company’s product and data integration team.

1. Can you tell us more about yourself? How did you get into entrepreneurship?
a. I started my career as a software engineer at a variety of companies, including Instacart and Houseparty. Instacart is where I met Andrew Wynn, my now co-founder and co-CEO.
b. In 2019, we founded our first company, Sheltr. Sheltr was a home maintenance startup that provides homeowners with routine preventative maintenance service and diagnostics to offer data-driven proactive care to catch issues before they become costly repairs. We were inspired to take this first step into entrepreneurship because XXX. A couple years later, and it became the first acquisition made by insurtech unicorn Hippo because of its intuitive and technological approach to building an insurance product that went beyond the customer interaction.
c. This first step into entrepreneurship taught me a lot, but most importantly, it set myself and Andrew up for success with our next endeavor: Ascend.

2. What was the inspiration behind designing Ascend services?
a. At Sheltr, Andrew and I witnessed firsthand while working on the distributor side of insurance, the challenges that existed on the back end for insurance sellers and how it impacted building strong customer experiences. We decided to start Ascend to fix this pain point for insurance sellers as well as customers, contributing to the much needed modernization of the insurance industry’s financial infrastructure.

3. Were there any challenges while tapping into the fintech markets considering the competition?
a. Insurance is an incredibly old and antiquated industry, and I think that a common challenge/misunderstanding that many people have when entering the space is thinking that they’re going to come in and turn the place upside down with their ground-breaking innovations. Ultimately, it’s important to remember that insurance is a very old and established product, and at its core, that’s not going to change. Insurance as a risk-sharing mechanism will still be the core offering. What will change is what we’re protecting (eg. hacks), how we’re protecting it (telematics), and how we’re interacting with our insurance providers.
b. Because of this, a big challenge is simply the nature of the space itself – there are these huge, bureaucratic, companies that have existed for a long time. And every single insurtech on the market is trying to outdo them – a massive and oftentimes impossible undertaking. I think what we’ve learned works best is to co-exist. Don’t fight to dethrone the legacies and incumbents, work with them instead.

4. Could you tell us more about Ascend and how has the company evolved over the last couple of years?
a. Ascend is the first modern insurance payments platform that provides automated all-in-one financing, collections, and payables. It saves distributors from labor intensive, expensive processes while providing customers with the great online checkout and financing experience they’ve come to expect. Ascend was built on the premise that, as the insurance industry moves from offline to online, insurance distributors–from brokers to MGAs to carriers–will need to provide a modern seamless customer experience with a payment infrastructure in order to keep pace with the increasing demand for high quality customer experiences. Ascend’s API provides distributors with the technology to sell more policies and increase customer experience. By using Ascend, customers can pay the full amount for the year upfront in full or with flexible financing that best fits their needs. It’s an online payments solution and a “buy now-pay later” model custom-built for insurance.
b. Since starting Ascend, we’ve seen immense growth that we only dreamed could be possible. Currently, we’re operating nationally in all 50 states working with industry-leading customers. Ascend customers have seen increases in policy purchase conversion due to the reduced friction when given the option of monthly flexible payments at point of sale. In some cases, customer adoption of financing has more than doubled from less than 40% (pre-Ascend) to 80% (post-Ascend). Additionally, millions of dollars of policies have been transacted through Ascend with the average value of each being nearly $10k, 61% of transactions are premium finance loans, the remaining 39% are policies paid in full while 33% of checkouts created convert to a transaction and 30% of all conversions are on the same day the checkout is created.
c. This year, my partner and I have been focused on forging partnerships with agency networks, insurtechs, MGAs, and AMSs to complement innovations being made across the insurance industry. Ascend recently announced its first AMS integration with NowCerts to provide agencies with a comprehensive solution that combines workflow management with the best of both payments and premium financing. They also announced an integration with HawkSoft’s insurance management platform designed for independent agencies. Additionally, The Agency Collective (The AC), Independent Insurance Agents of North Carolina (IIANC), Veruna, and Professional Independent Insurance Agents of Colorado (PIIAC) have endorsed Ascend as their preferred payments and financing platform for their vast member networks. Furthermore, we partnered with Stere to provide existing brokers, MGAs, and carriers with the best-in-class digital experiences.
d. Also this year, we announced that Ascend has raised $30M Series A in equity funding, bringing our total funding raised to $39M along with a $250M lending commitment to finance insurance premium loans through its platform facilitated by Hudson Structured Capital Management Ltd.

5. What’s your favorite part about working in this industry?
a. My favorite thing, which is also probably one of the most challenging parts of the job, is how quickly everything changes.

Technology is developing at a rate like never before, and almost every moment there’s a new company making headlines.

Yes, it can be intimidating to see the up-and-comers, and yes, there is a nagging pressure to always keep up with the latest tech so that your own doesn’t get outdated. But this also is what makes things exciting. I love seeing what the newest trend is, what companies are doing, and interacting with the growing community. It keeps you on your toes and encourages you to never stop. I am always on a quest to keep growing and developing our product, making it better and better, and making it more accessible and applicable to people everywhere. And this constant change in the industry helps keep that fire lit.

6. What makes Ascend unique? How does it stand apart from the competition?
a. Ascend puts user experience top of mind for all parties in the insurance payments process. For insurance customers, we provide an easy to use purchase flow with flexible payment options. For our insurance sellers, we are a single paperless solution that handles financing, collections, and payables.
b. Additionally, our API eliminates the need for digital brokerage, online sellers and distributors of commercial insurance to build their own payment infrastructure. Ascend integrates with the systems you already use to power a checkout flow that handles all forms of customer payment — from credit card and ACH to premium financing — and programmatically distributes funds for commissions and carrier payables

7. What are the biggest challenges you’ve faced when trying to grow your business?
a. Something that took me by surprise was just how much fundraising takes out of you! It’s a challenge mentally and physically. Moreover, it comes at an opportunity cost to the business – when you are fundraising you can’t spend time working on all the other critical functions like sales, hiring, and product development.

8. How do you see the current fintech scenario and its evolving possibilities to meet the growing customer demand?
a. In the past, we’ve seen the most convenient insurance distribution and acquisition mechanisms be wildly successful at customer acquisition even if the products aren’t as good, or the products are more expensive. Conversely, there are great insurance products out there that are fairly priced and cover the most real risks that people actually face. There’s probably a bunch of them out there that are hard to find. Even agents and brokers who do it all day have a hard time finding those sorts of diamonds in the rough. I think these two scenarios need to go in parallel because humans take the path of least resistance. If you have a good insurance product and business, you need to ensure that the distribution and experience around that product is convenient, or people simply won’t take advantage of it.

9. Can you give us a sneak peek into Ascend’s development plans?
a. Our biggest focus right now is still on forging partnerships with agency networks, insurtechs, MGAs, and AMSs to complement innovations being made across the insurance industry. While we’ve announced several over the past year, we still have quite a few up our sleeve that people can expect to hear in the upcoming months.

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FTB News Desk

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