Exploring ways to approach Insurtech innovation at Dig-In


Last week, I attended Dig-In: The Digital Future of Insurance in Austin, TX.

Nathan Golia, Editor-in-Chief of Digital Insurance, shared in his opening keynote that there were 1,300 attendees, 100+sponsors and exhibitors, 10 tracks and over 200 speakers.  


This was the largest conference I have attended this year and marked the mid-way point of my current conference blitz.      

There were a number of insightful panels on a wide array of topics, as well as an abundance startups and vendors both presenting and displaying their solutions.  The networking was aplenty too, with 40 tables set up for Brella meetings. 



For me personally, in addition to covering the event for Daily Fintech, I also intended on networking for business.  This includes finding potential carrier partners for some of the startups I’m working with.

This gives me a multi-pronged vantage point:

  • Being part of the ‘press’ means that the most common question I get asked is ‘is this on the record?’  The answer is no.  Both I and Daily Fintech treat anything that is not in the public domain as being confidential.
  • Being a ‘consultant’ means that the other most common question is ‘what are you trying to sell me?’  The answer is it depends. If you are an incumbent I will want to talk to you about one of our startup clients. If you are a startup, I will want to talk to you about our services to help you better connect with incumbents.

Between the networking and attending some panels/talks, I gathered some themes at the conference along the lines of some of the articles I have written over the past few weeks. 

This week, I focus on:

  • ‘Jumping in’ to innovation
  • Selling B2B Insurtech solutions
  • Culture is critical

‘Jumping in’ to innovation

Ken Rosen, EVP and Chief Claims Officer of Allstate, kicked off the conference with a talk about ‘The Future of Catastrophe Response’.  


He started off by stating our industry mission to ‘Help restore customers lives as quickly as possible’.

At the core of it, our purpose in this industry is to make people whole when they have a loss.  

Yes, there are other services and benefits we can give them throughout their policy lifecycle. However, if we can not pay a claim to them when they have a loss – fast and in a method that makes it easy and convenient for our policyholders, then we are missing the point of what we are here to do.   

He went on to explain that the hurricanes of 2017 are what prompted Allstate accelerate their work in digitization.  He showed how Allstate is using satellites to triage a loss and get granular imagery of where their clients are. They use drones to get specifics for each home/area that may be affected and AI for assessing claims.  

These solutions are currently being used and explored by many of the P&C carriers, both for cat and non-cat events.

It was Ken’s challenge to the audience which helped set the stage for me for the rest of the event.  He challenged everyone in the room to think ‘how we could jump in as an industry and push the envelope on behalf of customers to up our game’.  

As part of that, he went on to demonstrate that this means we all need to be testing, learning and iterating our innovation initiatives, saying we need to ‘truly listen to our customer’ and ‘push the limit’.

This is probably the single biggest challenge for our industry.

We are, by nature, a risk averse industry.  We do not like to do things that don’t have certainty.  Yes, we price products based on unknown events, however we have enough back data and underwriting controls in place to ensure we don’t bring extremely bad/unknown risks on the books.  

Trying out new processes, tools and ways of doing business is not within our core culture.  Innovation for our industry typically means ‘legacy system replacement’.

To really reinvent insurance, to really give a good customer experience, we need to have a different mindset about how we do things and how we engage with our customers.  We need to look at the pain points they have and identify how various customers want to deal with their Insurance providers.  We need to work with our customers on this, not just assume we know what they need.  Then, we need to find the right technologies (and potentially technology providers) to solve these problems.  

This can include changing business models completely, not just updating legacy systems.  We need to go into this with an open mind and explore options that will keep us relevant and important in the minds of our customers.

The next panel I attended took a view from the other side, looking at how technology providers are trying to solve this conundrum.  

Selling B2B Insurtech solutions

The B2B Insurtech – Best Practices in Empowering Incumbents panel, included Gregory Bailey, CEO of Denim, Jane Wang, CEO of Optimity and Dan Woods, CEO of Socotra.  It was moderated by Farron Blanc, VP, Innovation Studio Lead at RGAx.


The panel started with some of the ‘positives’ that these CEOs have experienced in partnering with carriers.  

This included discussion on what the ideal incumbent client is as well as how long it takes from first conversation to POC.

In regards to both of these points, Jane shared that to achieve the traction Optimity has, she not only focused on finding the right carrier partner but the right individuals within it. She looks for personalities within the carriers who have both political influence in an organization as well as the attitude of problem solving and learning. Her champions gets technology and is good at being knees-deep in execution. This combination has helped her in finding the right champions to help push their innovation forward (tip for startups out there…try and identify this person in your conversations!) 

For Optimity, they have had success in offering a light version of their product, which allows organizations to test out what they will be using.  Even though, first they didn’t want to because of fear of being copied, now their solution is more robust and it’s less of an issue.  By implementing a super light pilot, some times within weeks, they are able to prove out the business case and give the carriers a visceral experience.  These clients get more ideas on what they can do and plan full commercial implementations faster.

On the flip side of this discussion, Farron asked the panel of some ‘blockers’ as it relates to forming a partnership with a carrier.

Gregory shared that one of the biggest challenges his team faces is in regards to staff changes.  People leave and/or move to another department/company. Due to this, his company has learned to build a robust ‘nurturing and pipeline process’ when selling into a carrier.  This includes building a ‘triage’ to the organization, and having multiple entry points, from the C-suite all the way down to junior level employees, to ensure that they do not have to ‘restart’ the sale if their key contact leaves (another tip for startups out there…do this!).

Dan talked about the time horizon of innovation and explained that ‘if a carrier wants to get somewhere in 10 years, they should start experimenting now’ (similar to Ken’s presentation).  He also went on to explain how the RFP process can prohibit the carrier from ‘just trying the product’ (similar to Jane’s point above, the sooner they can try the product, the quicker they will know if they like it or not).  

I have been part of enough RFPs before (on the carrier side) to understand Dan’s point.

Carriers – I understand the meaning and purpose of an RFP.  Your vendors do too. There has got to be a better way to do this to make you feel comfortable and to streamline the process.  If only there were a guide out there to help.

There are multiple ways for carriers to go about their partnerships and innovation efforts.  The concept of build, partner or buy is a conversation many executives are having.

How to get to the answer of that question can differ from company to company..

Culture is critical

One of the increasingly popular options for re/insurers to scout technology and help solve problems for customers and within corporations, is the setup of an Innovation lab.

Kim Garland, SVP of Commercial Lines and Managing Director at State Auto and Tom Walker, President and CEO of Rev1 Ventures discussed the setup and operations of State Auto Labs.


Kim started by sharing the fact that State Auto is a mid-sized carrier that had been shrinking it’s in-force policies over the past 7-8 years made it a perfect candidate for Innovation.  Larger carriers will have a tough time with implementing ‘radical change’ and with the successful ones, it’s hard to change something that is going well and ‘status quo’.

Once determining that the State Auto was a good candidate for an Innovation lab, both Kim and Tom realized that the next focus needed to be on goal setting and cultural change, with a larger emphasis on culture.

Most of the conversation about Insurance companies adopting a culture of innovation is one that has been ongoing for some time now.  ‘The norms of innovation are different than the norms of running an insurance company’, stated Tom. I believe this is a concept that many of us in the industry have known and are currently coping with.

I’ve been seeing and hearing more about the domain expertise that startups/technology vendors must have and understand when dealing within the Insurance industry.  Tom further went on to explain that startups need to ‘recognize that they have just landed on a new planet’ when it comes to Insurance. Insurance is a highly regulated industry with different rules, regulations and processes than any other industry out there.  

The combination of both domain experience and technology expertise is going to equate to the winning strategy for Innovation.


Dig-In was a great conference and great opportunity to see and learn about a variety of different topics.  It has also reaffirmed some of the best practices and lessons learnt from B2B Insurtech sales/partnerships, something that I do in my day to day business

There is a healthy amount of excitement, frustration and fatigue that I am seeing and hearing from the attendees at the multiple conferences I am attending.

Excitement from incumbents to hear new ideas.  Excitement from startups to present their ideas and see their prospective clients and investors.

Frustration from incumbents because startups think they know their business better than they do.  Frustration from startups because incumbents don’t get it (or move to slow).

Fatigue from both sides because of the number of meetings, presentations and information being thrown at them.

This is good.

This is necessary.

Change is not easy.  Change does not happen overnight.

This continuing drive to push and challenge each other (while focusing on customer outcomes), is what will drive the changes needed in Insurance.

Stephen Goldstein is an experienced Insurance executive and Insurtech dealmaker with a core focus on growing revenue, launching go to market initiatives and advising industry leaders.

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