Digital Insurance Summit 2026
May 18 - 19, 2026
Westin Copley Place - Boston, MA
Day One – July 15, 2019 DIGITAL CUSTOMER ACQUISITION: Engaging and acquiring the modern insurance customer through digital commerce
7:30 am - 8:30 am
Continental Breakfast & Registration
8:30 am - 8:40 am
Welcome Remarks & Ice Breaker
Victoria Spadaccini -
Program Director,
Digital Insurance Summit
8:40 am - 8:55 am
Chairperson’s Opening Address
Alex Feldman -
EVP Business Development,
auto-savings.com
8:55 am - 9:15 am
Keynote: What is Innovation, Really? Forward-Thinking with a Risk-Adverse Mind-set
Scott Sanchez -
Chief Innovation Officer,
Nationwide
With so much talk about "innovation" it's time we break down what being "innovative" truly means. You'll discover how a risk mindset of insurance can actually be an asset to innovation as opposed to a hindrance, and explore Nationwide’s “design-thinking” approach, helping you re imagine your own ground-breaking approach to the digital customer journey.
9:15 am - 9:35 am
Peer to Peer Fireside Chat: The Future of Insurance – 2025 and Beyond
Ellina Shinnick -
Chief Marketing Officer,
HUB International
Richard McCathron -
Chief Insurance Officer,
Hippo Insurance
The power is now in the hands of the consumer and it’s changing the way companies do business. In this C-Level Fireside Chat we position two of the most forward-thinking pioneers in insurance together to interview each other, and explore the answers to the following questions and more:
· How consumer demand and influence is going to shape the next 5-10 years of the insurance industry and beyond
· What necessary shifts you need to make to survive and thrive long-term
· How you can leverage and identify new innovations in technology that create brand loyalty
9:35 am - 10:05 am
Panel: Using Advanced Personalization to Win Over New Customers
Michael Flynn -
Director of Marketing,
Metromile
Jeff Kroeger -
EVP – Strategy and Business Development,
Insureon
Byron Udell -
Founder, President and Chief Executive Officer,
Accuquote
Jeff Merkel -
Co-Founder,
Ladder
Kevin Kennedy -
Executive Vice President of Carrier Business,
EverQuote
Insurance innovators agree – it’s all about KYC (knowing your customer). With cutting-edge technology, you can collect huge aggregates of real-time data that empower you to identify the most valuable customers and then construct hyper-relevant policies, pay-per-use coverage, instantaneous underwriting, and stop and start coverage when the customer wants. Want to beat the competition? This is how you do it.
• Utilizing data and technology to set personalized premiums based on an individual’s risk
• Using machine learning/AI/personalization to drive acquisition campaigns and best target customers
• Utilizing data to customize the customer’s insurance plan
• Pinpointing the threshold of pain for customers and recognizing its impact on response time
10:05 am - 10:15 am
Panel Q&A: Using Advanced Personalization to Win Over New Customers
10:15 am - 10:55 am
Refresh & Recharge AM Networking Break
Stop by the Solutions Zone for a quick pick-me-up to keep your creative juices flowing throughout the day!
Also, this is your chance to collect stickers for your punchcard and take a swing "On The Green" - a friendly golf competition where prizes are just around the corner.
10:55 am - 11:20 am
Serving Consumers as Population of One: Providing Seamless End-to-End Consumer Experiences
Mariya Filipova -
VP of Innovation,
Anthem
With the convergence of exponential technologies, the pace of change is occurring at a rate never seen before. Additionally, a new level of consumer expectations are requiring insurance policies to accelerate new strategic bets, digitization, and the adoption of exponential technologies. That being said, gone are the days of developing five year digital road-maps. We will explore how policies must drive advancements through the use of technologies to:
- Enable a fail-fast mindset to accelerate innovation
- Empower consumers to understand and manage their health through simple, intuitive experiences
- Create transparency and accessibility to healthcare services, products, and solutions
- Deliver unprecedented insights to care processes, treatment plans, and products
- Define new consumer engagement strategies around achieving better health outcomes and cost of care reductions
11:20 am - 11:45 am
Learn & Poll Case Study: More Money, More Problems - Forming New Pricing Strategies
Anthony Tornatore -
Director Insurance Product Management,
Kin Insurance
Regardless of the customer experience, cost will always be a crucial factor in the purchasing decision. Find out how you can customize your pricing strategy to the exact needs of your customers based on their real-time behaviors as well as data on their lifestyles, risks, and environments. Be sure to attend as Anthony shares his lessons in:
•Tapping into new data sources that can predict risk and allow you to offer a personalized premium
•The emerging definition of risk in a cutting-edge world
•Discovering the brand new insurance service model
•Keeping a watchful eye: combatting pricing competition
•Keeping track of partner sites and other insurance sites—ensuring rate parity agreements are in-tack
•Segmenting data to push customers the best deals that are tailored to their interests
11:45 am - 12:25 pm
Talk Show Panel: Digital Revolution is a Culture Evolution
Ann Bair -
Chief Digital Officer,
Nationwide
Jeff Berezny -
Head of Global Product & Marketing,
Trov
Dedra Mitchell -
Senior Manager, Business Transformation,
Aflac
Joel Jackson -
VP of Marketing,
Pekin Insurance
We're on the cusp of 2020, roughly 250 years since the first insurance policy arrived to the American landscape. While some standards of business have remained, consumer technology has advanced light years, putting customers in the driver's seat and propelling an industry steeped in tradition to rapidly transform their customer acquisition and retention strategies. Where do you begin? Our all-star panel of insurance master minds come together to share their points of view, and then pose the question back to you, the audience, to work together to develop the sharpest path towards customer-first innovation, from within your organization all the way to the customer. You'll learn:
- The shift in the insurance industry that led to the need for consumer-centric digital strategies
- Working with the top: getting executives to champion digital change
- Thinking like a start-up: becoming nimble, agile, and efficiently executing A/B testing
- Delivering an exciting vision by building customer-driven design solutions
- Getting digital, product, and onsite teams to listen and leverage one another: delighting users, solving problems, and driving real business results
12:25 pm - 12:35 pm
Talk Show Panel Q&A: Digital Revolution is a Culture Evolution
It’s your turn! Our panelists answer your burning questions on the digital insurance revolution.
12:35 pm - 1:35 pm
Lunch For All Attendees
Track A:
Digital Marketing
1:35 pm - 1:45 pm Track Chairperson’s Opening Address
1:45 pm - 2:15 pm Engineering an Effective Omni-Channel Strategy
Cora Hall - AVP Group Benefits Marketing, The HartfordMany carriers rely on direct mail because it works and the ROI is seamless. Underwriters and actuaries prefer a sure thing and are skeptical of digital marketing investments that may or may not pay off. Our products are highly regulated and consumer interest varies dramatically by generation yet, we know channel preferences are changing and customer-centric experiences improve sales. In this session, you’ll learn how to build an Omni-Channel strategy from the ground up, embracing the challenges and transforming your culture to focus on test and learn.
Track B:
Emerging Technologies
1:35 pm - 1:45 pm Track Chairperson’s Opening Address
1:45 pm - 2:15 pm Case Study Revolution: Allstate’s Virtual Assist app and How it Helps Customers Streamline the Claims Process
Sean Beavers - Product Owner and Business Architect, AllstateVirtual Assist by Arity app is a live, on-demand video chat app that makes the customer experience even more convenient. Auto body shops can instantly show vehicle damage in real time to an auto technical Allstate representative so a supplement review and decision can happen instantly and the repairs can start faster. With no appointment and no waiting, you’ll clear up your floor space sooner.
Creative Board Rooms
1:35 pm - 2:15 pm Creative Boardroom – Staying Innovative and Flexible in a Highly Regulated Marketplace
Roman Geyzer - Senior Director of Product, Northwestern MutualInsurance is a highly-regulated marketplace, and companies often move faster than the regulations. While regulations are in place to protect the customer, it often feels as if it stops the industry from digital advancement. You'll determine best-in-class strategies to:
•Navigate the increasing rules on using and protecting customer data
•Handle state-by-state inconsistencies related to innovations in the insurance industry
2:15 pm - 2:55 pm Panel Interactive: Time Waits for No One: Improving the Speed of Change in Your Organization
Mike Ashkar - Chief Counsel Global Risk and Digital, Marsh Jen Swanson - former Vice President, Digital Product Management, Optum Abel Travis - Vice President of Underwriting and Product Innovation, AF Group Jonathan Metrick - Chief Marketing Officer, Policygenius Anthony Grosso - VP, Product Marketing and Industry Strategy, EIS Group, Inc.The digital revolution is making its way into insurance business strategies, but integration speed staggers. What are the main roadblocks that slow down implementation and how do we transform our approach so change becomes more immediate? After a 30 minute panel session, our panelists pose a specific question/challenge back to you, the audience, to discuss your takes on the topic together. You'll learn about:
•Changing rigid ways of thinking and getting your organization on-board to do business differently
•Creating room for unanticipated scenarios and training
•Implementing best practices on training
•How will roles and organizational structure change based on technology needs
•Understanding change is not just project development but also software development - empowering IT and digital marketing counterparts
•Prioritizing – what needs to happen in what order
2:55 pm - 3:05 pm Innovation Spotlight: Acquiring New Long-Term Policy Holders with Google Marketing Technology
Ashton Howe - Director of Marketing, Delve
3:05 pm - 3:25 pm Getting Customers To Not Just Think, But Do: A Behavioral Science Approach
Matt Wallaert - Chief Behavioral Officer, Clover HealthWhen we build insurance products, we often have very specific behavioral goals in mind, things we want customers not just to think and feel but actually do. Yet, our design process so rarely takes what we know about changing behaviors into account. Join behavioral scientist Matt Wallaert as he talks about “Competing Pressures Design”, a psychology-based method for thinking about product and service design, using science, startups, and plenty of practical examples to help you put theory into practice.
2:15 pm - 2:55 pm Marketing Beyond Digital to the Human Experience
Kim Brown - Head of Marketing and Communications, AMA InsuranceToday’s world is full of digital noise, countless options and commoditization across industries. It’s critical – now more than ever – for businesses to have clear and powerful differentiation and market presence to drive growth online. In this immersive and interactive program, you will discover
•How human-centric marketing can drive and develop breakthrough digital strategies that drive growth
•How to forge a clear path forward for your business in these times of high growth demands, constant change, unexpected disruption and hyper-connectivity
•The misunderstandings and old definitions attached to “digital”
• How to become the experience champion
• How to transform marketing strategy from technology-driven to human-driven
2:55 pm - 3:05 pm Innovation Spotlight: Use Cases of A.I. Solutions Driving Greater Conversion and Efficiency in Insurance
Matt Coughlin - Founder & CEO, XSELL Technologies Mike Hubbarth - AVP of Financial Services, XSELL Technologies
3:05 pm - 3:25 pm Transforming Your Team to Follow the Customer Journey
Roman Geyzer - Senior Director of Product, Northwestern MutualIn an industry focused on managing risks, making bold choices is not the expected norm. With that in mind, it takes true leadership and teamwork to develop and implement the vision, the support, and the building blocks that will allow your company a new digital future.
•How do you incentivize people to do new things and not be afraid of failure?
•How do you create an extraordinary employee experience that results in an extraordinary customer experience?
•Moving from what you’ve always done to brand new digital processes
•What do you need to build?
•How do you develop those skills?
2:15 pm - 2:55 pm Creative Boardroom - People, Process, and Technology: Driving Digital Transformation through Intelligent Automation
Chris Frankland - Founder, InsurTech360 & Head of InsurTech, ReSource Pro, Insurtech360What is Intelligent Automation and what role does it play within your Digital Transformation strategy? We will be discussing the critcial role Intelligent Automation has to play across your organization, from back-office operations to re-imagining the customer experience through chatbots and virtual assistants. We will be talking about the role of the Customer and finding the ideal balance between People, Process and Technology and how and where they are used across the Insurance Value Chain can dramatically improve or negatively impact the end Customer Experience.
- Your RPA & Intelligent Automation Strategy - where do you start?
- Traversing the Automation Maturity Curve - from RPA to Intelligent Automation
- Balancing People, Process and Technology across the Insurance Value Chain
- Building your Center of Excellence
2:55 pm - 3:25 pm Women Empowering Women in Insurance Meetup
Jen Swanson - former Vice President, Digital Product Management, OptumMeet other female insurance leaders in this peer-led discussion group focused on leadership, mentoring, work/life balance, and more!
3:25 pm - 4:05 pm
Sweet Treat PM Networking Break
Craving something sweet? Head over to the Solutions Zone for a treat!
Be sure to stop by a few booths to complete your punch card and swing to win a $10 Starbucks gift card at our "On The Green" golf game.
4:05 pm - 5:05 pm
Digital Insurance Roundtables
Vivian Arestia -
Assistant Vice President, DTC Marketing,
Metlife
Chris Frankland -
Founder, InsurTech360 & Head of InsurTech, ReSource Pro,
Insurtech360
Gerald Chiddick -
VP of Marketing,
Amerisure
Abel Travis -
Vice President of Underwriting and Product Innovation,
AF Group
Jeff Berezny -
Head of Global Product & Marketing,
Trov
Ian Sweeney -
General Manager of Mobility,
Trov
Paul Sims -
Senior Vice-President, Digital Automotive and National Account,
Assurant
Krishna Prasad -
Senior Program Manager,
X by 2
Julie Zimmer -
Chief Operating Officer,
Embroker
· Round Table #1: Navigating a Large Transformation Program: A Checklist for Insurers Krishna Prasad, Senior Program Manager, X by 2
· Round Table #2: Who is Your Audience? A Deep Dive into Consumer Purchasing Behavior and Buyer Personas Vivian Arestia, AVP Acquisition Marketing, Metlife
· Round Table #3: What can Insurtechs and Incumbent Insurers Learn from One Another? Chris Frankland, Insurtech Evangelist, Silicon Valley Insurance Accelerator, Founder of Insurtech360
· Round Table #4: Leveraging Social Media to Drive Website Traffic and Build Relationships – Gerald Chiddick, VP of Marketing, Amerisure
· Round Table #5: Strategic Applications of Wearable Technology - Abel Travis, Vice President of Underwriting and Product Innovation, AF Group
· Round Table #6: Making the Most Out of Your Agency and Broker Partners - Julie Miller, Chief Operating Officer, Embroker
· Round Table #7: Getting Leaders to Champion Digital Change Jeff Berezny, Head of Global Product & Marketing, Trov
· Round Table #8: Opportunities and Challenges in Using Customer Data to Personalize the Customer Experience Ian Sweeney, General Manager of Mobility, Trov
· Round Table #9 : Adjusting to selling B2B2C insurance products in a digitizing world Paul Sims, Senior Vice-President, Digital Automotive and National Account, Assurant
5:05 pm - 6:05 pm
Bourbon and Blues Cocktail Reception
Culture meets Cocktails! Mix and mingle with your peers, enjoy live blues music, and our specialty Bourbon cocktails in a celebration of the Windy City and the Digital Insurance Summit.
Sponsored by: Pyramid Solutions
