Deb Smallwood, Author at Insurance Thought Leadership



Deb Smallwood

Deb Smallwood

Deb Smallwood, the founder of Strategy Meets Action, is highly respected throughout the insurance industry for strategic thinking, thought-provoking research and advisory skills. Insurers and solution providers turn to Smallwood for insight and guidance on business and IT linkage, IT strategy, IT architecture and e-business. She has specialized understanding of distribution and underwriting automation.

Smallwood has held leadership roles in premier insurance companies, professional services firms and research advisory organizations, where she consistently demonstrated the ability to find new ways to leverage technology to achieve optimal business outcomes. Her skill set includes linking business strategy to IT strategy; development of business and IT road maps; selection, shaping and delivery of enterprise/core solutions; and implementation of right-sized governance models.

Before founding SMA, she served as chief transformation officer for Insurance Company of the West, where she was recruited to deliver as much IT capability to the business operations as possible in the least amount of time. Smallwood led companywide change that included developing and integrating the corporate business strategies into five strategic initiatives. Before joining ICW, she launched and served as managing director of TowerGroup’s insurance research and consulting practice.

As a partner at KPMG, she launched an IT consulting practice specializing in the assessment and management of IT risks. She began her career at Liberty Mutual, where she directed a variety of large-scale system development projects and rose to leadership of the commercial lines application development group.

Smallwood’s expert opinion and counsel is in demand by press, clients and major industry events. She is a frequent contributor to leading insurance trade journals and has been a keynote speaker at major conferences such as ACORD/LOMA Forum, NAMIC, ISOTECH and IASA. She is a graduate of the University of New Hampshire, with a B.S. in business administration.

Recent Articles by Deb Smallwood

Myth or Reality? Digitization Is Stalled

To assess whether digital transformation is stalled because of the pandemic, we really need to think about transformation from past investments, the current state in the context of the pandemic and the strategies planned for 2021.    Well, 2020 was quite a year! I want to make two key points that we’ve learned during the pandemic. […]

3 ‘Must Have’ Digital Investments

Disasters – such as pandemics – have a way of revealing the need for change. That’s why digital transformation has advanced five years in about eight weeks. Businesses of all sizes have embraced digital sales and service, and, due to lockdowns, just about everyone has experienced the increased need for digital engagement, with expectations only […]

10 Moments of Truth From COVID-19

In the midst of all the chaos, insurers are being put to test in real time. For all, it becomes the moment of truth for our industry and every individual company. The strength of our industry is shining through. Insurers have quickly adapted to the new norm. Insurance executives are mindful of how this pandemic […]

Standing Strong in the Moment of Truth

In a blink of an eye, the world – society and all of humanity – are being stressed at every level imaginable due to the rapid spread of COVID-19. No one could ever have imagined or planned what this could really be like … including our industry. But since the beginnings of insurance, we have […]

8 Key Changes for Customer Experience

Transforming the customer experience is a powerful way for an organization to shift and bring about quantum change, improving retention without huge IT investments that take years. A better customer experience will optimize operations, as well. In all my years of working in insurance and technology, I have never experienced anything with such power and […]

Thinking Big for True Transformation

A transformation journey is required for every company within our industry’s ecosystem that wants to remain relevant beyond 2030. So, how do you get past all the hype around disruption, digital and innovation and really set a course to transform? How do you start the journey – with clarity, focus and informed decisions – that […]

Accelerating the Transformation

The transformation journey requires a new lens. This lens provides a clear future-state vision that anchors both the outside-in lens (prioritizing customers and their experience) and inside-out lens (prioritizing operational optimization), which together propel the journey forward. Acknowledging that the world and insurance are changing at an unprecedented pace, the first step to defining our […]

Who Is Your Customer; How Is the Experience?

In today’s digital world, companies have to focus on customers and their experience. No longer is it just about optimizing the business and processing the transaction; the overall experience matters for retention and renewal. It is essential to create a seamless digital experience that is tailored and personalized, based on understanding customers and their needs. […]

Is Insurtech Wave Hitting a Riptide?

Has the insurtech wave hit a riptide? At Strategy Meets Action, we think it has. The riptide analogy generates a powerful image of a turbulent sea, where the strong finally reach the shore, but the weak succumb to the powerful currents and are pulled back out to the sea. The insurtech world is experiencing a […]

10 Essential Actions for Digital Success

Becoming a digital insurer is an essential requirement for being competitive in insurance today – but even more so for the future. Your digital strategy becomes the framework from which to leverage all other transformational initiatives, not only for the customer experience but for the employee and operational experiences, as well. This process requires clarity […]

Seeing Through Digital Glasses

Extraordinary change is taking place throughout the insurance industry and everything that surrounds it. The whole world is going digital. It’s the new reality, and there is no getting around it. But just the word or even the idea of digital has many people, insurers included, pondering the basic and fundamental questions: Why do we […]

Top 5 Themes in Commercial Lines

SMA has tracked the changing course of business and technology projects in the insurance industry for nine years. Our recent research study for our Strategic Initiatives in Insurance series and our work with insurers shows that the P&C commercial lines industry is going through change – change that is having a profound impact on strategies, […]

2018’s Top Projects in Personal Lines

SMA has tracked the changing course of business and technology projects in the insurance industry for nine years. Our recent research for the Strategic Initiatives in Insurance series and our work with insurers clearly support the fact that the P&C industry is changing, especially in the personal lines arena. And this change is having a profound impact […]

The 5 Big Initiatives in Commercial Lines

Transformation is underway in P&C commercial lines – finally! The nature and speed of the transformation will play out quite differently for small/medium/large commercial, workers’ comp and specialty lines. And the stage of the transformation journey may be very different based on business strategies, the appetite for innovation, emerging technologies, insurtech and the geographic scope […]

Innovation Is Really Happening

We talk about innovation all time. Yes, it is mandatory. Yes, your competitors are doing it. Yes, it means fundamental changes within an organization. But what does innovation really mean, and where do you start? An innovation is defined as a new method, process or product. For insurance, the quest to build something new or transforming has quickly […]

Innovation: No Longer an Option

Every year, for the last six years, SMA has completed its Innovation in Insurance research report. Our insights are based on targeted research, experience in the industry and insights from our customers. It is with our unique lens that we investigate and analyze innovation in insurance to share trends and findings that will guide the industry into […]

Innovation Pivots: 10 Lessons Learned

Some of the best innovation success stories are built out of the lessons learned from watching the attempts of others as they either falter or flourish. The following is a compilation of what we believe are the best practices for innovation, through anecdotal and use case examples. In an effort to help and inspire insurers […]

Key to Digitizing Customer Experience

Every aspect of the way we interact with goods and service providers is becoming digitized, but it doesn’t work to go partway. As insurers, we have to ask ourselves, “What does a complete digital experience for our customers and policyholders look like?” In my travels over the last year, I have run into experiences with very […]

Yes, Personalize — but Get it Right!

“Hello, undefined: How are you?” We’ve all seen bad marketing emails where what was supposed to be a personalized greeting or communication goes terribly wrong. These failed attempts at personalizing the customer experience have the exact opposite effect that they are supposed to when the data is bad. It would be better to go back […]

8 Exemplars of Insurtech Innovation

The winners of the SMA Innovation in Action Awards are Figo Pet Insurance, Meteo Protect, Motorists Insurance Group and Texas Mutual Insurance, among insurers, and Baseline Telematics,, Octo Telematics and Pristine, among service providers. SMA launched this awards program five years ago to recognize projects and solutions that have reshaped one or more of […]

Bridging From Today to Tomorrow, Part 2

In part one of this blog, we looked at the transformational changes insurers are facing and the need to build bridges between today’s world and the future. Now it’s time to look at “the hows” – How do you respond? … How do you set a call to build those bridges? … And how do […]

Bridging From Today to Tomorrow, Part 1

Change is constant; we all know that. External forces are conjoining with emerging technologies and changing our whole world, including the business of insurance. And changes bring challenges. How insurers face these challenges and bridge their current world to the future is the key to success. Our perceptions of change vary. For some, it feels […]

Pursue Innovation or Transformation?

People often use “innovation” and “transformation” synonymously. Both words evoke thoughts of change and modernization. Both words are important outcomes of the change management life cycle. We know innovation is occurring all around us, as people find ways to improve things. Alternately, transformation is the result of moving from one state to another. So, should we […]

What the Primaries Can Teach Us

Super Tuesday’s presidential primaries and all the associated media coverage made me reflect on how candidates interact with their constituencies and the lessons insurers can learn. I have been a New Hampshire resident all my life, and one of the special privileges of living in this great state is being able to vote in the […]

What We Can Learn From Google Compare

“The Google Compare service itself hasn’t driven the success we hoped for.” Google Compare announced in an email to its partners that it would be shutting its insurance and financial products comparison service tools in the U.S. and U.K. as of March 23. The lack of traction in both usage and revenue generation were named as two […]

Shift in Funding for Strategic Initiatives

Take a look at the financials of the insurance industry and industry projections, and it may seem like business as usual. But peek just under the surface at many insurers, and you’ll find a great deal of activity aimed at transformation. Typically, this activity takes the form of strategic initiatives—enterprise-wide programs that require sustained commitment […]

The 10 Top Trends From a Pivotal 2015

Many will pinpoint 2015 as a pivotal year – the turning point in the transformation of the business of insurance. External influencers and rapid technology advancements are resulting in major shifts in strategy, areas of focus and investment. Many insurers are thinking big – beyond the typical incremental change and toward bold moves that will […]

2 Key Tools for Innovation in P&C

Imagine this: two separate kingdoms, the kingdom of P&C insurers and the kingdom of agencies and brokers. Within each kingdom, each insurer and agency is represented by its own little house, and every little house has a door. Each door can open both ways and represents a way to communicate and share data – and […]

Innovation Spreads in U.S. State by State

Innovation can start simple. It does not always have to start with a big bang. We all know that doing anything in insurance across 50 states is often complex and expensive and a long process, but it is possible to begin with an idea around a new model, product, channel or line of business. Decide […]

Is Your Organization Open to New Ideas?

Recently, I wrote about innovation and changing the way we acknowledge, nurture and incorporate it into our organizational culture. There are many areas where our industry desperately needs transformation and innovation. Our very survival depends on new ideas. We at SMA are witnessing remarkable progress — innovation is on a bullet train! — but we […]

10 Reasons to Innovate — NOW!

We’re busy gearing up for the annual SMA Summit, where innovation will take center stage. In the spirit of the summit, I started to gather some inescapable facts that could inspire us all to innovate and improve – to truly become the Next-Gen Insurer. But, rather than peddle the same old innovation benefits and business […]

Insurance Impacts of FIS-Sungard Merger

Here we go again: Out of the blue, FIS agreed to acquire SunGard. The joining of two more global technology firms creates another giant in the financial services space. Why so many? Power of scale. Size allows companies to consolidate overhead, with the merger of people, processes, infrastructure and product offerings, allowing for profitable growth. […]

Venture Capital and Tech Start-ups

Unicorns – to some they are just mythical creatures of lore. To today’s tech world, a unicorn is a pre-IPO tech start-up with a billion-dollar market value. These are the companies driving innovation, technology and disruption in every corner of every business, and their impact is truly being felt across the insurance industry. The number […]

100 Ideas That Changed Insurance

Recently, I bought a copy of Time magazine’s publication, TIME 100 Ideas That Changed the World: History’s Greatest Breakthroughs, Inventions and Theories, in an airport book store while on a business trip. It was certainly a compact and interesting read, highlighting amazing innovations that we now accept as the norm of human existence on Planet […]

Rethinking Underwriting for Commercial Lines

It is time to step up automation in commercial lines, and you can do just that with a powerfully rich combination of enhanced technology capabilities in the key areas of underwriting and policy administration – a combination that lowers cost, simplifies doing business, makes it easier to enter new markets and significantly improves underwriting outcomes. […]

Getting Beyond the Policy Admin System

As SMA’s Karen Furtado wrote in last month’s blog post about core systems, “Now that the insurance industry recognizes modernization as an indispensable tool for remaining competitive, it is worthwhile to take a step back and look at the technical capabilities that insurers really need.” With underwriting, this requires a platform that extends beyond the […]

The 5 I’s of Underwriting

The benefits of next-generation underwriting for complex risks are quantifiable and real. So, when, where and how to start? When? Now. The sooner, the better. Where? It all starts with understanding the possible. You need to know what is realistically possible with the offerings that are available today. It is equally important to figure out […]

Shifts in Strategy: Making Sense of 2015

The insurance industry is in the midst of a historic shift. That might sound like an overstatement, but Strategy Meets Action’s research and observations from working with insurers back up this claim. For the past six years, SMA has been tracking and supporting the industry’s evolving maturity – by doing research and providing services – […]

How Does Your IT Budget Compare?

In my conversations with insurers, I am frequently asked about IT investments. People want to know what the trends are around IT budgets and how their spending on information technology compares with others. To help explore these topics, we analyzed insights from our portfolio of research and did some additional analysis. Working on this research project […]

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