Smart Choice named to IBA Hot 100 list for insurance industry power players in 2016

Smart Choice named a 5-Star Networks and Alliances winner by IBA in 2024

Accolades

Hired at Smart Choice in accounting department

2003

Showing up for your people

When Andrew Caldwell first took up the CEO seat at Smart Choice, it marked the pinnacle of an employment journey that’s spanned a lifetime. Having begun his career at Smart Choice in 2003 in an entry-level position, Caldwell quickly worked his way through the ranks – wearing many different hats along the way. Speaking to Insurance Business, he revealed that the secret to both his loyal tenure and the firm’s exponential growth is the company’s unparalleled, employee-first culture. “I feel like our culture is something that’s shaped my leadership,” he said. “At Smart Choice I’m proud that people don’t mind who’s above them or when they’re promoted – it’s never been a competition. It’s about getting people where they’re supposed to be and working together from there.”

It’s this level of empathy that’s shaped Caldwell’s time as both president and CEO at Smart Choice – and has led to significant expansion over the past decade. “We care about the people who work here,” added Caldwell. “And that’s stayed with me. I care about the entry-level person who is entering data because I sat in the seat. I care about compliance; I care about market research – because I did all of those roles. It’s important for a leader to have empathy for what everyone else in the organization does. And if you haven’t sat in the seat, at least for a little while, that can be tough to understand.” And while Caldwell’s contribution to defining Smart Choice’s culture is undeniably significant, he’s quick to point out that the embers of it were stoked by founder, and Caldwell’s personal mentor, Doug Witcher. As he told IB, Witcher may have changed roles but his presence and the legacy of what he built can still be seen, literally, on the walls of Smart Choice.

“Sadly, we’ve had a few people pass from cancer over the past 20 years,” Caldwell explained. “But a lot of our pictures in our office are of us coming together for them. We do the walks for charity, we get the T-shirts, we attend the funerals and the birthdays and the baby showers – we really show up for our people.”

Another unique aspect of Smart Choice under Caldwell’s leadership is that he ensures everyone is incentivized. As the fastest-growing network in the country, Caldwell is a firm believer that any successes are attributed and celebrated as a team. “When we have surplus revenue, everyone in the company – compliance, accounting, marketing – everybody gets a piece of it, and it works. This shared stake creates a dynamic where every new agent signed is a win for the whole team. People want to help them. People want to get them a code. People want to celebrate their first commission. Because, guess what – we’re all in this together.” This, as Caldwell pointed out, was Witcher’s system – but it’s one that he’s really pushed forward and embraced as part of Smart Choice’s core values. And so protective is Caldwell of their superbly honed culture that he’s incredibly cautious about Smart Choice’s mergers and acquisitions, of which they’ve executed a considerable $170 million worth.

As he told IB, early acquisition deals were straightforward – agents were already familiar with Smart Choice. But things evolved quickly – a staggering 39 acquisitions were completed over the last few years, all of which are aimed at strengthening, not rebranding, the network. And it’s a responsibility Caldwell takes very personally. “I spend the majority of each day talking to prospects who are asking us to buy them,” Caldwell said. “For me, the first step is that phone call. Before we get the teams on here and start talking financials and going through multiples, I like to have that initial conversation. [It’s a chance to] tell them how we lead and to ensure that’s what they want. Because, again, culture is vitally important to us.” And when companies start cutting people to meet goals, that’s a huge red flag for Caldwell. Smart Choice isn’t looking to gut the companies it acquires, or to ruin an employee’s livelihood in the name of a quick profit – and Caldwell’s certainly not interested in having that approach poison their culture.

Spotlight

“If you look around our offices, it’s Doug who hung up all the pictures,” he said. “He had this servant leadership sort of mindset. For example, Doug would ask us to read a different book every month – then we’d all get together and talk about it. Some people hate public speaking, and I didn’t realize it at the time, but here Doug was really rounding us out as people.” It’s a focus on family and fun that sets Smart Choice’s culture and employee mindset apart from other more “buttoned-down” firms. Regular get-togethers, including a United Way event where employees were encouraged to “pie” leaders in the face, have been instrumental in carving out important memories and making Smart Choice somewhere employees choose to stay. And it’s something that’s blurred the lines between personal and professional lives in the most wholesome way.

Smart Choice is a network of over 10,000 independent insurance agencies and more than 120 carrier partners. The nation’s fastest-growing agency network, Smart Choice partners with agents to help grow their book of business, maximize revenue, and deliver competitive insurance solutions to their customers. They provide agents with access to top-rated Personal, Commercial, E&S, and Life markets, as well as product training, and dedicated support from regional sales representatives. Collectively, their agency partners represent more than $12 billion in written premiums.

Company Profile

growth rate within insurance network

10,000+

agency partners

2024

8th consecutive year of 1k+ new agency additions

$100M+

acquisitions this year

last 12 months

time pro-forma earnings through acquisition and organic growth more than doubled

Bio

Spotlight

Milestones

Media

Accolades

Company Profile

Years of Experience

Tenure IN current position

2017 - Present

CAREER HIGHLIGHT

“It has been the highlight of my career to be mentored by three amazing leaders: Steve Bostian from an accounting standpoint, Paul Taylor from a sales standpoint, and Doug Witcher from a leadership standpoint. Getting three separate but meaningful perspectives helped prepare me to lead an organization of our size with such a varied opportunity”

Andrew Caldwell

CEO at Smart Choice

Where servant leadership meets serious scale – inside Smart Choice’s culture-first empire

Read on

“The first step is that phone call… [It’s a chance to] tell them how we lead and to ensure that’s what they want. Because, again, culture is vitally important to us”

Andrew Caldwell, Smart Choice

Milestones

2011

2012

2015

2016

2019

2021

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2012

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2015

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2016

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2019

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2021

Karen Adams

President and CEO at Fundserv

Before becoming CEO of Fundserv, Karen Adams held a variety of leadership roles around the world – and she learned that listening and understanding are key to both providing service and developing talent

Read on

Milestones

2011

2012

2015

2016

2019

2021

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2012

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2015

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2016

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2019

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2021

Karen Adams

President and CEO at Fundserv

Career highlight

Read on

IN Partnership with

In Partnership with

2003

2006

2011

2014

2024

2025

Hired at Smart Choice in accounting department

2003

Named commission accounting director

2006

Named EVP of business development

2011

Named president

2014

Smart Choice tripled EBITDA

2024

Named CEO – responsible for maintaining company’s core vision and principles, expanding size and scope of the network, and implementing strategies for revenue growth

2025

Milestones

‘We really show up for our people’

$170 million in M&As

Published September 16, 2025

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Best in Insurance

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Risk Management

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RSS

Sitemap

About us

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Terms & conditions

People

Specialty

Best in Insurance

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About us

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People

“When we have surplus revenue, everyone in the company – compliance, accounting, marketing – everybody gets a piece of it, and it works... every new agent signed is a win for the whole team”

Andrew Caldwell, Smart Choice

All of Caldwell’s careful decision-making and strategic overview permeates the operational core of Smart Choice and the company’s namesake – choice. “We want choice. Choice is in our name,” Caldwell said. The company has designed multiple entry points to support agencies at various stages of maturity. “And if you can’t qualify for a code, even if it’s through us, you can come through our internal side. It’s called Smart Start.” That internal program, supported by underwriters, contributes over $150 million in business, with $3 million in new commercial business monthly. As agencies grow, Smart Choice helps them “graduate out” and secure their own codes.

Freedom to succeed

Looking ahead to what the future holds for Smart Choice, Caldwell says his immediate priorities will be an ongoing focus on their people while continuing to build out the agency-acquisition side of things. But his vision is anything but cautious. The company is doubling down on specialization, particularly in commercial niches like trucking. “Trucking came up… and everybody’s raising their hands,” he recalled from a past agent meeting. Despite the risk complexity, Smart Choice launched a trucking division two years ago and has seen strong results. “What’s the next risk? What’s the next thing we can do for our agents? I’m willing to take chances around rounding out our offering for our customers.” For Smart Choice, the strategy remains clear: strengthen the network, empower the agents, and evolve with purpose. With over 10,500 agents and a growth model that blends flexibility, acquisition, and specialization, the company is setting the pace for what a modern insurance network can be – all under Caldwell’s careful eye. “We just want to continue to build on that,” Caldwell added, “and continue to grow.”

‘I’m willing to take chances around rounding out our offering’

Smart Choice named IBA 5-Star Networks and Alliances All-Star in 2025