In the photograph, Jeff Smedsrud is standing in Antarctica with a handset against his ear. Behind him are ice, dark water and a gathering of penguins. He wears a yellow jacket bright enough to settle any argument about where to look. It is an appealing place to imagine an unanswered business call. It does establish that his travels have taken him some distance from the usual conference hotel.
Smedsrud has completed marathons on all seven continents. His working life has its own changes of scenery: a magazine office, a rural membership association, publicly traded companies, an internet startup and a business that was bought by another business he had helped create. The unusual part is the returning. In 2018, HealthCare.com acquired Pivot Health, the company he founded after serving as HealthCare.com’s CEO. A career normally drawn as an ascending line had produced a rather useful loop.
An editor before an executive
The first job in this story involved a monthly magazine. In 1980, Smedsrud joined the association now known as Communicating for America as its editor. His father, Milt, had founded the organization in 1972, initially as the Creamery Association. Its audience included dairy farmers, and its purpose was collective buying power. It later widened its remit to other small businesses and self-employed people.
Editing put Jeff in the business of reaching those members before he was in the business of leading the organization. His education overlapped with that beginning. He attended Minnesota State University Moorhead from 1977 to 1981 and edited the college newspaper. There is a pleasing consistency in finding an editor on both sides of the graduation years: the audience changed, while the work still involved making information worth someone’s time.
He helped the association grow from fewer than 10,000 members to more than 80,000 over the following two decades. In 1993, he established its first Washington office. In 1997, he first became its CEO. Publishing, membership and representation sat within the same institution. Long before an online comparison site entered his résumé, he was working with people whose independent businesses gave them plenty to manage already.
Those early roles also complicate the familiar image of a startup founder appearing fully formed with a presentation and an idea. Smedsrud’s background included an existing organization, a family connection and years of operating work. The later businesses would use different technology. The challenge of reaching a dispersed audience was already familiar.
A familiar address, a new business
When Smedsrud became CEO of HealthCare.com in March 2014, he arrived with a substantial commercial record. He had sold four marketing businesses to publicly listed companies. His previous positions included senior vice president and chief marketing officer at The IHC Group, as well as president of American Independence Corp. This was a founding CEO with experience of what happens after a business gets large enough to require divisions, reporting lines and a buyer’s scrutiny.
The date needs care. The website had an earlier history; the new business launched in 2014. Smedsrud’s place in the story is as a co-founder and the founding CEO of that business. His fellow founders included Howard Yeh, Jose Vargas and Matias de Tezanos. An established internet address was the starting asset. Turning visitors into customers required an operating system around it.
One decision shows how practical that work could be. The team initially wanted to build its own data capability. It then recognized the infrastructure that would require and chose a partnership with Quotit. The decision redirected effort toward the customer experience while a specialist supplied an essential component. The ambition remained; the division of labor changed.
“Partnering with Quotit allowed our team to scale more quickly”
Jeff Smedsrud, discussing the company’s data partnership
There is less romance in choosing a supplier than in unveiling a product. It can still be a consequential founding decision. Every component a company builds must subsequently be maintained. Smedsrud’s account gives the infrastructure its proper weight: an expense in money and attention, with consequences for how quickly the rest of the company can move.
HealthCare.com
Pivot Health
HealthCare.com
The company that came back
Smedsrud led HealthCare.com from 2014 to 2016. He founded Pivot Health in 2016. Two years later, the companies came together through an all-cash acquisition. The financial terms were not disclosed. Pivot would continue operating independently, and Smedsrud would continue leading it day to day while joining the buyer’s management team.
The transaction brought together different commercial capabilities. HealthCare.com had developed a comparison and distribution platform. Pivot developed, managed and marketed proprietary products. By the time of the deal, the companies had already been working together. The acquisition extended a business relationship as well as reconnecting people with a shared founding history.
Howard Yeh was then HealthCare.com’s CEO. Smedsrud returned carrying responsibility for a company he had built separately. That distinction gives the deal its character. He was bringing an operation and a team into a company whose earlier work he knew from the inside. The new arrangement gave the combined business more of the journey between a visitor’s first search and a completed transaction.
By 2017, HealthCare.com had reached No. 148 on the Inc. 500 list. That ranking belongs to the company and its collective work, rather than to any one founder. Placed beside the Pivot acquisition, it marks how far the business had moved from its 2014 launch. Smedsrud’s second chapter there began within an organization already different from the one he had first led.
A form is not a conversation
Listen to Smedsrud discussing online commerce and the details tend to become smaller. In a 2019 interview, he described customers becoming less willing to fill in a vague form and wait for someone to call. He wanted a more specific exchange: establish what the person wants, understand the budget and connect that person to an appropriate next step.
His point concerned the machinery between interest and action. A company can count a submitted form while the customer is still waiting for a useful answer. Smedsrud’s emphasis was on making that interaction quicker and more relevant. He discussed online engagement, calls and chat as ways to refine an understanding of what a shopper was actually seeking.
He also had a compact complaint about the way older rules meet smaller screens: “How do you put a big 200 word disclaimer on a mobile app?” It is an operator’s question, with the awkward object left on the table for everyone to inspect. The screen has a finite size. The requirement has a word count. Someone has to make the two coexist.
The same discussion included consent and the proper use of customer data. Those details matter to the portrait because they reveal the scale at which he was thinking. The founder who had overseen business development and strategy was also talking about forms, handoffs and information people agreed to share. A digital business becomes tangible through precisely those encounters.
The Indiana connection
In October 2020, another part of the job involved explaining an expansion in Indianapolis. HealthCare.com was relocating headquarters functions and building a local operation. Smedsrud discussed a workforce spread across New York, Miami, Indianapolis and Guatemala City. For a company reached through a browser, the physical map had become considerable.
His explanation for Indiana included the usual business considerations: location, taxes and workforce. Then it took a family turn. Both his children had attended Indiana University, one at the Kelley School of Business and the other at the Jacobs School of Music. He had spent years visiting Bloomington and Indianapolis. The proposed business destination was already a place he knew through family travel.
That small detail makes the location decision easier to picture. Corporate moves generate agreements, employment targets and forecasts. People making them also accumulate impressions on ordinary visits. Smedsrud offered both accounts together. Indiana had a commercial case, and he had been there often enough to have an opinion beyond a spreadsheet.
The expansion was also a reminder of what an online enterprise can contain. Behind the web address were offices, agents and hiring decisions. The company’s work required people to answer questions as well as software to route them. A founder speaking about headquarters was addressing another layer of the same operating business.
Seven continents, then another chapter
In 2023, the Inter-Company Marketing Group gave Smedsrud its Don Kampe Lifetime Achievement Award. He had been a member since 2005. The recognition cited his sponsorship, speaking and participation, including encouraging employees to become involved. The record behind the award was built through repeated attendance and support, the sort of activity that rarely makes a dramatic announcement.
The award biography also noted his Seven Continents Club membership. Running a marathon on each continent supplies a memorable personal achievement without requiring it to explain every business decision. A race has a defined distance and a finish. Companies can be sold, combined or revisited. Smedsrud has pursued both kinds of undertaking; the differences are part of the interest.
His next founding chapter was Flex Benefits. By February 2025, he was appearing at ICMG’s Tampa conference as its founder and CEO, alongside Susan Plumer, Charlie Harris and Brendan McLoughlin. The discussion returned to technology, distribution and how companies serve customers. An award bearing the words lifetime achievement had left room for another working appearance.
At Flex, Brian Dow is president and chief operating officer. The team’s stated values include convenience, quality and relationships sustained through listening and responsiveness. Those are company commitments rather than guarantees of an outcome. They do, however, keep the customer’s experience close to the center of Smedsrud’s latest business chapter.
From the monthly magazine to the comparison platform, a recurring piece of work remains visible: finding a way to reach people, giving them something useful and organizing a business capable of delivering it. The titles have changed. So have the partners and the tools. Smedsrud’s career keeps producing another occasion to begin, sometimes in a new company, sometimes in a familiar one, and once with penguins in the background.