Carson Conant keeps changing the business. The question stays the same.

Carson Conant has a wonderfully modest remedy for the overlong business email: make the window smaller. The recipient will probably read it on a phone, he reasons, so the writer ought to experience the same confinement. A smaller stage discourages a longer speech. It is a tiny piece of engineering, applied to the human tendency to mistake having something to say for deserving everybody’s afternoon.

The habit offers a useful way into his career. Conant founded Mediafly in 2006 to make digital content easier to consume. The company eventually helped salespeople present it, measure it and adapt it to a buyer’s questions. Now he is a co-founder of Clever Solutions, working on AI-assisted custom software. Different businesses, familiar irritation: useful technology has a habit of arriving with too much ceremony.

The family business came with a soundtrack

Long before Mediafly, there was a publishing company with his surname on the door. His grandfather Lloyd Conant founded Nightingale-Conant with broadcaster Earl Nightingale in 1960. The business distributed personal-development recordings, carrying ideas about work, ambition and selling through successive generations of playback equipment. Records gave way to cassettes, then CDs, then digital distribution. The message travelled; the machinery kept changing its clothes.

Carson participated in that digital transition. The family connection remains professional as well as personal: Nightingale-Conant identifies him as an adviser and board member, and lists him under strategic technologies. Its catalog also includes Evolved Selling, credited to Conant and Tom Pisello. For a founder who later built software for sellers, the distance from the family business is shorter than the product descriptions suggest.

In conversation with sales author Andy Paul, Conant described regularly returning to Nightingale’s recordings, especially The Boss and The Strangest Secret. He connected the former to Mediafly’s treatment of customers: the people buying the product ultimately finance the enterprise and deserve sustained attention. There is something rather pleasing about a software executive taking instruction from an audio program older than his software company.

A radio idea takes an unexpected turn

His first route into business was media. He launched AdvantEdge Magazine in 2004, then saw an opportunity in the awkwardness of early digital listening. Podcasts existed, but getting them into people’s lives required more technical enthusiasm than he thought reasonable. He imagined aggregating free and paid content into something closer to personalized radio. Listening should feel easy enough to happen on the fly; the company’s name followed.

His account of the launch includes an admission that founders rarely put on the invitation: he waited too long. Trying to perfect the product delayed the encounter with paying customers. Looking back, he urged entrepreneurs to collect revenue early, test and adjust. The elegance of an unfinished possibility can be terribly persuasive when no customer has yet had the opportunity to object.

By 2010, Mediafly’s distribution technology was finding a distinctly corporate audience. RE/MAX worked with Mediafly and Roku to deliver business video to its affiliates. Secure company content could reach desktops, smartphones and televisions through an experience borrowed from consumer media. A tool imagined for listening and watching was acquiring a working life inside organizations.

That connection helps explain the move into sales. Companies already had material they wanted people to see; they needed practical ways to distribute it and understand its use. Conant’s business was moving toward the place where content met a commercial decision. The consumer idea had supplied useful machinery, even as the audience and the reason for watching changed.

The presentation ought to have manners

The sales-software argument became clearer as Mediafly grew. Enterprise systems often pleased the people administering them while exhausting the people expected to use them. Conant wanted a platform a salesperson would willingly open. Early customers including Goldman Sachs, PepsiCo and NBCUniversal brought different needs, helping shape the product. The buyer’s questions, meanwhile, deserved more influence over the meeting than the sequence of a preassembled slide deck.

By 2021, he was describing a business with more than 350 customers and a sharper emphasis on interactive, animated content. Mediafly had announced a $25 million growth round, with equity from investors including Boathouse Capital and senior debt from Sterling National Bank. Funding was helping support an approach in which the sales conversation itself mattered, alongside the systems surrounding it.

Conant’s thinking extended beyond the presentation. Discussing the customer journey with Ray Rike in 2022, he distinguished the buyer’s exploratory route from the seller’s wish for a tidy progression toward a decision. Buyers investigate, reconsider and compare. The seller would prefer a straight line, preferably ending this quarter. Human beings have proved persistently unwilling to arrange their uncertainty for the convenience of a forecasting spreadsheet.

He also questioned the handoffs between marketing, sales and customer success. A customer experiences a relationship; the supplier divides responsibility among departments. The gaps between those departments can become gaps in the experience. His interest in revenue enablement brought those activities into the same discussion, including what happens after the contract is signed.

Buying the missing pieces

Acquisitions gave that broader ambition physical form. In 2018, Mediafly bought Alinean, adding tools such as calculators for total cost of ownership and return on investment. Pisello, Alinean’s founder, emphasized understanding buyer challenges and business outcomes. The combined proposition let a seller discuss the economics of a purchase as well as its features. A handsome presentation could now arrive with arithmetic.

The iPresent deal addressed a different obstacle: getting started. Conant described the appeal of letting a small team begin using sales-enablement software without first committing the entire enterprise. In a conversation with Nathan Latka, he explained how a modest deployment could grow into a much larger account. He also discussed the mechanics of acquisitions, including combinations of cash, stock and contingent payments.

Presentify brought visual-communication capabilities in 2020. InsightSquared followed in 2021, then Aptology and ExecVision in 2022. By August that year, Conant was discussing five acquisitions in three years on the DealLab podcast. His job had expanded from developing a product to assembling capabilities and teams. Every new component also brought the less photogenic work of making a combined company function.

In August 2023, Mediafly announced that investment alongside a reported 164% increase in its customer base over the preceding 18 months. The company was aiming at large organizations with complex selling operations. Its expanding portfolio reflected an ambition to put content, coaching, value selling and intelligence closer together. Conant’s original concern with getting useful material to people had accumulated a considerable enterprise around it.

Strong opinions, lightly worn

Conant’s writing about hiring offers a more intimate view of how he wanted that enterprise to work. In 2020, he described three characteristics he sought: limited ego, careful listening and comfort with ambiguity. The first did not mean agreeable silence. He wanted people prepared to argue for an idea while remaining willing to abandon their ownership of it. Vanity, in this arrangement, receives no reserved parking.

Recruitment could begin six to twelve months before a position needed filling. He connected comfort with uncertainty to Mediafly’s first acquisition, when the team had to learn a process it had never undertaken. A founder changing the business needs colleagues who can tolerate a partially drawn map. Listening becomes practical equipment when everybody is encountering something new.

“I wake up every day with the goal to serve…”

Carson Conant, reflecting on his Mediafly team in 2022

His public appreciation of the team returned to the same theme: colleagues with conviction, technical ability and a sense of fun. The workplace earned outside recognition too, including a place on Inc.’s 2018 Best Workplaces list and recognition from Crain’s Chicago Business. Those awards belong to the organization. His repeated emphasis on the people behind it helps explain why they mattered to him.

A founder makes room for another chapter

In April 2023, Mary Shea joined him as co-CEO. The pairing brought together his experience building the company and her background in revenue technology, research and sales leadership. Conant said he had known her for more than a decade. The arrangement made an explicit place for a different set of strengths beside his own.

A year later, William Walsh became CEO. Mediafly’s announcement described Conant moving to executive chairman and chief strategy officer; subsequent company commentary placed the transition in early 2024. Walsh had arrived through the Aptology acquisition. A deal intended to add capabilities had also brought in the person who would take over running the business.

Conant’s current work places him back among a founding team. Clever Solutions lists him as chief strategist and AI solution architect, alongside Gregory McClendon, John McGill and Mohammed Hasan. Its stated focus is operational problems that companies struggle to solve economically: awkward workflows, software that fits poorly and systems expensive to replace. The company proposes combining AI, automation and human expertise to make those projects more practical.

It is an apt next problem for someone whose career began with the conviction that digital listening demanded too much effort. The tools have changed again. The attraction remains recognizable: find the point at which the machinery makes a sensible task unnecessarily difficult, then see whether it can be made easier. Somewhere in that work, one imagines, there is still a very small email window.