Humour, humanity, ‘hidden sort of heroism’

Eight weeks from now, Telpay Inc. might have something in common with Michelle Obama and Conan O’Brien.

The Winnipeg payments company is a finalist at this year’s Shorty Awards, a U.S.-based competition that counts the former U.S. first lady and late night TV mainstay/comedian among its previous winners.

The awards honour innovative work in digital and social media by brands, agencies and organizations. Telpay is a finalist in the “Branded Series” category for its original web series, Double Entry — a six-episode mockumentary in the style of The Office that celebrates bookkeepers and the everyday challenges they face.

The company, which is the largest independent processor of electronic bill payments in Canada, faces stiff competition in the category from global brands such as Amazon, Disney, Nasdaq and Visa.

Paul Vieira, the marketing professional and Telpay executive who created Double Entry, said he’s been flying high since he learned the series is up for a Shorty award, especially given there are entrants from all over the world.

“It’s just crazy — Telpay, this little company from Winnipeg, is up against these big brands,” Vieira said. “I’m pretty pleased. This has been a pretty interesting and great experience so far.”

The 54-year-old’s previous career background includes adult education and working in the provincial government’s immigration department.

More than a dozen years ago, he wrote and produced WindCity, a six-episode web series that took place in Winnipeg and showcased local businesses. (The Free Press was one of the series’ two media sponsors and the official online home of its episodes when it debuted in 2014.)

That experience led Vieira to work in film production for a few years before he took a communications and marketing role at Manitoba Public Insurance.

He joined Telpay in 2024, where he oversees marketing, sales and customer relations as the company’s chief experience officer.

Vieira said he pitched Double Entry to Telpay leadership not long after joining the 40-year-old company.

“I felt like we needed to sort of re-establish ourselves as a beloved brand with our target segment: the bookkeeper,” he said. “I’ve always said empathy is better marketing than advertising is, so we thought, what if we just told a story about them?”

Vieira spoke with bookkeepers to better understand the ins and outs of their profession. Those interviews informed the six episodes, which Vieira wrote over the course of six weeks last spring.

“I found that the profession was full of humour and humanity and a hidden sort of heroism,” he said.

“Each episode has a certain theme that we want to bring out that’s fairly relevant to the bookkeeping profession — things like how to manage difficult clients, navigate technology, how to price your work, how to cope with deadlines and tax season.”

Vieira hired local production company Foundation Film and Media to film the episodes on a shoestring budget in about a week last July. Each episode is around eight minutes long.

Telpay debuted the trailer for Double Entry in September at Ignite, an annual conference hosted by the Certified Professional Bookkeepers of Canada, before making the entire series available online at telpayoriginals.com.

The series reached more than 3,000 bookkeepers across the country within its first two months, Vieira said.

Goals for the series included educating through entertainment and creating curiosity about Telpay without ever mentioning the brand in the series.

“I think about how innovative and pioneering our leadership is to actually put investment into something (where) we don’t even talk about ourselves,” Vieira said.

Company president Mark Loewen said his first reaction to Vieira’s pitch for the series was “sounds expensive,” but he came around once he understood the goal was to build trust and emotional connection with bookkeepers.

He added he’s proud of Double Entry and the award nomination, and multiple stakeholders were involved in producing the series.

“A lot of people came together and worked really hard over the course of a couple weeks in the middle of the summer, and I’m happy to see that all that effort is being recognized,” Loewen said.

The 18th annual Shorty Awards will be presented during a ceremony on May 19 in New York City. Telpay has given Vieira the green light to attend, but he said he’s still deciding whether or not he’ll make the trip.

Telpay was founded in 1985 by Bill Loewen (Mark Loewen’s great-uncle). The company employs around 80 people and processes $28 billion in transactions annually.

aaron.epp@freepress.mb.ca