Media Room

Quick Facts

Who we are, where to find us, what we do best.

View Quick Facts


We’re passionate about our Community. You’ll find us leading conversations and creating solutions when it comes to issues like livability, education and our local tech ecosystem.

View Community


An insider’s view into how C-level execs stay on the leading edge of innovation and tackle the challenges of everyday business.

View SmartTalk

2018 SAGE Business Award winners announced
It was a spectacular Friday night at the Riverhouse Convention Center with the who’s who of Bend’s business community gathering for the 2018 SAGE Business Awards, presented by the Bend Chamber and U.S. Bank. Join the Bend Chamber in congratulating the 2018 SAGE Award recipients!

Large Business of the Year – Five Talent
Small Business of the Year – Powers of Automation
Nonprofit of the Year – Guardian Group
Citizen of the Year – Amy Tykeson
People’s Choice – Guardian Group

On the road with Kate Brown
Oregon Business
A light rain had turned the pavement shiny and slick as she sat in her official, unmarked Tahoe parked outside Five Talent, a tech company that’s working to “connect the dots” between education and economy through a program called Apprenti.

Five people land spots in tech apprenticeship program
Bend Bulletin
A single mother, Megan Ivey learned on a Tuesday last month that a Bend software consulting firm had chosen her as its apprentice.

FiveTalent Turns to Portland Labor Market
Bend Bulletin
Five Talent Software is opening a Portland office to overcome a labor shortage in Bend, which CEO Preston Callicott said has limited the firm’s growth over the past year.

Bend’s Innovation District
Cascade Business News
For a small community, it’s clear that Bend has big magnetic pull for entrepreneurs, investors and creatives eager to reinvent work and play. This drive doesn’t imply a lack of ambition either. True to its outdoor lifestyle and pioneering roots, Bend is in constant motion and in search of new ventures. It’s a mindset that impacts everything from kombucha to software, single track to food carts.

Five Talent’s Preston Callicott on Bend’s Startup Industry
Bend Magazine
Five Talent’s CEO on what it takes it to make it in Bend and how tech companies are working together to make this the most liveable city in America.

Coding education in Bend gains momentum
Bend Bulletin
Ryan Comingdeer, chief technology officer at the Bend software development firm FiveTalent, took his first computer programming course as a seventh-grader and landed his first job in programming as a sophomore. This was Comingdeer’s experience as a student in Oklahoma City public schools in the 1990s. Although computer science-driven jobs are among the highest-paying, fastest-growing in the modern economy, the effort to teach computer science and programming in Central Oregon public schools is fragmented.

Bend TechCrawl draws interest from industry participants
Cascade Business News
The Central Oregon branch of the Technology Association of Oregon (TAO-Central Oregon) hosted the 1st annual Bend TechCrawl. The unique and fun evening was the first statewide technology networking event with simultaneously TechCrawls in Bend, Eugene and Portland.

High housing costs deter Bend job applicants
Bend Bulletin
It’s happened to several Bend employers — they hire new employees, but the new hires quit weeks after moving to Bend when they’re unable to find a place to live. “I had a well-paid developer and his family move in state, and he had a wife and a little baby,” said Preston Callicott, CEO of Five Talent Software. “I put him up in a hotel, and two weeks after, he says, ‘I can’t find anything, we have to move back.”

A better future Bend? ‘Bend Livability Project’ launches
It’s the question on all our minds: How do we protect the livability of our community in the face of such dramatic growth and change? The answer is clear—it’s up to us to define our future together by learning about the challenges facing our town, understanding how we can shape the outcomes and engaging to implement innovative and effective solutions for our community.

Smart Technology Putting Business First
Oregon Business
Going into software development was a no-brainer for Ryan Comingdeer. “I took my first programming class in seventh grade,” he says. “I was kind of a geek from day one.” But when he started technology firm Five Talent in 2004, he discovered he had a knack for something in addition to writing code. Many clients came to him with problems that could be helped by technology, but they weren’t always considering the right solution. “They would contact us about an off-the-shelf e-commerce approach when they really needed a custom software solution,” Comingdeer says. “Or they would seek out more visitor traffic when they needed a better website to improve sales.”

High Desert starts model to promote innovation
High Desert Education Service District
High Desert is a publicly funded agency that provides various services to Central Oregon school districts, from legal and financial advice to special education and career and technical education support. Participants in i4 get help refining their ideas at workshops with local entrepreneurs before pitching to a five-person panel, including High Desert leaders and people from the private sector.

Californians help bring golden tech sector to Bend
Bend Bulletin
While Californians being drawn to Bend is not a new story, the new arrivals have had a profound impact on the tech scene in Central Oregon. When Callicott arrived in 2003, tech companies were still few and far between, meaning he had to commute back and forth to Silicon Valley to continue working in the industry before finally taking his current position at Five Talent, which he converted into a growing software consulting firm, in 2010.

Tech: Predictions from an industry insider, CEO of Five Talent Software sees bright future, worries about Bend housing
Bend Bulletin
Bend has become a rising star among tech clusters across the country. Finding experienced software developers has been a challenge, but Five Talent Software CEO Preston Callicott believes a four-year university will allow technology companies to recruit more talent locally.

Build vs. Buy: Weighing Custom Software against Off-the-Shelf Solutions from Five Talent in Bend, Oregon
Cascade Business News
Company leaders face this decision more often than they’d like and it’s not going away. How do you navigate the build vs. buy question and ensure you get a system that adapts and evolves as you do? Five Talent CEO Preston Callicott and CTO Ryan Comingdeer dive into the debate.

More than 1,000 rentals proposed in Bend
Bend Bulletin
“It’s hard enough for us to find software developers. They’re in extreme high demand,” said Preston Callicott, CEO of Five Talent, a software company in Bend. “Once you get them, and they come to town, they start saying, ‘Well, I can’t find a place to live.’” Callicott said he sometimes calls real estate brokers looking for unlisted vacancies, and, in one case, put up a new hire and his family in his own home while they looked for a place of their own.

IT’S A MAN’S MAN’S MAN’S WORLD, Male tech workers weigh in on the industry’s gender troubles
Oregon Business
Men in Oregon’s tech sector work in one of the country’s most forward-looking industries, one that prides itself on meritocracy and disruption. They live in some of the most liberal leaning cities in the country: Portland, Bend, Eugene. Add those two components together and you get a business sector that prides itself on being more collaborative and less competitive than its peers in the rest of the country.

Growing the tech scene in Bend. What Bend needs to do to take it to the next level
Bend Bulletin
Bend has been dubbed an entrepreneurial hot spot, as well as a growing tech cluster. It’s received national attention for its ecosystem that includes a startup accelerator called FoundersPad and the largest angel conference in the Pacific Northwest, the Bend Venture Conference. Yet, McDonald, a user-experience designer, had never heard of Bend until several months ago.

Five Talent Driving by the Finger
Cascade Business News
What makes a web development company unique in a town where nearly everyone and their brother is a “website developer?”  According to Preston Callicott, partner and chief operating officer with Five Talent, it’s the deep technical knowledge and the ability to use that in business applications. It’s being on the “bleeding edge” of technology.

Let’s Work Together

If you’d like to discuss a project you’re working on, drop us a line. We’d love to learn more about what you’re building.