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The CEO of the Year nominees from last year: Moz CEO Sarah Bird, Smartsheet CEO Mark Mader, Outreach.io CEO Manny Medina, Remitly CEO Matt Oppenheimer, and Textio CEO Kieran Snyder.

They run companies across various industries, from AI training to text analysis to wireless networks. But all five of our GeekWire Awards candidates for CEO of the Year share a similar trait: leadership that’s helped propel their respective companies to growth and success.

Over the next two weeks, we’re opening voting in 13 GeekWire Awards categories, with GeekWire readers choosing their top picks from finalists selected by our panel of judges from community nominations. Check back on GeekWire each day to cast your ballot. Winners will be revealed at the GeekWire Awards — presented by Wave Business — on May 10th at the Museum of Pop Culture in Seattle.

Last year’s winner in this category was Smartsheet CEO Mark Mader, whose Seattle-area company is preparing to go public this year. Other past winners have included Rover.com CEO Aaron EasterlyAvalara CEO Scott McFarlaneJulep CEO Jane Park and Elemental Technologies CEO Sam Blackman, who passed away last summer at the age of 41.

This year’s finalists include Michel Feaster of Usermind; John Legere of T-Mobile; Sandi Lin of Skilljar; Daryn Nakhuda of MightyAI, and Kieran Snyder of Textio. Read more about each of them and vote for your pick in the poll below. And a big thanks to our longtime partner, EY, for sponsoring this year’s CEO of the Year category. 

Tickets are on sale for the big Awards show, so head here to get yours before we sell out.

Michel Feaster
Michel Feaster, co-founder and CEO of Usermind in Seattle. (Usermind Photo)

Michel Feaster, CEO of Usermind: Michel Feaster likes to build software and teams, and as the co-founder and CEO of the Seattle-based startup Usermind, she’s getting to do both.

With more than 20 years experience in enterprise IT, Feaster helped start Usermind in 2013. The software-as-a-service product connects data from different sources, helping companies pay closer attention to the needs, wants, and rants of their customers.

Feaster was previously the vice president of products at Apptio, where she helped grow the company from 30 to almost 400 employees. She also managed product teams at Opsware, leading the acquisition of that company by HP Software for $1.6 billion, and held product and engineering roles at Mercury Interactive and Compuware.

Usermind raised a $23.5 million round this past January from investors including Northgate Capital, Andreessen Horowitz, Menlo Ventures and CRV.  Feaster was recently featured in Startups.co and she’s a past GeekWire Geek of the Week, telling us that “I feel like there is tremendous integrity and authenticity in building software that makes my customers’ lives better.”

T-Mobile CEO John Legere speaks at CES. (GeekWire Photo / Todd Bishop)

John Legere, CEO of T-Mobile: If you follow Legere on social media, you already know he’s a brand marketing whiz, constantly donning magenta or lambasting rivals.

But it’s more than just flash. Since joining T-Mobile in 2012, Legere has helped turn around the company, guiding it to 19 straight quarters — and counting — with more than one million net customer additions.

Since he became CEO, Legere drove an aggressive campaign in which T-Mobile branded itself the “Un-carrier,” with new pricing strategies, subscriber benefits and promotions that forced rivals to change their own packages and promotions.

The result? T-Mobile’s customer count now tops more than 72 million. Legere, known for guzzling Red Bull, running marathons and his popular Slow Cooker Sunday cooking show, ranked No. 20 on Glassdoor’s Employees’ Choice Awards last year among highest-rated CEOs.

Skilljar founders Sandi Lin and Jason Stewart. (Photo via Skilljar)

Sandi Lin, CEO of Skilljar: It’s never easy taking your early-stage startup through a pivot, but Lin’s leadership helped Skilljar change course for the better.

The Seattle startup just raised a $16.4 million investment round to fuel growth of its learning management platform for enterprises. Skilljar provides the back-end technology and software that lets companies build cloud-based training and onboarding programs for their own users. The company has more than 150 customers, including giant companies like Verizon, Tableau, Cisco, Spotify, Zendesk, and others.

Lin made the startup leap after working for several years at Amazon, where the MIT and Stanford grad saw the need for a way to better train Amazon Marketplace sellers. In 2013, she teamed up with her co-founder Jason Stewart and launched Everpath, the first iteration of Skilljar.

Everpath, a Techstars Seattle accelerator participant, was a platform for online instructors to host their lessons — like a search engine for online classes. But the company pivoted in 2014 to solve a similar problem that instead targeted larger companies and provided more opportunity to scale.

Skilljar tripled the number of customers, year-over-year, in 2016 and 2017, and tripled its revenue last year. Lin said she’s excited to usher in a “new era of customer training and enablement” in a market the company estimates to be $12 billion. It plans to grow from 40 to 100 employees this year.

Daryn Nakhuda.

Daryn Nakhuda, CEO of Mighty AI: Leading Mighty AI is Nakhuda’s latest startup adventure. The veteran entrepreneur, who previously co-founded Eyejot and has executive experience at companies like Spam Arrest, Mixpo, TeachStreet, Amazon, and Porch, now heads up Mighty AI, a Seattle startup that offers training data as a service for computer vision and natural language AI, providing the human insights that help make artificial intelligence engines smarter.

The technology is especially critical to the development of autonomous vehicles, and Mighty AI is now reportedly working with more than a dozen automakers. The company taps the insights of people to help make AI engines stronger in vehicles — for example, identifying objects along the road that could be potential obstacles.

Formerly known as Spare 5, Mighty AI recently opened new offices in Boston and Detroit. The 65-person startup has raised $27 million to date from backers that include Intel Capital, Accenture, Foundry Group, Madrona Venture Group, New Enterprise Associates and GV, the investing arm of Google.

Nakhuda, who helped start the company, took over as CEO in August as former CEO Matt Bencke stepped down after being diagnosed with pancreatic cancer. Bencke passed away this past October.

Kieran Snyder
Kieran Snyder.

Kieran Snyder, CEO of Textio: Snyder is doing something right at the helm of Textio. This is her second consecutive nomination for CEO of the Year, as Snyder was up for the award in 2017 as well.

The former Microsoft manager and past Geek of the Week is using text analysis to help companies craft better job listings or candidate emails. Textio looks at word choice, organization of the listing, style, and more when formulating its score. Customers who get a high score on Textio end up seeing more qualified and diverse candidates, and they fill positions faster, the company says.

It’s a noble pursuit, and one in which Snyder says she draw inspiration from her daughters, coaching their basketball team and studying how they relate to technology.

Snyder holds a PhD in Linguistics from the University of Pennsylvania, where she studied natural language processing and computational linguistics. She describes herself as a “language nerd and math nerd,” and has built her career around those two passions.

Snyder’s four-year-old startup recently raised a $20 million investment round, with plans to expand to other types of business interactions, such as recruiting emails and sales communications. Textio’s customers include Apple, Microsoft, Slack, Twitter, BP, Johnson & Johnson and others.

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