Vote for CEO of the Year: GeekWire Awards finalists find growth opportunities in uncertain times

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CEO of the Year finalists in the 2022 GeekWire Awards, clockwise from upper left: Sandi Lin of Skilljar; Anoop Gupta of SeekOut; Bill Richter of Qumulo; Maria Colacurcio of Syndio; Karl Siebrecht of Flexe; and Xiao Wang of Boundless.

Building and running a company is no easy task in the best of times, let alone amid the ongoing uncertainty of the past year. This year’s finalists for CEO of the Year in the GeekWire Awards have led their companies through global turmoil while finding new opportunities for growth along the way.

The six finalists for CEO of the Year in the 2022 GeekWire Awards are: Maria Colacurcio of Syndio; Sandi Lin of Skilljar; Anoop Gupta of SeekOut; Bill Richter of Qumulo; Karl Siebrecht of Flexe; and Xiao Wang of Boundless.

This category recognizes CEOs of Pacific Northwest technology companies with more than 100 employees. (The separate Startup CEO of the Year category in the GeekWire Awards is for those with 100 employees or fewer. CEO of the Year is presented by audit, tax, and consulting services company RSM US.

Last year’s winner of CEO of the Year in the GeekWire Awards was Kieran Snyder, CEO and co-founder of Textio, the augmented writing technology company.

Continue reading to learn more about this year’s finalists for CEO of the Year, and vote for your picks across all categories in the GeekWire Awards ballot below.

The GeekWire Awards recognize the top innovators and companies in Pacific Northwest technology. Finalists in this category and others were selected based on community nominations, along with input from GeekWire Awards judges. Community voting across all categories will continue until April 22, combined with feedback from judges to determine the winner in each category.

We’ll announce the winners on May 12 at the GeekWire Awards, presented by Astound Business Solutions. Contact [email protected] for more information.

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CEO of the Year, presented by RSM US, LLP

Maria Colacurcio of Syndio during the GeekWire Elevator Pitch finals at the GeekWire Summit in Seattle in 2019. (GeekWire File Photo / Dan DeLong)

Maria Colacurcio, CEO of Syndio. The workplace equity technology company further expanded its focus in February with the release of a new product called OppEQ, which lets companies analyze hiring, promotions, retention rates and other data by gender, race and other factors to identify, understand and address pay gaps in their organizations.

Colacurcio, who previously co-founded the workplace collaboration company Smartsheet, joined Syndio in 2018. The company, which won GeekWire’s Elevator Pitch competition in 2019, raised $50 million in new funding last year.

Sandi Lin, CEO and co-founder of Seattle’s Skilljar. (Skilljar Photo)

Sandi Lin, CEO and co-founder of Skilljar. The customer training platform and education company saw its growth accelerate amid the boom in online training and education during the pandemic. Skilljar rolled out a series of product upgrades in 2021 and was recognized for its rapid growth, along with several others in this category.

Lin, a former Amazon senior product manager, is an MIT civil engineering and Stanford MBA graduate who worked as an economic consultant earlier in her career. Skilljar raised a $30 million Series B funding round in October 2020.

SeekOut CEO and co-founder Anoop Gupta.

Anoop Gupta, CEO and co-founder of SeekOut. The company’s AI-powered recruiting technology is used by more than 1,000 companies. SeekOut, which won Startup of the Year honors at the 2021 GeekWire Awards, saw its annual recurring revenue triple in the last nine months of 2021, into the $25-to-$50 million range.

Gupta is a former technical assistant to Bill Gates who previously led Microsoft’s Unified Communications Group. SeekOut raised $115 million in new funding in January at a valuation of more than $1 billion.

Flexe co-founder and CEO Karl Siebrecht. (Flexe Photo)

Karl Siebrecht, CEO and co-founder of Flexe. The on-demand warehousing and fulfillment technology company offers retailers flexible logistics and cost savings through access to a network of distribution facilities and carriers. The company helps retailers compete with Amazon with same-day delivery and other capabilities.

Siebrecht, the former AdReady CEO, was previously president of aQuantive’s Atlas technology division, and then a Microsoft general manager. Flexe closed out an $80 million Series C funding round in January 2021.

Qumulo CEO Bill Richter. (Qumulo Photo / Andy Rogers)

Bill Richter, CEO of Qumulo. The cloud file storage and management company focuses on helping companies manage unstructured data. The acceleration of cloud technologies during the pandemic contributed to record growth in its business, Richter told us on the GeekWire Podcast last fall.

Richter was previously a venture partner at Madrona Venture Group, and a leader at Isilon Systems and EMC. Qumulo joined the ranks of Seattle’s unicorns with a valuation of $1.2 billion in a $125 million funding round in 2020. 

Boundless CEO Xiao Wang. (Boundless Photo)

Xiao Wang, CEO of Boundless. The Seattle-based company, which offers software and services to streamline the immigration process, has encountered more than its share of uncertainty in recent years. Shifting U.S. immigration policies and the shut-down in global travel created “a great environment to build resilience and the ability to adapt and evolve as an organization,” Wang told us on the GeekWire Podcast in December.

A former Amazon senior product manager, Wang immigrated to the U.S. from China at 3 years old, and went on to earn advanced degrees from Stanford and Harvard Business School. Boundless, which spun out of Pioneer Square Labs in 2017, raised $25 million in April 2021 in its latest funding round.


A big thanks to Astound Business Solutions, the presenting sponsor of the 2022 GeekWire Awards.

Also, thanks to gold-level and category sponsors: Wilson Sonsini, ALLtech, JLL, DreamBox Learning, Blink UX, BECU, Baird, Fuel Talent, RSM, Aon and Meridian Capital. And thanks to silver level sponsors: J.P. Morgan Chase and Material+.

If interested in sponsoring a category or purchasing a table sponsorship for the event, contact us at [email protected].


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