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Jessie Woolley-Wilson, CEO of DreamBox Learning, won Big Tech CEO of the Year honors in 2019. (GeekWire Photo / Kevin Lisota)

Editor’s note: The GeekWire Awards are now virtual on July 23. Watch live below.

Our five GeekWire Awards finalists for Big Tech CEO of the Year work across various industries but they share several leadership traits in common — namely the vision, fortitude, creativity, and that impossible-to-define X-factor it takes to helm the ship of a fast-growing tech organization.

Awards 2020 big tech ceo EYThis award recognizes the leader of a tech company with more than 200 employees. The five finalists for Big Tech CEO of the Year are Dan Lewis, CEO of Convoy; Matt Oppenheimer, CEO of Remitly; Karl Siebrecht, CEO of Flexe; Raj Singh, CEO of Accolade; and Yvonne Wassenaar, CEO of Puppet.

Community voting is now under way across across 13 GeekWire Awards categories. These community votes will be combined with feedback from more than 20 judges to determine the winner in each category. We’ll announce the results live on stage May 19 at the GeekWire Awards — presented by Wave Business — in front of more than 800 geeks at the Museum of Pop Culture in Seattle. You can register for tickets on the event site or below.

DreamBox Learning CEO Jessie Woolley-Wilson took home the prize in the Big Tech CEO of the Year category last year.

Submit your votes belowgrab your tickets, and scroll down for descriptions of each Big Tech CEO of the Year finalist. This category is presented by EY.

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Dan Lewis, CEO of Convoy

Convoy CEO Dan Lewis. (GeekWire Photo)
  • Lewis, a former Amazon and Microsoft manager, helped launch digital trucking startup Convoy in 2015. The Seattle startup, ranked No. 5 on the GeekWire 200, has grown rapidly and attracted investors such as Bill Gates and Jeff Bezos. Convoy raised a $400 million round this past November, valuing the company at $2.7 billion. Its technology facilitates transactions between trucking companies and shippers. “We think this is an area where we can have incredible impact on society because the supply chain is so big and so inefficient and there isn’t an optimal supply chain solution that’s available to anyone,” Lewis said in November.

Matt Oppenheimer, CEO of Remitly

Remitly CEO Matt Oppenheimer. (Remitly Photo)
  • Oppenheimer co-founded Remitly in 2011 to transform the $600 billion global remittance industry. His company is certainly well on its way. Remitly, ranked No. 4 on the GeekWire 200, helped customers send more than $6 billion in 2018. The company launched a new banking service last month, expanding beyond remittances for the first time. “We want to bring peace of mind to immigrants with a suite of financial services that work for them and that they can trust,” Oppenheimer said in January. Remitly has raised nearly $300 million and grown to more than 1,000 employees. Oppenheimer was previously nominated twice for CEO of the Year honors at the GeekWire Awards. Perhaps the third time’s a charm.

Karl Siebrecht, CEO of Flexe

Flexe co-founder and CEO Karl Siebrecht. (Flexe Photo)
  • It started with a conversation at a dinner party, and the rest is history. Siebrecht, a former executive at aQuantive and AdReady, co-founded Flexe in 2013 as a way for retailers to find warehousing space to meet the demand from online shoppers. Flexe operates much like Airbnb — instead of using technology to match travelers with open homes and apartments, it matches retailers with warehouses that have excess capacity. Its customers include Walmart, Ace Hardware, Staples, Toms, and others. “We believe this will be a very, very large category and we aspire to be the leader of it,” he said last year after the company raised a $43 million investment round. Flexe is ranked No. 72 on the GeekWire 200.

Raj Singh, CEO of Accolade

Accolade CEO Raj Singh at the 2018 GeekWire Summit. (GeekWire Photo / Dan DeLong)
  • Raj Singh already helped disrupt one industry as co-founder of Concur, an employee expense management company that sold for $8.3 billion to SAP in 2014. Now he’s aiming to do it again, this time in healthcare. Singh took the helm at Accolade in 2015 and the company, which helps employers help their workers navigate healthcare options, has continued to grow since then. Customers include large employers from a range of industries, such as Comcast, Lowe’s, Amerigas, and Temple University Health Systems. The company, ranked No. 7 on the GeekWire 200, brought on more than 500,000 new members in 2018 and is reportedly gearing up for an IPO. “We have to think about people as people,” he said at an event last month, “and understand all of their context, as opposed to thinking about people as conditions and attempting to wrestle them to the next step in their condition.”

Yvonne Wassenaar, CEO of Puppet 

Yvonne Wassenaar at the Portland, Ore. office at Puppet. (Puppet Photo)
  • After helping lead companies such as VMware, New Relic, and Airware, last year Wassenaar took over as CEO of Puppet. Founded 15 years ago, the Portland. Ore.-based, 500-employee cloud automation company helps customers develop software and has raised $150 million. In her role, Wassenaar is aiming to expand Puppet’s customer base to bigger companies, moving beyond “super users” of their tools. She wants to shift from talking about solutions for solving specific use cases, to putting their products into a business context. As the rare female CEO — just 6.6 percent of Fortune 500 CEOs are women — Wassenaar is eager to help other leaders diversify their corporate boards and employees. “Diversity and inclusion is one of the most important business topics on the agenda today,” she said in this Working Geek profile from November, “and the reason for that is technology is changing every aspect of life around us.”

A big thanks to our longtime awards presenting partner, Wave Business, for supporting this fun community event. Also, thanks to gold and category sponsors: BECU, BCRA, Blink UX, EY, JLL, Premera, Slalom, WSGR and First Tech Federal Credit Union. And to our supporting sponsors Bader Martin, Flyhomes, Moz, Funko, Killer Visual Strategies and Tagboard. If interested in sponsoring a category or another component of the GeekWire Awards, please contact us at

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