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From paratrooper to Yahoo CTO

From paratrooper to CTO — how Chris Wayne made his military transition a success

The similarities between being a paratrooper and being a chief technology officer for a large company might seem slim on the surface. But both environments thrive on chaos, and in both settings, a person needs to be able to pivot, adapt, and react.

That’s what Chris Wayne, a former sergeant from the 82nd Airborne and CTO of Yahoo! Small Business, has learned over the last 20 years. Now Wayne is doing what he can to help make the path from service member to civilian easier for those leaving the military. He left the Army in 2000 and says that it took a lot of hustle to get to where he is now, but the main lesson he’s learned is that everything is transferable.

“No one was hiring ex-paratroopers to go blow stuff up, so I had to figure out where I fit into the ecosystem. I was in a new city, with new people, and at a new school,” he said.

Wayne immediately recognized that he needed to ditch his ego if he was going to be successful in the civilian sector. No one cared that he was a decorated soldier, so he had to find other ways to make himself stand out from competing job applicants, which was challenging since he didn’t have much civilian work experience. The military taught him to sink his teeth into a role and make it the best possible experience it could be.

“When you leave the military, you’re used to working really hard. Some of those habits die hard,” said Wayne.

In the military, that meant going full charge until the job was done, not complaining, showing up for work on time, and making sure rules were followed. Wayne initially struggled to find work because it felt like none of his paratrooping qualifications matched what civilian employers were looking for. Then he realized the job description had less to do with the actual description and more to do with how the job is done. Wayne calls this looking for the “how” and not the “what.”

“So for me, I wanted something I could sink my teeth into. I asked myself what are my strengths? Those are waking up early, paying attention to detail, solving problems under stress, and working well with anyone,” he said.

All traits and characteristics honed during his time with the 82nd.

“You don’t go to job interviews and say, ‘I’m going to show up on time and not complain and do everything and ask for very little money.’ You just don’t say that. But that’s kind of the role you’re looking for,” he said.

That line of thinking led Wayne to a tech career, which, he says, is a lot like being a paratrooper.

“I enjoy it because I love solving complex problems, leading teams, and I love the chaos of tech. There’s always something new that’s changing, just like being in the military,” he said.

Wayne is adamant that transitioning service members do several things before hanging up their uniforms for the last time.

“You need to be focused on the tools the military offers for a transition and be more deliberate and diligent about what a graceful exit looks like,” he said.

That means establishing a base network of peers and colleagues online and in-person and clarifying the division between professional and personal networks.

Read Chris’s story on page 28 of the February issue of the Military Influencer Magazine.

“What the world knows about you is up to you. You need to get professional fast. Make sure you have a professional email address. Don’t post controversial things within your professional network and manage your brand aggressively,” he said.

Finally, the most important thing a soon-to-be veteran can do is find a mentor and a way to give back.

“Having a mentor is having someone tell you when you’re wrong. You have to surrender yourself to not having an ego and accept you’re probably wrong most of the time. You have to go out on this journey of self-exploration to make sure you’re finding the right solution instead of just needing to be right,” said Wayne.

Wayne credits his success in tech and at Yahoo! Small Business because the company’s values align with his own. He urges veterans to explore their value systems and find companies that have similar approaches.

“One of the reasons I’ve been so successful is because of the alignment with Yahoo! Small Business and what I’m trying to accomplish personally are really similar,” he said.

Recently, Yahoo Small Business! has made all of its resources available for free. After YSB saw a spike in people wanting to open businesses, Wayne led the charge to create the kind of change he says the world needs.

“We said let’s give away our products for free and how about we generate some goodwill because it’s the right thing to do,” he said.

Yahoo Stands by Small Business: Our Get Online Plan for SMBs is Now Free for a Year

This new, free offering in response to COVID-19 provides several valuable services, including:

  • Domain name registration (yourbusiness.com) with private domain registration included.
  • Professional, custom business branded email with 5 email addresses.
  • A website builder package with design tools and templates to help you quickly build and publish a professional website.
  • A business plan creator to help you plan your next steps and potentially help with documentation you many need for SMB relief initiatives.
  • A Localworks Scan to see how your business appears online in more than 70 directories and to help you decide what changes might be needed to keep customers up to speed with any changes you’re making with your business and services.
  • 10 GB storage and unlimited bandwidth so you don’t need to worry about running out of digital space.
  • Consultation time from a small business expert. We’ve been helping small businesses succeed for more than 20 years, and we want to share this expertise with you to be sure we’re both here working together for 20 more.
  • And of course, because we are in this with you, our support representatives are available 24/7 to make sure we address any questions you may have.

For more information about the Yahoo Small Business free Get Online program for small businesses, visit https://smallbusiness.yahoo.com/businessmaker/payitforward.

This new, free offering in response to COVID-19 provides several valuable services, including:

  • Domain name registration (yourbusiness.com) with private domain registration included.
  • Professional, custom business branded email with 5 email addresses.
  • A website builder package with design tools and templates to help you quickly build and publish a professional website.
  • A business plan creator to help you plan your next steps and potentially help with documentation you many need for SMB relief initiatives.
  • A Localworks Scan to see how your business appears online in more than 70 directories and to help you decide what changes might be needed to keep customers up to speed with any changes you’re making with your business and services.
  • 10 GB storage and unlimited bandwidth so you don’t need to worry about running out of digital space.
  • Consultation time from a small business expert. We’ve been helping small businesses succeed for more than 20 years, and we want to share this expertise with you to be sure we’re both here working together for 20 more.
  • And of course, because we are in this with you, our support representatives are available 24/7 to make sure we address any questions you may have.
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