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Recognizing 100 CEOs & C-level Executives

Wendy J Greenland



Location: Phoenix, AZ

Founded: 2001

Industry: Software

You can’t escape the truth, at least not if you want to succeed, says Openforce CEO Wendy J. Greenland.

“The greatest leadership lesson I’ve learned is that you must accept the brutal truth about how your customers and employees feel about your company,” she said. “I was still relatively new to Openforce when I was promoted into the CEO role after just a year and a half in the COO role. The only choice I had was to look head-on and ask our customers and employees to tell me everything that wasn’t working so that I could confront the brutal truth and act on it. As a company, we could no longer turn our head away from our problems. With that approach, we have achieved unprecedented membership growth in our company in the past two years.”

Openforce is a leader in technology-driven services that reduce costs and compliance risk for companies using independent contractors. The company’s mission is to connect independent contractors and the companies that need them.

Openforce was formed from the experience of its founders operating a company that used independent contractors. Frustrated by administrative inefficiencies and legal constraints, the team set out to build a solution that would help companies do it right. Twenty years later, more than 60,000 companies and contractors rely on Openforce as their outsourced provider for rapid and compliant onboarding, contracting, settlement processing, risk controls requirements and member benefits.

Greenland came to Openforce with 30 years of leadership experience: 25 of those years with technology and software companies. She began her career in telecommunications with Sprint as a technical training manager before moving on to business operations. In the early 2000s, Greenland co-founded a wireless telecom company called SCSConnect. She was co-owner of that business for 12 years and helped grow top-line revenue over 300% during her tenure.

She then shifted her career focus to the software industry. Greenland landed a position at InfinityHR, an HRIS and payroll software integrator, eventually rising to COO. Greenland joined Openforce in early 2019 and restructured the operations, marketing and sales teams. In August 2020, she was promoted to CEO and drove the company’s highest earnings in history in Q4 2020 while many companies were shuttering due to the economic impact of COVID-19.

Greenland was pushing boundaries for inclusion in the technology industry 20 years ago, before most companies recognized the need for diversified leadership teams. The trail she blazed to put women in leadership positions was further advanced when she joined Openforce as its COO and eventually took over as its first female president and chief executive.

Under Greenland’s leadership, Openforce has helped more than 100,000 companies and independent contractors reduce operating costs and mitigate risk. “The transportation and logistics industries, which represent the biggest customer base for Openforce, have experienced significant challenges over the past 24 months, yet under Wendy’s leadership Openforce has thrived,” the company said.

Presented by:

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Comerica Bank

Did you know?

Wendy loves 70’s and 80’s rock bands. She primarily likes to listen to Aerosmith, Journey, Guns N’ Roses, Queen, Pink Floyd, Bon Jovi, STYX, and Kansas to name a few! Her all-time favorite artist from that era is ‘The Piano Man’, Billy Joel.


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