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Can Work-From-Anywhere Really Work?

November 22, 2022 Digital Workplace
Dr. Kyle Elliott
By Kyle Elliott

Workers are demanding increased flexibility from their employers, and according to a recent survey by McKinsey, 87% of job holders who are offered the chance to work flexibly take their employer up on the opportunity.

Work-from-anywhere is one strategy being used by companies to attract and retain top talent in today’s competitive labor market. But is it working? Here are two examples of organizations that have recently deployed this talent strategy.

Attracting High-Caliber Talent Beyond Alaska

Several years ago, Cynthia Adams, the founder of philanthropic GrantStation, made the decision to close the company’s office in Fairbanks, Alaska, and move the organization to the cloud, with the hopes of attracting and retaining talent. “Our employment pool was slim, and it seemed we were constantly struggling to find reliable staff. And when we did find a good person, they’d often want to leave Alaska,” said Adams.

“The decision was easy: keep stellar staff and let them live wherever they want as long as it fit within their job description,” she explained. “Alaska is gorgeous, but it is a tough place to live,” Adams said. According to her, the state’s high cost of living and remoteness can make it even more difficult to attract and retain talent.

With fewer than 50 full-time employees, GrantStation is exempt from the requirement to provide health coverage, but according to Adams, the company still offers stipends toward health insurance costs. She explained that this exemption enabled GrantStation to sidestep any potential health insurance-related roadblocks in transitioning to a fully remote workforce.

Following the office closure, several of GrantStation’s employees immediately relocated outside of Alaska, including one to California and another to Spain. Both employees now live in Spain, and the company has since hired a third employee in the country. A decade later, only one of GrantStation’s employees remains in Alaska.

As of our November 2022 interview, a GrantStation employee was temporarily living in Amsterdam, while another had recently spent six months living in Norway where her husband had a teaching job. As the company’s CEO, Adams herself has lived in both Mexico and Chile.

Adams’ vision for a cloud-based company has paid off, as talent is drawn to the ability to work and live wherever they want. “I encouraged people to do this if they want to… it is a perk we can offer as a small business that makes everyone smile," she said.

“Retention is key for the work we do, so allowing our staff to spend time abroad, or to live abroad, is an attractive benefit that keeps our employees happy.”

Related Article: Why Your Return-to-the-Office Directives Fail — And What to Do About It

Improving Worker Flexibility During the Covid-19 Pandemic

GrantStation isn’t the only organization that has attracted and retained employees by pivoting its talent strategy.

In 2020, Feedback Loop’s Chief People Officer, Marjorie Ajero, made the decision to spend two months working abroad from the Caribbean. She enjoyed the experienced so much, she returned the following year and spent two and a half additional months working internationally.

As the company’s most senior human resources leader, Ajero was charged with setting and communicating the people vision and strategy for the organization. This included gaining buy-in from the CEO and CFO to permit employees to work internationally, mitigating organizational risk and setting the parameters and boundaries for this new way of working.

Ajero explained that her highly visible, executive-level role enabled her to model effective work-from-anywhere. It also required her to coach managers on setting expectations in this flexible model for approximately 100 employees.

According to her, the company operated using a professional employer organization (PEO), which made the process “really easy,” she said. Additionally, employees frequently mixed paid time off with remote work, enabling them to spend several months working and living across the globe.

Workers benefited greatly from Feedback Loop’s flexibility, Ajero said. For instance, one employee was able to finally visit family in their home country after being separated for more than two years due to Covid. Another employee traveled across the United States, spending a handful of months living in different states.

Several employees relocated outside of the New York City area, where Feedback Loop’s main office was located, to live with family or for a lower cost of living. Notably, the organization did not reduce salaries when employees chose to move to another city or state.

The benefits of Feedback Loop’s flexible model weren’t just tactical, either, clarified Ajero. “I encouraged people to take a little bit more time for themselves or to find things that, especially during the pandemic, brought them joy.”

“I think the other benefit was, we just showed the flexibility we were willing to give employees, and I think we gave a lot of people flexibility,” she said.

About the Author

Dr. Kyle Elliott, MPA, CHES (he/him/his) is the founder, career coach and executive coach behind


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