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Leading Remote (First): Learnings From A Pioneer

February 10, 2023



Leading Remote (First): Learnings From A Pioneer

Leading Remote (First): Learnings From A Pioneer

John Riordan, the so-called “Godfather of Remote” and Chairman of Grow Remote, an Irish-based social enterprise organization, has led fully remote teams and divisions for over 20 years including for multiple airlines, Apple, and Shopify in the US and internationally. John’s remote working division’s expertise enabled the office-based 60% of Shopify employees to transition quickly to fully remote in March 2020. John shares transferrable insights from his experiences leading remote, hybrid, and on-site empathetic customer services teams—emphasizing community.


[03:07] John Riordan starts in investment banking but quickly pivots to sales and marketing.

[03:49] John moves to the US loving the accent of positivity of personal marketing.

[04:55] The sheer size of American companies and amplification of scale quickly teaches John to be more structured and rigorous in his thinking and execution.

[07:14] John steps up to join Virgin Atlantic as VP of Sales and Marketing leading a much larger than at US Airways, spread across nine US cities.

[09:17] John is challenged to deliver on Marketing’s promises and transition to be VP Customer Service.

[10:40] John spends valuable time in the call centers and airports learning to empathize with customers.

[12:40] Humility as a leader comes with recognizing reliance on the team and the importance of choosing team members well.

[13:57] John learns from the staff what real empathy is.

[14:25] A seismic shift in outsourcing customer service happens post 9/11.

[15:53] In 2006, Apple calls researching how to create a remote-based customer service operations for the first iPhone launch.

[17:48] Why a remote-only call center was Apple’s sustainable option.

[18:55] The challenges of the very beginnings of remote work: teleworking or telecommuting.
Remote working was a small percentage of workdays in 2006.

[20:35] John starts selling remote services and finds a general lack of acceptance.

[21:33] The fully-remote services company originally started to serve underemployed and under-resourced workers.

[22:46] Fully-remote-served customer service was an important niche market.

[23:36] Key points of resistance to fully-remote services—especially “I don’t think I could do it myself”.

[24:30] Mavericks made the leap, but John sees the inflection point as happening in March 2020.

[25:09] The next move, with Apple, is fully on-site—a tough transition for John.

[22:55] The points of resistance from companies are easily managed, except for one.

[25:08] From consulting for remote work with Apple to working for Apple back home in Ireland, but in a traditional brick-and-mortar call center.

[26:22] Without knowing John’s a remote pioneer, Shopify calls about a fully remote leadership role.

[27:38] Ecommerce requires 24/7 support, but local coverage leads to constant churn out of the night shift.

[28:48] Shopify becomes 40% remote (customer service) and 60% office-based pre-pandemic.

[30:44] Learnings from a major office move helped prepare Shopify to go remote in 2020.

[32:40] John has to readjust to remote working—eg self-discipline. He tunes into team members who excel at remote working.

[34:12] Painful personal experiences teach John what does NOT work in hybrid meetings.

[35:30] Pre-pandemic, office-based leaders start staying at home to participate equitably in meetings.

[37:44] 24/7 coverage teaches asynchronous, well-documented hand-offs and timing adjustments to wait for local contributions.

[39:55] John leads the company-wide initiative to remote in March 2020, as decentralized communication is humanized and normalized.

[42:50] The three most important areas to focus on that ensured emergency remote working success.

[44:55] The HR department had already compiled a “how to” book of the customer service department’s remote work experiences which became very useful for the whole company.

[45:31] The biggest challenge Shopify faced was for people to embrace their own vulnerability.

[47:10] John’s seemingly ageist concern about the irrelevance of using a 2015 approach to solve a 2023 problem.

[49:09] The future is about communities, not companies, especially to reduce the isolation that often accompanies remote working.

[51:12] How remote workers need to proactively design their work weeks, including nurturing non-work activities and setting boundaries.

[51:35] IMMEDIATE ACTION TIP: To reduce feelings of isolation, encourage remote working employees to connect with people regularly—virtually and in person in their local area—supporting humans’ need for community.

[53:25] How John identifies people who have good work-life balance—he uncovers their passion!


“The last -- and toughest -- objection to telework from companies: I don’t think I could do it therefore I don’t think somebody else could do it.”

“The number one thing -- absolutely paramount -- was to embrace your vulnerability.”

“You may well go back to an office, but you're not going back just because you had one, there has to be a reason.”

“What are you doing to make your business stronger in ‘25, ‘27, ‘29? You can’t go back 5, 7, 8, 10 years and tell me what it used to be like because those conditions don't exist anymore.”

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