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Going “Remote First”: Automate, Communicate, and Document

August 19, 2022



Going “Remote First”: Automate, Communicate, and Document

Going “Remote First”: Automate, Communicate, and Document

Robert Keane, Founder and CEO of Cimpress and Vista (formerly VistaPrint) built a multibillion-dollar business from scratch starting more than 20 years ago. He transformed the original analog operations through digitalization in order to scale rapidly. Robert explains how this strategic move also set them up to go “remote first” in August 2020—listening to employees’ preferences—with the intent of building and maintaining competitive advantage for the business.


02:22] Robert identified the need and developed the business plan for Cimpress at INSEAD business school.

[03:38] Cutting edge (at the time) technology was essential to provide the services.

[04:45] The core customer proposition and need have not changed over 27 years.

[06:30] Pushing the early envelope for browser-based software.

[07:49] After raising venture capital money in ’99, the company turned profitable by 2003 and reached US$1 billion in revenues by 2011.

[10:30] End-to-end integrated digitalization allowed them to achieve significant growth.

[11:55] Robert’s purposeful approach for capturing competitive advantage through automation.

[13:53] To build the business, new recruits were selected who were intent to transform industries.

[14:45] Post the 2000 crash, the emphasis is “digital first”.

[15:20] Robert recognizes the digitization emphasis needs to be rebalanced with more customer focus.

[16:31] How Cimpress operated as a global distributed business pre-pandemic.

[18:57] Robert’s direct reports in China and Italy rang alarm leading to early contingency planning.

[20:00] The decision to go “remote first”.

[20:56] Management could compete for talent, and give certainty and guidance to employees.

[23:24] Employees were asked regularly about their interest in remote work which started shifting.

[23:53] Management respectfully addresses the minority of people who didn’t want to go fully remote

[25:36] People accept the fact that remote is not perfect.

[26:22] How has Robert’s changed his leadership style going fully remote?

[27:26] The importance of systemizing communication to inform, align, and connect people.

[29:35] Investment in asynchronous documentation is essential for “remote first” companies.

[31:09] Hiring people to lead Cimpress businesses who have entrepreneurial/founder mindsets.

[32:26] Robert is open to making mistakes and not believing there’s only one way forward.

[35:10] IMMEDIATE ACTION TIP: To integrate remote working effectively, run a thought experiment. If you started a company today, how would you architect it and incorporate remote working? Whatever percentage of time employees would be onsite and remote at this company, they would need clarity and certainty. Putting theory into practice for your current organization cannot happen overnight, but listen to team members to make choices about the direction you need to go.


“Our engagement scores, which we've tracked for years, are at all time high because people can combine their life and their work in ways that fits their personal needs.”

“People embrace the fact that remote is not perfect.”

“It’s important to constantly reiterate the importance of that nimbleness, that ability to take action and the willingness to fail, to fall down and get bruised and pick yourself up and pivot and move.”

“We started believing that the way we were doing things was the only way to do things. They just happened to be the right way to do things at a certain moment in time.”

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