Get the latest on Ed Tech industry news, hiring, recruiting, and more!

Category: Remote Work

Reflections After 20 Years of Remote Work

After the birth of my first child, I initially struggled with the same question faced by so many working parents: how did I want to balance my career with my growing family?

In my case, I found inspiration in the career of Ruth Bader Ginsburg. I learned that, at times in her life, she would simply make a decision that her husband and children needed to take precedence over her career. And yet, her brilliance and perseverance still took her to the pinnacle of her field. Her success gave me confidence that I could do anything, including building a working life that would give me more flexibility to spend time with family while maintaining my career.

This confidence allowed me to embark on a remote career 20 years ago, long before the current trend toward telecommuting. For me, this choice has proved incredibly rewarding. In this article, I wanted to take a moment to collect my thoughts and think through remote work in the context of both my personal experience (including a front-row seat to a shifting job market in my role as a recruiter) and the growing body of evidence after several years of post-COVID perspective.

A Personal Choice Becomes an Emerging Trend

When I approached my employer about transitioning to remote work, I was surprised to hear an enthusiastic reception. They trusted me to be productive, had confidence that I would continue to contribute at the same level remotely, and understood that retaining a valued professional was worth any logistical hiccups that came with this transition. Of course, at that time, technological productivity tools were far more limited. My position was ready to go remote because it focused on concrete deliverables that had to be generated on a tight, consistent schedule. As technology advanced over time, more and more positions at my employer became amenable to remote work, and ultimately my career shift became a trend-setting move in the company.

In many ways, I think my experience 20 years ago gets to the heart of the central issue with remote work today: productivity. More and more employers recognize that allowing for at least some remote work provides benefits including lower costs for office space, access to a broader geographic hiring pool, and improved employee retention. The key question will always be, "Can I trust employees to provide the same level of productivity in a remote setting?"

In this context, my experience highlights a common fact that I believe goes under-discussed in the current cultural debate over the future of remote work: remote work has always been an option for experienced professionals who have earned their employer's trust. For lawyers, programmers, salespeople, recruiters, marketers, and a huge array of other business functions, the flexibility of remote work has been accessible for decades (and for many consultants and traveling salespeople, a necessity!).

What makes remote work different today?

The fundamental shift now is not that remote work exists, it is that today’s collaboration technologies make it easier to collaborate remotely, track productivity, assign work, and provide timely feedback. These capabilities make remote work a possibility for early-career professionals, something that was very rare in the past, by lowering the threshold of trust needed with a remote employee. And they dramatically expand the set of job functions that can be supported remotely. Today’s digital collaboration tools have effectively democratized remote work.

Of course, not every company, industry, and/or career path is amenable to remote work. Some jobs simply require physical input and oversight from employees, while some companies prize the unique benefits of in-person collaboration. JPMorgan CEO Jamie Dimon remarked as the company returned to an in-office work policy that “I completely understand why someone doesn’t want to commute an hour and a half every day, totally got it. Doesn’t mean they have to have a job here either.” While this remark may be flippant, it also alludes to the new reality of the job market: professionals have a choice.

I certainly sacrificed some opportunities by transitioning to a remote career. But I gave myself the choice to invest in flexibility for myself and my family which has proved incredibly rewarding. And eventually, this flexibility led me to transition toward entrepreneurial opportunities that I may never have found time for in my earlier corporate career.

According to survey data from Forbes, 98% of employees want to work remotely at least some of the time. Looking forward, I believe the job market will evolve to reflect a balance of this overwhelming preference and the requirements of different employers and positions. Hybrid work, for example, can be a great option to balance remote flexibility with the need to be in-office for certain activities.

Takeaways from Two Decades of Working Remotely


  1. Remote work isn’t for everyone. Some people thrive on independence and self-motivation, while others need the energy and focus of a physical office.
  2. The right technology matters. For some jobs, a mobile phone is all that’s really needed for remote productivity. But most positions require a more sophisticated approach to digital collaboration, and finding the right mix of tools can be critical for unlocking effective remote workflows.
  3. Remote work isn’t just for employees. It can also be the foundation of small businesses that used to require a brick-and-mortar presence.
  4. Remote work can promote equity, providing greater choices for parents with careers, individuals with occupational disabilities, and people who live in remote/rural areas.
  5. Remote work isn’t always either-or. Hybrid work arrangements can provide greater flexibility for workplaces that still need at least a part-time in-office presence.


Learn More About Working Remotely in the Ed Tech Industry

HighFive Partners operates the biggest jobs platform in the Ed Tech industry, operated by a fully remote team. We feel fortunate to work from a beautiful place like Lake Tahoe, and we take pride in connecting job seekers who are interested in remote work with companies that embrace this approach.

We take a deeper look at why remote work is a great fit for the Ed Tech industry in our blog here. Or, if you're interested in browsing remote positions in the Ed Tech industry, I invite you to explore the remote section of our jobs platform here.