Upwork tapped this HR pro to make remote work ‘best in class’

Here’s this week’s edition of our Coworking series. Each week, we chat 1:1 with an HR Brew reader. Want to be featured in an upcoming edition? Click here to introduce yourself.

Upwork’s Director of Remote Organizational Effectiveness Jessica “JJ” Reeder is an inventor. What’s she inventing? A gold standard for remote work, so Upwork can deliver a “best in class” remote-first experience for employees.

“There are a lot of companies doing it very well, but nobody has truly cracked the nut,” Reeder said.

She’s working on “things like meeting effectiveness, things like transparency, things like how to offer benefits and flexibility for folks,” and those will look different for a remote-first organization like Upwork.

Reeder tried an office job when she began her career, but it “just didn’t work” for her, so she freelanced until 2017, when she found her way into a fully remote company, Toptal. She then took a job helping to make remote work better at GitLab. Reeder likened the experience to “getting a master’s degree in remote work.”

Reeder said HR pros can help leadership think through remote work and RTO by focusing on the why before diving into the how, but the how is important. For Reeder and Upwork, it involves a lot of experimentation and a heavy emphasis on communication while she learns and incorporates best practices from other remote-first orgs.

This interview has been edited for length and clarity.

What’s the best change you’ve made at work?

In October, Upwork launched an intranet, a private information hub for our organization. We previously had a mix of documentation practices and tools for sharing information, but we knew we needed an elevated solution. This is especially true because Upwork has a large contingent workforce in addition to traditional employees, and so we have a range of different offerings, benefits, and policies to serve many different worker types.

After spending the first half of 2023 vetting intranet providers, we decided to use Haystack as our solution. As of December 2023, I’m proud to share that we’ve migrated almost 1,000 pages of information to the platform.

What’s the biggest misconception people might have about your job?

Making decisions about an organization’s work model is not cut-and-dry. Not all companies can go remote, and the notion that returning to the office is a bad idea isn’t necessarily accurate. These decisions are difficult, nuanced, and take significant research to find the right solutions. I’m currently earning my masters in industrial organizational psychology at Harvard Extension, because I want to apply the latest thinking to Upwork and continue to evolve how we approach work. My goal is to act as a consultant and to bring knowledge and information, rather than just advocacy, to help the leaders I work with make great choices.

What’s the most fulfilling aspect of your job?

Honestly? Working remotely. I’ve been remote since 2006, and I try to integrate my personal experience to help others succeed in the virtual workplace.

Another fulfilling aspect of my job is the “why” behind what I do. The vision for the future of work is stunning: global teams representing the best people from anywhere in the world, working around the clock, while also having the freedom to design their own workdays. This ideal represents so much potential for companies to gain and keep the most talented people, while staying productive and profitable.

What trend in HR are you most optimistic about? Why?

DE&I. While “diversity” as an outcome has been an intention for some time in many companies, understanding equity is very much a maturing practice. Inclusion is only getting started, and I find this exciting because it’s something we (not just leaders) can all learn to be more intentional about. Especially as teams become more global, we are all getting a lesson in multiculturalism and how to be considerate and inclusive. This makes us all better people, and it helps us find ways to contribute, talk about problems, and connect with people.

What trend in HR are you least optimistic about? Why?

I don’t think this is a new trend, but at times you can really tell what people are talking to each other about behind closed doors, right? Some of the discussion around remote work that’s happening in the media is not reflected in research, but it seems to have a more anecdotal basis. I think some of this is backlash against the rah-rah attitude toward remote work that dominated during the pandemic, but some of it is good old fear-based bias.

There will continue to be outdated notions of remote work or people holding the belief that employees are less productive because of where they work. Whether it’s fear, bias, or not being adaptable to change, some organizations are still firm in their belief that remote work is not strategic.