Introduction

Hi, I am Heather Doshay, VP People at Webflow, where I lead the talent and people teams. Also, I am a Distributed/Remote Work Enthusiast and an SHRM senior certified served on the PeopleTech Partners Advisory and the Forbes HR Council.

Current Location?

Portland, Oregon

Current Gig?

VP People at Webflow

Current Computer, Mobile, etc.?

Apple devices: MacBook Pro

Where can we follow you on the Internet?

Linkedin. I quit Twitter as it was terrible for my mental health!

Describe how you work in 10 words or less?

Many Zoom meetings are punctuated by async Slack/Docs/Loom communications.

Tell us a little bit about your background & how did you get started with remote work?

I had the pleasure of working on my first distributed team six and a half years ago and realized both the inherent power and challenges that come with remote work. I managed a team in multiple time zones, made coworker friends all over the world, and instantly improved my written communication skills.

Ever since that experience, I have only sought opportunities to work and lead people teams at companies working to invest in remote work truly. However, for the first four years of my remote work experience, I was always in an office, and remote work was the "other".I decided to move away for two reasons:-

  1. I could be so much more impactful supporting remote work for others if I could personally empathize with it, and
  2. As an executive in SF, I found myself lived in a tiny studio apartment, and I wanted to move somewhere where I could put down roots. I was empowered by my then boss to go remote, and I've loved the experience ever since-- not sure I can go back to office life.

What job responsibilities do you have?

My mom still doesn’t understand what I do no matter how much I explain it but let me give this a shot: I lead our internal teams that attract, engage, and develop our people.

This includes our talent/recruiting team, our people and organizational development team, team engagement (workplace, remote work, events), IT, and executive support. Most of my day to day involves meeting with people across the company and helping solve problems or work through our various organizational opportunities.

What’s your workspace setup like?

My workspace is still a work in progress, and I redesigned it to spark more joy. It’s a small bedroom down the hall from my bedroom, and I tried to incorporate lively colors. I have one officemate, Charles Barkley.

What apps, gadgets, or tools can’t you live without?

So many! Google Suite, Zoom, and Slack power most of my existence, and I’m an Apple user all the way. But these are pretty basic answers.

Here are three lesser-known tools I can’t live without, especially as a remote professional: 1. Loom! Loom is an asynchronous recording tool where I can screen share and voice-over whatever I am looking at. It has probably saved me 100 hours of meetings and helped my looming (pun intended) Carpal Tunnel. Loom allows us to share a screen and record myself explaining any concept to the person on the other end for whom a live meeting isn’t possible (or realistic).

2. Peloton! Okay, so maybe this one is pretty widely known, but not how I use it- I don’t have the bike. I use the digital app, which has 5 and 10-minute mini-workouts- I can stretch if I’ve been sitting too long or if I can fit a 10-minute arms toning class on my lunch break, I feel more accomplished.

3. Prioritization notepad. This is a simple (paper omg) notepad that forces me to name the top 3 priorities of the day/week. I don’t use it consistently, but I find whenever I’m overwhelmed and have an essential deliverable I need to progress on that week, it keeps me focused.

How do you keep track of what you need to prioritize?

A lot of things. I set OKRs, have a great EA, use my prioritization notepad. I also use the Slack “remind me” snooze feature tons to create a to-do list with the Slackbot. I also block off action items on my google calendar. It’s organized chaos, if I’m totally honest.

It’s really easy to get sidetracked when you want to help someone with their priority, even when it isn’t yours.

How do you recharge or take a break?

Oh gosh, lots of things, and it’s never enough. One way I recharge, which I recommend, is what I call Selfcare Sundays! Every Sunday, I try to do at least two acts of self-care to start the week right. These can be anything as fancy as a spa treatment or buying myself a gift or as easy as taking a hike or catching up with a good friend on the phone.

I also take vacations of at least a week and then make my first day back a focus day, so I feel caught up versus going right back into meetings. That emotional-mental warm-up is so important.

What are you currently reading? What do you recommend?

I’m reading the Infinite Game by Simon Sinek. My CEO gifted it to me recently, and it’s an excellent read for anyone thinking about the long game and how to bring people along to work toward your vision with you. I recommend anything by Simon Sinek, and I am also pretty into The 15 Commitments of Conscious Leadership lately.

Advice for someone who is looking to switch to a remote job?‌

Test it out first. This is easier right now than ever before but make sure you understand the many pros and also the few cons. Remote work is ideal for so many people and me, but it’s not a match for all people. Also, practice asynchronous communications as much as you can.

What’s your best piece of advice you have received?

Ever?! Big question without an easy answer. Related to remote work specifically, I’d say knowing to move to a video call with someone when it’s clear async communication is escalating into frustration or conflict territory.

Also, and in all conflicts, staying on your side with what’s objective. If you conclude the other person’s motive or actions, prefacing any assumption with “there’s a story in my head when you do X, you mean Y” versus attacking that they mean why when they do X.

Validate assumptions.

What, according to you, are the pros and cons of remote work?

Cons are few: Can be lonely for some (I don’t typically experience this), it can be frustrating not to get an immediate response to quick questions. It can be tough to feel work/home separation if you can’t make room for a dedicated workspace.

Pros are many: Gain back 2+ hours back each day not getting ready for work and commuting, great for the sustainability of our world to have fewer vehicles on the road, communication has become more robust out of necessity, more time with my dog, ability to meet my introvert needs at lunch without the pressure of group dining, knowing people all over the world I wouldn’t have the chance to meet if I worked in an office in downtown Portland.


‌Want to work remotely like Heather? Go over our guide to see how companies hire remote employees and learn essential qualities a remote employee must-have.  If you are searching for a remote job, keep in mind to avoid common mistakes while applying. And while you're at it, join like-minded remote workers in our LinkedIn community.