Remote Work Interviews

Owl Labs (OL): How would you answer the question "tell me about your career" in a one-minute elevator pitch?

Jacqueline Jensen (JJ): I'm a former venture-backed startup founder, so right out of college, I started a startup and after raising money, I ran that for about four years. After that, I did different projects here and there that I was interested in, and then I decided to take a sabbatical in the fall of 2017.

I took a total break from work because I realized everything in my life revolved around work and working. I decided I wanted to find out what my life would look like if I took that out.

During that sabbatical, I spent time in the Balkans in Croatia and Montenegro and I tried to answer the question, what would I do if I could do anything just for fun? So, I wrote a book. I took an intro to programming course online for four months. And I just worked on my mental and physical health.

After that, I started working with Carl Richards, a New York Times columnist who wrote the forward to my book. As we were working on that project, he asked me about what I did for work. I told him I hadn't started looking at my next career move yet, and he said, "You should work with me." So that's how we started working together.

OL: Tell me a little bit about Prasada Partners, where you currently work with Carl as COO.

JJ: Prasada Partners is a small company — we don't have a website. We have a ton of individual projects we are working on right now.

Carl is an author, speaker, and columnist, and we're working on scaling and amplifying his content. For example, he creates cool Sharpie sketches in the Times, so we made a calendar of those sketches for people who love his art. We also work on scaling his content through speaking, and we brainstorm ideas for his next products.

OL: You've spent most of your career working remotely. When did that start for you?

JJ: I've been working remotely for almost all of my career. In my book, I write about when I was 22 years old — right out of college and getting ready to go full-time with my startup. At this point, I needed a paycheck to pay the bills. I was working with a nonprofit and I read a random blog post about remote work and working from anywhere and I thought to myself, "I want to do that."

So, I pitched our director at the non-profit by asking, "What if one day a week" — because I was just there part-time — "I worked outside the office? I'll still get everything done, I'll just work from another location one day a week."

To me, that was pretty bold. At the time, nobody in our 100-person organization was working remotely, and the director of the nonprofit said I could try it. I just read about this new thing and thought it would be cool, and from then on, I knew it was what I wanted to do. So really, my entire post-college career has been working remotely.

It's been interesting to build remote teams. I've worked with other remote folks, had my own autonomous projects going, and even worked remotely as a founder.

OL: Let's fast-forward to another role where you worked remotely. What was the structure like when you worked at Piktochart?

JJ: The team at Piktochart is "semi-distributed." I was team member 45 or so, and there are about 60-65 right now. At the time I joined, there were a few customer service folks who were remote to accommodate the different time zones of our customers in North and South America. But the majority of the team was working on-site, so remote work was still in the early stages of experimentation.

They wanted me to come to the island — Penang, Malaysia — to meet everyone who worked in-house for my first month on the job. It was a great visit, and the team has an awesome culture. When I left, I was asked, "Wait — how am I going to be part of the Monday morning meeting?" The team held a weekly standup on Monday mornings, and there wasn't a plan in place to get the information to me where I worked remotely. That conversation prompted the team to start recording meetings and sending recordings to remote team members around the world.

There were a lot of small learning moments like that, where the team had to figure out how to translate best practices into a format to accommodate the remote and hybrid team members.

OL: Based on your experiences with remote work, what do you think it takes structurally for a team to work remotely? Whether a team is a hybrid team or a remote-only team, what do structures need to look like for both of those situations to work?

JJ: For hybrid teams, where some people work remotely and some work in the company office, everyone on the team needs the options to be able to choose what is best for them depending on their preference or lifestyle needs — at work, or outside of work. If they have a sick parent and they want to try working remote, and they have the support to do that and the structure to do that and the systems in place to be successful, let them do it. Communicating remotely requires extra effort to be mindful of different time zones and after-work constraints, so it's all about communicating when you are and are not available and setting expectations about response times and meetings accordingly.

For the remote-only teams to work, people really need to understand what it is they're best at and most enjoy doing, and then being clear about that with their team. We all think we know, but we don't. I've written on Medium about an exercise that I was introduced to where you create a quadrant over time of what you're best at and how to properly communicate that to others, which I think works wonders on all teams, but particularly on remote-only or hybrid teams.

Prasada Partners is the first group I've worked with where video is totally central to collaboration, and that's been amazing. We use different tools (like Loom) to communicate asynchronously with video messages.

Video is helpful when working across different time zones. People are reading things at different times and they might not be in the same headspace as you are when you write it. It's easy to work video into your workflow to make hybrid and remote teams work more effectively together. Sometimes I'll record a video just talking through an email I wrote and include it as a link within the email to provide the recipient with some additional context.

Different tools help you create messages in the way team members want to digest them, build relationships with people you don't work with face-to-face, and provide additional context to prevent communication conflicts.

OL: Walk me through the quadrant.

JJ: The quadrant is built on the axes of passion and talent.

Ideally, you're spending much of your time in the top-right quadrant — where you're both passionate about the work you're doing, and you're talented at doing it. Other quadrants aren't as ideal — you're either talented but passionless, passionate but talentless, or you're neither talented nor passionate about the work you're doing.

This is the exercise: for 48 hours, to meticulously list everything you're working on. First, list everything out in a long list. Then, organize the activities into the quadrants that represent your perception of them.

Entrepreneurs can get stuck in the quadrant wherein they're good at something, but they hate doing it. Our team is trying to pull out tasks in the less-than-ideal quadrants and give team members tasks or roles so they're in the ideal quadrant more often — where they're full of passion and talent for the work they do. By doing this exercise ourselves and with our team, we can assign the right work and the right projects to the right people.

OL: Let's talk a little more in-depth about Prasada Partners and how it came about. What's the story of this new venture for you?

JJ: It's new for me, but it's been Carl's business for years. He was creating content for the Times, writing books, he speaking on stages around the world — he's been an influencer in his space for a long time. He saw peers who were in different industries who were also creating content, and he recognized he could make an even more successful business out of it, too.

He was looking for a CEO or COO type of person to augment his creativity, so he could keep creating, but someone could start executing on his vision. I'm a strong executor, but I don't always love brainstorming and coming up with new ideas. In my role, Carl tells me ten ideas, and I'll tell him which one I think would be the most impactful and the easiest to get from point A to B.

OL: How did Carl go from what he was doing to building educational resources to help financial advisors communicate better?

JJ: Carl is a creative communicator. He started his career in the financial services industry, where he was a financial advisor. Over the course of his career, he started to realize that a lot of advisors weren't awesome communicators.

Say, for example, a couple comes in and sits across from their financial advisor. They're in tears because they don't think that they've saved enough money to send their child to college. Or they come in after their partner has died and they've never managed money before. For these real-life financial situations, there's no spreadsheet or toolkit for advising. You need empathy and compassion. The way Carl sees it, financial advisors are acting almost as therapists sometimes, but he was seeing a disconnect between financial advisory training and the reality of dealing with human beings.

So he started to create content to bridge that divide. His books are about money, and he speaks often at financial services industry events. He also creates his sketches and his Times column.

But Carl also likes to communicate with humans.

So, for "humans," we cover topics like imposter syndrome, embracing insecurity or uncertainty, doing or starting something new, entrepreneurship, and being creative.

You'll see in his Times columns that there is an element of money in the content, but he also writes about having empathy and bearing witness to this other person's burdens that they're carrying. His writing is very broad, and Prasada Partners was created as an entity to create and distribute his content.

OL: What does your team look like right now? 

JJ: The team is made up of all contractors, and we have a team member who heads up online material that we created for financial advisors to be better communicators. That person stays solely in that area of the business and is like a CEO of that business under the umbrella of the entire company. We have a marketer, a designer, a researcher, a writer, someone working on community, and a proofreader who are all contractors. 

OL: When it comes to the team that you're building now, you mentioned that they're all contractors. Do some of them work full-time, and some of them part-time? Or are they all working part-time?

JJ: We're very invested in the idea of building a calm company. We're very focused on deliverables, and we're not focused on the time spent in front of a computer. I don't care if people are working 20, 40, or 60 hours a week. In fact, if people are working 40 or 60 hours a week, I would say should we hire someone else to pick up the extra work. Most employees (myself included) work somewhere between part-time and traditional full-time hours. 

OL: As a remote-only company building a whole team of people who are contractors, versus building a whole team of people who are full-time employees, do you think there's a difference between the two? Or are they fairly similar?

JJ: No, they're different. There are times when we've brought aboard people who are newer in their career, and the all-contractor team can be a difficult concept for them to grasp. They have an expectation of what work is supposed to look like coming out of school, but usually, once they get a taste of what the freedom looks like, it's exciting for them.

OL: What do you think the perception is? 

JJ: Whereas previous generations were paid and rewarded for time spent at their desks at the office, what we are doing is totally different. We work on a project-by-project basis and we want the work to be excellent. It's less about time spent and more about passionate experts working on deliverables they are interested in.

OL: Do you think there's a difference between building a remote-only team with contractors versus with full-time employees? 

JJ: The biggest difference is in the expectations of your employees — both their perception of the work and themselves. Unlike working on a team of full-time employees year after year, we look at our work as if we're all contributing to a project with our unique abilities. If we need someone else, we bring them on for a particular project. And if one project isn't a fit for someone, they'll work on something else. It feels more fluid, almost like a project lab. I don't know if that's because it's a startup or if it's because we all work remotely. On our team, there are plenty of folks who go to yoga class at noon, or single parents who do their work on nights and weekend, and we don't care — it's all about the deliverables.

OL: As you're building this remote team now, what are some of the processes you've started to put in place to make sure that the team is running as effectively as possible when everybody is distributed?

JJ: Something Carl started that we've formalized is what we refer to as "The Code." It's something we're still building over time, but essentially, it's our mutually agreed upon code of business for the way we work with each other, our audiences, and customers. We would talk informally about things we didn't want to do as a business — like playing pricing games with customers to get a quick sell — and we wanted to make sure the entire team was on the same page. So we've made a list of our principles that make up The Code and share it in a document with all new team members.

The first principle is, "We are generous in our assumptions."

If we get an email from a customer and it feels aggressive, being generous with our assumptions means assuming the customer might be having a bad day, and trying to help instead of getting defensive. If we get work back from another contractor and it's not up to our own standards, they may not have understood the instructions.

Another principle of The Code is to maintain calm communications. We don't put hectic or rushed words in our language. We never say we were busy as a way to apologize. Instead, we use calm language. For example, "I'm so sorry for my late reply, it's been really busy around here," is not something we would say.

We don't perpetuate the busy culture that's especially prevalent in the startup world. We take responsibility, we don't trick people, and the business is optimized for people who work here and for their happiness.

OL: What are some of the tools you use to effectively work remotely from a variety of different locations and points of view?

JJ: Video is definitely the top tool we use to communicate effectively. If a remote team asked me, "What's one thing to do to make this work," it's to implement video into your workflow. We use synchronous video, but we use asynchronous video just as frequently.

OL: What is the difference between the two? 

JJ: Synchronous video is live video communication — such as video meetings via Zoom, or a webinar via Google Hangouts. Asynchronous video is pre-recorded video content for later consumption. We record videos of our talking heads alongside screen shares or presentations, and then send them out in lieu of or along with emails or Slack messages. We're using video for everything. Today I recorded a video for Carl to explain that a final calendar order for this month had shipped, along with an email of the receipt. Updates like that are done using video to provide additional context and understanding for the recipient. 

OL: How do you embed those videos?

JJ: We use Loom. People aren't doing this very much. Because it's such a main part of my workflow now, it's shocking to me that this is the first team I've used it with. We can use Loom's browser extension to record videos while screen-sharing or presenting slides, and we can talk through everything we need to communicate to eliminate confusion or the need for back-and-forth.

We're also using Vidyard to do personalized video replies for his email and social media communication. When we see that someone has a positive response to his latest Times piece, Carl will quickly record a personalized thank you video that requires less time and effort than typing out a reply would.

OL: Are there any other tools that your team lives and dies by? 

JJ: Some of us use Trello and Asana for project and task management. We barely use Slack. We thought Slack would be stronger for us but it's not in this case.

OL: If you were tasked with building a 100-person all-remote team and making sure this team was successful doing remote work, how would you build it?

JJ: It's really important that people work in different time zones. I've come across some remote teams where everyone is in North America, and I don't think that's scalable to create an effective global team. It's not just about the time zones, it's about building a global-first team from the start, and setting up processes so time zone differences don't hinder people or cause cultural insensitivities.

Some people who are new to remote working freak out about time zones at first, and although there can be some sticking points, everyone eventually starts to work at their own cadence. On our team, there are no emergencies anyone needs to wake up in the middle of the night to solve. There should be no such thing as "I need this turned around in an hour," because if someone's on the other side of the world, that can't happen — so you have to plan in advance. Everyone eventually adjusts to it, and we find working on their own timetable makes for happier team members. 

OL: You can't always plan for everything when it comes to business. Let's say there was a huge PR fiasco, and you needed all hands on deck. What would you do?

JJ: I think we make up these crises more often than they actually happen. Imagine there was a situation where your entire website went down, and you needed a dev ops person to get it back up and running. There's a way to logistically plan team members' hours so that, if one dev ops person is asleep, and one is on vacation, there's another one "covering" in their time zone. It's all about trusting people in their role to do their job well. If there's a PR crisis, is it so big that it can't wait four to eight hours to be addressed? For most small companies, I don't think that's the case. I don't buy it. We've created a culture of busyness and a hectic pace, and I would like to unravel that. 

OL: What do you think is one of the big misconceptions among remote leaders about how to build remote teams effectively?

JJ: I think some people are nervous about going outside of their immediate time zone and country. I think that causes a lot of anxiety from leaders who I've talked to, for whatever reason. I think there's a lot of pressure around building company culture and that being make-or-break for your brand, and I sometimes wonder if the contractor route is a good way to get around that a bit.

We have people working on lots of different projects, whether they're paid or their own personal ones, and they don't need an in-house mentor. They don't need a crazy vacation package or big perks. Usually, they actually went away from that to start working on their own things if they're a contractor. I think the pressure to hire people full-time and build a culture is sometimes overrated. If you can get more entrepreneurial-minded people who aren't there with you full-time but instead work as contractors, that's a good thing, because they're usually self-starters with a knack for effective problem-solving. They want to do what they are passionate about and then unplug from work.

OL: Do you think that it's valuable to have a headquarters if you're a remote-friendly (not remote-only) company? Do you think that helps or hinders employees?

JJ: I think it hurts employees. Why create that divide? I view it as creating a divide between team cultures — those who work remotely and those who work in-house.

In fact, I've heard of teams where even if two people happen to be in the same city, either visiting or living, they never get together in-person to be on a call with other people who are all remote.

Everyone has headphones, and everyone is on the computer, no matter where they are in the world. No one skirts the remote culture, even if they happen to be in the same city.

People are just human beings, and no one is being intentionally malicious about this stuff — remote is just a new way to work, and it takes deliberate practice. If you don't have a boundary in place, it's not going to work. No one will learn how to communicate differently and they will default to non-remote communication.

OL: How do we get those who work remotely to feel that they are more integrated or connected or part of the transparency of the organization if they're not in a specific location?

JJ: I think it's okay to acknowledge that remote work is not for everyone. It's okay if people like to work in an office — and they should go work in an office. We should also, at the same time, understand that there are people who do not want to be in an office, and provide opportunities for both types of people to succeed. In my experience, remote workers are usually self-starters who like to work autonomously, which are important things to identify about yourself so you're not unhappy at work. It's a different way of looking at work and at life. For people who need to be in an office, they should seek out companies that offer meaningful work-life balance with facilities that help them work effectively. 

OL: Is it possible to achieve a balance between remote and office work, to create a hybrid or semi-distributed team?

JJ: There are a lot of companies who are trying to make hybrid, or semi-distributed teams work, but frankly, I've never met a team that's cracked that balance perfectly. If working from an office or working remotely is extremely important to someone,  they should find a team that's in-office or remote only. There are plenty of talented people in the world, but a lot of them probably wouldn't be a good fit to join our team because we can't provide an office experience with in-person connection. I think that's okay to acknowledge.

Our use of video helps us get closer to achieving that balance. We're all in different time zones, and we work asynchronously, but video helps us communicate like humans. It's on our team members to go to meetups, have mentors, meet other like-minded professionals should they wish to have connections like that. People on our team aren't communicating to us that they wish they had some place to go with coworkers — instead, they seem to appreciate being able to simply do what they're best at work.

OL: When you think about the future of remote work and where it's going, given the trajectory of how much it's changed in just the last few years alone, what do you envision remote work looking like? How will people engage with and do remote work differently in 10-20 years?

JJ: According to the London Business School, more than half of us will be working remotely by 2020. At their 2014 Global Leadership Summit, a group of 600 people was asked what percentage of their companies' full-time workforce would be working remotely by 2020, and 34% said more than half and 25% said more than ¾. Remote work is not slowing down — it's growing fast.

The future of remote work is also going to offer a lot more empathy in general, and more human tools coming out are making it a lot easier for us to go through a mental shift that allows for more empathy for people's lives — at work, and outside of work.

During my sabbatical, I spent a lot of time coping with the fact that work wasn't the center of my life anymore. I had to become comfortable waking up and not doing any work that day — and being okay with that. In the future, I think there's going to be a radical shift in everything workers do, and how they do it. Their relationships with their families and their personal lives will start to be impacted, too. I think the big question we're going to start asking as more workers go remote will be, "How do we make it more human at work when we're leaning so much on technology?"

OL: Where you think the future of where remote work is going? What do you think is the biggest gap that needs to be filled as far as technology and the ways in which we communicate go, as well as how we think about remote work in general?

JJ: In our culture of being busy, we're all in this constant feedback loop where all we hear is how entrepreneurs work 60, 80, 100 hours each week, and that we should be moonlighting and working weekends to see success. There are so many instances of messaging and policies that reinforce the hectic pace of the "culture of busy." If glorifying "busy" was removed from a lot of company cultures — both hybrid and remote-only — that would have a huge impact on work-life balance and the prevalence of remote work.

It's no wonder that some leaders think, "We can't have someone work in another country, what if there's an emergency?" Or we see people checking their phones late at night when they're with their families. I'd love if we could remove that culture of busy or just dial it down, and instead remember that we're having fun building cool products together.

Key Takeaways

Here are the key takeaways from Jacqueline's insights about building an effective remote-only team:

1. The culture of busy is making work-life balance difficult to achieve.

Jacqueline advocates for the dismantling of the "culture of busy" that's sometimes glorified in the startup world. She believes in a workplace culture that's about deliverables and impact, rather than face time or time spent in the office.

2. Synchronous and asynchronous videos are key for effective communication and collaboration for remote-only teams working across different time zones.

Jacqueline frequently cited the use of video technology as critical to her team's success. She says using synchronous live video in tandem with asynchronous pre-recorded video helps her team communicate faster and more effectively than email or Slack alone.

3. Spending time identifying the daily responsibilities you're passionate about and talented at is a worthwhile monthly or quarterly self-reflection practice.

Using Jacqueline's passion:talent quadrant, you can take stock of your satisfaction at work by identifying the tasks that you're most and least passionate about and talented at to determine if you should evolve the scope of your role to be happier at work.

To learn more, read our State of Remote Work report.