Interview with Tyler, a director of customer success models how to start a remote work career

In early 2019, I had been studying for an educational leadership master's degree. I intended on becoming an assistant principal or a technology coordinator with a school district, but I kept running into roadblocks.

My spouse met someone who was working remotely as a Salesforce administrator, and that sparked my journey from being a technology-oriented educator to becoming an education-oriented technologist. Eventually, I was hired as a customer success manager at Hubstaff.

Hubstaff is a time tracking, project management, and proof of work solution tool built to accelerate remote work and empower more kinds of work to go remote. As director of customer experience, I lead the customer success and customer support functions.

I like the flexibility most of all.

Secondary public education is a VERY co-located environment: bells every hour to send another set of people to a mandatory meeting outside of your control.

I still feel like I'm in a honeymoon period with it; check back with me in another 18 months? The only frustrations I've felt so far are mostly unrelated to remote as a mode of business.

Physical hardware:

• Lots of screen space (27" iMac + 24" second screen);
• a studio headset and microphone plugged into a powered USB audio interface;
• a great webcam;
• and noise-canceling headphones for when others are in the house or when I'm traveling.

I can't say enough about taking charge of your environment and schedule.

As a customer-facing people leader, I highly recommend investing in your A/V setup. Every penny has been worth it for the increased bandwidth on video and audio calls.

Software tools: I have a typical stack.

Internal comms:

• Slack for chat;
• Zoom for calls.

External comms:

• Calendly for scheduling;
• Zoom for calls;
• Gmail for email.

We use GSuite for internal documents, and our external knowledge base is built using WordPress.

Hubstaff runs on Hubstaff, so we track our time using our tool, and I really love Hubstaff Tasks for managing projects. Hubstaff Tasks is exactly what you would expect from a PM tool: project boards and task cards.

However, Tasks has an Agile layer of standups, sprints, epics, timelines, etc. that make it really great to break big tasks down into manageable chunks that really move the needle in a flexible and adaptable way. I've been exploring lots of other tools, but that's the core.

I mostly work from our home office (especially now during the pandemic), but I also enjoy working from coffee shops, gym lobbies, commuter trains, and burrito joints.

One of my favorite things about remote work is the opportunity to listen to your own rhythms and be intentional about your working environment.

I love that my main workspace faces exterior light. I get to see the outdoors and it really makes me feel productive.

I get up early before my children and work 60-90 minutes before they wake up. Then, I cook breakfast for our whole crew (six family members); these are some of my most productive work times.

Then we all go our separate ways to school, work, etc., but I usually workout following breakfast. After showering and putting on my work clothes, I usually knock out smaller tasks and take any meetings just before or just after lunch.

I also really enjoy the opportunity to greet my children home from school in the afternoon. Maybe I'm weird, but I put everything I am intending to do in my calendar as an event. Future me often thanks past me all the time for taking the time to decide what I am doing when.

I report to our CEO, and we collaborate on what's important to move forward on each week. Many tasks that I touch on have a direct revenue impact, so it is fairly easy to measure and prioritize the things that move the needle for us

I know I am biased, but I think using a time tracking tool is really helpful. When I am working, I track my time. When I am not working, I don't.

It really helps me to know how much I've already worked in a day, week, month, etc.; if it's Thursday AM and you've already tracked 45 hours that week... uh oh. Having that little bit of friction to have to track time really helps separate things.

Don't wait for permission to do or seek the thing you want to do.

Study GitLab, Automattic, Basecamp, Buffer, Doist, Workplaceless and others (Hubstaff, too) that have been doing this much longer than you have and share their learnings on the internet.

Subscribe to the podcasts, read the blogs, even contribute to the GitLab handbook as I did. Honestly, I became a successful remote worker just following the guidelines here: RemoteOnly.org. This guide recently got an update earlier this year and added lots of GitLab branding.

In spite of that, it’s still a fantastic compilation of resources for remote job seekers, workers, leaders, and companies.

Remote is a forcing function for intentionality as an organization and that carries over to CX.

You really have to answer the question of: "What do we want customers to feel in these moments interacting with our product or our team?" especially when we don't get to meet nearly all of them.