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Mastering Remote

Technology Podcasts

Single topic deep dives. Bite-sized episodes. Expert advice to help you work smarter and manage better — remotely. For distributed team leaders and remote professionals. Podcast FKA "Outside the Valley."

Single topic deep dives. Bite-sized episodes. Expert advice to help you work smarter and manage better — remotely. For distributed team leaders and remote professionals. Podcast FKA "Outside the Valley."


United States


Single topic deep dives. Bite-sized episodes. Expert advice to help you work smarter and manage better — remotely. For distributed team leaders and remote professionals. Podcast FKA "Outside the Valley."






Employees vs Contractors: How to Stay Compliant When Remote – Dee Coakley of Boundless | S2E5

Hiring remote team members internationally? You might want to figure out how to deal with the legal employment, local payroll, and taxes before getting into trouble. Our guest Dee Coakley faced exactly this problem in her previous experience as COO, which led her to co-found and head Boundless as CEO. She breaks down how to minimize the risks when hiring remotely, explains what an Employer of Record is, and shares why using one can give your organization a competitive edge in recruiting.


How a Strong Employer Brand Helps Recruit Top Talent – Diane Tate of Mozilla | S2E4

If you want to hire good people, you should do employer branding. Companies today must be able to tell a compelling story of their workplace in order to capture the attention of top candidates. In this episode, you’ll hear how senior manager Diane Tate built Mozilla’s employer branding initiative from scratch and how you can do it for your organization.


How to Lead Through Uncertainty – Dominic Price of Atlassian | S2E3

Wartime leadership is challenging. In this episode, we discuss strategies to help you navigate through it. Atlassian’s Work Futurist Dominic Price shares “plays” he uses that can make you a more effective leader right now. We also cover what he learned from the “Reworking Work” pandemic research, how you can break old habits to remove obstacles to your growth, and how to create a more experimental culture to foster innovation.


How to Raise Funds Remotely – Joe Blair of Cota Capital | S2E2

Fundraising is tough, and even tougher for remote founders who can’t meet investors face to face. In this episode of Mastering Remote, early stage VC Joe Blair shares what it really takes for distributed companies to raise money – including how pitching is actually like building a sales funnel and why he thinks remote is underhyped.


How to Transition to 100% Remote – Chris Winn, Creative Market CEO | S2E1

Switching the way you work from in-office to all remote is no easy task. Chris Winn took on this challenge when he became the CEO of Creative Market, knowing he had to “pick a lane” or risk his team evolving into two separate cultures. Chris shares his journey of managing change and building a healthy remote culture in this episode of Mastering Remote.


Chris Ruder (Spikeball): Shaping Up Your Company's Culture and Values - S1E30

In this episode, we talked about how shaping up company culture and values, the “a-ha” moment when Chris realized that an office is not really required to get things done, how Chris deliberately works on processes and culture within the company, and his advice for companies starting out with remote work.


Recruiting and Remote Work in a Post-COVID World - S1E29

This week’s episode is a replay of our recent webinar Recruiting and Remote Work in a Post-COVID World. We invited remote work thought leaders to talk about how the recruiting landscape will shift in the “post-COVID” world, how remote work will play a huge role in employer branding, building the infrastructure for your remote team, and more.


Jennifer Aldrich (InVision) - Why Remote Work is More Than a Job Perk - S1E28

In this episode, we talked about how InVision’s culture has adapted to their rapid growth, how their “design-first principle” has impacted their culture, the difference between a community and an audience, and her personal story on how remote work changed her life.


Remote Engineering Team Best Practices: AMA with TaxJar and Help Scout - S1E27

Another special episode this week! This is the first Outside the Valley episode not hosted by me (you’re welcome). This week’s episode is a replay of our recent AMA session with CTO of TaxJar Matt Anderson. The AMA was hosted by our VP of Sales Mike Fossi, and a special co-host: VP of Engineering of Help Scout (and previous podcast guest), Megan Chinburg. It’s a conversation between engineering leaders of two awesome remote companies talking about how the COVID-19 pandemic has affected their...


Brooke Hurford (Workfrom) - Building a Community of Remote Workers - S1E26

For this week’s episode, we have Brooke Hurford, COO and co-founder of Workfrom, a platform connecting professionals to real-world spaces and virtual offices. We talked about how Workfrom is designed to help remote workers interact better, the benefits of remote work to local communities, how Techstars mentorship helped her and her co-founder, and more.


All About Pair Programming: AMA with Ben Orenstein of Tuple - S1E25

Welcome back! For this week’s episode, we’re going to replay our live AMA session with Ben Orenstein, co-founder and CEO of Tuple. We covered a lot of grounds in this session, including the benefits of pair programming in remote teams, best practices in pairing, the ups and downs of running a bootstrapped startup, and more!


Remote Work FAQs - Live with the Arc Team - S1E24

This week we have a special episode on the podcast! In this episode, we have our very first roundtable chat with other Arc team members. During this chat, we talk about our recently-launched Remote Work FAQs. We created this resource hoping to help companies who need to go remote because of the COVID-19 pandemic. This episode’s guests are members of different teams at Arc. We get their perspective on how the current remote work transition has been affecting their team, processes, and more....


Darren Murph (GitLab) - Why Companies Should Go All-Remote - S1E23

This week on the podcast, we have Darren Murph, Head of Remote at GitLab, book author, and Guinness World Record holder! We talked about why GitLab uses “all-remote” to describe the company’s remote identity, how hybrid model remote teams can lead to anxiety and guilt, GitLab’s handbook-first approach, and why “story-telling ability” is essential in remote teams.


Steph Smith (Integral Labs) - The Main Qualities of Effective Leadership - S1E22

Today we have Steph Smith, author, developer, and Senior Analyst at Integral Labs and The Hustle! In this episode, we talked about the “give and take” approach in remote hiring and why you should actively hire “givers”, the three must-have aspects of effective leadership, how to be a better communicator through deliberate practice, and more!


Laurel Farrer (Distribute Consulting) - Re-skilling Via Remote Work - S1E21

Today we have Laurel Ferrer, CEO of Distribute Consulting and founder of the Remote Work Association! In this episode, we talked about how remote work can help the development of rural areas by enabling entrepreneurship, strengthening local technology culture, and re-training the local workforce to utilize their skills for remote work opportunities. We also talked about how to measure the impact of transitioning a company to remote-first or fully distributed, how to measure productivity...


Ken Weary (Hotjar) - How to Regain Productivity in Your Remote Team - S1E20

Today we have Ken Weary, VP of Operations at Hotjar! In this episode, we talked about the reason why Hotjar prefers asynchronous communication, why software tools aren’t as important, and the “Tribes” system Hotjar uses in project ownership. We also talked about Hotjar’s onboarding process, meeting culture, documentation principles, and why being a self-starter is the number one attribute to have as a remote worker.


Fred Perrotta (Tortuga Backpacks) - Encourage Remote Team Risk-Taking - S1E19

Today we have Fred Perrotta, Co-founder and CEO of Tortuga Backpacks! In this episode, we talked about the challenges of developing a physical product when you’re a 100% distributed team, building an epic place to work, and applying the principle of “players and coaches” in your company. We also talked about Fred’s million-dollar mistake, how to figure out if someone can be a good remote worker, and why you should always do project post-mortems. If you’re enjoying the podcast, please...


Jesse Mecham (YNAB) - Building a Helpful & Kind Remote Team Culture - S1E18

Today we have Jesse Mecham, Founder and CEO of You Need A Budget (YNAB)! In this episode, we talked about how Jesse started YNAB in 2004 and how it evolved to be a remote company, his approach in delivering feedback and criticism, and the deliberate steps that Jesse took along the years to become a better remote leader Jesse also shared about YNAB’s cultural manifesto, unique questions the team uses to assess new team members, and the impact of remote work on Jesse’s family life. If you’re...


Max Makeev (Owl Labs) - Making Remote Meetings Better - S1E17

Today we have Max Makeev, Co-founder of Owl Labs, the company that created the Meeting Owl. This is the first-ever episode that we recorded live in Arc’s office, so the audio is noticeably different! In this episode, we covered how their flagship product, Meeting Owl, was created, and the struggles Max and his co-founder faced in the early days of Owl Labs, We also talked about the unique challenges of building a hardware startup, how Max prepares for — and runs — meetings, and his...


Laura Roeder (MeetEdgar) - How to Build a Company That Doesn't Need You - S1E16

Today we have Laura Roeder, CEO and founder of MeetEdgar! In this episode we covered how Laura built a company that can run without her, why MeetEdgar has a “CEO” _and_ a “President,” and the importance of transparency in company culture. We also talked about why MeetEdgar doesn’t believe in deadlines, why they use the title “advocates” instead of “managers,” and how you can give better criticism and feedback in a remote team. Laura also has a special gift for Outside The Valley listeners!...