Mastering Remote: Recent Episodes

Christine Orchard at Arc

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."

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What you’ll learn in this episode:

  1. Know when to hire a remote team member as an employee versus contractor
  2. How compliance can be actually help you recruit and retain great talent
  3. How to evaluate an employer of record before selecting one

Resources mentioned:

  • Boundless
  • Gavin Sheridan’s Twitter list of experts on COVID
  • Morning Brew
  • Coda
  • Asana

Presented by Arc.dev, making it easy to find remote developers, pre-vetted and tailor-matched to you.

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What you’ll learn in this episode:

  1. Why a strong employer brand can help attract hard-to-hire candidates
  2. How to research and build your employer value propositions from scratch
  3. The metrics to help measure the effectiveness of your employer brand story

Resources mentioned:

  • Mozilla’s employer value propositions
  • Job Portraits agency
  • Anand Giridharadas @AnandWrites
  • Mozilla’s Spotify playlist
  • “The Four Loves” by C.S. Lewis

Presented by Arc.dev, making it easy to hire remote developers, pre-vetted and tailor-matched to you.

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What you’ll learn in this episode

  1. Several exercises to help you be a more effective leader, especially now
  2. How to keep your old habits from holding you and your team back
  3. How to turn experimentation into a core part of your organization’s DNA

Bonus: Why and how Atlassian decided to embrace being a hybrid organization.

Resources mentioned

  • Atlassian Team Playbook 4Ls Retrospective
  • Atlassian Team Playbook “Health Monitors”
  • Report: Reworking Work: Understanding The Rise of Work Anywhere
  • "Radical Candor," by Kim Scott

Presented by Arc.dev, making it easy to hire remote developers, pre-vetted and tailor-matched to you.

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What you’ll learn in this episode:

  1. How to ace your next VC interview and get funded
  2. How to overcome the trust deficit when raising capital remotely
  3. What unexpected challenges founders will face and how to overcome them

Resources mentioned:

  • Distributed Valley
  • Cota Capital
  • Remote Startup Expo 3.0
  • Remo virtual events platform
  • Del Johnson on Twitter
  • “Lead the Field” by Earl Nightingale

Presented by Arc.dev, making it easy to hire remote developers, pre-vetted and tailor-matched to you.

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What you’ll learn in this episode:

  1. How to transition from an office-based to fully distributed company (and culture)
  2. How to get team buy-in and handle people leaving as change occurs
  3. Why meaningful work is the secret to strong remote team connections

Resources mentioned:

  • Creative Market
  • “Hiring Your Dream Team,” video of Chris speaking at Calibrate 2018
  • Kara Swisher, journalist and host of the “Sway” podcast
  • Microserfs by Douglas Copeland

Hosted by Arc.dev, making it easy to hire remote developers, pre-vetted and tailor-matched to you.

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Topics also covered on the podcast episode:

  • The history of SpikeBall
  • Why playfulness and kindness is essential to SpikeBall’s company culture
  • Identifying traits that makes someone suitable for remote work during the interview process
  • SpikeBall’s onboarding process for new employees

Mentioned resources:

  • Chris Ruder
  • Spikeball
  • Ken Weary of Hotjar: How to Regain Productivity in Your Remote Team
  • Basecamp

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Topics also covered in this episode:

  • How recruiting teams can adapt to shifts in the talent market.
  • Creating a job description that attracts the right candidate.
  • Purposefully building infrastructure so your remote team can be sustainable and succeed.
  • The importance of culture when bringing new hires together in remote teams.
  • Practices or processes that might continue even after the pandemic is over.
  • Soft skills recruiters should be screening for when evaluating remote candidates.

Mentioned resources:

  • Laurel Farrer
  • Distribute Consulting
  • Mathew Caldwell
  • RocketPower
  • Greg Russell
  • Snapdocs

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Topics also covered on the podcast episode:

  • How culture and onboarding evolved at InVision as they experienced rapid growth
  • What companies should know about building a community
  • Challenges Jennifer faced as a community builder
  • Why remote work is a life-changer for disabled individuals
  • Advice for remote job-seekers

Mentioned resources:

  • InVision
  • Clark Valberg
  • Jennifer’s Twitter
  • Remote work is more than a job perk—for people with chronic illness, it’s life changing
  • Job openings at InVision

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Topics also covered in this episode:

  • How COVID-19 pandemic has affected Matt and Megan’s working routines
  • How Matt and Megan kept the morale and culture of their engineering teams intact during this challenging time
  • How they go about figuring out meetings and setting goals for their teams
  • The hiring processes and interview questions at TaxJar and Help Scout

Mentioned resources:

  • TaxJar
  • Help Scout
  • Matt Anderson
  • Megan Chinburg
  • Basecamp
  • Fellow.app
  • Help Scout’s 12-Step Remote Hiring Process

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Topics also covered in this episode:

  • Why Brooke was initially attracted to remote work
  • Brooke’s experiences with isolation while working remotely
  • How Workfrom helps remote workers to interact with each other
  • How Brooke thinks COVID-19 will impact the dynamics of remote work in the future
  • Why remote work is a big benefit to local communities

Mentioned resources:

  • Workfrom
  • Brooke’s Twitter
  • Darren Buckner
  • Techstars
  • Techstars Anywhere
  • Codementor
  • James Clear

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Mentioned resources:

  • Tuple
  • Ben’s Twitter
  • How to pair with a junior developer
  • Basecamp
  • Shape Up
  • The Manager’s Handbook
  • Clearbit
  • Alex MacCaw
  • Extreme Programming
  • Learntopair.com

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Topics also covered on the podcast episode:

  • How our communication style and processes have evolved
  • How we designed our workspaces at home
  • Handling criticism and feedback in remote teams
  • How remote work affected our routines and daily life

Mentioned resources:

  • Zoom
  • Notion
  • Airtable
  • Kap
  • Loom
  • Liam Martin: How to Be a Remote Executive
  • Workstation Popcorn method
  • MOFT stand
  • Tuple

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Topics also covered on the podcast episode:

  • How Darren got the rare title of “Head of Remote”
  • Why GitLab choose “all-remote” as their company identity
  • Why hybrid remote teams can lead to guilt and burnout
  • Why “storytelling ability” is important in GitLab
  • GitLab’s “handbook-first” approach
  • Darren answering questions from Twitter

Mentioned resources:

  • Darren’s Twitter
  • Darren’s Instagram
  • Andreas Klinger of AngelList: Normalizing Hiring Outside Silicon Valley
  • GitLab’s Guide to All-Remote
  • The importance of a handbook-first approach to documentation
  • GitLab Handbook
  • Informal Communication in an all-remote environment
  • GitLab onboarding
  • GitLab communication

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Topics also covered on the podcast episode:

  • What attracted Steph to remote work
  • The “give and take” approach in remote hiring
  • How Steph learned to be a better communicator
  • Can you deliberately train communication skills?
  • How to encourage top-down empathy in an organization
  • Why humility should be at the core of leadership
  • The three must-have qualities of effective leadership
  • Frameworks for remote decision making
  • Is there a middle ground between “delegating” and “being hands-on” for CEOs?
  • How Steph adapted to remote life and still finding time to be creative

Mentioned resources:

  • The Hustle
  • Trends
  • Nomad(hubb)
  • Eunoia
  • FeMake
  • Ken Weary of Hotjar - How to Regain Productivity in Your Remote Team
  • Must-Have Qualities for Effective Leadership
  • Best Practices for Managing Remote Teams: A Psychological Perspective
  • Give and Take: Why Helping Others Drives Our Success by Adam Grant
  • Jason Fried
  • Basecamp
  • Sam Parr
  • Steph’s website

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Topics also covered on the podcast episode:

  • How Laurel persuaded the executives of his previous company to experiment with remote work
  • Why Laurel thinks compliance is the number one thing companies should figure out before going remote
  • How Laurel measures the cost of transitioning to remote work (as well as the metrics for measuring whether this transition has been successful)
  • Why remote work can strengthen local technology culture
  • How remote work can enable both re-skilling and up-skilling
  • How the right training can enable older members of the workforce to get modern remote opportunities
  • How can leaders help new remote workers develop their self-discipline (without micromanaging!)

Mentioned resources:

  • Distribute Consulting
  • Remote Work Association
  • The Joe Rogan Experience podcast with Naval Ravikant
  • Josh Pigford
  • Baremetrics
  • Could remote work be economic development’s new secret weapon
  • Rural Online Initiative
  • Liam Martin: How to Be a Remote Executive
  • Laurel’s Twitter
  • Laurel’s LinkedIn

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Topics also covered on the podcast episode:

  • How Ken and his spouse manage their children’s education while being digital nomads
  • Why Hotjar decided to always default to asynchronous communication whenever possible
  • How Hotjar realized that productivity was going down
  • Hotjar’s meeting culture and requirements
  • How Hotjar’s utilizes the “Tribes” system in project ownership
  • Why being a self-starter is important as a remote worker
  • Hotjar’s onboarding process and documentation principles

Mentioned resources:

  • Hotjar
  • Running Remote
  • WeWorkRemotely
  • Slido
  • David Darmannin, CEO of Hotjar
  • Trello
  • Hotjar Team Manual
  • Confluence
  • Laura Roeder - Build a Company That Doesn’t Need You
  • Hotjar is hiring!
  • Ken’s LinkedIn

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Topics also covered on the podcast episode:

  • The challenges of developing a physical product as a 100% remote company
  • How you can create an “epic place to work”
  • How Fred applies the principle of “gentle guidance” as a remote leader
  • Tortuga’s hiring process
  • Signals to find out if someone can work remotely well
  • Fred’s one million dollar mistake
  • The importance of project post-mortems in remote teams

Mentioned resources:

  • The 4-Hour Workweek by Tim Ferriss
  • A Place to Do Epic Work
  • David Heinemeier Hansson
  • Basecamp
  • Organizing Teams by Players and Coaches by Help Scout
  • Laura Roeder of Meet Edgar: Build a Company That Doesn’t Need You
  • Who by Geoff Smart
  • Naval Ravikant
  • Meetup.com
  • Notion
  • I F*cked Up (and You Can Too)
  • Decentralized Decision Making
  • Shape Up by Basecamp

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Topics also covered on the podcast episode:

  • How Jesse started YNAB back in 2004 and found his CTO remotely
  • How Jesse delivers feedback and criticism as a remote CEO
  • YNAB’s unique ritual for all-hands meetings
  • YNAB’s hiring and onboarding process
  • The growing pains experienced while scaling a remote company
  • The unique interview questions that YNAB asks when hiring
  • Jesse’s past mistake in hiring and how YNAB learned from it
  • How remote work has influenced Jesse’s family life

Mentioned resources:

  • Jesse Mecham
  • You Need A Budget (YNAB)
  • Hiten Shah: Figuring Out Your Own Remote Work Structure
  • YNAB Podcasts Library
  • Please Stop Talking About Company Culture
  • Getting Things Done by David Allen
  • YNAB cultural manifesto
  • Jason Fried
  • Basecamp
  • Shape Up by Basecamp

Available now on your favorite podcast players:

  • iTunes
  • Google Podcast
  • Castro
  • Overcast
  • Spotify
  • Stitcher
  • Player.fm
  • Tune In

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Topics also covered on the podcast episode:

  • How Max started in the world of robotics and helped created Roomba
  • The very first prototype of Meeting Owl
  • How Max and his co-founder found early adopters and gathered feedback
  • How can a hardware startup vet their suppliers?
  • Does a 100% distributed team need a Meeting Owl?
  • Unique use-cases of Meeting Owl
  • Max’s number one piece of advice for founders who want to be better at meetings
  • The most important things Max learned when he was still the CEO
  • Why Max had to record an apology video for customers
  • How Max thinks remote work will affect the future
  • What’s next for Owl Labs

Mentioned resources:

  • Max Makeev
  • iRobot
  • Owl Labs co-founder Mark Schnittman
  • Get Meeting Owl
  • Y Combinator
  • Foxconn
  • Flextronics
  • Zoom
  • Lisette Sutherland
  • Rebecca Corliss
  • Collaborations Superpowers: Interview with Rebecca Corliss of Meeting Owl
  • Owl Labs CEO Frank Weishaupt
  • Megan Chinburg of Help Scout: A Look Into Help Scout's Hiring Process
  • 5 Ways to Have Killer Meetings
  • 2019 State of Remote Work Report by Owl Labs

Available now on your favorite podcast players:

  • iTunes
  • Google Podcast
  • Castro
  • Overcast
  • Spotify
  • Stitcher
  • Player.fm
  • Tune In

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Topics also covered on the podcast episode:

  • Laura’s current role and why MeetEdgar has a “President”
  • Why Laura decided to create a company that can run without her
  • Mistakes and challenges Laura made while growing MeetEdgar
  • The importance of transparency
  • Why you should not put criticism on Slack
  • Why meetings are essential for remote teams
  • Is MeetEdgar small by design?
  • How MeetEdgar thinks about documentation
  • Why MeetEdgar doesn’t have “managers” but “advocates”
  • Why Laura doesn’t believe in deadlines

Mentioned resources:

  • Laura’s blog
  • MeetEdgar
  • One free month of MeetEdgar (Code: PODCAST)
  • Liam Martin of Time Doctor: How to be a “Remote Executive”
  • MeetEdgar President Sarah Park
  • Justin Mitchell of YAC Chat: Remote Team “High-Res” Communications
  • “Away” controversy
  • Krister Haav of Toggl: Creating a Playful Culture in Remote Teams
  • David Heinemeier Hansson
  • Dave Teare
  • REWORK Podcast: Venture Capital and Control with Dave Teare
  • Basecamp
  • Tettra
  • Holacracy
  • Trello
  • Asana
  • The MeetEdgar Company Handbook

Note: Laura's new software for coaches, Paperbell, is now available!

Available now on your favorite podcast players:

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  • Breaker
  • Castro
  • Overcast
  • Spotify
  • Stitcher
  • Player.fm
  • Tune In

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Topics also covered on the podcast episode:

  • How remote work helped Kieran in his career and personal life
  • Why geographical boundaries shouldn't limit career opportunities
  • The hardest part of remote leadership
  • Why remote hiring is one of the best things you can do for company growth.
  • Using "squads" in distributed teams
  • Avoiding too many processes in distributed teams
  • The "goldfish face" problem in meetings
  • How presenting on Zoom can be awkward
  • Things HubSpot do to recreate the “watercooler feeling”
  • Kieran's advice to companies who want to hire remotely

Mentioned resources:

  • HubSpot
  • Salesforce
  • Marketo
  • Andreas Klinger of AngelList: Normalizing Hiring Outside Silicon Valley
  • Kevan Lee
  • Buffer
  • Nicholas Holland
  • How to Be a Remote Leader with Nicholas Holland
  • Wade Foster
  • Zapier
  • How to set your growth team up for success
  • Paul Thompson
  • Megan Chinburg of HelpScout: A Look Into HelpScout’s Hiring Process
  • Balsamiq
  • Peldi Guilizzoni of Balsamiq: Continuous Learning as A Company’s DNA
  • The GoldFish Face? 5 Truths about Remote Working
  • Airtable
  • Donut
  • Growth TL;DR

Available now on your favorite podcast players:

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  • Breaker
  • Castro
  • Overcast
  • Spotify
  • Stitcher
  • Player.fm
  • Tune In

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Topics also covered on the podcast episode:

  • 04:12 — How Tammy realized that working in an office is not really for her
  • 07:00 — What fascinates Tammy the most about remote work
  • 08:27 — How remote work can improve the education sector
  • 13:30 — How Workplaceless started
  • 16:46 — Why companies and managers need training to successfully become “remote”
  • 21:51 — Why creating a career map is important for remote companies
  • 24:54 — The #1 fear of companies who are trying to go remote
  • 30:24 — The three pillars framework you can start with when proposing a remote initiative to your boss
  • 32:37 — Is it possible to hire for potential?

Mentioned resources:

  • Running Remote conference
  • Workplaceless
  • Zoom
  • Andreas Klinger
  • Andreas Klinger: Normalizing Hiring Outside Silicon Valley
  • Goplaceless Remote Readiness Assessment
  • Claire Lew
  • Claire Lew: Building Social Trust in Remote Teams
  • Why are American companies so bad at re-skilling?
  • Jason Fried
  • Asana

Available now on your favorite podcast players:

  • iTunes
  • Google Podcast
  • Breaker
  • Castro
  • Overcast
  • Spotify
  • Stitcher
  • Player.fm
  • Tune In

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Topics also covered on the podcast episode:

  • 04:10 — How Liam realized that overworking and hustle culture is dangerous
  • 09:00 — The main difference between “entrepreneur” and “executive”
  • 14:15 — The top two things that Liam needed to re-teach himself to be a better remote executive
  • 24:14 — The million-dollar mistakes that Liam and his co-founder made
  • 30:17 — Why it is crucial to extract the “sacred knowledge” of your key team members and document it
  • 37:14 — How Liam created a document to help his direct reports work with him more effectively
  • 41:39 — The most surprising feedback Liam received from his direct reports
  • 44:45 — Why Liam and the team started Running Remote
  • 48:37 — The unspoken difficulties about running a conference

Mentioned resources:

  • Running Remote conference
  • Time Doctor
  • Staff.com
  • “Karoshi” phenomenon
  • Zero to One
  • Mark Faggiano: Creating Remote Employee Culture
  • “Dunbar’s number”
  • Trainual
  • Gitlab Handbook
  • Dmitri Zaporozhets
  • Rob Rawson
  • Nick Francis
  • Amir Salihefendić
  • Twist
  • Jing
  • The Pesto Podcast with Liam Martin
  • Myers-Briggs test
  • Intercom
  • Egor Borushko
  • The 4-Hour Workweek
  • Tim Ferriss
  • Andrew Warner
  • Andreas Klinger
  • Andreas Klinger’s Running Remote keynote
  • Hiten Shah: Figuring Out your Own Remote Work Structure
  • Jennifer Aldrich
  • Remote work is more than a job perk—for people with chronic illness, it’s life changing by Jennifer Aldrich
  • Fiverr
  • Wade Foster
  • Zapier
  • Lori McLeese
  • Automattic
  • John Eckman
  • 10Up
  • Sara Sutton
  • FlexJobs
  • Running Remote YouTube Channel

Available now on your favorite podcast players:

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  • Breaker
  • Castro
  • Overcast
  • Spotify
  • Stitcher
  • Player.fm
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Topics also covered on the podcast episode:

  • 03:31 — What makes DigitalOcean’s hybrid team model successful
  • 06:42 — Examples of the “remote-first mindset” at DigitalOcean
  • 08:03 — Early resource investments by DigitalOcean to make remote work run smoothly
  • 09:16 — The growing pains of DigitalOcean’s remote processes
  • 13:49 — Eddie’s most surprising finding in the DigitalOcean Remote Developer Experience Report
  • 21:26 — How the rise of remote work helps foster communities of local developers
  • 34:29 — Advice for developers who wants to start their own meetup

Mentioned Resources

  • Digital Ocean
  • IRC
  • Currents: The Remote Developer Experience
  • SendGrid
  • Twilio
  • THAT Conference
  • Zoom
  • Owl Labs
  • Tulsa Remote
  • Eddie’s Twitter
  • Eddie’s GitHub

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We covered:

  • 02:31 — How Megan started her engineering leadership career
  • 08:40 — The differences between managing a remote vs co-located engineering team
  • 18:06 — How Help Scout screens for value alignment and technical competence
  • 35:38 — Help Scout’s onboarding process for new hire
  • 40:10 — Why documentation is important when onboarding new engineer
  • 41:00 — One of the best things Help Scout did early on to grow a solid remote team
  • 43:35 — How Megan sees her responsibilities as a VP of Engineering
  • 49:30 — Top two pieces of advice Megan would give to other engineering managers

Mentioned resources:

  • Help Scout
  • Nick Francis
  • Denny Swindle
  • Andreas Klinger: Normalizing Hiring Outside Silicon Valley
  • AngelList
  • Basecamp
  • Help Scout’s 12 Step Remote Hiring Process
  • Leah Knobler
  • How to Knock Your Virtual Job Interview Out of the Park
  • Help Scout “Fika”
  • Mark Faggiano: Creating Remote Employee Culture
  • Mark Faggiano
  • I, Me, We, Us - Creating team ownership with better language
  • Megan’s LinkedIn
  • Help Scout Blog

Available now on your favorite podcast players:

  • iTunes
  • Google Podcast
  • Breaker
  • Castro
  • Overcast
  • Spotify
  • Stitcher
  • Player.fm
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We covered:

  • 04:25 — How Hailley convinced her previous company to allow remote work
  • 06:33 — Advantages of remote work for Hailley’s productivity
  • 11:30 — Why Buffer has a super transparent culture (and how this affects Buffer)
  • 13:55 — Why Buffer gives internal team members opportunities to apply for new job openings
  • 20:03 — Do you need to have experience in remote work to have a job at Buffer?
  • 23:36 — Buffer’s onboarding process and what’s so special about it
  • 28:50 — What are some unique internal communication processes within Buffer?
  • 35:00 — Why Buffer started offering paid sabbaticals
  • 41:12 — Buffer’s unique all-hands meeting
  • 50:15 — Hailley’s most surprising finding from the last State of Remote Work survey

Mentioned resources:

  • Buffer
  • Joel Gascoigne
  • Open Startup movement
  • Transistor.fm
  • Baremetrics
  • Buffer Open Blog
  • Todoist
  • Hiten Shah: Figuring Out Your Own Remote Work Structure
  • “Peldi” Guilizzoni: Continuous Learning as A Company’s DNA
  • Balsamiq
  • Loom
  • Angel List
  • Hailley’s Twitter
  • Make Work Work podcast

Available now on your favorite podcast players:

  • iTunes
  • Google Podcast
  • Breaker
  • Castro
  • Overcast
  • Spotify
  • Stitcher
  • Player.fm
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We covered:

  • 4:30 — How John keeps in touch with the Credo community.
  • 7:00 — Has John's mindset about remote work changed over the years?
  • 11:05 — The difference between managing a client vs managing a product.
  • 14:30 — How a leader can be better at writing expectations, especially in a remote organization.
  • 20:00 — What soft skills John looks for when hiring a remote contractor.
  • 28:32 — How remote freelancers can "sell" themselves better.
  • 32:28 — John's thoughts on building a profitable business outside of Silicon Valley.
  • 35:06 — Can you build connections remotely?

Mentioned resources:

  • Credo
  • Codementor
  • Credo team page
  • Don’t Hire Remote Workers by John Doherty
  • Claire Lew - Building Social Trust in Remote Teams
  • John Mueller
  • Matt Cutts
  • Million Dollar Consulting
  • Indie Hackers
  • Basecamp
  • Zillow
  • Union Square Ventures
  • Fred Wilson
  • Pieter Levels
  • Nomad List
  • Brennan Dunn
  • Double Your Freelancing
  • Indie Hackers’ interview with John Doherty
  • Jason Calacanis
  • John Doherty's interview on This Week In Startups
  • John Doherty’s Twitter
  • John Doherty’s Instagram

Available now on your favorite podcast players:

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  • Breaker
  • Castro
  • Overcast
  • Spotify
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We covered:

  • 02:31 — Why Peldi moved back to Italy to build Balsamiq
  • 07:26 — What Balsamiq does to maintain a self-aware and continuous learning culture
  • 10:16 — Why “experiment culture” is important in Balsamiq
  • 13:35 — Why Peldi prefers not placing too much weight on his own “voice” within the company
  • 21:15 — The un-sexy part of remote hiring (legal challenges, paperwork, etc.)
  • 28:05 — A peek into Balsamiq's hiring process
  • 29:50 — Balsamiq's onboarding process and how it has evolved over time
  • 32:46 — How Peldi moved away from doing the things he's good at

Mentioned resources:

  • Balsamiq
  • Peldi’s Indie Hackers Interview
  • Balsamiq Career Page
  • How TaxJar Creates a Remote Company Culture with Mark Faggiano
  • Baremetrics
  • Josh Pigford’s tweet
  • Zapier
  • Know Your Team: The Heartbeat podcast episode with Peldi
  • Buffer
  • Buffer’s co-founder Leo Widrich
  • Peldi’s Twitter
  • Peldi’s LinkedIn

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We covered:

  • 2:27 — How Hiten Shah started his very early internet business
  • 4:00 — Why Hiten and his co-founder Marie Prokopets wrote the Remote Work Report
  • 6:10 — The most surprising finding from the Remote Work Report
  • 8:10 — How a remote manager can help remote team members figure out their ideal daily structure
  • 10:10 — What exactly is “overcommunicating”?
  • 12:37 — Why understanding people is the most important challenge remote companies need to tackle
  • 14:00 — Hiten’s hiring process and the biggest differences in hiring remotely between then and now
  • 24:00 — Questions people should ask themselves when they’re building a remote team.
  • 29:09 — Where Hiten usually does his best work

Mentioned resources:

  • FYI
  • Kissmetrics
  • Crazy Egg
  • Quick Sprout
  • The Remote Work Report
  • The Startup Chat Podcast
  • The Remote Show Podcast episode with Hiten Shah
  • Notion
  • Marie Prokopets
  • 11 Best Practices for Working Remotely
  • 58 Must-Read Remote Work Resources
  • Automattic
  • Buffer
  • How To Build Social Connections and Trust in Remote Teams with Claire Lew
  • Why Hiring Outside Silicon Valley is the New Normal with Andreas Klinger
  • Hiten’s Twitter

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We covered

  • 05:54 — What fascinates Ho Yin the most about remote work
  • 08:41 — Challenges and lessons Ho Yin faced while transforming to be a remote startup leader
  • 13:08 — How Ho Yin’s hiring process changed
  • 19:38 — Ho Yin’s “superpower” that helps him manage his remote team better
  • 21:35 — Why recording is a powerful tool for creating processes in remote teams
  • 24:59 — Resources that helped Ho Yin to be a better remote leader
  • 26:54 — What is Remo?
  • 34:21 — Use cases for Remo
  • 40:58 — How Ho Yin’s transition to being a remote startup leader affects Remo’s product roadmap
  • 49:11 — Advice to startups that want to start hiring remote team members
  • 50:45 — Why it’s important for remote startup CEOs to have a deep bond with early remote team members

Learning resources:

  • Remo’s Remote Company Transition Plan
  • Workplaceless
  • Lisette Sutherland
  • Laurel Farrer

Mentioned resources:

  • Remo
  • Riotly Social Media
  • Zapier
  • Automattic
  • Running Remote
  • Running Remote Podcast with Ho Yin Cheung
  • How TaxJar Creates a Remote Culture by Prioritizing Employee Experience
  • Help Scout
  • Loom
  • Using Voice to Bring "High-Resolution Communication" to Remote Teams
  • The Sims
  • Remote Work Summit

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We covered:

  • 01:02 — What is “Head of Remote” actually?
  • 02:00 — Why remote work came naturally to Andreas
  • 04:37 — How investors’ perceptions about remote work have changed over the years
  • 06:24 — Why building an engineering team inside Silicon Valley is now questionable
  • 11:08 — Is there such a thing as a “network effect” in remote work?
  • 15:45 — Why Andreas wrote Managing Remote Teams - A Crash Course
  • 19:48 — Systemizing “trust” inside a remote team
  • 23:35 — Why onboarding is crucial for new hires
  • 28:37 — Why you need to “refactor” your organization every few months
  • 35:04 — The misperception of the “digital nomad” trend
  • 40:30 — Is “remote readiness” is a thing?
  • 43:40 — How to start transitioning into a remote team
  • 47:12 — Andreas’ general advice to those who want to start/scale remote companies, especially regarding hiring
  • 50:30 — Why pair programming is an underrated way to assess your remote candidates

Mentioned Resources:

  • AngelList
  • Product Hunt
  • Ryan Hoover
  • Seedcamp
  • Running Remote
  • Andreas Klinger’s talk at Running Remote
  • Andrew Chen
  • Mullet model
  • Remotive
  • Managing Remote Teams - A Crash Course by Andreas Klinger
  • Zapier
  • Creating a Fun and Playful Culture in Remote Teams with Krister Haav
  • Toggl Startup Simulator
  • “Your company should be your best product”
  • Pieter Levels
  • Pieter Levels tweet about ‘digital nomads’
  • Nick Francis
  • Help Scout
  • Andreas Klinger's Twitter

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We covered:

  • 01:28 — How Justin got his first startup gig in high school
  • 06:06 — What is YAC?
  • 07:46 — Why voice communications are better than written documents
  • 12:44 — Using voice for async communication and clarity
  • 26:33 — How YAC launched via Product Hunt Maker’s Festival
  • 33:29 — Why Silicon Valley companies are doing themselves a disservice by not hiring outside the valley
  • 37:04 — Why remote work can create a ‘disconnect’ between the CEO and CTO
  • 41:12 — Why high-resolution communication is crucial for remote startups
  • 45:23 — The role of voice in the future of remote work and other aspects of daily life.
  • 48:50 — Using voice communication to increase accessibility

Mentioned resources:

  • SoFriendly
  • YAC
  • Hotjar
  • Zapier
  • Product Hunt
  • The $400,000 Tweet
  • Justin Jackson
  • Roche Healthcare
  • Zoom
  • Makers Weekly episode with Justin Mitchell
  • Request for Startups 1: Remote tools for remote teams by Tyler Tringas
  • Twist
  • Doist

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We covered:

  • 07:23 — Why “playfulness” is important to Toggl’s culture
  • 11:51 — Does brand authenticity = a higher employee retention rate for Toggl?
  • 13:51 — How Toggl “transfers the vibe” of team culture within the organization
  • 20:45 — The hiring and onboarding process at Toggl
  • 35:45 — Is it possible for remote teams to hire for potential?
  • 40:13 — Krister’s advice for companies who want to start hiring remote employees

Mentioned Resources:

  • Toggl
  • Teamweek
  • Hundred5
  • Krister’s Toggl page
  • Toggl Unicorn Startup Simulator
  • 5 Ways to Have Killer Meetings
  • What We’ve Learned Building a Remote Culture by Nick Francis

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We covered:

  • 03:00 — The 3 pillars of good leadership and how Claire codified these
  • 08:40 — Attributes of a good remote team leader
  • 10:05 — The importance of “affective trust” in a team
  • 16:10 — Can empathy be trained?
  • 19:40 — Asking the right questions as a leader
  • 29:50 — Claire’s thoughts on hybrid teams (half remote, half co-located)
  • 34:11 — How can employees “manage up” better?

Mentioned resources:

  • Know Your Team
  • The Heartbeat Podcast
  • How To Build Social Connection in a remote team
  • Basecamp
  • The Watercooler
  • Zapier
  • Wade Foster
  • MeetEdgar

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We covered:

  • 03:00 — Why Mark is passionate about remote work
  • 06:30 — The point during company scaling when it started to become harder to convey the company’s core values 06:30
  • 10:40 — The importance of employee onboarding, and why Mark decided to personally onboard new employees until the company grew to a team of 20
  • 16:00 — The importance of the Employee Experience Team and People Ops to TaxJar
  • 25:00 — How TaxJar’s transparency helped build trust among potential customers and new hires
  • 31:00 — How remote job applicants can stand out
  • 42:45 — Why it is now easier to raise money as a distributed startup

Mentioned resources:

  • TaxJar
  • Life at TaxJar
  • SaaS Insider - Mark Faggiano episode
  • Trello
  • Jira
  • Basecamp