Debugging Work

Derek Hatchard•podcast.debuggingwork.com

Modern work does not have to be a nightmare. This podcast is about finding ways to make work more enjoyable, productive, and even fulfilling. Host Derek Hatchard (founder of Posthaste.ai, ex-Salesforce product+engineering) talks with guests about their areas of expertise and experiences making work better.

Last refreshed: August 23rd, 2025 at 2:32 AM ⓘ

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Episodes

Brad DiPaolo on modern recruitment and candidate nurturing

Brad Polo is the Founder & CEO of Candidate Hub. He has 25+ years in sales, marketing, and recruitment. Key Topics Discussed The Recruitment Problem Only 10% of recruiters actually go back to their candidate database The "biggest lie recruiters tell": "We'll keep your resume on file" Traditional ATS systems aren't built for candidate nurturing, just processing hires Candidate Hub's Solution Marketing automation for recruitment - bringing quality candidates to recruiters' inboxes daily Creati...

Jun 17, 2025•53 min•Ep. 7

Lynn Osler on building a strong remote first culture

Lynn Osler is an HR and Culture Specialist. She has worked in a variety of sectors from retail startups to large health care organizations. She is currently a human resources generalist at Pagefreezer, a remote-first software company. In this episode, Lynn shares some of the tools and practices they use to create a strong remote culture and safeguard the well-being of team members. Links from the episode: https://ca.linkedin.com/in/lynnosler https://www.amazon.ca/Coaching-Manual-Definitive-Princ...

Mar 11, 2025•34 min•Ep. 6

Jamar Parris on quitting his job in tech to take a sabbatical

Jamar Parris started his career on the technical side, working as a full stack engineer and systems architect. He was a tech lead at Buddy Media, which is Derek and Jamar first crossed paths after Salesforce acquired the company in 2012. His background has always been a blend of the technical and business sides. About 10 years ago, he switched from engineering to product management and has worked primarily in fintech and e-commerce, including companies you know like PayPal and Braintree. The pan...

Feb 25, 2025•43 min•Ep. 5

Rob Smith on stepping into new roles, moving from corporate to fractional executive leadership, launching a conference, and being chronically curious

Rob Smith was cajoled into filling out a paper application in a pub that turned into a 25 year career at 3M where he says he kept being asked to step into roles he wasn’t qualified for. After leading many initiatives in digital transformation, ebusiness, commerce, marketing automation, business strategy, and more, Rob reimagined his career and became a fractional executive, providing access to his experience and expertise to companies that otherwise would not be able to afford an executive of hi...

May 10, 2024•45 min•Ep. 4

Najla Elmachtoub on human-centered on-call practices, leading with empathy, retrospectives, and knowing what is just enough to do and then letting go

Najla Elmachtoub is an engineering leader. In her most recent role as a Director of Engineering at Etsy, she led product teams across several domains including mobile, machine learning, adtech, and more. Prior to Etsy, Najla worked at a fintech startup in New York as an engineering manager and a product manager. She believes in growing teams with empathy, bringing people along for tough decisions, and advocating for others. In this episode, Najla shares how she applies human-centered thinking to...

Mar 28, 2024•34 min•Ep. 3

Dr. Leeno Karumanchery on DEI and helping organizations engage inclusion in a way that drives positive, sustainable and measurable change

Leeno Karumanchery is a sociologist with a PhD focused in Diversity and Inclusion. Dr Karumanchery has 30+ years of experience in the field, he is widely published and is an internationally sought after speaker, facilitator and consultant. He is co-founder and head of behavioural sciences of MESH Diversity where his research underpins the MESH Diversity software platform. Leeno combines his education, research and expertise to help organizations engage inclusion in a way that drives positive, su...

Mar 28, 2024•47 min•Ep. 2

Sergio Pereira on building remote teams, fractional CTOs, and fostering human connections

Sergio Pereira was an advocate for remote work years before the pandemic forced everyone to think about it. Over the past decade, Sergio has worked in full-time and fractional CTO roles, hiring and leading teams distributed all over the world. He is the creator of the Remote Work Academy, the Remote Jobs Braintrust, and the Remote Work newsletter. Links from the episode: Jobs CoPilot The Bootstrapped Founder Podcast with Arvid Kahl The Pragmatic Engineer newsletter from Gergely Orosz Remote Work...

Mar 28, 2024•35 min•Ep. 1

Trailer - Debugging Work

Introducing the Debugging Work podcast. Modern work can be a hot mess. This podcast is for discussing ways in which work doesn’t work. Host Derek Hatchard talks with guests about their areas of expertise and experiences making work better.

Mar 26, 2024•59 sec

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