Debugging Work

Hosted by Derek Hatchard

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Jun 2025

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About the show

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.

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8 recent

June 17, 2025Episode 752 min

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 DiscussedThe Recruitment ProblemOnly 10% of recruiters actually go back to their candidate databaseThe "biggest lie recruiters tell": "We'll keep your resume on file"Traditional ATS systems aren't built for candidate nurturing, just processing hiresCandidate Hub's SolutionMarketing automation for recruitment - bringing quality candidates to recruiters' inboxes dailyCreating "virtual benches" of candidates segmented by role/industryLead scoring for candidate engagement to prioritize follow-ups90%+ reduction in sourcing costs for clientsThe Sports Analogy: Building Championship TeamsThree ways to build teams:Free Agency (job boards) - expensive, competitiveTrades (staffing firms) - costly at 25% of salaryThe Draft (nurturing future talent) - most overlooked but strategicMajor Industry IssuesGhost job postings - Brad calls this "extremely unethical"Hiring managers need recruitment KPIs - treating hiring as urgent but not prioritizing interview schedulingPay inequity - average internal raise is 2-5%, but external job moves yield 12-15% increasesRemote Work ImpactAtlantic Canada lost its competitive advantage of lower cost of livingNow competing globally for talent while trying to retain local workforceCompanies need new strategies beyond "better way of life" messagingLightning Round RecommendationsPodcast: Chad and Cheese (HR's most dangerous podcast)Person/Product: Adam Gordon and Poetry (recruiter enablement platform)Superpower: Ability to change and adapt quickly to new technologyConnect with BradLinkedIn: https://www.linkedin.com/in/braddipaolo/Email: brad@candidatehub.ioMentioned Resources"Don't Work for Beer" videoPoetry by Adam GordonChad and Cheese podcastHow Music Got Free

March 11, 2025Episode 634 min

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/lynnoslerhttps://www.amazon.ca/Coaching-Manual-Definitive-Principles-Personal/dp/1292084979. https://www.audible.ca/pd/The-Coaching-Manual-5th-Edition-Audiobook/B0CBW3LW6Q https://sanfordosler.ca/ --This episode is sponsored by Posthaste.ai Stay up-to-date on Debugging Work by following Derek Hatchard on LinkedIn and subscribing to the Debugging Work newsletter.

February 25, 2025Episode 543 min

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 pandemic led to some reevaluations for Jamar and his husband, which led them to quitting their jobs at the end of 2022 and taking a sabbatical. When Derek and Jamar spoke in 2024, Jamar was setting down roots in Lisbon, Portugal. Links from the episode:https://blog.jamarparris.com/p/in-search-of-a-different-approachhttps://blog.jamarparris.com/p/my-new-reality-in-2024https://www.linkedin.com/in/jamarhttps://www.lennysnewsletter.com/p/redefining-success-purpose-and-belonginghttps://pathlesspath.com--This episode is sponsored by Posthaste.ai Stay up-to-date on Debugging Work by following Derek Hatchard on LinkedIn and subscribing to the Debugging Work newsletter.

May 10, 2024Episode 444 min

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 his caliber.He is also the founder of FRAK, an in-person conference for fractional executives and the fractionally curious. And as if that isn’t enough, Rob is the CTO of Atomic Elevator, a syndicate of marketing professionals combining AI with human insights to create successful product launch strategies.Links from the episode:FRAK – A Conference for Fractional Pros - https://fractionalconference.com/Atomic Elevator - https://www.atomicelevator.com/The Go-GiverValue Proposition Design: How to Create Products and Services Customers Want The Speed of TrustMy First Million PodcastThe Tim Ferriss ShowReclaim AI (Smart Scheduling App for Teams)--This episode is sponsored by Posthaste.ai Stay up-to-date on Debugging Work by following Derek Hatchard on LinkedIn and subscribing to the Debugging Work newsletter.

March 28, 2024Episode 334 min

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 engineering leadership. And stick around for her story about moving to Mexico City to open Etsy’s first office in Latin America.Links from the episode:Commodore VIC-20 (Wikipedia)The Universe in Your Hand: A Journey Through Space, Time, and BeyondJournalist Motaz Azaiza مُعْتَز عزايزة ⚡️ (@motaz_azaiza)Najla Elmachtoub on LinkedIn--This episode is sponsored by Posthaste.ai Stay up-to-date on Debugging Work by following Derek Hatchard on LinkedIn and subscribing to the Debugging Work newsletter.

March 28, 2024Episode 247 min

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, sustainable and measurable change.Links from the episode:Leeno Karumanchery on LinkedInMESH DiversityThe McKenna Institute | University of New Brunswick--This episode is sponsored by Posthaste.ai Stay up-to-date on Debugging Work by following Derek Hatchard on LinkedIn and subscribing to the Debugging Work newsletter.

March 28, 2024Episode 134 min

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 KahlThe Pragmatic Engineer newsletter from Gergely OroszRemote Work AcademyRemote Work NewsletterMastering Remote Work (video course)https://twitter.com/SergioRocks--This episode is sponsored by Posthaste.ai Stay up-to-date on Debugging Work by following Derek Hatchard on LinkedIn and subscribing to the Debugging Work newsletter.

March 26, 20240 min

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.