Built for HR leaders, People Ops professionals, and Founders navigating the future of work, Freedom of Work is the human resources podcast for teams serious about building global. Episodes cover everything from global hiring and talent acquisition to remote work strategy, AI in HR, and international employment. Whether you're scaling across borders or rethinking how your team works, Freedom of Work has the expert conversations you need. This podcast is hosted by RemoFirst.com, an Employer of Record solution that manages every aspect of a company's global employment needs.
Why Payroll Has No Net for Global Remote Teams with William Tincup
Host Leah Cottham talks with William Tincup, Editor, Analyst, and Advisor at WRKdefined, about what really happens when global remote teams try to buy and adopt HR tech. William brings 25 years of experience as an outsider to the HR world, which gives him a sharp eye for the gap between a dazzling demo and software people actually use.
The conversation covers why practitioners need to ask if a tool solves a real problem before they get sold on it, and why adoption is only a midway step toward getting people to love business critical software. William explains why payroll and compliance have no room for error with distributed teams, how to triple your implementation timeline for a realistic launch, and what he looks for in acquisitions long after the deal closes. He also shares practical advice for HR and TA leaders evaluating vendors, from viewing live software to talking with customers who are just like you.
Key topics covered:
[00:00] Intro
[00:49] Calling out the BS in HR tech
[03:17] Why outsiders question the establishment
[04:41] Where marketing and HR overlap
[07:16] How Covid sped up remote work
[09:02] The gap between demos and adoption
[11:36] Building products from customer feedback
[14:17] Why every software change disrupts users
[17:58] Adoption isn't the goal, love is
[18:20] Triple your implementation timelines
[23:52] Why payroll has zero margin for error
[30:04] What makes companies worth buying
[33:57] Startups are bands that clash
[36:31] Spotting customer concentration risk
[39:09] How to evaluate vendors before scaling
[47:53] Actionable AI and the future of work
[51:46] Getting comfortable with failure
Listen now to learn how to choose HR tech that survives contact with reality.
1 Sept 2026
Can We, or Should We? Rethinking AI in Recruiting (Federico D'Alessio @ FD)
Host Leah Cottham sits down with Federico D'Alessio, Talent Leader and AI Builder, for an honest conversation about where AI genuinely helps hiring teams and where the human touch still matters. Federico shares how 15 years in tech and SaaS recruiting led him to start building his own AI tools after realizing recruiters were repeating the same tasks thousands of times.
Federico walks through Mike, his multilingual AI voice recruiter that handles first stage screening, and Talent Signal, a tool that pulls public information from communities like Hacker News to surface active candidates. He explains why AI should remove repetitive admin work rather than replace recruiters, and why understanding the business and building trust with hiring managers stays firmly human. He also shares a simple way to start experimenting with AI today using small painful tasks first.
Key topics covered:
[00:00] Intro
[00:49] From Italy to tech recruiting
[02:36] When AI stopped being a buzzword
[03:16] Automating repetitive recruiter tasks
[06:27] The ChatGPT moment that changed everything
[07:42] Discovering AI voice platforms
[09:54] Meet Mike the AI recruiter
[13:07] Why building AI is expensive
[15:12] Talent Signal spots ready candidates
[18:50] Where AI actually saves recruiter time
[21:13] Why AI won't replace recruiters
[24:43] Start small with painful tasks
[30:20] Tackling bias in AI hiring
[33:10] The recruiter of the future
If you want a clear and practical view of how AI fits into hiring without over engineering it, this episode is worth your time.
12 Aug 2026
4x the Applicants, 0x the Quality: The AI Recruitment Dilemma (Heather Erickson @ Obra)
Host Leah Cottham sits down with Heather Erickson, COO at Obra, to unpack why hiring feels broken and what teams can do about it. Heather brings a career spent at the intersection of HR, technology, and operations, and she explains how AI has flooded hiring inboxes with applications that all look the same.
The conversation digs into a clear shift happening now. Applications have quadrupled since AI took off, yet quality has not kept pace, leaving hiring managers to waste time verifying whether candidates are even real people. Heather makes the case for going outbound, searching directly for candidates by skills rather than keywords, and building real relationships with job seekers. She also shares practical advice on hiring globally, why skills come first and location second, and how partnering with an employer of record removes the payroll and paperwork barriers to international growth.
Key topics covered:
[00:00] Intro
[00:43] Meet Heather COO at Obra
[03:11] How Ai bots flood hiring inboxes
[06:03] Why job seekers feel ghosted
[07:20] Detecting fake Ai candidates on camera
[09:33] Using Ai the smart way
[10:02] Building global teams that win
[11:53] Why Ai engineers demand going global
[13:50] Applications quadrupled since Ai
[15:47] Hiring is just like dating
[18:47] Why networks beat crowded inboxes
[20:33] 83% now chase passive candidates
[21:38] Matching skills not keywords
[25:15] Skills first then location and culture
[30:00] Make the first move yourself
[32:07] What success looks like 12 months later
[36:02] Putting the job seeker first
If you are tired of drowning in AI applications or wondering how to find top talent across the globe, this episode gives you a clear path forward. Press play and rethink how you hire.
Who has been a guest on Freedom of Work
Names identified in recent episode analyses. Showing up to five guests.
Natalie Lineton
Juan Pablo Carstens
Fernando Alves
Anthony Vaughan
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
YouTube views
277,801
Score snapshot 15 Sept 2025
Apple Podcasts (US)
5.0 / 5
1 ratings
Spotify
5.0 / 5
2 ratings
Podcast Authority Score: 45 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
59
Social presence
0
YouTube
76
Engagement
0
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Guest appearances
Books guests
Based on episode analysis; this does not confirm that the show is currently accepting guests.
Questions about Freedom of Work
Who hosts Freedom of Work?
Leah and Leah Cottham host the show. Published by RemoFirst.
How often do new episodes come out?
The show publishes bi-weekly, based on its RSS feed.
Does Freedom of Work take guests?
Yes. Guests have been identified in episode analyses.
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