What actually happens between a flashy product demo and a team that's still using the software a year later? In this episode of Freedom of Work, Leah Cottham sits down with William Tincup, a 20-plus-year HR and talent acquisition (TA) veteran who's studied the industry from nearly every angle: agency marketer, user adoption consultant, market analyst, media host, and now advisor to more than 25 HR tech boards.

William brings a practitioner's skepticism to a topic every people leader faces: how do you choose HR tech that a distributed, global team will actually use? Drawing on his experience watching companies get built, bought, and occasionally broken, he lays out a clear-eyed framework for evaluating vendors, spotting real problems versus manufactured ones, and understanding why payroll and compliance sit at the top of the risk hierarchy for any remote-first organization.

What We Cover

The demo trap. Every demo is designed to dazzle. William explains why the real question isn't "can this technology do it?" but "do we actually have this problem?" and how practitioners can separate genuine need from a solution in search of one.

Why culture had to be redefined. Pre-pandemic, William says most companies equated culture with the office itself. He walks through how remote-first teams have had to rebuild what culture means without a physical headquarters, and why he sees mandatory return-to-office policies as a step backward.

The hidden cost of every software change. Even small product updates create change management work for the end user. William explains why speed of iteration, especially with AI, means practitioners need built-in, contextual training rather than assuming intuitive design is enough.

Adoption isn't the finish line, love is. William argues that getting a team to use new software is only the midpoint. The real goal is getting people to depend on it the way sales teams depend on Salesforce or finance teams depend on QuickBooks: as business-critical, not just another tool.

Why payroll gets zero room for error. Across every HR tech category, William ranks payroll and compliance as the two areas where mistakes carry the highest cost, especially for global, remote teams managing pay and regulations across multiple countries.

What due diligence really looks like in M&A. From customer concentration risk to independently verified sales pipelines, William shares what he's learned advising on acquisitions, including why he judges a deal's success by whether the acquired leadership team is still there a year later.

How to actually vet a vendor. His advice for HR and TA leaders scaling globally: insist on live software over polished decks, and talk directly to a similar-sized customer who'll tell you the truth about implementation, not just the vendor's chosen reference.

Where HR tech goes next. William closes on why he's optimistic about AI's role in HR, not as a replacement for people, but as a layer that turns siloed data into actionable insight, freeing teams from the tasks no one wanted to do in the first place.

About William Tincup

William Tincup is Editor, Analyst, Advisor and Host at WRKdefined, a podcast network covering everything related to work. He's studied HR and TA for more than 20 years, from the practitioner and technology sides alike, and has been featured as an HR and future of work expert in the New York Times, Wall Street Journal, Harvard Business Review, Fortune, CNN, Bloomberg, TechCrunch and WIRED. William is a venture partner at Evergreen Mountain Equity Partners and Future Wrk Ventures, and sits on the Boards of Advisors for more than 25 HR and TA tech companies, advising on go-to-market, positioning and strategy. He holds a BA in Art History from the University of Alabama at Birmingham, an MA in American Indian Studies from the University of Arizona, an MBA from Case Western Reserve University, and SHRM-SCP and SPHR certifications.