Sinead Condon, Chief People Officer at Guidewire Software

Episode SummaryWhat does it take to scale a company in today’s volatile market—and why is curiosity the secret leadership skill we underestimate? In this episode of Built by People, we sit down with Sinead, Chief People Officer at Guidewire Software, whose career spans decades in tech, Agile consulting, and large-scale business transformation.From founding her own tech firm in Ireland to leading HR at a global insurer tech company, Sinead shares hard-won insights from scaling organizations in complexity and uncertainty. She dives into the critical importance of educating employees on financial operations, building organizational resilience, and challenging the assumptions that often stall progress.You'll hear Sinead’s take on the evolving role of the CPO, why relationships matter more than ever in solving complex business problems, and how to build a culture where every team member understands their impact on the bottom line.Key Timestamps[00:45] – Sinead’s tech-driven career journey from Ireland to Silicon Valley[02:49] – The biggest challenge: Scaling and operationalizing in a post-COVID world[05:22] – Why employee financial acumen matters in transformation[07:53] – The danger of assumptions and the power of relationships[09:47] – Sinead’s parting advice: Be curious and lead beyond your laneTakeawaysClarify the evolving role of CPOs in organizational strategy and operationsEducate teams on financial and operational levers to build trust and transparencyAvoid reactive leadership by absorbing information before actingBreak down silos by helping employees understand their role in the broader company missionLead with curiosity—not just within HR, but across all areas of the businessOur SponsorPrevi is an employer network that provides private pricing for employees. Joining the Previ network allows employees to save on necessities they already pay for, such as cell phone service and insurance. Previ saves the average employee $2,200/year. ⁠Join at no cost to the company.⁠