What I Learned from Two Powerful Customer Roundtables at the Rippling Roadshow

Today at the Rippling Roadshow in Chicago, I had the opportunity to host two roundtable discussions with talent leaders and hiring managers from across the country. These weren’t just surface-level chats — they were deep dives into the realities of today’s hiring experience, and the pain points keeping people up at night.

Here’s what stood out:

🧩 The Feedback Loop is Broken

Several leaders shared frustrations with hiring workflows that look great on paper — sourcing, screening, interviews — only to realize after a hire that the candidate wasn’t the right fit. Why? Because feedback from panel interviewers wasn’t clearly shared or was missing altogether. Decisions were being made in silos.

Opportunity: This signals a need for better alignment tools and tighter integration across hiring stakeholders — feedback should be captured, surfaced, and acted on before decisions are made.

🚩 Resume Red Flags & the Rise of “Professional Storytelling”

Everyone acknowledged a rise in resumes that were either too good to be true or exaggerated. One leader put it bluntly: “We’ve stopped calling them lies — they’re just really creative versions of the truth.”

Opportunity: There’s a growing desire for objective validation earlier in the funnel — background checks, skills assessments, and behavioral indicators need to be fast, credible, and candidate-friendly.

⏳ Time is the Real Competitor

Delays in background checks, clunky interview stages, and slow internal processes are costing companies top talent. Several leaders shared stories of candidates dropping off mid-process because they accepted another offer — not because they weren’t a fit, but because someone else moved faster.

Opportunity: Speed and clarity win. Employers need to create seamless, transparent journeys that keep candidates engaged and informed.

🧭 Culture Is Still Confusing

One surprising takeaway: many candidates feel disconnected from company culture during the hiring process. Despite “culture” being a top-of-funnel message on career sites, candidates often walk away unsure what the company actually stands for.

Opportunity: Infuse real culture into each touchpoint — from recruiter convos to interviews to offer letters. Authentic storytelling and candidate-first communication are key.

🎢 The Interview Gauntlet

A major source of friction? The interview process itself. Too many steps. Unclear expectations. And inconsistency in what’s being evaluated. One HR leader joked, “Sometimes I think we scare the best people off by making them jump through so many hoops.”

Opportunity: Re-evaluate the structure and purpose of interviews. Clear communication, consistent formats, and streamlined decision-making build confidence on both sides.

Final Thought:

What struck me most was that every challenge raised wasn’t just a recruiting problem — it was a business problem. Hiring is the front door to your brand, your product, and your future. And broken experiences at that door impact everything downstream.

As product marketers, it’s our job to listen to these stories and translate them into better solutions. This wasn’t just a conversation — it was a call to build with empathy, speed, and alignment.

Let’s keep listening. Let’s keep building.