The Squawk – Details, episodes & analysis

We begin our very first episode on The Squawk with Bob van Winden. Bob shares his extensive experience in scaling customer support operations across major tech companies like Google and Stripe, and now at Bridge, a fintech startup. He reflects on how he accelerated his career thanks to unique professional opportunities available in Support and Operations, the importance of balancing anecdotes with data when it comes to CX, and the key lessons from hyper-scaling operations over the past decade.

The customer experience space is changing fast. The Squawk is a short, sharp and focused deep dive on one guest and their one big idea about how CX is changing for the people involved. The conversation is deep, tactical and specific. Perfect for a quick commute and guaranteed to leave you with something new to think about – or implement – for your CX operation.

Timestamps:

• 00:00 Introduction to Bridge and Bob's Journey
• 04:45 Transition from Google to Stripe and customer support
• 06:26 Focusing on Customer Support and Managing Vendors instead of Product or Hyper Scaling at Stripe
• 12:12 Counterintuitive Lessons from Growth: Anecdotes and Data
• 13:57 Balancing Anecdotes and Data as Stripe Grew
• 16:36 Balancing In-House and Outsourced Support Teams
• 19:03 The Evolution of Operations in the AI Era
• 20:28 The Cambrian Explosion of Operations Startups
• 21:44 Lightning Round: Insights on Customer Support Metrics and Experiences

Where to find Bob:

LinkedIn: https://www.linkedin.com/in/bobvanwinden/

☝️Subscribe to this channel - New episodes in Season 1 is out every 2 weeks!

We’re launching a new podcast! The customer experience space is changing quickly. The Squawk is a short, sharp and focused deep dive on guests from leading companies. Hear Steve Hind speak to CX, Product and Operations Leaders at Clay, Linear, Stripe (to name a few), and their one big idea about how CX is changing for the people involved. Here’s a sneak peek. We can’t wait to share Season 1 with you—stay tuned!More about us:LinkedIn: https://www.linkedin.com/company/lorikeetcx/ Website: https://www.lorikeetcx.ai/Blog: https://www.lorikeetcx.ai/blog

What if your support team didn't just answer tickets, but shipped code to the product?

That's exactly what Vicky Firth, founding CX lead at Granola, has built. A team where every agent has Cursor open next to their inbox, makes small code changes themselves, and rebuilds the internal tools they use every day instead of waiting on engineering. In this episode, Vicky breaks down how to:

- Equip a "non-technical" CX team to read, troubleshoot and ship code

- Hand the keys back to support by letting them own their own internal tools

- Turn the support function into the team that engineers actually want to collaborate with

Follow The Squawk podcast for hot takes and big ideas in CX, perfect for your commute and packed with insights you can actually use.

Timestamps:

00:00 - Cold open & intro

01:17 - Vicky's career: biology to support engineering to Accurax to Granola

04:04 - Lessons from supporting NHS frontline workers through COVID

06:17 - What Granola is and Vicky's goals as founding CX lead

09:11 - Deep dive: how the CX team uses Cursor day-to-day

13:16 - Working with engineering, reviews, pitfalls, and trust

17:30 - Where to start if you're a CX leader

19:13 - Career paths, recruiting, and the future of CX

23:43 - Lightning round

29:32 - Wrap-up

Where to find Vicky:

LinkedIn: https://www.linkedin.com/in/vicky-firth-505b15105/

What if support wasn't just a cost center, but your company's best talent pipeline?

That's exactly what George Dilthey, Head of Support at Clay, built - a system that recruits new grads into support, then rotates them across the business. In this episode, George breaks down how to:

• Turn support into a talent exporter that feeds product and GTM teams
• Develop expert generalists ready for an AI-driven workplace
• Build structured career pathways that retain top performers

Follow The Squawk podcast for hot takes and big ideas in CX - perfect for your commute and packed with insights you can actually use.

Timestamps:

00:41 - Intro to George & Clay

03:38 - Inside “The Wheel” rotational program

08:02 - AI, new grads & the rise of the “expert generalist”

12:00 - The Wheel as a talent engine for Clay

22:05 - Lightning Round

Where to find George:

LinkedIn: https://www.linkedin.com/in/george-dilthey/

In this episode of The Squawk, we sit down with Jared Ellis from Culture Amp. Jared shares his journey from being the first support specialist to leading an AI-first customer experience transformation. Key topics include shifting from productivity metrics to quality of experience, improving AI through frontline feedback, emerging career paths in support teams, and challenging the conventional wisdom of slow AI rollouts by moving quickly with well-planned "escape hatches."

Follow The Squawk podcast for hot takes and big ideas in CX. Perfect for a short commute and guaranteed to leave you with actionable insights to implement in your CX operation.

Timestamps:

00:41 Introduction to Culture Amp and Jared's Role

02:12 Jared's Journey and AI Adoption in Customer Support

05:03 The Impact of AI on Customer Experience Measurement

09:07 Metrics shift: from speed (FRT) to quality of experience in an AI-first model.

19:00 Lightning Round

Where to find Jared:

LinkedIn: https://www.linkedin.com/in/jaredellis/

All companies care about product quality, but Linear actually has a zero bug policy with teeth.

We sat down with Alexandra Lapinsky Wilson, who leads Product Ops and CX at Linear.

Linear wants to bring the magic back to software, and Alexandra's teams are making that real for users every day.

Hear Alexandra's insights on how CX is critical to delivering on the zero bug promise

1. If a user thinks something is broken, it's a bug. No "that's expected behavior" excuses allowed
2. CX does real work before bugs hit engineering: troubleshooting, gathering logs, providing context
3. CX gets staffed on every product project from discovery through launch

Follow The Squawk podcast for hot takes and big ideas in CX. Perfect for a short commute and guaranteed to leave you with actionable insights to implement in your CX operation.

Read more about Linear's zero-bug policy here: https://linear.app/now/zero-bugs-policy

Timestamps:

0:54 - Retail to Software Career

7:32 - Zero Bug Policy Explained

10:24 - Identifying bugs for eng, collaborating with product

16:38 - Hiring Philosophy, Org

19:03 - Lightning Round Q&A (great support, favorite metrics)

Where to find Alexandra:

LinkedIn: https://www.linkedin.com/in/alexandra-lapinsky-wilson/

☝️Subscribe to this channel - New episodes in Season 1 are out every 2 weeks!