The Squawk

Lorikeet

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.

Episodes

  1. How Stream Built an AI Support Agent with One Part-Time Engineer | Nick Rogers

    13 May

    How Stream Built an AI Support Agent with One Part-Time Engineer | Nick Rogers

    Stream's AI support agent resolves 80% of their customer tickets. It was built by one engineer, working part-time, inside a 60-person product and engineering team. In hundreds of conversations with CX leaders evaluating self-build, this is the exception. Most attempts stall between an impressive hackathon demo and a system reliable enough for production. Nick Rogers, Chief Product and Technology Officer at stream (formerly Wagestream), explains why his team is one of the few that crossed that gap. Nick walks through the test he'd give any leader weighing build versus buy (his answer: if you need to ask, partner), the "wait for the frontier" tempo of trying, failing, and coming back when a new model release shifts what's possible, and the results of stream's recent model bake-off, including the model that surprised the team for being worse than expected. Follow The Squawk podcast for hot takes and big ideas in CX. Perfect for a short commute and guaranteed to leave you with something new to think about, or implement, for your CX operation. Timestamps: 00:00 - Cold open 00:41 - Intro to Nick & stream 01:55 - Nick's career path 04:00 - Why stream's self-build is the exception 05:07 - The chronological story: GPT-3.5 to Gemini 2.0 Flash 07:50 - The culture that lets stream try and fail 09:15 - Eval methodology: golden datasets and A/B testing in production 11:30 - 70% to 80% deflection, a 33% reduction in tickets 11:55 - The model bake-off and the Claude Opus surprise 13:20 - Latency versus quality tradeoffs 14:46 - "How many of your 60 engineers work on this?" - effectively one 16:18 - Why talent matters (Joel on Software's "high notes") 17:39 - The self-build vs buy test: "if you need to ask, just buy" 19:30 - The "wait for the frontier" strategy 20:58 - Risk: from wild hallucination to agentic actions 24:41 - Knowledge management as the new CX job 26:42 - Lightning round 28:51 - Recommended reading: Hackers and Painters by Paul Graham 29:48 - Wrap-up Where to find Nick: LinkedIn: https://www.linkedin.com/in/rogersnm/

    30 min
  2. Scaling Support at Google, Stripe, and Bridge: Lessons in Building World-Class Operations

    07/10/2025

    Scaling Support at Google, Stripe, and Bridge: Lessons in Building World-Class Operations

    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 Journey04:45 Transition from Google to Stripe and customer support06:26 Focusing on Customer Support and Managing Vendors instead of Product or Hyper Scaling at Stripe12:12 Counterintuitive Lessons from Growth: Anecdotes and Data13:57 Balancing Anecdotes and Data as Stripe Grew16:36 Balancing In-House and Outsourced Support Teams19:03 The Evolution of Operations in the AI Era20:28 The Cambrian Explosion of Operations Startups21:44 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!

    26 min

About

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.