
Growing engineering headcount in the world of AI with Allan Leinwand, CTO of Webflow
From Engineering Unblocked by Swarmia
June 30, 2025 · 46 min · Season 3 · Episode 24
About this episode
Allan Leinwand discusses the role of a scaling CTO and the impact of AI on engineering and hiring processes.
In this episode of Engineering Unblocked, Rebecca sits down with Allan Leinwand, Chief Technology Officer at Webflow and serial engineering leader who has scaled teams at Slack, ServiceNow, and Shopify. Allan shares his unique perspective on what it takes to be a successful “scaling CTO” — the type of leader who comes in at inflection points to help companies hockey-stick their growth. Allan also offers insights on navigating the AI revolution in engineering — from how it’s changing the hiring process and accelerating junior developer growth, to using it for everything from code completion to writing performance reviews. With his background spanning from early Cisco networking to modern SaaS platforms, Allan brings a unique long-term perspective on technology evolution and what it means to build engineering organizations that can scale to serve millions of users worldwide. Find the transcript at: https://www.swarmia.com/podcast/allan-leinwand-webflow/ Timestamps (0:00) Introductions (1:37) Allan's role as CTO (6:04) Staying in touch with the reality of software engineers (8:40) Similarities between leadership roles (11:09) Encountering founder mentality (13:00) The key to success…
People in this episode
Host: Rebecca
Guest: Allan Leinwand
Topics covered
- engineering leadership
- AI in hiring
- scaling teams
- performance management
- junior developer growth
- technology evolution
Keywords
- CTO
- AI revolution
- hiring process
- performance reviews
- engineering organizations
- junior developers
- team scaling
Mentioned in this episode
Organizations: Webflow, Slack, ServiceNow, Shopify, Cisco, SaaS
More episodes of Engineering Unblocked
- AI's unglamorous wins for developer productivity with Tara Hernandez from MongoDB · February 11, 2026 · 48 min
- What a year of hands-on AI coding teaches you about good software with Lada Kesseler · January 19, 2026 · 42 min
- Being a CTO when everything is exploratory with Rob Zuber from CircleCI · January 7, 2026 · 54 min
- Managing up, down, and the robots with Michael Lopp aka Rands · September 12, 2025 · 49 min
- Develop, deploy, operate: Three stages of delivering business value with Titus Winters from Adobe · July 31, 2025 · 46 min
- How to hire normal engineers and help them do great work with Charity Majors from Honeycomb · July 22, 2025 · 36 min
Explore listener stats, chart rankings, contacts and more on the Engineering Unblocked podcast page.