Growing engineering headcount in the world of AI with Allan Leinwand, CTO of Webflow

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 as a CTO
(16:23) How Webflow uses AI
(19:37) How AI is affecting the hiring process
(21:44) Hiring juniors
(25:35) How AI is changing other roles
(27:22) Webflow's approach to performance management
(32:32) Mitigation strategies to maintain productivity
(36:27) How Allan approaches reorgs
(39:46) Who Allan feels accountable to
(42:58) Creating a culture of accountability

Follow Allan on LinkedIn: https://www.linkedin.com/in/aleinwand/

Follow Rebecca on LinkedIn: https://www.linkedin.com/in/rmurphey/