The Engineering Leadership Podcast

Ali Dasdan, CTO @ Dropbox, joins the pod to share insights on the company’s large-scale AI adoption and research as a foundation of successful engineering leadership. First, Ali shares insights on why he continues publishing research despite his role as a CTO and how research / curiosity can drive better trust within your organization. He shares about how his research ultimately guided decision making regarding redrawing Dropbox’s entire architecture and the importance of creating a record of the company’s progression as the rearchitecture occurred. The bulk of the conversation centers around how Dropbox is adopting AI, including tools like Nova and Dash, within both EPD and non-EPD departments.

ABOUT ALI DASDAN
Ali Dasdan is a C-suite technology executive with 25+ years building, scaling, and leading global engineering, product, and technical-operations organizations of up to ~1,000 people across a dozen industries, in public companies, high-growth startups, and enterprises in Silicon Valley and London.
Today he is CTO of Dropbox, serving over 700 millions of users on an exabyte-scale platform with $2.5B+ revenue, where he also leads the AI strategy and AI enablement. Previously EVP and CTO of ZoomInfo and VP of Engineering at Atlassian (Confluence Cloud, Trello, Jira Work Management). As CTO (at Turn, Vida, Poynt, ZoomInfo, and Dropbox) he defines and owns company-wide technology strategy; in divisional roles (eBay, Atlassian, Tesco, Yahoo) he led engineering for revenue-critical parts of the business.

SHOW NOTES:
Why Ali continues to publish research as a CTO (1:51)
How research results can alter decision making as an eng leader (3:30)
The connection between research & organizational trust (4:29)
Redrawing the org’s architecture to learn more about it (6:00)
What kinds of info help eng leaders better understand the business / technology (8:12)
Building a record of the org’s progress & development (10:13)
Where Dropbox is at in their AI adoption journey (11:58)
AI @ Dropbox in EPD vs. non-EPD functions (13:36)
Frameworks for implementing AI at the highest level (15:23)
The engagement / ownership model @ Dropbox (16:58)
Insights on Nova, Dropbox’s code review AI workflow (18:59)
Incorporating human-driven feedback into the AI loop (21:12)
What the immediate future looks like for automated developer tools (23:54)
How AI has directly impacted productivity @ Dropbox (27:15)
Addressing bottlenecks related to AI adoption (30:35)
Using AI infrastructure to assist in non-EPD functions (32:33)
Dash as a contextual AI platform (35:39)
Ali’s experience with specialized models vs. foundation models (38:10)
Rapid fire questions (39:48)

This episode wouldn’t have been possible without the help of our incredible production team:
Patrick Gallagher - Producer & Co-Host
Jerry Li - Co-Host
Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/
Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/
Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

In this episode, Jerry discusses key insights on delegating to agentic tools while maintaining high levels of engineering ownership with Ozzie Osman, co-founder @ Monarch. Ozzie shares what it looks to pursue two paths when it comes to AI: agentic-forward and human-orchestrated pipelines. They also cover the specific AI tools that are used in Monarch, including Devin and Voltron; assigning tasks to be AI-first vs. human-led; determining which pieces of customer feedback lead to new features; and common challenges when it comes to AI-generated code and what the human review process for it looks like.

ABOUT OZZIE OSMAN
Osman (Ozzie) Osman is co-founder of Monarch. He is the lead author of the Holloway Guide to Technical Recruiting and Hiring. He has built products and engineering teams at companies including Quora and Google. Ozzie has also started two companies that have been acquired, and advised dozens of other startups.

Sinch is the communications infrastructure the AI era runs on.
There's a layer of infrastructure behind every text, call, and login code your product sends, and it works exactly like plumbing: nobody thinks about it until it's the reason something broke.
Most providers route through 4-6 intermediaries; Sinch connects in 1-2 hops, direct carrier relationships across 600+ connections, handling 900 billion interactions a year across 60+ countries.
Routing, compliance, fraud prevention handled automatically rather than manually managed by the business sending the message!
Sinch is the reliability layer underneath AI-driven customer communications; the infrastructure that determines whether an AI agent's output actually reaches a real person as a delivered text, connected call, or verified interaction.
Check it out here!

SHOW NOTES:
Introducing Ozzie & his role @ Monarch (2:37)
Where Monarch is at in terms of technology transformation / user adoption (5:20)
Insights on how Monarch is embracing AI with a security-forward mindset (7:21)
What it looks like to pursue both agent- and human-orchestrated AI pipelines (11:00)
Dissecting how an MCP shared infrastructure improves productivity (13:11)
Inside the enablement team @ Monarch (15:25)
Why Monarch uses Devin / prioritizing autonomy (16:33)
How to fine-tune an agent to make it reusable (18:40)
Strategies for determining what is an AI-centric vs. human-centric task (20:47)
Understanding when & why Devin fails (24:49)
Devin’s role in assisting the human-orchestrated processes (26:39)
What a typical flow looks like throughout an SDLC (28:05)
The importance of ownership in engineering when reviewing AI-generated code (29:31)
Frameworks for prioritizing feature requests based on user feedback (35:15)
Ozzie’s perspective on the role of engineering teams (40:03)
Final thoughts on navigating AI-related anxieties (43:08)

This episode wouldn’t have been possible without the help of our incredible production team:
Patrick Gallagher - Producer & Co-Host
Jerry Li - Co-Host
Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/
Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/
Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Jakub Oleksy, SVP of Software Engineering @ Github, joins the podcast to discuss how Github is addressing some of the biggest challenges facing the industry when it comes to infrastructure scaling, customer capacity, and using AI to add value to your org’s processes and eng leaders’ decision-making. He shares how scaling looked different at Github six years vs. today, how they navigated the migration to Azure, and what AI transformation looks like individually & at the team level. Jakub also discusses insights for eng leaders when it comes to investing in yourself & your people and making cross-functional decisions.

Sinch is the communications infrastructure the AI era runs on.
There's a layer of infrastructure behind every text, call, and login code your product sends, and it works exactly like plumbing: nobody thinks about it until it's the reason something broke.
Most providers route through 4-6 intermediaries; Sinch connects in 1-2 hops, direct carrier relationships across 600+ connections, handling 900 billion interactions a year across 60+ countries.
Routing, compliance, fraud prevention handled automatically rather than manually managed by the business sending the message!
Sinch is the reliability layer underneath AI-driven customer communications; the infrastructure that determines whether an AI agent's output actually reaches a real person as a delivered text, connected call, or verified interaction.
Check it out here!

SHOW NOTES:
The current focus @ Github & what scaling looks like (1:21)
Signals that previous scaling methods are no longer viable (3:00)
Migrating to Azure / impact on the engineering org (5:55)
Strategies for orchestrating massive, widespread change across the org (7:28)
How to control the scope while scaling / rebuilding (10:16)
Ownership dependencies & potential rollback with Github’s service migration process (11:50)
Embrace excitement when it comes to prioritization, scaling, & problem solving (14:15)
Addressing capacity & configuration challenges earlier on (16:49)
Github’s “new norm” for processes / organization (18:23)
How to address legitimate vs. illegitimate traffic (21:02)
Keeping up with rapidly changing technology / AI advances (21:31)
Github’s method for tackling the context layer of its AI toolage (27:14)
Where Github is on the AI adoption curve (29:30)
Navigating the transition from individual AI adoption to team-level transformation (31:36)
An example of team-level AI adoption @ Github (33:39)
Jakub’s advice to eng leaders on building infrastructure teams / investing in people (34:36)
How platform leaders can improve their cross-functional change making ability (38:39)
Reducing complexity for platform teams to improve ability to scale (40:42)
An example of a successful transformative moment @ Github (42:34)
Rapid fire questions (46:28)

This episode wouldn’t have been possible without the help of our incredible production team:
Patrick Gallagher - Producer & Co-Host
Jerry Li - Co-Host
Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/
Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/
Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Benny Chen, Co-Founder @ Fireworks AI, joins the show to discuss his founder journey and share valuable insights on navigating common founder / product dev challenges in today’s agent-first landscape. He and Jerry cover strategies for creating effective messaging, staying competitive in a crowded market space, hiring top-tier talent / what qualities to look for in high-performing engineers, navigating the cultural shift to managing agents, creating data flywheels & how this can help your customers, and more.



ABOUT BENNY CHEN

As co-founder and early product architect, Benny Chen shaped Fireworks AI’s infrastructure strategy, spearheading the design of scalable systems to support high-throughput AI model serving. Benny’s contributions established the technical foundation for Fireworks AI’s robust and cloud-native architecture, which underpins its ability to meet enterprise demands.

Formerly Meta’s Ads Infrastructure Lead, Benny optimized large-scale ad-serving pipelines and developed significant expertise in distributed systems and cloud infrastructure. He holds a B.S. in Computer Science from Stanford University, bringing both leadership and technical depth to the Fireworks AI management team.



Sinch is the communications infrastructure the AI era runs on.

There's a layer of infrastructure behind every text, call, and login code your product sends, and it works exactly like plumbing: nobody thinks about it until it's the reason something broke.

Most providers route through 4-6 intermediaries; Sinch connects in 1-2 hops, direct carrier relationships across 600+ connections, handling 900 billion interactions a year across 60+ countries.

Routing, compliance, fraud prevention handled automatically rather than manually managed by the business sending the message!

Sinch is the reliability layer underneath AI-driven customer communications; the infrastructure that determines whether an AI agent's output actually reaches a real person as a delivered text, connected call, or verified interaction.

Check it out here!



SHOW NOTES:

Moving from an early idea to a rocket ship (1:13)

Insights on developing / communicating your core message as an early founder (2:40)

Role of open source & inference @ Fireworks AI (4:24)

How Firework AI’s company messaging evolved over time (6:07)

Popular customization features today (7:25)

Strategies for staying competitive in a crowded market (9:11)

Defining the customer data flywheel & how it helps users (11:25)

Common types of data that companies can collect to train their AI models (13:53)

The customer’s next steps after creating a data flywheel (15:53)

Benny’s perspective on acquiring engineering talent as a founder (16:43)

Common traits shared by high-performing engineers @ Fireworks (19:05)

How AI has altered which traits founders prioritize when hiring (20:45)

Navigating the shift from engineering work to managing agents (22:40)

Frameworks to ensure agents are doing the right thing (25:23)

Aligning your metrics with the outcome you’re trying to follow (27:37)

What a typical day looks like for Benny as a founder (28:31)

Advice for founders / eng leaders looking to embrace AI adoption (29:19)

Rapid fire questions (31:15)



This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

In this episode, Pooja Brown (Founder @ Inventry.ai) shares her insights on balancing being a founder & technologist, especially within the mid-market manufacturing industry. We cover why founders need to lead with curiosity as they seek out customer problems to solve, strategies for solving complex problems related to supply chain, and strategies for selling your products. Pooja also dissects important fundraising tactics, how to identify areas that AI tooling can enhance within your business, reading customer signals, and bolstering your engineering skills by leveling up business capabilities.

 

ABOUT POOJA BROWN

Pooja Brown is a technology executive and founder focused on building AI-native platforms that power real-world operations across industries. She has led engineering at scale at companies like Stitch Fix and DocuSign, building systems that combine data, workflows, and machine learning to drive everything from personalization and supply chain to digital agreements used by hundreds of thousands of businesses.Her experience spans multiple verticals including retail, enterprise SaaS, education technology, and real estate, where she has consistently focused on embedding AI directly into core business systems rather than layering it on top.

Pooja is currently the founder and CEO of Inventry.ai, where she is building autonomous AI agents that help mid-market manufacturers run procurement and supply chain operations more effectively. Across her career, she has focused on turning complex operational data into systems that don’t just generate insights, but actually drive decisions and execution.

 

Sinch is the communications infrastructure the AI era runs on.

There's a layer of infrastructure behind every text, call, and login code your product sends, and it works exactly like plumbing: nobody thinks about it until it's the reason something broke.

Most providers route through 4-6 intermediaries; Sinch connects in 1-2 hops, direct carrier relationships across 600+ connections, handling 900 billion interactions a year across 60+ countries.

Routing, compliance, fraud prevention handled automatically rather than manually managed by the business sending the message!

Sinch is the reliability layer underneath AI-driven customer communications; the infrastructure that determines whether an AI agent's output actually reaches a real person as a delivered text, connected call, or verified interaction.

Check it out here!

 

SHOW NOTES:

What shaped Pooja’s entrepreneurship journey & background (3:20)

Looking for the right problem & leading with curiosity (6:47)

Insights on solving problems related to supply chain (10:42)

Building systems for chaos / complexity (12:46)

Adopting a beginner’s mindset when solving complex problems (15:40)

Dissecting fundraising strategies & decision making (19:28)

Emerging business patterns that eng leaders need to capitalize on (26:32)

Understanding how customers make decisions on what products to adopt (29:09)

Selling strategies for the mid-market manufacturing industry (37:08)

Integrating AI tools to augment current business capabilities (41:03)

Engineering skills that enhance sales processes (44:43)

Communication frameworks when working with customers (47:21)

Rapid fire questions (50:06)

 

This episode wouldn’t have been possible without the help of our incredible production team:

Patrick Gallagher - Producer & Co-Host

Jerry Li - Co-Host

Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/

Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/

Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/

Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.