The Engineering Leadership Podcast

Amit Gupta, Partner @ SNR Ventures, joins Jerry to discuss his unique eng leadership journey and how that led him to his second career as an investor / coach. We cover some of the lessons learned throughout his time working as VP of various startups and how those experiences shaped his desire to start his own consulting business. Amit defines what a coaching tree is and his philosophy when it comes to mentorship, picking the right projects, and determining what a team needs to work effectively together. Throughout the conversation, we revisit why effective engineering coaching also includes mentorship around company building. Lastly, Amit discusses why eng leaders make good investors and how investing was a natural continuation off of engineering for him.

ABOUT AMIT GUPTA
Amit Gupta has held leadership roles at multiple high-growth companies from early-stage through the public markets, including Qualcomm, INQ Mobile, Lookout, and Benchling. He combines concentrated, early stage investing with a passion for helping technical founders with company building. In some cases that materializes into a role helping in the trenches and in others a more passive, help as needed voice. Amit has helped countless companies directly and as an advisor to Y Combinator Continuity.

The CAFE(S) framework is a research-backed definition of context quality for AI agents.
DX collaborated with researchers at Capital One, Google, and UVic to give teams a shared standard for reviewing agent context by breaking it into five properties: clarity, actionability, fidelity, efficiency, and security.
Your agent is only as good as its context and the CAFE(S) framework establishes a shared language around context to help you better understand how & why agents go wrong.
Check it out here!

SHOW NOTES:
Amit’s transition from Qualcomm (1:05)
Talent acquisitions challenges faced when starting a company (4:58)
Lessons learned from Amit’s time @  Qualcomm (8:24)
Strategies for building a support networks as an eng leader (9:41)
An example of effective mentorship in Amit’s career (11:00)
Defining work-life integration & how that influences Amit as a coach (12:55)
Transitioning from a second startup / starting his own consulting business (14:05)
Why the work at Benchling wasn’t as hard as the first couple startups (16:21)
Amit’s favorite behavioral interview question (17:40)
Shared traits of great teams who perform well together (18:56)
Frameworks for determining good leaders vs. good managers (20:38)
Ways to feed your high-aptitude leaders (23:18)
An example of a rewarding coaching scenario (25:25)
Amit’s perspective on investing as an extension of building (29:38)
Strategies for determining which bets will be successful (32:16)
Considerations for the eng leader to investor pipeline (34:43)
Rapid fire questions (39:53)

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.

Zohar Einy, CEO & Co-Founder @ Port, shares best practices for building a software factory, how software factories impact the organizational structure of your org, and scaling strategies. He and Jerry discuss why software factories can contribute to a significant ROI, tools for helping your teams navigate the transition from building a product for agents vs. people, and what scary (but healthy) decision-making looks like as an eng leader in a post-AI world. Zohar also shares some of his core beliefs when it comes to developing talent & hiring young engineers @ Port.

ABOUT ZOHAR EINY
Zohar Einy is the co-founder and CEO of Port, the agentic SDLC platform helping companies like GitHub, Visa, and PwC build and scale their AI Software Factories. Port has raised $158M, backed by General Atlantic, Accel, Bessemer Venture Partners, Team8, and TLV Partners.
The idea for Port began during Zohar and co-founder Yonatan Boguslavski’s time as engineers in the IDF’s Unit 8200, where they built a platform to help developers move more quickly at scale. After recognizing the same challenge across the broader market, they founded Port in 2022.

The CAFE(S) framework is a research-backed definition of context quality for AI agents.
DX collaborated with researchers at Capital One, Google, and UVic to give teams a shared standard for reviewing agent context by breaking it into five properties: clarity, actionability, fidelity, efficiency, and security.
Your agent is only as good as its context and the CAFE(S) framework establishes a shared language around context to help you better understand how & why agents go wrong.
Check it out here!

SHOW NOTES:
Introducing Zohar & his background / main focus (1:02)
Defining what a software factory is & what that means for the industry (1:50)
Parallels between a physical factory vs. a software factory (3:50)
How the software factory model impacts organizational structure (5:27)
What certification means in the context of software factories (8:46)
Best practices for building a new software factory (10:48)
Don’t make the ability to scale an afterthought (12:15)
Navigating the balance between control & automation when building from scratch (13:17)
How to know when a team / function merits its own software factory (14:37)
Transitioning from a pre-AI to post-AI world as a large company (16:18)
Inside Port’s rebuild using AI & navigating the team through the transition (18:00)
The team’s reaction to building for agents vs. humans (20:25)
Approaching decision-making with a healthy dose of trepidation (21:48)
Characteristics that make for good hires today (22:51)
Examples of product-related decisions that felt scary in the moment (25:03)
Lessons learned while Port transitioned to building for agents (27:27)
How to measure the ROI of software factories (29:05)
Insights on how to best allocate resources across a mature company (31:10)
Hiring hungry, young talent vs. hiring established talent (32:56)
Rapid fire questions (35:30)

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.

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.