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NEW - EPISODE 275
Automating the product development workflows and supporting bottom-up experimentation
with Iccha Sethi
In this episode, we’re diving into how orgs can leverage AI to create more autonomous processes when it comes to product development and quality control with Iccha Sethi, SVP of Engineering @ Vanta. Iccha shares how as an eng leader, it’s imperative to continue to be hands on, and she shares her experience replicating Vanta by vibe coding and what it taught her. She not only breaks down Vanta’s product development workflow and the ways in which AI has automated it, but she also shares the guardrails & checkpoints in place that ensure quality. Additionally, Jerry and Iccha discuss individual and team accountability within Vanta’s fast product cycle. Lastly, they cover the AI DX team, who it is comprised of, and its role within Vanta while still maintaining a culture of experimentation when it comes to AI.
On this show, we uncover stories and examples of great leadership in software engineering, explore the experiences of industry leaders, as well as share actionable insights from leadership and management thought experts artful and skilled in the application of leadership.
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EVENTS, PODCASTS AND MORE
FEATURED STORY
Oct 27, 2026
Developing the modern builder framework and managing the cross-pollination of roles at scale
with Pratima Arora
In this episode, Pratima Arora, Chief Product and Technology Officer @ Smartsheet, dives into what it means to be a modern builder as product, design, and engineering roles converge into today’s post-AI world. She and Jerry discuss why the modern builder model is disrupting traditional engineering processes / responsibilities as individuals embrace a breadth of skills while maintaining individual expertise. They cover how to encourage “cross-pollination” of roles, maintaining product quality while improving iteration speed, facilitating bottom-up contributions, creating context / knowledge graphs to inform agents, examples of good product builders, and what this means for hiring.
FEATURED STORY
Oct 20, 2026
Best practices for scaling AI adoption across a large org & the trade offs you will have to make
with Sagnik Nandy
In this episode, Sagnik Nandy (CTO & EVP of Engineering @ Docusign) joins Jerry to discuss keys to success when it comes to peer-led AI transformation. Sagnik shares how they approached AI adoption internally @ Docusign with the use of both champions & multipliers, understanding trade offs associated with AI adoption, determining which tasks to assign to agents, frameworks for measuring the ROI of agentic tools, and how it helps bring value to your customers. He also discusses how to measure the customer productivity index (CPI) and what it takes to mitigate customer issues when scaling AI internally.
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- Rudest Buddhist
Sept 1, 2020
LATEST
Episode 275: Automating the product development workflows and supporting bottom-up experimentation
with Iccha Sethi
In this episode, we’re diving into how orgs can leverage AI to create more autonomous processes when it comes to product development and quality control with Iccha Sethi, SVP of Engineering @ Vanta. Iccha shares how as an eng leader, it’s imperative to continue to be hands on, and she shares her experience replicating Vanta by vibe coding and what it taught her. She not only breaks down Vanta’s product development workflow and the ways in which AI has automated it, but she also shares the guardrails & checkpoints in place that ensure quality. Additionally, Jerry and Iccha discuss individual and team accountability within Vanta’s fast product cycle. Lastly, they cover the AI DX team, who it is comprised of, and its role within Vanta while still maintaining a culture of experimentation when it comes to AI.
Nov 03, 2026
Episode 274: Developing the modern builder framework and managing the cross-pollination of roles at scale
with Pratima Arora
In this episode, Pratima Arora, Chief Product and Technology Officer @ Smartsheet, dives into what it means to be a modern builder as product, design, and engineering roles converge into today’s post-AI world. She and Jerry discuss why the modern builder model is disrupting traditional engineering processes / responsibilities as individuals embrace a breadth of skills while maintaining individual expertise. They cover how to encourage “cross-pollination” of roles, maintaining product quality while improving iteration speed, facilitating bottom-up contributions, creating context / knowledge graphs to inform agents, examples of good product builders, and what this means for hiring.
Oct 27, 2026
Episode 273: Best practices for scaling AI adoption across a large org & the trade offs you will have to make
with Sagnik Nandy
In this episode, Sagnik Nandy (CTO & EVP of Engineering @ Docusign) joins Jerry to discuss keys to success when it comes to peer-led AI transformation. Sagnik shares how they approached AI adoption internally @ Docusign with the use of both champions & multipliers, understanding trade offs associated with AI adoption, determining which tasks to assign to agents, frameworks for measuring the ROI of agentic tools, and how it helps bring value to your customers. He also discusses how to measure the customer productivity index (CPI) and what it takes to mitigate customer issues when scaling AI internally.
Oct 20, 2026
Episode 272: Building your support network, picking the right projects, and why eng leaders make good investors
with Amit Gupta
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.
Oct 13, 2026
Episode 271: Building software factories and making the transition from a pre-AI to post-AI world as a large company
with Zohar Einy
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.
Oct 06, 2026
Episode 270: Utilizing AI to assist in EPD and non-EPD functions & how curiosity can drive organizational change
with Ali Dasdan
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.
Sep 29, 2026
Episode 269: Implementing scalable and powerful agentic tools across your organization
with Ozzie Osman
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.
Sep 23, 2026
Episode 268: Navigating from individual AI adoption to team-level transformation while scaling
with Jakub Oleksy
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.
Sep 17, 2026
Episode 267: Hiring top-tier talent, leveraging open source models, and staying competitive in the age of AI
with Benny Chen
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.
Sep 02, 2026
Episode 266: Applying Agentic AI to the Supply Chain, Building Systems to Withstand Chaos, and Leveraging your Curiosity
with Pooja Brown
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.
Aug 25, 2026
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