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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.
ABOUT ICCHA SETHI
Iccha Sethi is SVP of Engineering at Vanta, where she leads the engineering organization building products that help businesses earn and prove trust by automating security and compliance. Previously, she led engineering teams at GitHub across products including Actions, Codespaces, npm, Packages, and Pages. Her career also includes engineering and leadership roles at InVision, Atlassian, and Rackspace.
Iccha focuses on connecting engineering decisions to business outcomes, building reliable products at scale, and exploring how AI and agentic systems are reshaping software products and engineering organizations. She brings the perspective of both a hands-on technical leader and an executive leading engineering organizations. Outside work, she enjoys reading science fiction and fantasy.
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:
This episode wouldn’t have been possible without the help of our incredible production team:
Jerry Li - 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, 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.
ABOUT PRATIMA ARORA
Pratima Arora is the Chief Product and Technology Officer at Smartsheet. In this position, she is responsible for the company’s product management, product marketing, user experience, pricing and packaging, and digital and product partnerships.
An accomplished technology executive, Pratima has more than 20 years of experience as a product and technology leader with a passion for building innovative tools that solve real problems.
She has held senior product leadership roles at Atlassian and Salesforce, working on some of the companies’ highest-revenue products. Most recently, she was Chief Product and Technology Officer at Chainalysis, where she led the global R&D organization for one of the world’s top blockchain data platforms.
She holds a B.S. in Physics, an M.S. in Computer Science, and an MBA from UC Berkeley’s Haas School of Business.
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:
This episode wouldn’t have been possible without the help of our incredible production team:
Jerry Li - 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, 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.
ABOUT SAGNIK NANDY
Sagnik Nandy is the Chief Technology Officer and Executive Vice President of Engineering at Docusign responsible for engineering, cloud operations, and technology strategy that enables customers globally to run their organizations on Docusign.
Most recently, Sagnik served as the President and Chief Development Officer for Workforce Identity at Okta where led engineering development and operations, product management, and design and user research. Earlier, he joined Okta as their CTO, overseeing the engineering and business technology arms of the company.
Prior to Okta, Sagnik served as the Vice President of Engineering at Google where he oversaw several critical components of Google’s core advertising business, the backbone of the company’s growth and revenue. During his 15 years at Google, Sagnik also helped build Google’s Measurement and Analytics offerings and took several products from inception to becoming market leaders.
Sagnik has a bachelor’s degree from the BITS, Pilani (Birla Institute of Technology and Science Pilani) and a Ph.D. in computer science and engineering from UC San Diego.
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:
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.
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:
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 EINYZohar 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:
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:
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:
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:
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.
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.
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.
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.
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.
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.
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.
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