Enterprise Ready
EnterpriseReady is a podcast about building successful enterprise software companies. Hosted by industry veterans, it features conversations with founders, product leaders, and engineers who have scaled products for large organizations. Topics include infrastructure, compliance, product design, go-to-market strategies, open-source business models, and more. The show offers practical insights for anyone building software for the enterprise market.
Episodes
Episode 56: Dimitri Sirota of BigID
In this episode, BigID CEO Dimitri Sirota discusses the company’s journey, capitalizing on GDPR’s emergence to become a leader in data and AI security, compliance, and governance. He shares how an early pivot to target Chief Privacy Officers, strategic channel partnerships, and a focus on solving one critical problem fueled rapid growth. Dimitri also explores how AI is transforming BigID’
Episode 55: Jake Stein of Common Paper
In this episode, Jake Stein (co-founder of Common Paper, Stitch, and RJMetrics) joins Grant Miller to talk through the evolution of B2B contracts and how software—particularly AI—is transforming the sales process. Jake shares the origin story of Common Paper, lessons learned from previous startups, and how he’s leveraging AI with their new product "Jerry" to streamline contract negotiatio
Episode 54 - Kubelist Crossover with Marc Campbell and Benjie De Groot
In this special crossover episode of EnterpriseReady and The Kubelist Podcast, Replicated co-founders Grant Miller and Mark Campbell join Benji DeGroote to unveil SecureBuild—a new open source initiative delivering zero-CVE container images with commercial-grade SLAs. They trace Replicated’s 10-year journey from pioneering on-prem software delivery to redefining modern software distributi
Episode 53: Ev Kontsevoy of Teleport
In this podcast conversation, Grant Miller, CEO of Replicated, interviews Ev Kontsevoy, co-founder of Teleport (formerly Gravitational), reflecting on their past competition and the evolution of their respective companies. They discuss how their perspectives on competition have matured, evolving from emotional reactions to seeing competitors as allies who share a similar vision. Ev shares
Episode 52: Tristan Handy of dbt Labs
In this relaunch episode of the EnterpriseReady Podcast, host Grant Miller, CEO of Replicated, sits down with Tristan Handy, founder and CEO of dbt Labs. They dive into the evolution of dbt from a consulting project to an open source CLI tool with a thriving enterprise product and ecosystem. The conversation explores the strategic nuances of commercializing open source software, scaling d
Episode 51: Matt Mochary
In episode 51 of EnterpriseReady, Grant Miller speaks with leadership coach, investor, and filmmaker Matt Mochary. Together they explore themes on executive coaching, building trust, scaling businesses, conflict resolution, and customer retention. Additionally, Matt unpacks the characteristics of CEOs that drive the most success.
Episode 50: Matias Woloski of Auth0
In episode 50 of EnterpriseReady, Grant speaks with Matias Woloski of Auth0. This talk contains unparalleled lessons on utilizing authentication and authorization services, landing your first enterprise customer, making smarter hiring decisions, and understanding the complexity of the CTO role.
About the Guest
Matias Woloski is an engineer with a passion for building frictionless product
Episode 49: Omri Gazitt of Aserto
In episode 49 of EnterpriseReady, Grant speaks with Omri Gazitt of Aserto. They began with a dive into Omri’s early beginnings in enterprise software, including his time at Microsoft working on the .NET framework and XML team at Microsoft, and the lessons learned that would lead to the creation of Azure. Finally, Omri unpacks what led him to found Aserto, a solution to enterprise-grade ac
Episode 48: Sanjay Poonen of Snyk
In episode 48 of EnterpriseReady, Grant Miller is joined by Sanjay Poonen. This expansive conversation draws on Sanjay’s long and storied career in software, from the early engineering days at Apple and Microsoft to his executive and entrepreneurial experience building and scaling multi-billion dollar businesses like VMware. Together, Grant and Sanjay unpack invaluable lessons on engineer
Episode 47: Mark Lorion of Tempo
In episode 47 of EnterpriseReady, Grant speaks with Mark Lorion of Tempo. They discuss Mark’s programming background and early enterprise software roles, the importance of seeking customer data at the source, and deep insights on enterprise marketing.
About the Guest
Mark Lorion is an entrepreneurial and analytical software executive currently serving as CEO of Tempo Software, Board Dire
Episode 46: Donald Fischer of Tidelift
In episode 46 of EnterpriseReady, Grant speaks with Donald Fischer of Tidelift. Donald shares lessons from his early career journey in product and venture capital, and together they discuss the importance of supporting open source creators at scale.
About the Guest
Donald Fischer is the CEO and Co-Founder of Tidelift. He was previously VP of Online Services at Red Hat and a senior consul
Episode 45: Ed Anuff of DataStax
In episode 45 of EnterpriseReady, Grant speaks with Ed Anuff of DataStax. They discuss the importance of onboarding engineering, the carrying costs of legacy software, and building consumer trust that lasts for years.
About the Guest
Ed Anuff has over 25 years experience as an entrepreneur, creating innovative consumer and enterprise products and starting and selling several companies, a
Episode 44: Job van der Voort of Remote
In episode 44 of EnterpriseReady, Grant speaks with Job van der Voort, CEO of Remote. They discuss Job’s pivot from neuroscience to startups, his experience building opinionated software at GitLab, and the future of remote work.
About the Guest
Job van der Voort is the CEO of Remote and the host of the Remote Work Podcast. He was previously VP of Product at GitLab in the time that the co
Episode 43: Neha Sampat of Contentstack
In episode 43 of EnterpriseReady, Grant speaks with Neha Sampat, CEO & Founder of Contentstack. They discuss Neha’s career journey into enterprise and how Contentstack is accelerating the shift from monolithic suites to agile technology stacks.
About the Guest
Neha Sampat is the Founder & CEO of Contentstack. She previously founded Built.io and Raw Engineering. She was one of “50
Episode 42: Quinn Slack of Sourcegraph
In episode 42 of EnterpriseReady, Grant is joined by Quinn Slack of Sourcegraph. They explore Quinn’s self-taught development career, insights on finding perfect product-market fit, and the pain points large orgs face when managing massive codebases.
About the Guest
Quinn Slack is CEO and co-founder of Sourcegraph and a board member at Hack Club. He was previously Forward Deployed Engine
Episode 41: Wade Foster of Zapier
In episode 41 of EnterpriseReady, Grant speaks with Wade Foster of Zapier. They unpack Wade’s career journey, how Zapier was founded and self-funded, and lessons learned on maintaining camaraderie among distributed teams.
About the Guest
Wade Foster is Co-Founder & CEO of Zapier and a graduate of the University of Missouri.
Episode 40: Alexis Richardson of Weaveworks
In episode 40 of EnterpriseReady, Grant is joined by Alexis Richardson of Weaveworks. They discuss Weave GitOps, insights on brand revitalization, and the storied career journey that led Alexis from finance to startups to enterprise software.
About the Guest
Alexis Richardson began his career journey in finance as a trader at Goldman Sachs before founding 3 startups– MetaLogic, Cohesive
Episode 39: Loris Degioanni of Sysdig
In episode 39 of EnterpriseReady, Grant Miller is joined by Loris Degioanni of Sysdig. They discuss Loris’s storied career journey, the creation of Sysdig, tactics for better understanding enterprise customers, and the future of open source.
About the Guest
Loris Degioanni is the CTO and Founder of Sysdig. He was previously Senior Director of Technology at Riverbed Technology, as well as
Episode 38: Brandon Heller of Forward Networks
In episode 38 of EnterpriseReady, Grant speaks with Brandon Heller of Forward Networks. They discuss tactics for improving enterprise networks, tips for hiring engineers, and insights on the many roles co-founders play as they launch their companies.
About the Guest
Brandon Heller is Co-Founder and CTO of Forward Networks and a co-host of the podcast, Seeking Truth in Networking.
Episode 37: Jay Simons of Bond
In episode 37 of EnterpriseReady, Grant speaks with Jay Simons of Bond. They unpack the many lessons Jay has learned from his long and celebrated software career, including growing Atlassian from a startup to the massive, publicly-traded behemoth it is today.
About the Guest
Jay Simons is the former president of Atlassian. He is currently a General Partner at Bond and a Board Member at Z
Episode 36: Shannon Williams of SUSE
In episode 36 of EnterpriseReady, Grant speaks with Shannon Williams of SUSE. They unpack Shannon’s many years working with cloud-native and open source communities, his pioneering of Infrastructure as a Service, and the future of open source.
About the Guest
With over 20 years of experience working in startups, Shannon Williams is currently Chief Revenue Officer of SUSE. He is also a go
Episode 35: Karthik Ranganathan of Yugabyte
In episode 35 of EnterpriseReady, Grant speaks with Karthik Ranganathan of Yugabyte. They discuss Karthik’s enterprise journey, the fruits of maintaining a customer-driven ethos in business, and building modern databases. All this, and much more, are discussed in our latest episode of the EnterpriseReady Podcast.
About the Guest
Karthik Ranganathan is the Founder & CTO of Yugabyte, t
Episode 34: Gene Kim of Tripwire
In this episode, Grant interviews Gene Kim, Co-founder and former CTO of Tripwire. A giant in the world of DevOps, Kim is the author of the successful books, The Unicorn Project (2019), The Phoenix Project (2013), and The DevOps Handbook (2016). Listen as Gene and Grant discuss how enterprise organizations should structure their internal development priorities, the rise of the DevOps ecos
Episode 33: Shishir Mehrotra of Coda
In episode 33 of EnterpriseReady, Grant is joined by Shishir Mehrotra of Coda. They discuss important lessons for building and launching products, as well as Shishir’s role as a technology leader at YouTube in it’s pivotal early years, just after the Google acquisition.
About the guest
Shishir Mehrotra is the Co-Founder and CEO of Coda, a cloud-based document editor. He was previously th
Episode 32: Mike Gregoire of Brighton Park Capital
In episode 32 of EnterpriseReady, Grant speaks with Mike Gregoire of Brighton Park Capital. They discuss strategies for growing through a recession, the changing role of modern enterprise salespeople, and the internal metrics Mike uses when evaluating acquisitions.
About the guest
Mike Gregoire is a Partner at Brighton Park Capital and is a member of the Investment Committee. Previously,
Episode 31: Rob Zuber of CircleCI
In episode 31 of EnterpriseReady, Grant speaks with Rob Zuber, CTO at CircleCI. They discuss Rob’s expansive range of disciplines and the perspectives he’s gained on topics like fundraising, hiring, mentoring, scaling, and delivering value to customers.
About the Guest
Rob Zuber is a startup expert and the CTO of CircleCI. He previously co-founded Distiller, Copious, and YooHoot.
Episode 30: Alex Solomon of PagerDuty
In episode 30 of EnterpriseReady, Grant speaks with Alex Solomon of PagerDuty. They dive deep into product assortment, incident response management, on-call alerting, and company culture insights.
Alex Solomon is the CTO and Co-Founder of PagerDuty. Prior to PagerDuty, he was a software development engineer at Amazon.
Episode 29: Mitchell Hashimoto of HashiCorp
In this episode, Grant sits down with Mitchell Hashimoto, founder of HashiCorp. The two dive deep into the history of HashiCorp, its products, its go-to-market, its success, and many of the challenges it faced along the way.
Mitchell provides a candid view into the company’s inner workings, starting with how he and his co-founder, Armon Dadgar, transitioned to become enterprise software
Episode 28: Adam Gross of Heroku
In episode 28 of EnterpriseReady, Grant speaks with Adam Gross, seasoned enterprise investor and advisor. They discuss the inevitability of platform change, how software deployment has evolved, and how the enterprise application ecosystem might develop in years to come.
Adam Gross is an enterprise investor and advisor. He was previously the CEO of Heroku, SVP of Marketing and Sales at Dr
Episode 27: Christian Beedgen of Sumo Logic
In episode 27 of EnterpriseReady, Grant speaks with Christian Beedgen, CTO & Co-Founder of Sumo Logic. They discuss Christian’s background, security analytics, the challenges faced by first generation on-prem software companies, and the evolving security landscape.
Christian Beedgen is the CTO & Co-Founder of Sumo Logic, a secure, cloud-native, machine data analytics service. He
Episode 26: Alex Miller of StackOverflow
In episode 26 of EnterpriseReady, Grant is joined by Alex Miller, former GM at Stack Overflow. They discuss Alex’s background, what Stack Overflow Enterprise does, Alex’s four constituencies of enterprise software, and much more.
About the Guest
Alex Miller is the former General Manager of Stack Overflow, where he previously held the titles of Vice President of Operations and Chief of St
Episode 25: Jonathan Ellis of Datastax
In episode 25 of EnterpriseReady, Grant speaks with Jonathan Ellis of DataStax about Apache Cassandra and the complexity of distributed storage systems, as well as recruiting, interviewing, and hiring executives and engineers.
Episode 24: John Whaley of UnifyID
In episode 24 of EnterpriseReady, Grant joins John Whaley of UnifyID to discuss the process of monetizing university research, how technology enables businesses, and how inherent human behavior threatens security.
About the Guest
John Whaley is the Founder and CEO of UnifyID, an identity platform based on implicit authentication. He previous founded Moka5, and was taught Program Analysis
Episode 23: Abby Kearns of Cloud Foundry Foundation
In episode 23 of EnterpriseReady, Grant is joined by Abby Kearns, executive director of Cloud Foundry. They discuss enterprise infrastructure, the future of the cloud, technological ecosystems in China, and open source business models.
Abby Kearns is the Executive Director at Cloud Foundry Foundation. She’s had an immense technology career spanning operations, product marketing, product
Episode 22: Derek Steer of Mode
In episode 22 of EnterpriseReady, Grant chats with Derek Steer, CEO of Mode. Together they pull back the curtain on data science tools, and how enterprise software companies can use data analysis to drive business forward.
Derek Steer is the CEO of Mode, a data analytics and business intelligence tool. Derek previously held analytics positions at numerous renowned companies including Yam
Episode 21: Michel Feaster of Usermind
In episode 21 of EnterpriseReady, Grant interviews Michel Feaster, CEO and Co-Founder of Usermind. They discuss Michel’s journey from gas station employee to enterprise software CEO, as well as the relationship between product, product marketing, and marketing.
Michel Feaster is the Co-Founder and CEO of Usermind, responsible for company vision, strategic direction, planning and executio
Episode 20: Yvonne Wassenaar of Puppet
In episode 20 of EnterpriseReady, Grant is joined by Yvonne Wassenaar, CEO of Puppet. They discuss her experience serving on boards of enterprise software companies, transitioning from a single product company to multiple products, and the role of professional services.
Yvonne Wassenaar is a seasoned C-level executive with broad experience scaling, diversifying, and transforming business
Episode 19: Mark Geene of Cloud Elements
In episode 19 of EnterpriseReady, Grant speaks with Mark Geene, CEO and Co-Founder of Cloud Elements. They discuss Mark’s early days in enterprise, integrations between apps and APIs, and the go-to-market lessons learned along the way.
About the Guest
Mark Geene is the CEO and Co-Founder of Cloud Elements, a cloud API integration service. He was previously Vice President of [TenFold}(htt
Episode 18: Elizabeth Zalman of strongDM
In episode 18 of EnterpriseReady, Grant is joined by Elizabeth Zalman, Founder & CEO of strongDM. They discuss enterprise software go-to-market, remote teams, product prioritization frameworks, and SOC 2 certification.
Elizabeth Zalman is the Co-Founder & CEO of strongDM. Previously she was Co-Founder and CEO of the cross-device profile company Media Armor. After its acquisition,
Episode 17: Ben Hindman of Splash
In episode 17 of EnterpriseReady, Grant joins Ben Hindman, Co-Founder & CEO of Splash. They discuss Ben’s path into enterprise software, the community-driven power of events, and the freemium business model.
About the Guest
Ben Hindman is the Co-Founder & CEO of Splash, the world’s first event marketing software. He was previously National Events Manager at Thrillist in New York.
Episode 16: Spence Green of Lilt
In episode 16 of EnterpriseReady, Grant speaks with Spence Green, Founder and CEO of Lilt. They discuss language translation services for enterprises and governments, the rigor required to deliver enterprise software, and the internationalization of products.
About the Guest
Spence Green is the Founder and CEO of Lilt, a machine-assisted language translation company. He graduated from St
Episode 15: Jeff Williams of Contrast Security
In this episode of the EnterpriseReady Podcast we interview Jeff Williams, founder and CTO of ContrastSecurity. We explore Jeff’s early career in cyber security where he worked as a security consultant as the internet started to gain early traction. From there, we dive into his founding role at a security consulting firm where he stayed very involved with the security community through hi
Episode 14: Michael Pryor of Trello
In this episode of the entepriseready podcast, we hear from Michael Pryor the founder and CEO of Trello. Micheal has had an incredible career as one of the founders of FogCreek Software which has spun out products such as FogBugz, StackOverflow, Glitch and of course, Trello which was acquired by Atlassian for $425 million dollars back in 2017. We cover a wide range of topics primarily fro
Episode 13: Rahul Vohra of Superhuman
In this episode of the EnterpriseReady podcast we sit down with Rahul Vohra, founder and CEO of Superhuman. Superhuman recently announced a $33m series B from A16Z which was their first funding announcement despite having raised over $17m previously. I have Rahul give us some details about his fundraising history and strategy which is quite unique. Rahul and I spend a lot of time discussi
Episode 12: William Morgan of Buoyant
Welcome back to the EnterpriseReady podcast. Today we are talking with William Morgan, CEO, and Founder of Buoyant, a company that primarily focuses on contributing to the open-source ServiceMesh project, Linkerd. Linkerd was born out of William and his co-founder Oliver’s experience building infrastructure at Twitter, where they were responsible for reducing the frequency in which the in
Episode 11: Bob Tinkerer of MobileIron
In this episode of the EnterpriseReady podcast, I sit down with Bob Tinker, co-founder of MobileIron, a company that he served as CEO of, from founding through IPO before stepping down in 2016. Bob recently co-authored a book called Survival to Thrival, in which he lays out the foundations for building and growing an enterprise software company. We focus on several of the frameworks that
Episode 10: Joel Wallenstrom of Wickr
In this episode of the EnterpriseReady podcast, we sit down Joel W. CEO of Wickr, a secure messaging and communications platform. We learn a bit about Joel’s background in the cyber security industry, with a focus on his time running 3rd party security firms. From there, we dive into the history of Wickr, which started as a consumer, mobile first communications tool on the back of perfect
Episode 9: Zack Blum of Fleetsmith
Welcome back to the EnterpriseReady podcast, today our guest is Zack Blum, Founder and CEO of Fleetsmith. In the episode we dive into the founding story behind Fleetsmith and then move into how they brought the product to market. Given the nature of the business, the story of Fleetsmith is intertwined with lessons about what all companies should be doing for internal security. We also spe
Episode 8: Dave Cole of Tenable
Welcome back to the EnterpriseReady Podcast! Today our guest is Davle Cole, who at the time of recording was the Chief Product Officer at Tenable, but has recently left to start a stealthy startup in the security space. This episode is long, but that’s because Dave has such a great history of bringing enterprise software to market and there were so many topics for us to dig into. Dave sha
Episode 7: Paul Querna of ScaleFT (Acquired by Okta)
In this episode of EnterpriseReady we are speaking with Paul Querna, the CTO and Cofounder of ScaleFT, which was acquired by Okta not too long ago. Paul likes to say that ScaleFT is in the business of granting people and machines access to the systems and endpoints they should be reaching. We get some back story on the company’s founding and then we focus on the Zero Trust concepts that S
Episode 6: Andrew Peterson of Signal Sciences
This episode I’m joined by Andrew Peterson, CEO and Co-founder of Signal Sciences an application security company building a nextgen WAF that is deployed throughout the Fortune 500. Before starting Signal Sciences, Andrew and his two co-founders built up scar tissue solving security problems at Etsy, a company known for pioneering many of the devops practices that are common today. This e
Episode 5: Edith Harbaugh of LaunchDarkly
Today we are talking with Edith Harbaugh, the CEO and Co-founder of LaunchDarkly, one of the first “feature flags as a service companies” where they offer a feature management platform aiming to help teams build better software. We’ll get some backstory on how she got into enterprise software and some of the lessons she learned building advanced enterprise features, including an elaborate
Episode 4: Open Source with CoreOS’s Alex Polvi
In episode 4 of EnterpriseReady, Grant chats with Alex Polvi, co-founder and CEO of CoreOS, which was recently acquired by Red Hat, to dive into detail about the nuances of building and selling an enterprise product that has an open source core.
About the Guest
Alex Polvi is the Co-founder and CEO of CoreOS, which was recently acquired by Red Hat. Alex got his start in open source when h
Episode 3: Product-Market Fit with Segment’s Peter Reinhardt
In episode 3 of EnterpriseReady, Grant chats with Peter Reinhardt, co-founder and CEO of Segment, to discuss how finding and maintaining product-market fit helped grow his enterprise-facing company.
About the Guest
Peter Reinhardt is the CEO and founder of Segment, a Customer Data Infrastructure platform for businesses.
Episode 2: The Early Days of GitHub with Tom Preston-Werner
In this episode we interview Tom Preston-Werner, founder and former CEO of GitHub. We mainly focus on Tom’s time at GitHub, where he built and scaled one of the most important developer tool companies in the world. However, many might not realize that Github is also one of the most successful enterprise software companies of the modern era. With over half of their revenue coming from larg
Episode 1: Delivering Software That Enterprises Love with Chef's Adam Jacob
In this episode Grant interviews Adam Jacob, founder and CTO of Chef. Adam has been building Chef for over 10 years and during that time he has learned a LOT about how to deliver software that enterprises love. He has an incredible perspective and we were so glad to have him as one of our first guests.
Adam Jacob is co-founder and CTO of Chef, formerly known as Opscode, a configuration m
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