The Software Leaders Uncensored Podcast

In this episode, Trevor Calhoun, CEO of TPN Health, shares insights into building a scalable digital infrastructure for behavioral health, navigating industry regulations, and leveraging AI to improve provider networks and patient outcomes.

In this episode, Steve Taplin interviews Bobby Tahir, a four-time CTO and current CTO Advisor of Aldrich Capital Partners, to explore patterns in engineering leadership, AI adoption, organizational change, and technical debt management. They discuss how AI is transforming product and engineering teams, the challenges of scaling organizations, and strategies for CTOs navigating the evolving tech landscape.

In this episode, Steve Taplin interviews Shimon Ben-David, CTO of WEKA, about their innovative high-performance storage solutions for AI and HPC workloads. They discuss the company's growth, technical challenges, industry impact, and leadership insights.

In this episode, Steve Taplin interviews Cary Gahm, Co-Founder & Co-CEO, and Ed Thomas, Co-Founder of GoTu, who share their journey in building an innovative dental staffing platform. They discuss the challenges of scaling, regulatory compliance across states, and leveraging AI and technology to solve industry-specific problems.

In this episode, Steve Taplin interviews Stephen Chen, CTO at NuCompass Mobility, about AI adoption, security challenges, and managing a hybrid engineering team. They explore how technology impacts relocation services, the importance of human elements, and strategies for effective leadership in tech.

In this episode, host Steve Taplin interviews Nathan Strum, CEO of Abby Connect, about the evolving role of AI in customer service. They discuss hybrid models, technical challenges, industry-specific regulations, leadership lessons, and future trends in AI-driven customer support.

In this episode, John Grunas, Director of Technology at Hema-Tec Inc., shares insights on managing technology in healthcare, navigating regulatory challenges, and leveraging AI for healthcare solutions. Discover practical strategies for tech leadership in regulated environments and the future of healthcare technology.

In this episode, Aron England, Chief Product and Technology Officer at Accruent, shares insights on managing a global software organization, integrating AI into development, and leading innovation in the built environment industry.

In this episode, host Steve Taplin interviews Sylvain Kalache, head of AI labs at Rootly AI, and shares insights on how AI is transforming incident management, the role of AI in reliability engineering, and leadership lessons in the era of GenAI. Discover how companies are leveraging AI to improve operational efficiency and the importance of human-centered leadership.

In this episode, host Steve Taplin interviews Joseph Solomon, Director of Engineering at MyOme, and shares insights on scaling engineering teams in the healthcare biotech sector, balancing product development with regulatory compliance, and leveraging AI to accelerate growth.

In this episode, Steve Taplin interviews Abe Jarrett, Senior Vice President of Software Engineering at Origence, about engineering leadership in FinTech, managing technical debt, team collaboration, and the future of AI in financial services.

In this episode, Steve Taplin interviews Nick Gattuso, Founding Team and Head of Engineering at Somethings, about building and scaling a mental health platform for teens, focusing on engineering strategies, leveraging AI, and maintaining quality at scale.

In this episode, Steve Taplin interviews Wendy Dole, Director of Engineering at Direct Supply, about the intersection of AI, healthcare, and senior living. They explore how technology is transforming the industry, addressing workforce shortages, regulatory challenges, and the future of AI integration.

In this episode of Software Leaders Uncensored, host Steve Taplin interviews Bradley Friemel, Vertical CTO - Rentals at Fullsteam, and shares insights on managing multiple SaaS verticals, handling legacy code, leveraging AI for prototyping, and navigating private equity pressures in fintech. Learn practical strategies for technical leadership and innovation.

In this episode, Steve Taplin interviews Jonathan LaCour, CTO at Mission Cloud, about navigating acquisitions, building effective remote teams, and leveraging software-as-a-service in a service business. They explore leadership strategies, product development, and the future of AI in tech.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Martin Mrugal, CEO of Alchemer, about the evolution of customer feedback platforms, the integration of AI in software development, and the importance of data-driven decision-making in leadership. They discuss the challenges of innovation speed, the future of surveys, and how to build a customer-centric culture. Martin shares insights on making tough decisions as a CEO and offers practical advice for tech leaders navigating today's fast-paced environment.

In this episode of Software Leaders Uncensored, host Steve Taplin interviews Guyte McCord, CEO of Graphika, discussing his career journey from CRO to CEO, the challenges of remote work, the impact of AI on product development, and the importance of building trust within technical teams. They explore the complexities of scaling a tech company, addressing technical debt, and navigating the hype surrounding AI. Guyte shares insights on effective productivity systems and offers advice to tech leaders on deeply understanding problem spaces.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Todd Persen, CTO of Hydrolix, about his journey in the observability space, the growth of Hydrolix, and the challenges of managing a global engineering team. They discuss the importance of trust in leadership, the balance between product and engineering, and the role of AI in engineering workflows. Todd shares insights on learning from failures and the significance of shortening release cycles to enhance customer value.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Maha Virudhagiri, CTO of Coalition, about the intersection of cyber insurance and technology. They discuss Maha's journey to Coalition, the challenges faced by engineering teams, the adoption of AI tools for productivity, and the importance of a high agency culture in a remote work environment. Maha shares insights on managing tech debt, onboarding engineers, and the significance of tracking meaningful metrics while avoiding complexity in organizations. He concludes with valuable advice for tech leaders on building effective teams and fostering a productive work environment.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Michael Cieri, EVP of Software at BILL, about the company's mission to support small and medium-sized businesses (SMBs) through innovative financial management solutions. Michael shares insights from his extensive career in technology, emphasizing the importance of understanding customer needs, the challenges of integrating AI into workflows, and lessons from past product development and pricing experiences. He also discusses the significance of building trust with SMB clients and offers advice for tech leaders navigating the evolving landscape of technology and AI.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Eric Poff, CTO of Verve Labs, about his journey to becoming a technology leader, the innovative projects at Verve Labs, and the importance of human-centered AI. They discuss the engineering work model, the significance of communication within teams, and the balance between product and technology roles. Eric shares insights on experimentation, vibe coding, and the metrics that matter in engineering, as well as common mistakes organizations make. The conversation concludes with Eric's no-nonsense advice for tech leaders navigating today's challenges.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Brian Bauer, VP of AI Products at Rational Exponent. They discuss the transformative impact of AI on the banking sector, the development of their flagship product re:agent, and the importance of understanding the business needs of banking to create effective AI solutions. Brian shares insights on team dynamics in a remote work environment, the significance of collaboration between product and engineering teams, and the innovative approach of vibe coding for rapid prototyping. He also highlights common mistakes in AI development and offers valuable advice for tech leaders navigating the evolving landscape of AI.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Jeff Prince, CTO of XOi, about the evolution of engineering leadership, challenges in field service management, and the integration of AI in software development. They discuss the importance of aligning product and engineering teams, effective onboarding of new engineers, and key metrics for engineering success. Jeff shares insights on dealing with non-technical stakeholders and the lessons learned from failures in his career. The conversation concludes with advice for tech leaders navigating the industry's complexities.

In this episode of Software Leaders UNCENSORED, host Steve Taplin speaks with Ben Ede, an engineering director at Envoy, about his career transition, leadership philosophy, and the evolving role of AI in software engineering. They discuss the importance of CI/CD processes, breaking down work into manageable tasks, and effectively tracking engineering metrics. Ben shares insights on managing tech debt, the Run, Grow, Transform framework, and the significance of quality meetings for team alignment. He concludes with advice for tech leaders on the value of asking questions to foster understanding and collaboration.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Ajay Chankramath, a seasoned engineering leader and CEO of Platformetrics. They discuss AJ's unique approach to consulting, focusing on proven solutions rather than bespoke ones, and the importance of enhancing developer experience in tech companies. AJ shares insights on building the ideal developer experience, overcoming executive pushback, and his journey as an author and entrepreneur. He concludes with valuable advice for tech leaders on providing value with existing tools rather than chasing new ones.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Michael Terry, a seasoned software engineer and co-founder of Sanctuary Software Studio. They discuss Michael's extensive journey in software development, the evolution of his company, and the challenges faced in the current tech landscape, including talent management, onboarding, and the impact of AI on business models. Michael shares insights on maintaining a hybrid work model, the importance of continuous learning, and strategies for integrating new tools and workflows into their processes. The conversation concludes with Michael's advice for tech leaders navigating these changing times.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with William Steenbergen, co-founder and CTO of Federato, about the transformative role of AI in the insurance industry. They discuss the challenges of underwriting, the importance of addressing the coverage gap, and how Federato's platform is revolutionizing the insurance lifecycle. William shares insights on team dynamics, the impact of rapid growth, and the significance of fostering a collaborative culture through initiatives like demo days. He concludes with valuable advice for tech leaders navigating the complexities of scaling their businesses.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Matt Ryan, founder and CTO of Kythera Labs, about his journey from the corporate world to the startup landscape. They discuss the evolution of Kythera Labs, innovations in healthcare data solutions, the challenges of managing remote engineering teams, and the importance of clarity in technical communication. Matt shares insights on leveraging AI in healthcare, lessons learned from AI implementation, and the future goals for Kythera Labs as they aim to scale their offerings in 2026.

In this episode of Software Leaders Uncensored, host Steve Taplin interviews Nathan Miller, CEO of Rentec Direct, discussing the evolution of property management software, the integration of AI, challenges in the rental industry, and the impact of changing algorithms on customer acquisition. Nathan shares insights on fraud prevention, the importance of market testing ideas, and the dynamics of building a cohesive software engineering team. He emphasizes the need for tech leaders to adapt to new challenges and offers advice for aspiring entrepreneurs.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Matt DeBergalis, CEO and co-founder of Apollo GraphQL. They discuss the evolution of Apollo, the impact of AI on software development, the importance of APIs, and the challenges of hiring in a rapidly changing tech landscape. Matt shares insights on building a culture of accountability, navigating the hype around AI, and the future of AI in enterprises. He emphasizes the need for continuous shipping and adapting to change as key strategies for tech leaders.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Herb Hogue, CTO of Myriad360, about the evolving landscape of AI infrastructure, the challenges of talent acquisition in tech, and the rapid changes in technology. Herb shares insights from his extensive career, discussing the importance of adaptability, the complexities of data center planning, and the future implications of quantum computing. The conversation emphasizes the need for tech leaders to remain grounded amidst the hype surrounding AI and to focus on building effective teams and infrastructures.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Michael Campbell, CEO of Fusion Risk Management, about the importance of operational resilience in today's unpredictable business environment. They discuss Michael's journey to his current role, the innovative projects at Fusion, and the impact of AI on software development. Michael emphasizes the need for ruthless prioritization in tech leadership and shares valuable advice for navigating the rapidly changing landscape of technology.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Ken Johnson, CTO and co-founder of Dry Run Security. They discuss Ken's journey into the tech world, the innovations in software security that Dry Run is implementing, and the challenges faced by engineering teams in a rapidly evolving landscape. The conversation also touches on the impact of AI on software development, the importance of communication within teams, and strategies for engaging non-technical stakeholders. Ken shares valuable insights and advice for tech leaders navigating the complexities of modern software development.

In this episode of Software Leaders Uncensored, Steve Taplin sits down with Edward Calvesbert, VP of Product Management for IBM WatsonX, to discuss what’s real, what’s hype, and what’s breaking inside enterprise AI today. Edward explains how Watson evolved into WatsonX, why 95% of enterprise AI projects are failing, and why strong data foundations and semantic layers matter more than the model itself. He breaks down the difference between demos and production AI, the emerging reality of agentic voice systems, and how text-to-SQL and conversational BI are the current innovation frontier. Edward also shares candid insights on governance, legacy data, vendor lock-in, productivity with GenAI coding tools, and what it really takes to go from prototype to enterprise-ready at global scale.

In this episode of Software Leaders Uncensored, host Steve Taplin sits down with Peter Horadan, CEO of Vouched, and one of the few tech leaders who has helped scale multiple “boring” backend automation companies into multi-billion-dollar giants. Peter walks through his journey from Microsoft in the pre-internet era to leading engineering at Concur, Avalara, and launching Lockstep before its acquisition by Sage. He reveals why digital identity is on the verge of a massive transformation, how mobile driver’s licenses and cryptographic IDs will replace today’s broken verification, and why AI agents logging in as humans is the next huge security nightmare. Peter also shares candid lessons on remote culture, AI coding limits, leadership, and why anyone with the itch to found a company should stop waiting and start building.

In this episode of Software Leaders Uncensored, Steve Taplin talks with Behnam Bastani, CEO and co-founder of OpenInfer, and former AI executive at Meta, Roblox, Google, HP, and Kodak. Behnam breaks down why the future of AI will live at the edge—not the cloud—and how his team is building a fully integrated hardware–software ecosystem that delivers low-cost, private, on-device AI inference. He explains OpenInfer’s breakthrough “Mementos” technology that lets engineers move between Claude, Copilot, Gemini, and other tools without losing context or history. Behnam also discusses Bay Area culture, talent retention, global instability, hardware regulations, AI adoption failures, and why innovation requires embracing chaos instead of fearing it.

In this episode of Software Leaders Uncensored, host Steve Taplin talks with Jimi Li, CTO of ALM, whose career spans startups, GE, L’Oreal, Coach, News Corp, consulting, and now leading a fully digital legal-industry intelligence company. Jimi shares how he evolved from a two-person startup engineer to global technology leader, and why transformation is 80% psychology and communication—not architecture. He breaks down AI’s real value, the productivity leakage problem, the rise of human-in-the-loop systems, and why every tech leader must build an AI-powered second brain. Jimi also explains how ALM moved from publishing to data and intelligence, how to lead globally distributed engineering teams, and why asking the right questions will matter more than knowledge itself.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Tanner Hackett, CEO of Counterpart, about his entrepreneurial journey, the pivot to insurance technology, and the innovative approach of agentic insurance. They discuss the challenges of tech adoption in the insurance industry, the importance of building a remote engineering team, and insights on fundraising and capital efficiency. Tanner shares his thoughts on maximizing team utility, leveraging AI, and the value of learning from failures, as well as advice for tech leaders navigating a rapidly changing landscape.

In this episode of Software Leaders Uncensored, host Steve Taplin talks with Mathias Herzog, CEO of Korn Ferry Digital Business and President of Global Technology Industries at Korn Ferry. Mathias shares his journey from consulting in San Francisco to executive roles at Salesforce, Automation Anywhere, and now leading a $400M SaaS division inside a $3B global firm. He breaks down the challenge of unifying IP, data, and tech stacks from 20 acquisitions, and explains how Korn Ferry is productizing decades of talent science into a unified platform. Mathias also discusses agentic AI, the future of talent development, the difficulty of vetting AI-assisted candidates, and why leaders must focus, listen first, and avoid shiny-object distractions.

In this episode of Software Leaders Uncensored, Steve Taplin interviews Jim Sullivan, Founder & CEO of eDiscovery AI, whose rare background as both a technologist and an attorney gives him a unique advantage in transforming the legal industry. Jim shares how AI now outperforms humans in document classification, why 40,000 doc-review attorney roles are at risk, and how blurry scans, handwriting, foreign languages, and spreadsheets are no longer barriers for machine intelligence. He breaks down the hiring crisis caused by AI-assisted interviews, the rising cost of SOC 2 compliance, and the security pressures forcing his engineering team back into an office. Jim also explains why most AI pilots fail, why fun is the real founder superpower, and how embracing failure—not avoiding it—is the fastest path to breakthrough innovation.

In this episode of Software Leaders Uncensored, Steve Taplin sits down with Corey Ercanbrack, Chief Product & Technology Officer at Vasion, to unpack his 30-year journey from Intel → Landesk → InsideSales → Vasion. Corey explains how he scaled Vasion from 3 engineers to 150+, transitioned from on-prem to a cloud-native SaaS platform, and unified product + engineering under the CPTO role. He breaks down the realities of remote-first engineering, why nearshore LATAM talent is a game changer, and how AI agents will redefine print automation, document workflows, and the future of UI. Corey also shares candid lessons on acquisitions, leadership, engineering culture, and the race to upskill teams for the AI era.

In this episode of Software Leaders Uncensored, Steve Taplin sits down with Jose D. Perez-Diaz, VP of Engineering at Vetspire, to trace his journey from algebra teacher → software developer → CTO → tech leader in veterinary medicine. Jose shares how Vetspire is redefining veterinary EMRs with AI-native features like patient summarization and agentic scribing that let doctors make eye contact again instead of typing notes for hours. He breaks down how universities shape market dominance, why UX must follow human intention (not clicks), and how distributed teams require written-first cultures to avoid apathy and isolation. Jose also gets brutally honest about leadership: documentation over meetings, removing antagonists fast, and telling stories that align teams around a shared destination.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Justin Farris, VP of Product at Read.AI. They discuss Justin's unique career journey from film to tech, the importance of networking, and the innovative AI solutions being developed at Read AI. Justin shares insights on aligning product and engineering teams, the evolving role of product management, and the challenges of implementing generative AI in large organizations. The conversation emphasizes the need for clear communication, rapid prototyping, and learning from failures in the tech industry.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Jameel Al-Aziz, CTO of Bastion, about his career journey from self-taught coder in Kuwait to leading a startup focused on stablecoin issuance. They discuss the challenges of building a robust engineering team, the importance of practical security measures, and the evolving landscape of crypto and AI in engineering. Jameel shares valuable lessons learned throughout his career and offers advice for tech leaders navigating the complexities of the industry.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Chris Dean, CEO and founder of Treasury Prime, about his unconventional journey from academia to the tech startup world. Chris shares insights on the importance of embracing failure, the dynamics of building effective teams, and the challenges of leading in the fast-paced tech landscape. They discuss the impact of AI on software development and FinTech, the complexities of legacy banking systems, and the significance of maintaining a sustainable work culture. Chris emphasizes the value of choosing the right people and problems in tech leadership, offering practical advice for navigating the evolving industry.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Andy James, CTO of Stead Impact Ventures, about his extensive career in technology and the evolving landscape of software development. They discuss the importance of leadership, collaboration between product and engineering teams, and the impact of AI on the future of tech roles. Andy shares insights from the Founders Symposium aimed at building innovators and leaders, and emphasizes the need for authenticity and core values in tech leadership.

David Funck, Chief Technology Officer at Avaya, joins Software Leaders Uncensored with host Steve Taplin to share his remarkable journey from professional actor to technology executive. With decades of experience building and scaling enterprise communication systems, David has led teams through M&A deals, global product rollouts, and massive digital transformation. In this conversation, he opens up about Avaya’s next-gen contact center platform, Infinity, and how AI is reshaping the way humans and machines collaborate. From leading 900+ engineers worldwide to simplifying legacy systems and learning when to let go, David delivers real-world lessons on leadership, focus, and future-proofing enterprise software.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Gajus Kuizinas, co-founder and CTO of Contra, a unique talent marketplace that eliminates commission fees. Gajus shares his unconventional career journey from an arts background to the tech industry, detailing the innovative technology choices at Contra and the challenges faced in the evolving landscape of AI. He introduces the concept of Loom-Driven Development, discusses the implications of vibe coding, and offers insights on growth hacking and the importance of maintaining a long-term vision in entrepreneurship. Gajus emphasizes the need for tech leaders to navigate expectations and stay true to their core principles while building their companies.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Todd Albert, VP of Engineering at CYPHER Learning. They discuss Todd's unconventional career path, the importance of learning from failures, and the impact of AI on job recruitment and engineering processes. Todd shares insights on managing a remote engineering team, balancing priorities in software development, and the challenges faced in generative AI projects. He emphasizes the significance of networking and having a clear vision in entrepreneurship, along with the necessity of saying no to maintain focus and effectiveness as a leader.

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Vernon O'Donnell, CEO of Voxel, about his career journey, the mission of Voxel in enhancing workplace safety through AI and computer vision, and the challenges faced in the tech industry. Vernon shares insights on the importance of customer-centric leadership, the evolution of AI, and the lessons learned throughout his career. He emphasizes the need for trust in one's instincts as a leader and the significance of adapting to market changes.