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The Software Leaders Uncensored Podcast
Steve Taplin
138 episodes
16 hours ago
Software Leaders Uncensored isn’t your typical tech podcast—it’s a candid dive into the minds of the industry’s top innovators. Each episode is a raw, behind-the-scenes conversation with the leaders who are shaping the future of software—how they’re building, scaling, and dominating in their markets. This is where cutting-edge tech meets unfiltered storytelling.
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Technology
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All content for The Software Leaders Uncensored Podcast is the property of Steve Taplin and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Software Leaders Uncensored isn’t your typical tech podcast—it’s a candid dive into the minds of the industry’s top innovators. Each episode is a raw, behind-the-scenes conversation with the leaders who are shaping the future of software—how they’re building, scaling, and dominating in their markets. This is where cutting-edge tech meets unfiltered storytelling.
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Technology
Episodes (20/138)
The Software Leaders Uncensored Podcast
Tom Cook on LegitScript, AI Confusion & The Challenge of Being a CPTO in 2025

In this episode of Software Leaders Uncensored, host Steve Taplin interviews Tom Cook, CPTO at LegitScript. They discuss Tom's career journey from engineer to CPTO, the importance of aligning product and engineering teams, and the challenges of managing remote teams. Tom shares insights on navigating the complexities of AI implementation and the current challenges tech leaders face. He emphasizes the need for a customer-centric approach and the significance of understanding unique data positions in today's tech landscape.

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16 hours ago
34 minutes 31 seconds

The Software Leaders Uncensored Podcast
Michel Floyd on Fractional CTO Life, Building AI Products Fast & Staying Curious in Tech

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Michel Floyd, a fractional CTO, about her career journey, the transition from a full-time to a fractional role, and the challenges faced by tech leaders today. They discuss the importance of MVPs, the impact of AI on software development, and the necessity of curiosity and adaptability in a rapidly changing tech landscape.

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1 day ago
21 minutes 17 seconds

The Software Leaders Uncensored Podcast
Ihab Rimawi on My-Fi.AI, Values-Based Investing & Personalizing Finance with AI

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Ihab Rimawi, CEO and founder of My-Fi.AI, about his journey in technology and the founding of his current venture. They discuss the importance of personalized investment strategies, the challenges of data sourcing, and the dynamics of remote team collaboration. Ihab shares insights on work culture, the significance of focusing on processes over technology, and valuable lessons learned throughout his career.

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4 days ago
23 minutes 2 seconds

The Software Leaders Uncensored Podcast
Marlon Misra on Assembly, YC Lessons & Building the Client Portal of the Future

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Marlon Misra, CEO and co-founder of Assembly. They discuss Marlon's journey from product management to entrepreneurship, the insights gained from Y Combinator, and the evolution of Assembly as a platform for professional service firms. Marlon shares valuable lessons learned from his early ventures, the importance of client interactions, and the recent launch of their AI assistant. The conversation also touches on work culture, the challenges of the tech landscape, and advice for today's tech leaders.

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5 days ago
31 minutes 56 seconds

The Software Leaders Uncensored Podcast
Michael Smith on Fortium Partners, Fractional CIO Leadership & Why Business First Beats Tech First

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Michael Smith, a seasoned IT professional with nearly 30 years of experience. They discuss Michael's career journey, his transition to Fordium Partners, and the challenges faced by tech leaders in today's economic climate. The conversation delves into the role of AI in business, the importance of understanding business operations for IT leaders, and the lessons learned throughout Michael's career. He emphasizes the need for perseverance and continuous learning in the ever-evolving tech industry.

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6 days ago
32 minutes 24 seconds

The Software Leaders Uncensored Podcast
Raj Bakhru on Datasite, M&A Deal Intelligence & The Future of Agentic Diligence

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Raj Bakhru, GM of DatasiteI, about his career journey from a developer to leading a successful AI company. They discuss the importance of innovation in the tech industry, the challenges of M&A, and the lessons learned throughout Raj's career. The conversation also touches on the future of AI in the M&A space and offers valuable advice for tech leaders navigating the rapidly changing landscape.

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1 week ago
31 minutes 31 seconds

The Software Leaders Uncensored Podcast
Claire Fang on Fullstory, CPTO Leadership & Falling in Love with the Problem

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Claire Fang, Chief Product and Technology Officer at Fullstory. Claire shares her unique career journey from computer engineering to product management, discussing the challenges and benefits of her combined role. The conversation delves into the importance of aligning product and engineering teams, navigating gender dynamics in tech, and the current projects at Full Story, particularly in AI integration. Claire offers valuable insights for women in tech and shares her perspective on the future of AI in the industry.

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1 week ago
30 minutes 47 seconds

The Software Leaders Uncensored Podcast
Sam Clemens on Reprise, Demo Engineering & Scaling Product with AI

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Sam Clemens, CEO of Reprise, about his entrepreneurial journey, the challenges of demoing software, and the integration of AI in business. They discuss the importance of education in entrepreneurship, the dynamics of engineering teams, and the impact of macroeconomic factors on business decisions. Sam emphasizes the need for tech leaders to stay connected with customer needs and the evolving roles in the age of AI.

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1 week ago
28 minutes 44 seconds

The Software Leaders Uncensored Podcast
Tobe Sullivan on PFF, AI in Game Strategy & Engineering at the Speed of Sports

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Tobe Sullivan, head of engineering at Pro Football Focus (PFF). They discuss Toby's journey from a football player to a technology leader, the innovative projects at PFF, the challenges of managing vast amounts of data, and the role of AI in engineering. Toby shares valuable leadership lessons and offers advice for tech leaders navigating the complexities of the industry.

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1 week ago
33 minutes 4 seconds

The Software Leaders Uncensored Podcast
Ryan Debenham on GRIN, Building “Living” Software & Why Engineers Make Great CEOs

In this episode of Software Leaders Uncensored, host Steve Taplin interviews Ryan Debenham, CEO of GRIN, who shares his journey from software engineer to CEO. They discuss the evolution of influencer marketing, the challenges of leading a tech company, and the impact of AI on software development. Ryan emphasizes the importance of building a strong team, navigating company restructuring, and adapting to the rapidly changing tech landscape. He offers valuable insights for tech leaders on leveraging AI and fostering a culture of innovation.

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1 week ago
34 minutes 53 seconds

The Software Leaders Uncensored Podcast
Steve Marshall on Aidentified, AI Prospecting & Why Focus Beats Features

In this episode of Software Leaders Uncensored, host Steve Taplin interviews Steve Marshall, Chief Product Officer at Aidentified. They discuss the importance of aligning product and technology teams, the role of AI in enhancing prospecting solutions for financial advisors, and the challenges of leading product development in a remote environment. Marshall shares insights from his career journey, the innovative projects at Aidentified, and valuable lessons learned in product management. He emphasizes the need for effective communication, focus on core ideas, and the importance of understanding the true problems being solved in product development.

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2 weeks ago
27 minutes 40 seconds

The Software Leaders Uncensored Podcast
Dan Zimmerman on TreviPay, B2B Payments AI & Leading as a CPTO

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Dan Zimmerman, the Chief Product and Technology Officer at TreviPay. They discuss Dan's journey from a help desk engineer to an executive leader, the innovative solutions TreviPay is bringing to the B2B payments space, and the importance of integrating product and technology roles. The conversation also delves into the challenges and opportunities presented by AI in the tech industry, as well as advice for tech leaders navigating these changes.

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2 weeks ago
28 minutes 49 seconds

The Software Leaders Uncensored Podcast
Frank LaSota on Zyter|TruCare, Agentic AI & Solving Healthcare’s Hardest Problems

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Frank LaSota, CTO of Zyter|TruCare, about his extensive career in technology and leadership. They discuss Frank's journey from software development to executive roles, the challenges and innovations in healthcare technology, and the importance of effective leadership in navigating the complexities of AI integration. Frank shares insights on the current projects at Zyder, the dynamics of remote work, and offers valuable advice for tech leaders looking to thrive in a rapidly changing industry.

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2 weeks ago
31 minutes 1 second

The Software Leaders Uncensored Podcast
Bill Rokos on Parsec Automation, Manufacturing Software & Building a Career of Loyalty

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Bill Rokos, CTO of Parsec Automation, about his unique career journey and the evolution of the manufacturing software industry. They discuss the challenges and opportunities presented by AI in manufacturing, the importance of adapting technology to fit existing processes, and the need for effective delegation in leadership roles. Bill shares insights on the future of technology innovation in manufacturing and offers practical advice for tech leaders navigating the rapidly changing landscape.

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2 weeks ago
26 minutes 6 seconds

The Software Leaders Uncensored Podcast
Olly Downs on Curinos, AI in Banking & Turning Data into Decision Intelligence

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Olly Downs, CTO of Curinos, about his extensive career in technology and AI. They discuss the evolution of AI in the banking sector, the challenges of managing software engineering teams, and the importance of aligning technology with business needs. Ali shares insights on the current state of AI implementation, the lessons learned from failures, and offers advice for tech leaders navigating these complex times.

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2 weeks ago
23 minutes 52 seconds

The Software Leaders Uncensored Podcast
Alex Pape on Assetmark, WealthTech Innovation & Leading as a CPTO

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Alex Pape, Chief Product and Technology Officer at Assetmark. Alex shares his unconventional career journey from finance to technology, emphasizing the importance of combining product management and engineering roles. He discusses the challenges and innovations in the wealth management sector, particularly in integrating private market investments. The conversation also delves into the impact of AI on software development, lessons learned from failures, and advice for tech leaders navigating the industry.

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2 weeks ago
32 minutes 15 seconds

The Software Leaders Uncensored Podcast
William Benner, CEO and CTO of Pangolin, on Laser Show Tech & Turning Passion into a Global Business

In this episode of Software Leaders Uncensored, host Steve Taplin interviews William Benner, the president and CTO of Pangolin Laser Systems. They discuss Benner's journey from a passion for electronics and music to founding a leading company in the laser show industry. The conversation covers the evolution of Pangolin, the current applications of their technology, the importance of niche markets, and the integration of software engineering and artificial intelligence in their products. Benner shares valuable lessons learned over nearly 40 years in business and offers advice for tech leaders navigating today's challenges.

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3 weeks ago
24 minutes 4 seconds

The Software Leaders Uncensored Podcast
Matt Peters on CAI, AI in Government & Leading with Extreme Ownership

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Matt Peters, CTO of CAI, about his unique career journey, the company's approach to client relationships, and the challenges of integrating AI into their services. They discuss the evolving landscape of public sector AI adoption, the dynamics of software engineering teams, and the critical role of expectation management in technology leadership. Matt shares valuable insights on leadership lessons learned, shifts in hiring practices, and the impact of AI on future roles in the industry.

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3 weeks ago
29 minutes 51 seconds

The Software Leaders Uncensored Podcast
Jared Shepard on Hypori, Veteran Leadership & Building Secure Tech from the Battlefield

In this episode of Software Leaders Uncensored, host Steve Taplin interviews Jared Shepard, an Army veteran turned entrepreneur. Jared shares his inspiring journey from being a high school dropout and homeless to becoming a successful CEO of multiple tech companies. He discusses the challenges and lessons learned in entrepreneurship, the importance of secure technology in the military, and the innovative solutions his companies are developing. Jared emphasizes the need for veterans to receive support in their transitions to civilian life and the significant contributions they make to entrepreneurship. The conversation concludes with valuable advice for tech leaders on product knowledge, leadership, and the importance of learning from failure.

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3 weeks ago
30 minutes 31 seconds

The Software Leaders Uncensored Podcast
Jared Crapo on Carta Healthcare, Why Great Products Are Built by Iteration, Not Big Bangs

In this episode of Software Leaders Uncensored, host Steve Taplin speaks with Jared Crapo, a seasoned tech entrepreneur with extensive experience in healthcare technology and product management. They discuss Jared's journey through nine tech startups, the unique challenges of the healthcare industry, and the transformative role of AI in improving efficiency and outcomes. The conversation also delves into the importance of collaboration between product and engineering teams, the impact of generative AI on software development, and the necessity of training the next generation of software engineers. Jared shares valuable insights and advice for tech leaders navigating the complexities of building and scaling successful businesses in today's fast-paced environment.

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3 weeks ago
25 minutes 40 seconds

The Software Leaders Uncensored Podcast
Software Leaders Uncensored isn’t your typical tech podcast—it’s a candid dive into the minds of the industry’s top innovators. Each episode is a raw, behind-the-scenes conversation with the leaders who are shaping the future of software—how they’re building, scaling, and dominating in their markets. This is where cutting-edge tech meets unfiltered storytelling.