The Pair Program Podcast

CTO Wisdom with Freedom Dumlao | Beyond The Program

Welcome to CTO Wisdom. In this series, we interview technical leaders who have stepped into executive positions.Todays guest host, Eric Brooke, speaks with Freedom Dumlao, CTO at Vestmark, in this episode of CTO Wisdom. We sit down with Freedom to explore his unconventional journey into tech and the leadership lessons hes learned along the way. From programming on a black-and-white TV as a kid to leading engineering teams at Zipcar and Wayfair, Freedom shares valuable insights on building high-performing teams and navigating executive responsibilities.

Together, they dive into topics such as:

• How a passion for making sparked a tech career
• Lessons from managing managers and scaling teams
• Navigating the CTO role with empathy and accountability
• The future of AI in engineering organizations
• Why shipping culture beats everything

About todays guest: Freedom Dumlao is the CTO at Vestmark, with a background in leading engineering teams at companies like Flexcar, Zipcar, Wayfair, Drift, and Amazon. He brings deep experience in scaling technology organizations and driving innovation across both startups and large enterprises.

About todays host: Eric Brooke has a rich and varied leadership career leading up to 21,000 people and Billions in revenue, throughout 14 countries. In their career, they have been an Executive six times (e.g. President, CEO, CMO, and CTO) and a Board member of multiple organisations. Eric has been a CTO of scaling startups from 0 to 120 engineers. As an adviser and mentor, they have helped multiple other startups scale both in Canada and the US. As well as supporting multiple startup incubators such as 1871 in Chicago and TechStars.Exploring your next tech role? Get insider job advice and the latest startup & govtech openings delivered straight to your inbox.

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Combating Deepfakes with AI Innovation: Reality Defender & BAH Ventures | The Pair Program Ep61

In this episode of The Pair Program, we’re joined by Ben Colman (CEO and Co-Founder of Reality Defender) and Wes Blackwell (Managing Director at Booz Allen Hamilton) for a fascinating discussion on AI and national security. They dive into the dangers of deepfakes, the role of AI detection tools, and how public and private sectors can stay ahead of this evolving threat. Whether you’re curious about how deepfakes are disrupting banks or the ethics behind AI moderation, this one’s for you.

Here’s what we get into:

• Why deepfakes are the new cybersecurity threat
• Real-world fraud examples using AI-generated media
• The technical challenges of detecting synthetic content
• The ethics of AI detection and censorship
• How startups and government can work together to combat AI misuse

About Ben Colman: Ben is the CEO and Co-Founder of Reality Defender, a deepfake detection platform helping enterprises and governments identify AI-generated threats. With a background in cybersecurity and data science, he’s led innovation at Goldman Sachs and Google, and holds an MBA from NYU Stern.

About Wes Blackwell: Wes is Managing Director at Booz Allen Hamilton, where he invests in cutting-edge technologies that advance national security. His focus spans AI, quantum, cyber, and robotics – backing founders building high-impact, over-the-horizon solutions.

 Exploring your next tech role? Get insider job advice and the latest startup & govtech openings – delivered straight to your inbox. Subscribe here: https://www.myhatchpad.com/newsletter/

How We Hatched: Kevin Larrabee, Head of Product at DataShapesAI

In this episode of How We Hatched, we’re joined by Kevin Larrabee, the Head of Product at DataShapesAI. In our conversation, Kevin takes us through the transformative role AI plays in Electromagnetic Spectrum (EMS) applications. He also shares how DataShapesAI is using AI-driven solutions to enhance spectrum awareness and improve signal monitoring.

Here’s a glimpse of what we talked about:

• The fascinating intersection of military operations and AI-driven tech solutions
• How Kevin navigated the transition from Army officer to startup product lead
• Why DataShapesAI is focusing on EMS applications and what that means for the future
• The challenges and opportunities in developing dual-use technology for defense and commercial sectors

About Kevin Larrabee: Kevin Larrabee is the Head of Product at DataShapesAI, a leader in Artificial Intelligence for Electromagnetic Spectrum (EMS) applications. He leads the product strategy and execution, driving advancements in AI-driven spectrum awareness, signal monitoring, and automated frequency management. Kevin is a 21-year Army veteran who has led multiple analytical teams across USASOC, CENTCOM, and the Army Staff.

Exploring your next tech role? Get insider job advice and the latest startup & govtech openings – delivered straight to your inbox. Subscribe here: https://www.myhatchpad.com/newsletter/

The Dual-Use Debate: Crafting Smarter Startups from the Start | The Pair Program Ep60

Today on The Pair Program, we’re joined by Gene Kesselman, Director of Mission Innovation Experimentation at MIT, and Jake Chapman, Managing Director at Marque Ventures. Together, they dive into the evolving landscape of dual-use technology and the future of defense innovation. Gene and Jake explore opportunities, tough realities, and bold reforms shaping tech development for mission and market impact.

Some of what we dive into:

• Why dual-use strategy is more than just a category
• Common pitfalls startups face in defense tech
• How venture capital sees national security innovation
• The critical role of non-dilutive funding and SBIR programs
• Urgent reforms needed in government acquisition and budgeting processes

Tune in for real-world insights and sharp debate!

About Gene Keselman: Gene is a Lecturer at MIT Sloan School of Management, Executive Director of MIT Mission Innovation Experimental (MIx), and Managing Director of MIT’s venture studio, Proto Ventures. A seasoned entrepreneur and Air Force Colonel, he brings extensive expertise in innovation, defense, and dual-use technology strategy.

About Jake Chapman: Jake is the Managing Director of Marque Ventures, an early-stage venture firm focused on national security capabilities. He previously led a turnaround of the Department of Defense’s internal venture arm and serves as an adjunct at RAND, where he works at the intersection of finance and national security.

Exploring your next tech role? Get insider job advice and the latest startup & govtech openings – delivered straight to your inbox. Subscribe here: https://www.myhatchpad.com/newsletter/

How We Hatched: Nicolas Chaillan, Founder & CEO of Ask Sage

On today’s episode of How We Hatched, we sit down with Nicolas Chaillan, Founder & CEO of Ask Sage and former Chief Software Officer for the U.S. Air Force and Space Force. From launching startups at age 15 to transforming tech adoption in national defense, Nick shares lessons from his unconventional path and offers insights on building secure, scalable AI.

Key topics we cover:

• Ask Sage’s origin and mission to democratize generative AI
• Overcoming government tech barriers through agile innovation
• The cultural clash between startups and defense
• Scaling AI in the U.S. Army
• Advice for aspiring defense tech entrepreneurs

About Nicolas Chaillan:

Nicolas Chaillan is the Founder & CEO of Ask Sage, a generative AI platform helping government and enterprise teams work smarter with secure, scalable AI. As the former Chief Software Officer of the U.S. Air Force, he led major modernization efforts across defense. Today, he’s focused on accelerating innovation and productivity across the public sector.

Exploring your next tech role? Get insider job advice and the latest startup & govtech openings – delivered straight to your inbox. Subscribe here: https://www.myhatchpad.com/newsletter/