The Pair Program

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.Today’s 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 he’s 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 today’s 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 today’s 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/

The Future Frontlines of Defense: 3D Drones and Strategic Logistics | The Pair Program Ep59

Dive into the future of defense technology with Chad McCoy of Firestorm Labs and Jeff Wright, military strategist and special ops veteran. Explore how 3D printing drones and new logistic strategies are paving the way for innovative solutions in the INDOPACOM theater. We’ll discuss everything from the myths of Pacific warfare to practical tech integration at the edge—where logistics meet frontline operations.

Key Topics Covered:

• Debunking Pacific Warfare Myths: Reassessing historical assumptions about INDOPACOM conflicts.
• 3D Drone Innovations: Highlighting rapid drone manufacturing and its impact on defense logistics.
• Logistics XCELL Solutions: Exploring its role in streamlining operations in contested regions.
• Tech Deployment at the Edge: Discussing the strategic importance of proximity and connectivity.

About Jeff Wright: Jeff is a technology-focused strategist, currently transitioning from a career in special operations to lead his drone startup full-time. As the former architect for autonomous systems employment at USINDOPACOM, his work directly contributed to the DoD’s “Replicator” initiative. He is the Founder & CEO of SplashOne Robotics, dedicated to developing small, purpose-built ‘fighter drones’ to redefine air superiority.

About Chad McCoy: Chad is a retired Senior SOCOM leader and former Pararescueman with 23 years of military experience. After serving as AFRL-RW Munitions Innovation Institute Director, he co-founded Firestorm to revolutionize defense technology. His company develops rapid-production unmanned aerial systems (UAS), reshaping tactical applications in national security.

About Rob Murtha: Rob is the CEO and Founder of Adjective, a company dedicated to product strategy and innovation. With extensive experience in product development and design, he specializes in building user-centric solutions that drive engagement and business growth. Rob is passionate about transforming ideas into impactful products through strategic thinking, data-driven decision-making, and a deep understanding of user needs.

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/

Scaling Horizontally: EpiSci’s Strategic Play in Dual-Use Tech | The Pair Program Ep58

In this episode of The Pair Program, we’re joined by David Rothzeid (Principal at Shield Capital) and Bo Ryu (CEO of EpiSci) to unpack the challenges and opportunities in building and scaling dual-use technology. From startup funding paths to shifting dynamics in the defense sector, our guests dive into the future of autonomy, venture capital’s growing role in national security, and what it really takes to bridge commercial innovation with government adoption. Whether you’re a founder, investor, or just tech-curious. This one’s packed with insight!

Key topics covered:

• Why “dual-use” is an outdated term and what’s replacing it
• The shifting relationship between commercial tech and national security
• How venture capital is shaping the next wave of defense innovation
• Building scalable autonomy without owning the hardware
• Lessons from startup exits, fundraising, and navigating SBIR programs
• The value of focus and trust when entering complex markets

About Bo Ryu: Bo is the Founder and CEO of EpiSci, a technology startup specializing in Tactical AI and autonomy software for defense applications. With a Ph.D. in Electrical Engineering from Columbia University, Bo brings nearly 30 years of experience across aerospace, communications, and AI systems. EpiSci was recently acquired by Applied Intuition, accelerating the company’s mission to deliver scalable, multi-domain autonomy for defense and commercial markets.

About David Rothzeid: David is a Principal at Shield Capital, a venture capital firm investing at the intersection of commercial innovation and national security. With over $300M in assets under management, David leads investments in frontier technology startups and brings deep insight into how founders can navigate the defense innovation ecosystem—from early-stage funding to long-term impact.

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: Feross Aboukhadijeh, Founder & CEO of Socket

How do we secure open-source software in a world where supply chain attacks are on the rise? In this episode of How We Hatched, we sit down with Feross Aboukhadijeh, founder & CEO of Socket, to discuss the growing security threats in open-source development and how Socket is helping companies stay protected. Feross shares his journey from open-source enthusiast to startup founder, lessons learned from early ventures, and insights into the evolving cybersecurity landscape.

They delve into:

• The rise of supply chain attacks in open-source software
• Lessons from Feross’ journey in open source and startup life
• The challenges of funding open-source projects
• How Socket is redefining developer-first security
• The future of open-source security and what’s next for Socket

About Feross:

Feross Aboukhadijeh is the founder and CEO of Socket, a developer-first security platform that protects companies from software supply chain attacks. With over a decade of experience in open source, Feross has written some of the most-downloaded JavaScript packages. He also teaches CS 253 Web Security at Stanford University. Thousands of organizations rely on Socket to safely discover, audit, and manage open-source software at scale.

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: Feross Aboukhadijeh, Founder & CEO of Socket

How do we secure open-source software in a world where supply chain attacks are on the rise? In this episode of How We Hatched, we sit down with Feross Aboukhadijeh, founder & CEO of Socket, to discuss the growing security threats in open-source development and how Socket is helping companies stay protected. Feross shares his journey from open-source enthusiast to startup founder, lessons learned from early ventures, and insights into the evolving cybersecurity landscape.

They delve into:

• The rise of supply chain attacks in open-source software
• Lessons from Feross’ journey in open source and startup life
• The challenges of funding open-source projects
• How Socket is redefining developer-first security
• The future of open-source security and what’s next for Socket

About Feross:

Feross Aboukhadijeh is the founder and CEO of Socket, a developer-first security platform that protects companies from software supply chain attacks. With over a decade of experience in open source, Feross has written some of the most-downloaded JavaScript packages. He also teaches CS 253 Web Security at Stanford University. Thousands of organizations rely on Socket to safely discover, audit, and manage open-source software at scale.

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/

Cracking the Code: How Startups Can Win with MSP Partnerships | The Pair Program Ep57

How do startups break into the market without a massive sales force? And what do Managed Service Providers (MSPs) really look for in vendor solutions, beyond the sales pitch? In this episode, Tim Winkler and Mike Gruen sit down with Brian Luckey (CIO at Integris) and Ian Y. Garrett (CEO & co-founder of Phalanx) to explore the high-stakes world of vendor-MSP relationships. They dive into how cybersecurity startups can leverage MSP partnerships to scale, the biggest pain points MSPs face, and what separates a winning product from one that never gets traction.

Key Topics Discussed:

• Why Managed Service Provider (MSP) partnerships can be a startup’s secret weapon
• The must-have features MSPs demand from vendors
• How automation and AI are reshaping cybersecurity
• The biggest mistakes vendors make when pitching MSPs
• What the future holds for MSP services and security

If you’re in tech, you won’t want to miss this one!

About Brian Luckey: Brian Luckey is a transformational leader with 20+ years in IT, operations, and service delivery, Brian specializes in scaling businesses, optimizing performance, and driving innovation. As CIO at Integris, he enhances IT infrastructure, customer experience, and revenue growth for businesses of all sizes. With two MBAs and a Ph.D. in Management Information Systems, he blends strategic vision with hands-on expertise to implement cutting-edge technologies, streamline processes, and foster high-performing teams.

About Ian Y. Garrett: As CEO and co-founder of Phalanx, Ian is revolutionizing secure file sharing for startups and SMBs. A former US Army Cyber officer and defense sector data scientist, he has firsthand experience tackling cybersecurity challenges at scale. Combining his operational expertise with Ph.D.-level research in AI and cybersecurity, Ian is building automation-driven solutions that eliminate human error and simplify data protection in an increasingly complex digital world.

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/