The CTO Compass

Hiring has become one of the hardest problems CTOs and CIOs face, and most tech leaders are still using a playbook that no longer works.

There is no longer a deep talent pool. Long interview processes lose top candidates. Remote work has changed what “good” looks like. And AI is forcing leaders to rethink experience, roles, and team design entirely.

In this episode, Mark Wormgoor speaks with Bill Kasko, President and CEO of Frontline Source Group, a national staffing and executive search firm. Bill began his career in IT security and infrastructure before spending more than 20 years helping companies hire and scale teams, giving him an expert view of what actually works in today’s market.

You’ll learn:

1. Why there is no longer a true “talent pool”, and how to hire without one
2. How to design tech roles around outcomes instead of outdated requirements
3. Where great tech talent actually comes from today
4. How remote work has changed hiring signals and expectations
5. Why adaptability matters more than years of experience in the AI era
6. The one leadership habit that consistently separates strong tech teams from weak ones

If you’re a CTO, CIO, or senior tech leader and you frequently need to hire, this episode will help you rethink how you build teams.

00:00 Starting Out in IT

08:29 Infrastructure and Security Today

15:46 Where To Start With Recruitment

24:34 What's The Secret with Recruitment

30:50 Approaching Remote Work

36:56 The Hiring IT Landscape

42:33 Hiring In Today's Market

46:52 Hiring Retention

50:26 Communication is Important!

Bill Kasko is a seasoned business leader and entrepreneur with extensive experience in strategic planning, business development, and organizational growth. With a proven track record of driving results across multiple industries, Bill brings valuable insights into leadership, innovation, and sustainable business practices.

• Website: https://www.frontlinesourcegroup.com

• LinkedIn: https://www.linkedin.com/in/billkasko/

• Instagram: https://instagram.com/frtline

• YouTube: https://www.youtube.com/@frontlinesource

Matt Dixon, a seasoned tech leader and fractional CTO, shares insights on aligning technology with business goals, addressing revenue leaks, and the importance of mindset in leadership. He discusses the role of a fractional CTO, the significance of metrics that matter, and the challenges of managing technical debt. Matt emphasizes the need for effective team dynamics and the dangers of shiny object syndrome in tech. He also explores the future of AI in business and the evolving role of CTOs in modern organizations.

00:00 Tech, Business, and Leadership

04:16 Revenue Leaks and Fractional CTO Work

08:41 Working with Existing Tech Teams

13:02 Managing Expectations and Misunderstandings

16:39 Code Program and Misaligned Priorities

20:58 Technical Debt and Shiny Object Syndrome

26:47 What CTO's Should Be Doing

28:55 AI in Tech and Business

Matt Dixon is the Founder and CEO of Front Range Systems, serving as a Fractional CTO for growth-stage companies generating $10-75 million in revenue. With over 25 years of technology leadership experience, Matt specializes in identifying and eliminating "revenue leaks": the invisible operational inefficiencies that cost companies significant money through manual processes and misaligned systems.

Now based in Nashville, Matt focuses on logistics, insurance, healthcare, and sports industries, delivering operational clarity and measurable cost reductions within 90 days.

When he's not helping CEOs fix their operations, you'll find him on track days pushing limits behind the wheel or traveling with his wife.

• Website: https://frontrangesystems.com/

• LinkedIn: https://www.linkedin.com/in/mattdixon/

• Instagram: https://www.instagram.com/fractionalctomatt

• YouTube: https://www.youtube.com/@FractionalCTOMatt

What if the way we talk about tech leadership is completely wrong?

In this episode, Telle Whitney - Silicon Valley chip designer turned CEO and co-founder of the Grace Hopper Celebration - joins us to break down the myths that hold technology leadership back. She unpacks the dangerous illusion of meritocracy, the myth of the lone genius, and why many CTOs and CIOs unknowingly lead cultures that silence key voices. Drawing from her book Rebooting Tech Culture, Telle offers actionable insights for building inclusive, creative, and high-impact organizations, starting at the executive and board level.

Listen to learn how today’s tech leaders can:

1. Rethink hiring and strategy for real boardroom impact
2. Build cultures that amplify innovation (not just output)
3. Spot the hidden signals that sabotage diversity and creativity
4. Lead with courage, even when you feel like an imposter

00:00 From Theater to Computer Science

05:39 The Grace Hopper Celebration

11:27 Rebooting Tech Culture

20:12 Meritocracy and The Lone Genius

26:15 What a Company actually needs

32:44 Does Inclusivity Improve The Output?

34:28 AI4ALL

38:43 Taking Risks

Telle Whitney is a consultant, senior executive leader, and recognized expert and advocate for diversity and women in technology. Telle has been called "a pioneer for the promotion of women technologists" and was named one of Fast Company's Most Influential Women in Technology. Telle served as CEO of the Anita Borg Institute from 2002 to 2017 and cofounded the Grace Hopper Celebration of Women in Computing conference. Prior to joining the Anita Borg Institute, she was vice president of engineering for Malleable Technologies. She holds a PhD in computer science and is now a speaker and consultant helping executives and their companies create cultures where diverse teams thrive.

1. Telle Whitney's book: Rebooting Tech Culture: How to Ignite Innovation and Build Organizations Where Everyone Can Thrive
2. Website: https://www.tellewhitney.com/
3. LinkedIn: https://www.linkedin.com/in/telle-whitney/

In this episode, executive coach and former scale-up CEO Loic Potjes joins us to help CTOs, CIOs, and tech leaders break out of the "busy but stuck" cycle. We explore how to bring strategic clarity to your leadership, define a powerful USP, and position your company for exponential (not just incremental) growth.

🎯 Learn how to:

1. Escape the trap of surface-level innovation
2. Use AI as a strategic co-pilot, not a tactical bolt-on
3. Transform from technical expert to strategic leader
4. Lead with clarity, purpose, and structure, especially in fast-scaling environments

00:00 Worldwide CEO Experience Perspective

06:23 Transitioning for the Future

11:30 Personal Growth as a CEO

14:07 Business-Tech Mistakes

21:52 Change and Improvement

29:22 Coaching Growth

34:49 Business AI Integration

41:50 Navigating the AI Hype

48:10 Simplifying Your Pitch

Loic has a global perspective and 25 years of experience as a corporate/scale-up CEO, chairman and tech investor, and therefore uniquely qualified to partner with CEOs across diverse industries and growth stages. He has successfully launched, structured, and grown companies across mature and emerging markets, managing up to 4,000 employees at a time, with core expertise in go-to-market strategies, new technologies, innovation, and mergers & acquisitions.

• Website: https://www.disruptiveleap.com

• LinkedIn: https://www.linkedin.com/in/loicpotjes/

Hollis discusses the intricacies of raising capital, emphasizing the importance of multiple interactions with potential investors. He highlights the average of 32 touchpoints required to secure a significant investment and explores how AI can streamline this process without compromising the quality of engagement.

00:00 Beginnings with Technology and Career

06:20 When to use Tech and People

08:08 Implementing Tech into Real Estate (Raise AI)

12:45 Streamlining "32 Touch points" with AI

19:31 Building a Team and AI Adoption

24:06 AI Future-proofing and Relationships

28:36 Why Real Estate AI and Building Culture

33:02 The Future of Raise AI

William Hollis, known as “Hollis,” is the Founder & CEO of Raise AI, where he helps real estate capital raisers and fund managers use AI-powered automation to streamline investor communication, increase deal visibility, and raise capital faster. A self-taught software engineer turned real estate investor, Hollis specializes in bridging cutting-edge AI technology with the real-world challenges of capital raising.

Born and raised in Hollis, Queens, NY, he has built his career at the intersection of AI, automation, and real estate. Before founding Raise AI, Hollis developed AI solutions for global brands like Disney and Nike, then applied those same efficiencies to real estate by launching 24 Capital Group in 2022 and 24 Tech Systems in 2024. Today, through Raise AI, he empowers dealmakers with scalable, intelligent systems that replace manual follow-ups and outdated workflows—helping them move from hustling for capital to raising it effortlessly.

• RaiseAI: https://theraiseai.com/

• Website: https://williamhollis.com/

• LinkedIn: https://www.linkedin.com/in/rei-hollis/

Scott Morris, a veteran HR leader turned startup founder, discusses his transition from a successful corporate career to launching Propulsion AI, an innovative company focused on AI-powered HR solutions. He highlights the significant challenges in traditional HR practices, particularly the lack of clarity in role expectations and the misalignment of employee engagement. Scott introduces Athena, an AI teammate designed to enhance role design and improve hiring processes, ultimately aiming to create a more effective and engaged workforce. The discussion also touches on the future of hiring, performance management, and the importance of understanding the value of operational roles within organizations.

00:00 - Risks, Startups, and HR

07:35 - Solving The Problem with Hiring

14:39 - Athena and Propulsion

21:20 - Importance of Operational Roles

25:04 - Athena as a Teammate

29:41 - Collaborating with Tech

32:08 - Culture in the Hiring Process

34:32 - Are You Ready to Hire?

38:41 - Future of HR Tech

41:44 - Hiring and Managing Advice

With more than 25 years of HR leadership - including two decades at the C-suite level - Scott Morris has navigated talent management across five distinct industries and two continents. He's led HR strategy for nimble tech startups with 250 employees and orchestrated comprehensive workforce solutions for enterprises exceeding 15,000 employees. His experience spans the full spectrum of organizational complexity, guided by a core philosophy: if it feels comfortable, you're behind.

Scott is now Founder & CEO of PropulsionAI, building the first HR team made entirely of AI - digital teammates that coach managers through strategic talent decisions using proven frameworks. These AI coaches clarify how roles connect to business outcomes, transform hiring and performance management, automate labor-intensive documentation, and help organizations simultaneously raise employee engagement and productivity.

• Website: https://getpropulsion.ai/

• LinkedIn: https://www.linkedin.com/in/mscottm/

Mark and Margaret explore how leaders can operate effectively in unpredictable environments, emphasizing curiosity, reflection, and making decisions without perfect information. They discuss the limits of efficiency, the risks of relying too heavily on metrics, and how AI may weaken independent thinking. Margaret shares real examples of leaders who improved their organizations by listening more, empowering their teams, and building trust. They also examine extreme work cultures, the importance of maintaining personal autonomy, and how strong social connections in remote teams support better collaboration and problem-solving.

00:00 - The World of Uncertainty

03:57 - Curiosity in Business

10:15 - Measurements, Data, and KPIs

12:51 - Letting AI think for Us

16:29 - Growing Leadership Skills

26:31 - CEO Coaching Experience

33:29 - 9-9-6 Mentality

38:00 - Business Trends

40:00 - Social Capital with Global Teams

45:40 - Margaret's Essential Question

Dr. Margaret Heffernan began her career producing BBC radio and television programmes, including dramas, documentaries, and the first broadcasts featuring Simon Schama. After moving to the United States, she led multimedia initiatives for Intuit, The Learning Company, and Standard & Poor’s, later serving as CEO of InfoMation Corporation, ZineZone, and iCast. Recognized as one of Streaming Media’s “Top 25” and The Hollywood Reporter’s “Top 100 Media Executives,” she is also the author of seven influential books, including Willful Blindness, A Bigger Prize, and the best-selling Uncharted. Her TED talks have been viewed more than fifteen million times, and her next book, Embracing Uncertainty, will be published in 2025.

A Professor of Practice at the University of Bath, Heffernan mentors global CEOs through Merryck & Co., speaks at major international conferences, and chairs the board of DACS. She has advised high-profile public inquiries, was inducted into the Thinkers50 Hall of Fame in 2023, and is a frequent BBC Radio 4 broadcaster. She also writes for the Financial Times and serves as a parish councillor.

• Website: https://mheffernan.com/

• X: https://x.com/M_Heffernan

• Ted: https://www.ted.com/speakers/margaret_heffernan

• Substack: https://heffernanm.substack.com/

David Soileau discusses the potential of AI and automation in optimizing customer service and order processing. He emphasizes the importance of accurate order entry to reduce the need for customer service interactions and highlights the benefits of automating documentation processes. The discussion also touches on the shift towards self-service options, reducing manual data entry, and streamlining operations to enhance efficiency.

00:00 – Gopher’s Origin & Pivot

04:18 – Why Logistics Needs Tech

07:40 – Going Digital in Old Industries

10:16 – AI Features: Pic-to-Ship & GoPilot

12:12 – Tech Challenges & Early Mistakes

16:21 – Team, CTO, and Automation

20:07 – Fixing Legacy Logistics

24:23 – Techstars, Expansion & Future of AI

David is an entrepreneur and founder passionate about building companies that transform industries and create lasting impact. As a Co-founder of Gophr, he's part of a team redefining logistics and procurement. By combining pricing intelligence, technology, and service, they’re delivering a faster, smarter, and more cost-effective way for industrial and construction businesses to move materials and products. Their vision is to save teams time, reduce costs, and reshape the future of logistics. He's also a founder of Embark, a business incubator designed to launch and scale ventures that matter. At Embark, they provide entrepreneurs with the tools, network, and mentorship needed to transform ideas into thriving businesses. Alongside these ventures, David owns Integrity Homes, a residential construction company built on trust, craftsmanship, and long-term relationships. Whether it’s homes, logistics systems, or startups, his passion is taking ideas from the ground up and scaling them into businesses that create real impact. David thrives on solving big problems, building strong teams, and driving sustainable growth. Always open to connecting with leaders, innovators, and partners who share a vision for building what’s next.

• Website: https://gophrapp.com/

• LinkedIn: https://www.linkedin.com/in/davidtheguy

• Youtube: https://youtube.com/@gophrapp

How do you lead when AI is changing everything about how we work?

Mike Todasco, former Senior Director of Innovation at PayPal and Visiting Fellow at the SDSU AI Lab, talks about what it really takes to build an AI-first organization. Mike shares hard-won lessons from running innovation inside Paypal, why most teams get stuck in “pilot hell,” and how leaders can build a culture that embraces experimentation instead of fearing it.

Mark and Mike also explore the human side of tech leadership: creativity, curiosity, adaptability, and how to stay grounded as AI accelerates. From PayPal’s innovation tournaments to the future of work and the rise of solopreneurs augmented by AI, this episode gives CTOs and tech leaders a clear, practical view of what’s coming, and how to prepare.

00:00 Who Is Mike Todasco?

02:42 What AI-First Really Means for Companies

04:32 How Leaders Can Drive AI Adoption

07:56 Inside PayPal’s Innovation Culture

15:31 Getting Executive Buy-In for Innovation

21:06 The Leadership Skills That Matter in the AI Era

32:42 The Future of Work: Humans + AI

39:43 When AI Feels Overwhelming (Mike’s Advice)

Michael Todasco is the former Senior Director of Innovation at PayPal, where he spent over a decade leading initiatives to design, test, and scale disruptive ideas across the company. He is currently a Visiting Fellow at San Diego State University’s Artificial Intelligence Lab, where he explores the intersection of AI, creativity, and the future of work. In addition, he is pursuing his MFA in Creative Writing at Johns Hopkins University, blending his passion for storytelling with his expertise in technology. A frequent speaker and writer on AI, innovation, and creativity, Michael helps audiences rethink how to stay relevant and human in a rapidly changing world.

• "How to Win Friends and Influence People" by Dale Carnegie

• LinkedIn: https://www.linkedin.com/in/todasco/

• Website: https://todasco.lovable.app/

Coby Skonord founded IdeaWake, an innovation crowdsourcing platform. He addresses common misconceptions about innovation in organizations, the role of technology leaders, and the importance of integrating innovation into company culture. Koby also shares insights on overcoming budget constraints, navigating security challenges, and the impact of AI on innovation processes. He emphasizes the need for a sustainable innovation culture that is measured and integrated into the organization's goals.

00:00 – Leaving EY to Build Ideawake

02:35 - Why Innovation Fails Inside Big Organizations

03:47 - Building a Culture That Enables Innovation

05:26 - Turning Ideas into Impact

09:38 - Innovation in Healthcare and Regulated Industries

10:37 - The CTO’s Role in Driving Innovation

13:50 - Escaping the Budget Trap

19:35 - Breaking Through Enterprise Barriers

26:36 - The Future of Innovation and the Role of AI

Coby Skonord helps corporate innovation, improvement, and HR teams more effectively tap into the wisdom of employee ideas.

Over the last decade he's led the team at Ideawake, an innovation management platform used by thousands of companies like KraftHeinz, SiriusXM, and Jason's Deli power their employee ideas program focused on growing revenue, reducing costs, and improving efficiency.

• Website: https://ideawake.com/

• LinkedIn: https://www.linkedin.com/in/coby-skonord/