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Matt Watson is the CEO of FullScale and previously bootstrapped an SaaS company to $35 million ARR before a $150 million exit.

In this episode, you're going to learn what skills CTOs need to become CEOs, why understanding sales and marketing is crucial for tech leaders, how to delegate effectively to focus on big-picture strategy, why communication and collaboration are key to scaling engineering teams, and what AI’s role is in shaping the future of software development.

Matt Watson is the founder and former CTO of one of the early SaaS companies, VinSolutions, which he bootstrapped in 2003 to $35 million ARR before a $150 million exit in 2011. In 2018, he founded FullScale to help himself and others scale their teams with talent from the Philippines at 70% less cost. He also hosts the Product Driven podcast and writes a weekly newsletter about the gap between business and software engineering.

Timestamps:

[00:00] Introduction

[05:30] Starting a company by solving a real problem

[07:15] Bootstrapping an SaaS business to $35 million ARR

[08:40] Challenges of building a product without a playbook

[10:20] Different types of CTO roles

[11:50] Why startup CTOs need a product mindset

[13:05] The natural transition from CTO to CEO

[14:30] What makes a good CTO

[15:40] The importance of sales and marketing for CTOs

[17:00] Selling to developers is harder than it seems

[18:30] Why engineers struggle with delegation

[19:50] The real reason 10x developers exist

[21:10] How bureaucracy slows down engineering

[22:35] Why startups move faster than big companies

[24:00] Software corrosion and how products degrade over time

[25:30] Why big companies struggle with innovation

[27:00] The hidden cost of maintaining legacy software

[28:40] Teaching the next generation of developers

[30:20] The impact of AI on software development

[31:50] How AI is changing the role of engineers

[33:15] AI adoption rates among software developers

[34:50] Why junior developers benefit most from AI

[36:10] The balance between using AI and learning fundamentals

[37:45] Why developers need to improve communication skills

[39:00] The key to becoming a successful CTO

[40:30] Why being the best known is more important than being the best

Offshore your tech team with the talented engineers at FullScale.

Connect with Matt on LinkedIn.

Resources Mentioned:

Product Driven Podcast with Matt Watson | Spotify or Apple

VinSolutions | Website

Stackify | Website

GitHub Copilot | Website

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In this episode, you'll learn the top mistakes founder engineers make when starting a business, why early technical decisions can have long-term business consequences, how to choose co-founders with complementary strengths, the importance of understanding business fundamentals as a technical founder, and strategies for picking the right tech stack for your startup's needs.

Dr. Georgios Christou graduated from Carnegie Mellon University with a dual degree in Cognitive Science and Computer Science, he also has a Master’s and Ph.D. in Computer Science from Tufts University. Since 2003, he has worked at Cyprus College and holds the rank of Associate Professor. Dr. Christou founded and was the director of the Games Research Center of European University Cyprus, through which a computer game development start-up company emerged. Dr. Christou was also the coordinator of perhaps the only Microsoft-branded degree in the world, Microsoft's Bachelor in Information Systems.

Dr. Christou moved to the Cyprus International Institute of Management where he held a dual role, as the Chair Associate Professor of Computer Science and the Chief Technology Officer of eCREDO Ltd., a Fintech company in Cyprus. He was responsible for the Technology strategy of the company. Currently, Dr. Christou is a freelance consultant for Fintech companies.

Dr. Christou has many publications in scientific journals, as well as presentations at international conferences. His research examines the ways that video games can serve as social “third-places” and how this can be designed. He also examines the nature of player experience, the motivations that pull us towards playing video games, and the ways that we interact with them, as novices and as experienced players. The insights into these behaviours have been used towards creating entertaining e-Health experiences as well as novel interactions, such as playing video games through brain-computer interfaces.

Timestamps:

[04:06] Combining academia and industry experience

[05:26] The challenges of a failed startup

[07:04] Importance of product velocity

[08:26] Creating early income streams

[10:11] Choosing better co-founders

[12:20] Balancing communication styles

[13:46] Complementary knowledge in co-founders

[15:22] Common mistakes in startup presentations

[17:37] Learning from startup competition feedback

[19:29] Lessons from Amazon's business strategy

[21:00] The impact of early tech choices

[22:36] Matching the tech stack to the niche

[23:38] Overhauling poorly chosen technologies

[26:08] Planning for long-term scalability

[27:31] Managing decision-making complexity

[28:26] Avoiding the sunk cost fallacy

[30:01] The importance of asking the right questions

[33:09] Flexibility in choosing tech stacks

[34:40] Parallel tech stacks for different domains

[35:37] Learning the business side of startups

Follow Dr. Georgios Christou on LinkedIn to learn more.

Resources Mentioned:

The E-Myth Revisited by Michael E. Gerber | Book or Audiobook

Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

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Stephan Schmidt is a CTO coach and the author of “Amazing CTO”.

In this episode, you're going to learn why hiring the right people is the foundation of success and how to assess candidates effectively. Stephan shares his strategy for running weekly one-on-one meetings and why they should focus on alignment rather than status updates. You'll also hear about the importance of trust in leadership and practical ways to build it within your team. He explains why surprises undermine leadership and how to present ideas and decisions without creating resistance. Finally, Stephan emphasizes the value of early and consistent delegation as a tool for scaling leadership and empowering team members.

As a CTO and CPTO Coach, Stephen helps CTOs, CPTOs, VPs of Engineering, Heads of Development, and other tech leaders to master their challenges and achieve their goals. With over 25 years of experience as a CTO, consultant, and executive in various startups and enterprises, he has a wide range of skills and insights to share with clients.

Stephen’s coaching services include training workshops, one-on-one sessions, and fractional/ interim management. He focuses on topics such as people management, communication, recruiting, leadership, lean start-up, e-commerce, and bridging business and technology. He is passionate about working with people and developing them, as well as explaining technology in a clear and engaging way. Stephen is currently coaching several CTOs and tech managers from different industries and countries, and he enjoys seeing them grow and succeed.

Timestamps:

[00:00] Introduction

[05:05] Early career and becoming a manager

[07:44] First training on people management

[09:15] Learning from a great boss at eBay

[11:05] Building trust with junior developers

[13:07] Shifting decisions to the team

[16:22] Managing through late-night crises

[18:11] Importance of hiring the right people

[20:04] Common mistakes in one-on-ones

[22:07] Best practices for weekly one-on-ones

[23:15] Aligning remote teams effectively

[25:35] Benefits of skip-level meetings

[27:12] Spending 50% of the time on people

[29:02] Helping employees identify career goals

[30:20] The role of trust in leadership

[32:22] Avoiding surprises in leadership

[34:06] Overcommitting to solutions for success

[36:38] Focusing on effectiveness over efficiency

[39:07] Writing clear job descriptions

[41:04] People-first vs process-first management

[43:06] Why surprises harm team alignment

[45:09] Stephan’s advice for new CTOs

Find your Dream CTO Job with Inkmi.

Connect with Stephan through LinkedIn.

Resources Mentioned:

Amazing CTO | Website

Turn the Ship Around by L. David Marquet | Book or Audiobook

Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

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David Wascha is a seasoned product and tech leader with experience at Microsoft, MOO, Travelex and Zoopla.



In this episode, you're going to learn when to combine product and tech leadership roles and when not to, why the distinction between tech-enabled and deep tech businesses matters for leadership structure, how to avoid tension and misalignment between product and tech teams, the importance of representing and advocating for all functions as a leader, and practical strategies for new CTOs to build trust and effectively lead cross-functional teams.

Timestamps:

[08:23] Lessons learned from mistakes at Microsoft

[11:00] Transitioning to product-focused roles

[13:45] Adopting customer-focused strategies at Microsoft

[16:10] Moving to the UK and joining MOO

[17:32] Differences in product management between the US and UK

[19:08] Expanding MOO’s product lines and markets

[20:44] First combined product and tech leadership role

[23:13] When to combine product and tech roles

[24:35] Distinguishing between tech-enabled and deep tech businesses

[25:31] Avoiding tension between product and tech teams

[27:09] Challenges with re-platforming

[29:12] Handling legacy systems and updates

[31:04] Balancing product and tech priorities

[32:27] The importance of titles and team representation

[34:16] Managing relationships with other executives

[36:25] Challenges of stakeholder management

[37:46] The cost of misalignment in leadership

[39:12] Tips for avoiding executive misalignment

[40:27] Building trust as a new tech leader

To learn more from Dave, connect with him on LinkedIn.

Resources Mentioned:

MOO | Website

Photobox | Website

Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

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In this episode, you'll learn how to streamline your recruiting process, craft compelling job ads, evaluate candidates effectively, and create an exceptional onboarding experience.



Timestamps:

[03:48] Deciding when to hire

[04:27] Importance of employer branding

[05:32] Creating a role description

[06:13] Writing a job advert

[07:09] Talent sourcing strategies

[07:56] Using recruiters effectively

[08:48] The role of headhunters

[09:48] CV screening tips

[10:22] Benefits of group interviews

[11:02] Designing coding assessments

[12:08] Architectural and standards evaluations

[12:46] Assessing cultural fit

[13:16] The pressure release test

[14:22] Crafting effective interview questions

[14:57] Using situational achievement assessments

[15:45] Typical interview stages

[16:33] Selling the role during final interviews

[17:38] Tracking candidate funnel metrics

[18:16] Scoring and benchmarking candidates

[18:59] Blind voting in group interviews

[19:56] Enhancing candidate experience

[20:45] Communicating rejection feedback

[21:52] Tools for managing recruiting processes

[22:28] Making and presenting job offers

[23:39] Engaging new hires before start date

[24:35] Structuring onboarding processes

[25:58] Leveraging probation periods

[26:54] The value of a coordinated recruiting approach

[27:34] Investing in the recruiting process

[28:04] Training teams on recruiting skills

[28:51] Defaulting to no hire when unsure

[29:20] Creating an amazing onboarding experience

Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

Join The CTO Playbook Slack Community to connect with other CTOs!

Roman Labunsky is the co-founder and CTO of an early-stage cybersecurity startup based in Israel.

In this episode, you're going to learn how Roman's experience leading a military tech unit during wartime shaped his approach to building resilient teams and processes. You will discover strategies for managing onboarding and handovers under extreme constraints, the value of starting simple to scale effectively, and why clear communication and adaptability are key to succeeding in high-pressure environments.

Roman is the CTO and co-founder of a cybersecurity startup specializing in third-party risk management. He is 40 years old, married and a father to a 2-year-old girl. Roman lives in Israel with his family and two dogs.

He has been in the tech industry for over two decades, holding various engineering roles including software developer, team lead and software architect in both startups and enterprises across the security space. Between 2017 and 2023, he served as VP of R&D for a startup in the Kubernetes security space, where he led the company through growth and eventual closure when funding ran out.

Over the past year, Roman co-founded and served as CTO of a technological military unit in the Israeli Defense Force. With the unit now firmly established, he is focusing on his startup.



Timestamps:

[03:00] Roman’s journey into tech leadership

[05:20] Building a new military tech unit

[07:35] Early challenges in a high-stakes environment

[09:56] Adapting to military operations during wartime

[12:10] Overcoming bureaucratic barriers for faster delivery

[14:54] Managing short-term volunteers effectively

[17:07] Why traditional onboarding didn’t work

[18:13] The role of documentation in smooth transitions

[20:07] Setting a two-day onboarding goal

[22:23] Standardizing processes for efficiency

[24:18] The importance of automation for rapid delivery

[26:30] Navigating bureaucracy as the war progressed

[27:54] Conducting offboarding interviews for improvements

[30:37] Challenges of leading large-scale projects

[31:54] Starting simple with team structures

[34:24] Avoiding imported processes and frameworks

[35:10] The reality of rewriting code in early startups

[36:58] Streamlining recruitment for large-scale hiring

[39:26] Balancing risk and speed in recruitment

[42:33] Choosing tools that teams will actually use

[45:07] Delegating decisions to the teams

[46:43] Fixing breakages instead of overplanning

[48:12] Importance of communication for alignment

Connect with Roman on LinkedIn.

Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.