The CTO Playbook

Ritavan is a machine learning expert, author of Data Impact, and has worked in industries such as banking, energy, and real estate.Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.In this episode, you're going to learn how to avoid complexity traps in data-driven decision-making, how to leverage unique advantages to create real business value, why alignment across teams is critical for success, the importance of simplifying processes to reduce inefficiency, and the role of data in driving growth while maintaining focus on customer needs.Ritavan is an entrepreneurial technology leader with a decade of experience focused on data-driven business impact. He has authored peer-reviewed papers, given invited talks at global conferences, and holds an international patent. Known for his first principles approach to building and scaling data-driven solutions across industries, Ritavan combines deep technical expertise with strategic vision and an execution-focused mindset. His latest book offers actionable insights to accelerate data-driven impact for non-software native businesses.Timestamps:[00:00] Introduction[06:30] Working with large volumes of data in diverse fields[07:45] The challenge of scoping problems in the real world[09:00] Lessons learned from his time at Societe Generale[10:25] Identifying and solving real-world problems in data[11:40] Impact of working in high-stakes environments like energy markets[12:55] The importance of owning P&L in business[14:05] Ritavan’s journey into real estate technology and venture capital[15:35] Scaling businesses from seed to post-series B[16:45] The challenge of growing in legacy businesses[17:50] A different approach to solving problems in traditional industries[19:05] The role of technology in modern businesses[20:15] Defining leverage and its role in business growth[21:35] Aligning teams for maximum impact[23:00] How military strategies inform business alignment[24:25] The power of clarity in decision-making[25:40] How to use data to drive alignment across teams[26:50] Simplifying processes to avoid overcomplication[28:10] The need for refactoring systems at every level[29:25] Avoiding complexity and streamlining operations[30:30] The risk of inefficiency when complexity builds up[31:45] How simplification leads to better optimization[32:50] The importance of optimizing after simplifying[34:05] Iterative optimization in business processes[35:15] Building an empirically valid model of your business[36:30] Balancing stochasticity and regularity in decision-making[37:40] The importance of continuously evolving business strategies[39:00] Why satisficing is suboptimal and how to avoid it[40:20] The need to maximize every opportunity for growth[41:35] Transitioning from a scarcity to an abundance mindset in business[42:50] The difference between industrial and data-driven paradigms[44:05] How airlines are an example of using data for customer loyalty[45:15] Why traditional models in energy markets need rethinking[46:30] Case study: Octopus Energy’s approach to consumer involvement[47:50] Streamlining processes for customer involvement and efficiency[49:00] Importance of leveraging data for more efficient consumption[50:10] Rethinking industries by going back to first principles[51:25] Why businesses must evolve with modern tools and technology[52:40] Maximizing impact through data-driven business strategiesIf you want to stop being just a consumer of AI products and start being a producer of data impact to delight your customers and grow revenue profitably, pre-register for Ritavan’s new book, Data Impact.Follow Ritavan on LinkedIn.Resources Mentioned:Data Impact by Ritavan | WebsiteThe Collapse of Complex Societies by Joseph Tainter | Book or AudiobookWhat Your Business Can Learn From Peter Drucker | ArticleFind more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

Daniel Jarjoura is the Managing Director at Avolta, specializing in helping engineering-led companies prepare for mergers and acquisitions.Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.In this episode, you'll learn the importance of building products that solve broad problems for developers, how to use open source as a growth tool while monetizing through premium services, why GitHub metrics can help predict future success, how to scale from a developer-led market to enterprise sales, and the 18-24 month process to plan for a successful M&A exit.Daniel Jarjoura specializes in 'developer-first' companies, open source, AI, cloud, infrastructure and cybersecurity. Prior to his current role, Daniel served as a CTO advisor for four years and founded The Unicorn CTO, a community and leadership training program dedicated to CTOs. A software engineer by training, Daniel began his career managing tech, product and support teams before transitioning into entrepreneurship. Over the last 12 years, he launched two companies: Startup42, one of France’s first tech startup accelerators, and H2 Innovate, an innovative platform offering on-demand expertise. Additionally, Daniel founded and directed the entrepreneurship department at EPITA, a leading software engineering school in France, for ten years.Timestamps:[00:00] Introduction[05:00] Startup42: A tech startup accelerator for engineers[07:00] Challenges faced by engineer-led startups[09:00] Business model for Startup42[12:05] Lessons learned when transitioning to a second company[14:00] Shifting towards advisory work for CTOs and developers[16:00] Due diligence and M&A transactions in small cap companies[19:00] The importance of scaling to enterprise sales[21:10] Developer-first companies and the importance of solving broad problems[24:00] Evaluating market demand and finding alternatives[26:10] The difference between developer-first and VC-compatible companies[29:00] How to determine if your company is ready for VC funding[31:00] Open source as a tool for growth[36:05] The evolution of open source and its business model[39:00] The challenges of scaling developer-first companies[42:00] How to approach sales in a developer-first startup[44:30] Scaling from selling to developers to selling to enterprises[47:00] How cultural differences affect sales strategies in the US and Europe[50:00] How to position your company for an exit[52:00] The importance of getting noticed by the right acquirers[54:10] Strategies for attracting M&A attention[56:00] The 18-24 month preparation for a successful M&A exitConnect with Daniel on LinkedInResources Mentioned:The Unicorn CTO | WebsiteGitHub | WebsiteGitLab | WebsiteMongoDB | WebsiteAngelList | WebsiteDatadog | WebsiteH2 Innovate | WebsiteStartup42 | LinkedInEPITA | WebsiteFind more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

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.Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.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 startupsFollow Dr. Georgios Christou on LinkedIn to learn more.Resources Mentioned:The E-Myth Revisited by Michael E. Gerber | Book or AudiobookFind more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

Stephan Schmidt is a CTO coach and the author of “Amazing CTO”.Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.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 CTOsFind your Dream CTO Job with Inkmi.Connect with Stephan through LinkedIn.Resources Mentioned:Amazing CTO | WebsiteTurn the Ship Around by L. David Marquet | Book or AudiobookFind more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

David Wascha is a seasoned product and tech leader with experience at Microsoft, MOO, Travelex and Zoopla.Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.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 | WebsitePhotobox | WebsiteFind more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

Discover essential strategies for streamlining your recruiting process. Learn how to create compelling job ads, evaluate candidates effectively, and design an outstanding onboarding experience. Explore the importance of employer branding and the role of headhunters. Gain insights into group interviews and coding assessments. Get tips on enhancing candidate experience and communicating rejection feedback. Uncover the value of a coordinated recruiting approach and training teams on effective hiring skills.

Roman Labunsky is the co-founder and CTO of an early-stage cybersecurity startup based in Israel.Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.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 alignmentConnect with Roman on LinkedIn.Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

In this episode, it’s a CTO Christmas Tale! You'll learn the importance of steady leadership, how to manage tech debt effectively, the risks of rushing features, and why balanced teamwork leads to success.Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.Timestamps:[00:50] Two CTOs prepare for a funding race  [01:34] Rallying the team with bold demands  [02:13] Adopting a steady approach with a coach’s advice  [02:52] Rushing features led to technical chaos  [03:29] AI assistant mocks poor planning  [04:04] Team fixes festive tech mishaps  [04:35] Holiday hackathon fails disastrously  [05:21] Leadership inspires calm and efficient teamwork  [05:58] Demo glitches with embarrassing bugs  [06:30] Smooth presentation wins investor funding  [07:28] Reveals coach’s lessons for steady progress  [08:24] Both CTOs learn valuable leadership lessons  Find more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

Alena Ipanova is an expert in cultural intelligence and intercultural leadership.Build your own CTO Playbook at www.theCTOplaybook.com — the leadership platform built for the full CTO journey. Coaching, podcast, and community to help you lead with clarity, confidence, and strategic impact.In this episode, you're going to learn what cultural intelligence is and why it matters for CTOs, how to assess and improve self-awareness as a leader, ways to bridge cultural differences within global teams, strategies for adapting communication styles effectively, and the importance of continuous learning and feedback in fostering inclusivity and collaboration.Alena is an Intercultural Leadership and Team Development Trainer and Coach. She helps leaders and teams develop Cultural Intelligence, build inclusive workplaces, and create high-performing teams.With 15 years of experience and a background in psychology, coaching, and intercultural leadership, Alena combines research with best practices from her work across industries. Her goal is to support leaders and teams in developing a global mindset and an inclusive company culture.Alena’s work is centred on her clients' real needs. She aims to provide solutions that continue to help them long after each project ends. Alena approaches diversity, equity, and inclusion (DEI) by considering not only visible differences but also cognitive diversity, psychological safety, and practices that promote a sense of belonging and teamwork.In her personal life, Alena is an adventurous traveller and curious learner, always interested in people and cultures. She lives with her family in a new country each year.Timestamps:[03:00] What cultural intelligence means[05:10] Misconceptions about cultural differences[07:15] Challenges of working in multicultural teams[09:25] Why self-awareness is essential for leaders[12:40] How feedback improves self-awareness[15:30] Common pitfalls in cultural leadership[17:45] Differences between personal and organizational norms[20:20] Signs of poor cultural awareness in teams[22:50] Simple exercises for self-assessment[25:15] How the global disk assessment works[27:30] Bridging communication gaps in diverse teams[29:50] How team culture mapping improves dynamics[32:05] Building relationships through informal check-ins[34:15] Why curiosity matters in cultural intelligence[36:20] Adapting communication styles to different contexts[38:10] How to improve team meetings with better questions[40:05] Practicing and unlearning old communication habits[42:30] Importance of leaders modelling inclusive behaviour[44:15] Encouraging curiosity in diverse teams[45:45] How to leverage cultural diversity for better outcomesIf you would like to connect with Alena you can book a call with her and follow her on LinkedIn.Resources Mentioned:Cultural Intelligence | WebsiteFind more from Adam on LinkedIn and YouTube, and explore coaching, cohorts, and how you can stay up to date at theCTOplaybook.com, helping you build your own playbook for your path at your pace.

Adrian Stanek, a seasoned CTO and leadership mentor with 24 years in tech, shares invaluable insights on effective leadership. He discusses the four key traits that make a leader worth following, emphasizing the importance of credibility and vision. Adrian highlights common pitfalls new leaders face, such as dictating deadlines, and stresses the value of enabling teams rather than commanding them. He also explores the evolving dynamics of leadership in the IT sector and the impact of hybrid work environments on team collaboration.