The CTO Playbook

Join The CTO Playbook Slack Community to connect with other CTOs!Zach Goldberg is a seasoned CTO and author of “The Startup CTO's Handbook”.In this episode, you're going to learn the key lessons Zach gained from leading multiple startup engineering teams, common mistakes CTOs make when managing growth, how to build a culture of continuous learning and high performance, why external thought leadership matters for tech leaders, and much more.Zach Goldberg is an executive coach, the author of the 10k+ GitHub star book, “The Startup CTO’s Handbook” and the CTO of Gruntwork. Zach graduated from the University of Pennsylvania Magna Cum Laude with a degree in Computer Science and Engineering. He’s been the CTO of seven startups including WiFast, Sticks and Brains, AutoLotto, Trellis Technologies, GrowFlow, Towards Equilibrium Inc. and most recently Gruntwork, as well as an Entrepreneur in Residence at Tencent and an Associate Product Manager at Google.Timestamps:[01:34] Zach shares his journey from engineer to CTO  [02:47] The origins of The Startup CTO's Handbook  [05:11] Key lessons learned from managing engineering teams  [06:18] Balancing management responsibilities in growing teams  [07:39] Different challenges with various management styles  [10:22] The value of culture in retention and hiring  [12:02] Creating a culture of learning in tech teams  [13:21] Ensuring managers support learning opportunities  [15:31] Measuring coaching success with feedback loops  [17:11] Why skip-level meetings can improve transparency  [19:12] Benefits of connecting with lower-level team members  [23:05] Encouraging documentation and writing skills  [24:33] Why writing is a valuable skill for tech leaders  [27:18] Writing documentation for different user perspectives  [28:38] How consuming your own product builds empathy  [30:36] Practical examples of fostering empathy in engineering  [32:30] Zach’s advice for new CTOs entering growth organizations  [33:30] How to handle mistakes and setbacks as a leader  [34:44] Value of CTO coaching and leadership developmentWant Zach Goldberg’s advice? Book a discovery call today to get an introduction to what Executive Leadership Coaching can help you achieve.  Find Zach through The Startup CTO Coach’s Website and on LinkedIn.Resources Mentioned:The Startup CTO's Handbook by Zach Goldberg | Book or AudiobookTurn the Ship Around! by David Marquet | Book or Audiobook Extreme Ownership by Jocko Willink and Leif Babin | Book or AudiobookFind 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!Thorgeir Einarsson is a seasoned CEO and advisor who has helped hundreds of tech startups secure funding and navigate acquisitions.In this episode, you're going to learn why CTOs play a crucial role in fundraising and M&A deals, common mistakes CTOs make that can kill a deal, the importance of transparency during technical due diligence, how AI is changing the expectations for tech leaders, and why a CTO’s communication skills are as important as their technical knowledge.Thorgeir Einarsson is the founder of Elevera Advisers and has created, built and sold tech companies in Europe, the US, Asia and Africa for the last 35 years. Thorgeir co-founded Pitchago in 2020, which is an innovative SaaS platform for incubators & entrepreneurs to self-assess their startups and build a level-up action plan.Timestamps:[05:00] Introduction to Thorgeir’s background in fundraising  [06:33] Differences between M&A and raising capital  [08:01] Role of a CTO during M&A and fundraising  [09:33] Importance of preparation in fundraising  [10:10] Changes in the CTO role with AI advancements  [10:33] Should a non-founder CTO act like a founder?  [12:36] Why investors worry about non-founder CTOs  [14:34] Due diligence process explained  [15:23] What to include in a technical presentation  [16:53] Should you hide flaws during due diligence  [18:24] How startups handle imperfect technology  [20:14] Learning from past M&A deals[21:28] How a CTO can sell their vision effectively  [23:17] Focus on solving real problems with technology  [24:04] Why a CTO should communicate the company vision  [25:31] Examples of successful CTOs in M&A deals  [26:49] The importance of reading the room during negotiations  [28:49] Challenges of dealing with different tech stacks in M&A  [29:45] Why CTOs need to have a bit of attitude  [30:24] Avoiding the “not invented here” mindset  [31:59] How a CTO’s openness impacts M&A success  [33:18] Influence of a CTO in deal negotiations  [34:36] Balancing technical and business perspectives  [36:00] When is a complete technology rewrite necessary?[37:08] The evolving importance of the CTO role  [39:20] How AI is changing the software industry  [41:05] Global trends and their impact on CTOs  [43:48] Building a scenario-based product roadmap  [45:06] Preparing for uncertain market conditions  [46:00] How to decide on a major tech overhaul  [47:51] Why the CTO should work closely with the CEO  [49:59] Introduction to Pitchago’s assessment tool  [50:45] How Pitchago helps with funding readiness[52:59] How CTOs can become better communicators  Get a thorough 360-degree Pitchago Assessment of your venture in just 5 minutes for free! Find Thorgeir Einarsson on LinkedInResource Mentioned:Pitchago | WebsiteElevera Advisers | WebsiteThree Types of Online Attacks with Mikko Hypponen | TEDx TalkFighting Viruses, Defending The Net with Mikko Hypponen | TEDx TalkFind more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

In this episode, Adam talks about how to create a strong engineering strategy and prioritize creating roadmaps that align with company goals while effectively communicating your strategy to the entire team.Timestamps:[02:19] Aligning the engineering strategy with company goals  [06:00] Creating a roadmap for the engineering strategy[13:40] Building a process roadmap  [24:03] Prioritizing and executing the engineering strategy Join The CTO Playbook Slack Community to connect with other CTOs!Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

In this episode, Adam and Todd talk about why tech and product leaders need to expand their roles in today's market, why many startups struggle with tech debt and product debt, how AI is reshaping the responsibilities of engineers and CTOs, what the future holds for fractional CTO roles, and what Todd thinks about the shifting demands on tech leaders and the future of the CTO role.Todd is an experienced CPTO now doing fractional work, startup advisory, and working on his own SaaS platform. Todd offers consulting services for businesses seeking responsible growth and transformation. He is also working on a customer data platform that will unlock the true potential of AI and CRM in the new technology landscape.Timestamps:[06:19] The challenges of scaling tech teams during hypergrowth  [12:09] Why smaller teams can achieve more with the right structure   [24:18] How fractional roles fit into today’s tech leadership landscape[27:10] The evolution of the CTO role and what’s next for leaders  [37:10] The future of no-code and low-code tools [41:53] The importance of financial training for tech leaders  [45:35] Predictions for the role of CTOs over the next decadeConnect with Todd on LinkedIn. Join The CTO Playbook Slack Community to connect with other CTOs!Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

Magnus Lenngren is an engineering leader and a three-time unicorn builder.In this episode, you'll find out how to scale remote-first engineering teams effectively, the key challenges leaders face when growing teams quickly, the biggest mistakes to avoid during hypergrowth, why strong company culture is critical in scaling, and how to keep employees engaged and productive in a remote setting.Magnus is an experienced CTO and Director of Engineering, skilled at scaling engineering teams, especially in Fintech, with experience at Collector Bank, Klarna, and now Mews among others. Magnus is also an investor, having led Collector’s corporate venture capital division. Magnus is currently focused on scaling Mews’ remote engineering teams.Timestamps:[11:05] How to scale remote teams effectively  [16:28] Benefits of building a remote-first team  [22:13] Providing co-working spaces for remote employees  [35:17] Using new hires for onboarding other employees  [41:05] Applying the Conway/Yawnoc strategy to reshape teams  [46:22] Mistakes leaders make when scaling fast  [51:03] Focusing on continuous improvement over fixed metrics  [57:13] Balancing efficiency with hyper-growth challengesConnect with Magnus on LinkedIn.Join The CTO Playbook Slack Community to connect with other CTOs!Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

Zoe Cunningham, an award-winning technology professional and Director at Softwire, discusses her insights on networking. She reveals common misconceptions about networking, emphasizing its value for career growth. Zoe offers practical tips for building genuine connections, especially for introverts, and provides strategies to prepare for events. She also shares how to make networking feel less transactional and encourages a focus on nurturing authentic relationships over time. Discover how a relaxed mindset can make networking a rewarding experience.

Join The CTO Playbook Slack Community to connect with other CTOs!In this episode, Adam interviews Adem Bilican, the CTO at Relai, the App, about Bitcoin's value and its potential as a global currency. Adem discusses the technological advancements in Bitcoin, such as the Lightning Network, and offers insights into overcoming barriers to adoption.Adem Bilican, is the co-founder and CTO at Relai, Europe's number one Bitcoin app. We provide an app for your mobile phone that users can use to easily buy and sell Bitcoin while keeping full ownership.Timestamps:6:15 Improving mobile wallets to boost Bitcoin user adoption. 20:50 Using renewable energy for more efficient Bitcoin mining. 25:35 Leveraging Bitcoin’s capped supply to increase long-term value. 29:10 Introducing the Lightning Network for instant Bitcoin transactions at zero cost. 38:30 Ensuring user control with self-custodial wallets in the Relai app. 44:50 Securing your Bitcoin wallet with reliable backup and restore options.Get the Relai App to help you buy and manage your Bitcoin and follow Adem on X.Resources Mentioned:Mastering Bitcoin by Andreas Antonopoulos | Book or AudiobookMastering the Lightning Network by Andreas Antonopoulos | Book Bitcoin Nashville | WebsitePlan B Forum in Switzerland (Oct 2024) | WebsiteBitaxe Mining Device | Website 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 learn more about how to be a great CTO!In this episode, Adam discusses how CTOs can transition from firefighting to strategic leadership by following a structured, disciplined approach.Timestamps:5:19 Create time blocks for strategic work to avoid constant firefighting.9:51 Build trust by empowering your team through delegation.16:07 Focus on documenting why and how, not just what, to improve processes.23:38 Block off time for your top priority and protect it fiercely.Resources Mentioned:Michael Lopp | LinkedInFind more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.

Dipak Mistry, a senior architect with 25 years in the field, shares his expertise on technical presentations. He emphasizes the importance of storytelling and tailoring presentations to the audience. Dipak introduces his 'five S's' framework that ensures clarity and engagement. He discusses avoiding distractions by focusing on core objectives and highlights the value of templates for consistency. Overall, his insights aim to help IT professionals deliver impactful messages while aligning their presentations with business goals.

Join The CTO Playbook Slack Community to learn more about how to be a leader!In this episode, Adam interviews Carol Palombini, a psychologist and leadership coach specializing in psychological safety. Carol offers insights on how fostering psychological safety can drive team innovation and what leaders can do to create safe, effective work environments.Carol Palombini is a seasoned Psychologist and Tech Leadership Coach. Her passion lies in being a catalyst for transformation among tech leaders who face challenges such as communication issues, imposter syndrome, burnout, and the intricate demands of tech leadership roles.Timestamps:3:30 Assessing for a team's psychological safety.8:06 Foster healthy conflict for innovation and team growth.15:30 Create a psychologically safe environment by managing emotions.19:08 Conduct exit interviews to uncover reasons for talent loss.29:02 Reward and recognize behaviours that foster psychological safety.Build your dream team with personalized solutions that actually get results. Book a complimentary 30-minute call with Carol.Also, be sure to follow Carol on LinkedIn.Resources Mentioned:re:Work With Google | Archived WebsiteFind more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.