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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 development
Want 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 Audiobook
Turn the Ship Around! by David Marquet | Book or Audiobook
Extreme Ownership by Jocko Willink and Leif Babin | 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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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 LinkedIn
Resource Mentioned:
Pitchago | Website
Elevera Advisers | Website
Three Types of Online Attacks with Mikko Hypponen | TEDx Talk
Fighting Viruses, Defending The Net with Mikko Hypponen | TEDx Talk
Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.
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Saknas det avsnitt?
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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.
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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 decade
Connect 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.
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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 challenges
Connect 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.
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Zoe Cunningham is a director at Softwire and author of Networking Know-How.
In this episode, you will learn what most people get wrong about networking and why it’s so misunderstood. Zoe talks about simple ways to build genuine connections without feeling awkward, how introverts can excel at networking with the right approach, how to prepare for networking events to make them more enjoyable, and why investing in networking now pays off in the long run.
Zoe Cunningham is an award-winning technology professional and currently a Director of Softwire Technology, voted the #1 Best Place to Work in the UK 2023. She won Business Leader of the Year at the UK Women in IT Awards 2019 and has been selected by the BBC as the Brightest Woman in Britain.
Zoe has published three books, including "Networking Know-How" the tech leaders’ handbook for building a network and extending their professional reach.
Timestamps:
[05:09] Why networking is often misunderstood
[07:59] How to build genuine one-on-one connections
[10:33] Why networking is crucial for career growth
[13:54] Misconceptions about elevator pitches
[16:41] How to make networking less transactional
[24:06] Tips for boosting confidence at networking events
[27:22] Easy phrases to break the ice during networking
Check out Zoe’s book “Networking Know-How” and find her on LinkedIn.
Join The CTO Playbook Slack Community to connect with other CTOs!
Resources Mentioned:
CTO Craft | Website
Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.
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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 Audiobook
Mastering the Lightning Network by Andreas Antonopoulos | Book
Bitcoin Nashville | Website
Plan B Forum in Switzerland (Oct 2024) | Website
Bitaxe Mining Device | Website
Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.
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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 | LinkedIn
Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.
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Join The CTO Playbook Slack Community to learn more about how to be a great CTO.
In this episode, Adam interviews Dipak Mistry, a senior architect with 25 years of experience. Dipak shares his structured approach to presentations, emphasizing the importance of storytelling, conflict and resolution, and a clear narrative to make technical information more relatable and engaging.
Dipak Mistry helps small, medium and corporates business's grow and become efficiently sustainable by aiming to deliver value and achieve each business's mission. Dipak delivers a Technology Presentation Training Program that helps IT Professionals elevate their careers and in turn give great presentations that is specialized for different audiences.
Timestamps:
5:27 Know your audience to tailor the presentation effectively.
13:04 Build presentations with consistency for easier decision-making.
19:51 Focus on the key objective of the presentation to avoid distractions.
27:39 Use a structured framework to create clear and impactful presentations.
33:12 Get pre-approval from stakeholders to streamline decision-making.
Visit the Unity Edge Website and follow Dipak on LinkedIn.
Resources Mentioned:
The Golden Circle by Simon Sinek | Ted Talk
Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.
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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 Website
Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.
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Join The CTO Playbook Slack Community to learn more about the five-step playbook!
In this episode, Adam dives into the challenges of transitioning from a technical leader to a strategic CTO, outlining a five-step playbook to help navigate this journey successfully. He also shares insights on overcoming common obstacles and embracing a leadership mindset.
Timestamps:
8:45 Make fewer decisions by delegating responsibilities.
12:33 Adopt a learning mindset for your new role.
18:47 Learn the language of the business to succeed.
27:35 Empower your team by stepping back from technical details.
Resources Mentioned:
Crossing the Chasm by Geoffrey A. Moore | Book or Audiobook
What Got You Here Won't Get You There by Marshall Goldsmith and Mark Reiter | Book or Audiobook
Turn The Ship Around! by L. David Marquet | Book or Audiobook
The Five Dysfunctions of a Team by Patrick M. Lencioni | Book or Audiobook
The CTO Playbook episode on The 2 Most Critical Components of a CTO Career with Andy Skipper | Spotify or Apple
Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.
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Join The CTO Playbook Slack Community to learn more about empathic, dynamic reteaming!
In this episode, Adam interviews Daniel Walters, a seasoned CTO coach and consultant. Daniel shares his experiences on leading change within organizations, focusing on collaboration, dynamic reteaming, and the emotional impact of restructuring.
Daniel Walters is a Technology Strategy Consultant and CTO coach based in Auckland, New Zealand. With over 25 years of experience in technology leadership across various sectors, he specializes in systems thinking, technology strategy, and situational leadership.
Daniel has held leadership roles, including CPTO at Weirdly and CTO/CIO at Seek Asia, and has consulted for notable organizations like Kiwi Rail and New Zealand Super Funds. While in Malaysia he successfully established a development centre for Experian Marketing Services. He was part of a small team at Prestariang that won a concession to replace Malaysia's immigration systems nationally (MYR8.6bn). He also helped integrate JobsDB and Jobstreet into Seek to successfully fend off global competitors whilst raising the quality of product experiences for candidates and hirers.
Daniel started his career in his hometown of Melbourne, Australia where he was part of Hitwise' leadership that oversaw growth and eventual sale (USD240m). His blog 'Great CTOs Focus on Outcomes' is dedicated to supporting CTOs' success.
Timestamps:
4:15 How to use empathy to lead change effectively.
10:05 Strategies for CTOs' to implement dynamic reteaming successfully.
15:22 Why internal hiring is crucial for fostering innovation.
20:48 Leveraging team identity to boost morale and performance.
26:11 The 90-day strategy for assessing organizational needs.
32:34 How to avoid common pitfalls in restructuring as a CTO.
39:19 Why empathy should drive your leadership decisions.
To get more tips check out Daniel's Blog: Great CTOs Focus on Outcomes on Substack and connect with Daniel on LinkedIn.
Resources Mentioned:
Six Simple Rules by Yves Morieux and Peter Tollman | Book or Audiobook
Team Topologies by Matthew Skelton and Manuel Pais | Book or Audiobook
Domain-Driven Design by Eric Evans | Book
Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.
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Join The CTO Playbook Slack Community to learn more about startups and scale ups!
In this episode, Adam interviews John Broome, a seasoned product leader with over 20 years of experience. John shares insights on generative AI, collaboration between CTOs and CPOs, and the importance of being customer-centric in product management.
John Broome is a product and operations practitioner having worked in customer service, development, sales, marketing and project management for the past 20 years. Spending most of his time managing products and UX leadership throughout finance, gaming, e-commerce and now hospitality. John is currently the CPO and COO at Chico Hotel Solutions in Stockholm, helping hotels to increase revenues, reduce costs and improve their guest experience.
Timestamps:
3:39 Bridging the gap between business goals and product strategy.
10:46 Prioritizing customer needs over what they say they want.
16:33 Constructing effective teams despite budget constraints.
24:56 Collaborating to avoid idle engineers and wasted resources.
33:33 Balancing the capacity for product and technical development.
38:08 Leveraging generative AI as a tool, not a replacement.
51:01 Holding product managers accountable for prioritization decisions.
Connect with John on LinkedIn
Resources Mentioned:
Chico Hotel Solutions | Website
Find more from Adam on LinkedIn and YouTube and check out Adam's CTO coaching company Synova Tech.
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If you are finding this podcast helpful, please rate and review so other CTO's can join the conversation.
In this episode, Adam explores the different types and stages of a CTO's journey, offering insights and practical strategies to help you identify your strengths and align with your organization's needs.
Timestamps:
3:15 Understand the stages of CTO growth.
4:30 Determine what type of CTO your organization needs now.
7:20 Assess your strengths and weaknesses using a SWOT analysis.
10:24 Identify the gaps between your skills and organizational demands.
13:06 Consider coaching and feedback to accelerate your growth.
Resources Mentioned:
The Startup CTO's Handbook by Zach Goldberg | Book
The Unicorn CTO: Daniel Jarjoura's Startup CTO Growth Cycle | Website
SaaS Academy | Website
Realforce | 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, Adam speaks with Andy Skipper, the founder of CTO Craft and a seasoned CTO coach. Andy delves into the benefits of coaching for new CTOs, the growth of the CTO Craft community, as well as offers advice for navigating leadership challenges.
CTO Craft helps thousands of CTOs and Senior Engineering Leaders build skills, experience and resilience, to survive the pressures and demands of the most senior technology role in modern business, as well as provide real commercial impact within their organizations. CTO Craft helps both new and experienced CTOs by providing a safe space for learning and growth among one of the largest peer networks of senior engineering leaders in the world.
Alongside the free community, they help hundreds of CTOs through private mastermind Circles, one-to-one CTO coaching, conferences and other resources. The CTO Craft mission is to increase the success of technology-enabled startups and scale-ups by providing CTOs with the skills and support they need.
Prior to coaching and mentoring new leaders, Andy held CTO roles at Made.com, Comic Relief, and interim roles at dozens of companies such as JustPark, Intu, Threads Styling, Living Maps, Spyscape, VONQ and The School of Life, and has advised and invested in several massively successful businesses in the UK, as well as many VC firms and accelerators.
Timestamps:
3:00 Addressing leadership gaps through coaching.
10:36 Emotional intelligence improvements in personal life.
16:39 Convincing CEOs about coaching benefits.
20:28 Value of external mentoring groups.
24:03 Networking opportunities at CTO events.
29:11 Managing personal expectations in leadership roles.
31:50 Importance of CTOs focusing on the first team.
Stay connected with Andy on LinkedIn
Resources Mentioned:
CTO Craft | Website
CTO Craft Events | Website
CTO Craft | YouTube
Patrick Lencioni's Books | Amazon
Find more from Adam on LinkedIn and YouTube.
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In this episode, Adam interviews Warren Beazley, a seasoned CTO recruiter, about how tech leaders can effectively communicate their professional identity and attract ideal clients. Warren shares insights into leveraging LinkedIn for networking, strategic job searching, and the importance of personal branding.
Based in the UK, Warren is one of the best CTO recruiters, even going by the tagline "The CTO Recruiter". Warren has been hiring CTOs since 1997 and has an extensive network, a proven methodology, and a desire to help. He has hired against every brief he has had since 2015!
Connect with Warren on LinkedIn and book a 15 min Intro Call!
Resources Mentioned:
Edison Hill Search | Website
Find more from Adam on LinkedIn and YouTube.
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In this episode, Adam interviews Steven Renwick, who dives deep into the relationship between the CEO and CTO in early-stage startups. Steven shares his journey with Adam at Satago, emphasizing the importance of vision alignment and efficient software deployment.
Steven Renwick is a British technology entrepreneur living in Berlin, with a unique combination of experience in healthcare, fintech and technology. He is a product-focused CEO/founder with a passion for building businesses that actually make a difference in people's lives. In an earlier life, he started out working as a consultant in the pharmaceutical and biotechnology industry, advising on IP valuation, deal structuring, and M&A.
In November 2021 he co-founded Tilores, a start-up that specializes in helping tech scale-ups to radically transform their data infrastructure efficiency using Tilores, their entity resolution technology, while dramatically cutting prototyping time and decreasing operating costs. With Tilores, scale-ups can achieve unlimited processing scalability without adding a single machine or headcount to the tech budget.
Steven founded Satago in 2012 to help SMBs use technology to improve credit control and cash flow, before pivoting the company into a fintech business providing invoice finance through software. He raised ~£5M (debt & equity) to develop the business from VCs and Angels and grew the team to 16 people. He exited Satago in 2017. The company is currently listed on the Alternative Investment Market (AIM) in London.
Connect with Steven on LinkedIn
Resources Mentioned:
Tilores | Website
Satago | Website
Palantir | Website
GraphQL | Website
Find more from Adam on LinkedIn and YouTube.
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Welcome to the CTO Playbook! I'm Adam Horner, your host, with over 30 years in the tech industry and more than a decade as a CTO. In this podcast, we cover essential topics, strategies, and practical advice to help CTOs excel. Join me as we explore my journey, share insights from industry leaders, and build your unique CTO playbook. Whether you're navigating the rapid changes in technology or handling growing responsibilities, you're not alone. Tune in for valuable resources, community support, and expert interviews.
In this episode, Adam shares his journey to becoming a CTO, the challenges he faced, and the reasons for starting this podcast. He also emphasizes the importance of building a personalized CTO playbook and the evolving role of the CTO.
Resources Mentioned:
Synova Tech | Website
Find more from Adam on LinkedIn and YouTube.
