Contributors · 26
- Chase Mckee
- Christian Marin
- Jonathan Gerber
- Josh Ladick
- Gus Bartholomew
- Victor Santoro
- Volen Vulkov
- Dileep Kumar Pandiya
- Cyrus Partow
- Elisa Branda
- Joshua Odmark
- Joe Davies
- Barbara McMahan
- Michael Sumner
Q&A2024-12-09
Ever wondered how to climb the ranks to become a successful CTO? In this article, insights from seasoned Founder & CEOs and Presidents are shared to light your path. The first piece of advice emphasizes mastering reverse engineering user needs, while the last highlights the importance of harnessing the power of storytelling. Dive into these twenty-six expert insights to learn more.
Contributors · 26
Chase Mckee<Founder & CEO, Rocket Alumni Solutions>To aspiring CTOs, my advice is to master the art of reverse engineering user needs into tangible solutions. At Rocket Alumni Solutions, we invited school administrators to workshops instead of direct pitches, uncovering their challenges and boosting our lead conversion rates by 30%. Understanding your audience's core needs is invaluable.
Another key is leveraging frameworks like competitive intelligence. By analyzing competitor pricing and market trends, I orchestrated strategic negotiations to secure deals 40% above initial offers. Developing an eye for market dynamics helps you stay ahead in tech leadership.
Lastly, refine your technical and cross-functional communication skills. As a student, I juggled building a startup while at Brown University. This taught me the importance of conveying technical concepts to non-technical stakeholders. Today, having a solid grasp of both tech and business narratives is crucial for CTOs driving innovation.
Christian Marin<CEO, Freezenova>When I started FreezeNova, I learned that being a successful CTO isn't just about knowing the latest tech stack - it's about making tough decisions that balance innovation with practical constraints. Just recently, I had to choose between adopting a trending technology or sticking with our reliable stack, and what helped me most was having a deep understanding of both the business impact and technical implications. My advice is to actively seek opportunities to make strategic technical decisions, even if they're small ones, and always document your thought process and outcomes to learn from them.
Jonathan Gerber<President, RVW Wealth>As someone who manages a large financial firm, I've learned that understanding the business impact of technical decisions is absolutely critical. When we upgraded our client management systems last year, I made sure to involve both our tech team and financial advisors in the planning process, which helped us avoid costly mistakes. I suggest aspiring CTOs spend time learning financial fundamentals and practice translating technical concepts into business value - it's been a game-changer for getting buy-in from stakeholders.
Josh Ladick<President, GSA Focus>I discovered that mastering risk management was crucial when I helped small businesses navigate government contracts. Just last year, I had to quickly pivot our technical strategy when new compliance requirements emerged, saving several clients from losing their contracts. I'd recommend focusing on developing your ability to spot potential risks early and create practical backup plans - it's not just about technical skills, but about protecting your company's future.
Gus Bartholomew<Co-founder, Leafr>I discovered that the most crucial skill for aspiring CTOs isn't just technical expertise - it's being able to translate complex tech concepts into business value. When I started Leafr, I spent countless hours learning to communicate with non-technical stakeholders, which helped me secure buy-in for our sustainability initiatives more effectively than any coding skills could. From my experience building our platform, I'd strongly recommend focusing on developing your strategic thinking by taking on projects that connect technical decisions to business outcomes, even if they seem challenging at first.
Victor Santoro<Founder & CEO, Profit Leap>For aspiring CTOs looking to advance, I'd recommend honing your ability to merge diverse expertise with cutting-edge technology. With my background in both medicine and business, I've learned the importance of taking a diagnostic approach to identifying and solving business challenges. For instance, when I co-designed HUXLEY, an AI business advisor, the key was integrating real-world business insights with AI to transform small law firms' operations, leading to over 50% revenue growth year-over-year.
Focus on developing a strong framework for strategic innovation. At Profit Leap, we use the 8 Gears of Success framework to drive significant upgrades in small business processes. This involves not only adding AI tools but also realigning business models to open up exponential growth.
Lastly, always prioritize collaboration. I've started seven companies, and every successful project has hinged on fostering a culture where multidisciplinary teams work seamlessly. Your role as a CTO isn't just about tech leadership but facilitating a space where innovation thrives through collaboration and shared vision.
Volen Vulkov<Co-founder, Enhancv>When I was on my path to becoming a CTO, the most important step I took was to become deeply involved in multidisciplinary initiatives. During one such endeavor, I collaborated closely with the marketing and sales teams to introduce a new product. This event showed me the value of knowing how technology fits into corporate objectives and customer requirements.
One specific skill I worked on was improving my communication abilities. In a discussion with non-technical stakeholders, I understood how important it was to articulate technical concepts in a simple and approachable manner in order to acquire their trust and support. This skill proved crucial in moving technology ventures forward.
I urge aspiring CTOs to immerse themselves in a variety of business areas beyond technology. Seek out ways to interact with other departments and see how your technical skills may help solve larger business problems.
Dileep Kumar Pandiya<Principal Engineer, ZoomInfo>If I could share one piece of advice with aspiring CTOs, it would be this: focus on blending technical expertise with strategic thinking. It's not just about knowing the technology, it's about understanding how to use it to solve big problems and drive the company forward.
From my experience leading projects in Enterprise Technology and AI, one thing that stands out is the importance of designing systems that are not just effective today but scalable for tomorrow. For example, when I worked on re-architecting platforms to enhance data flow or integrating AI to streamline operations, the key was aligning these innovations with clear business goals. That's where the real impact lies.
Another area to focus on is collaboration. Being a CTO means working across teams, listening to diverse perspectives, and translating technical complexities into a language everyone can understand. It's a skill that takes time to develop, but it's invaluable when you're building trust and alignment with both technical teams and business stakeholders.
Lastly, never stop learning. Technology moves fast, and staying curious is essential. Dive into new areas like AI, cloud computing, or data platforms, and don't hesitate to share your knowledge. Personally, participating in think tanks, mentoring others, and contributing to industry panels has been an incredible way to stay sharp while giving back.
To grow as a CTO, focus on becoming a strategic leader who connects people, technology, and vision. Build solutions that last, nurture strong teams, and always stay open to learning.
Cyrus Partow<CEO, ShipTheDeal>As someone who's built and sold tech companies, I can tell you that being a CTO isn't just about coding anymore. When I was scaling ShipTheDeal, I learned that understanding business goals and communicating them clearly to the tech team was just as crucial as knowing the latest tech stack. I'd suggest spending time in cross-functional projects - maybe lead a major platform migration or architecture redesign - because that's where you'll learn to balance technical decisions with business needs.
Elisa Branda<Founder & CEO, NuvolediBellezza>Focus on building both technical expertise and leadership skills. In my early years, I spent too much time perfecting technical skills but overlooked communication and team alignment. One moment stands out: I was leading a project, but the team wasn't on the same page. It caused delays, and I realized I needed to explain the "why" behind decisions, not just the "how."
For aspiring CTOs, learn to simplify complex ideas for non-technical stakeholders and foster collaboration. Gain experience managing cross-functional teams, as this will prepare you to bridge gaps between tech and business needs. Also, stay hands-on with emerging technologies to make informed decisions. Balancing these areas helped me lead teams more effectively and drive results.
Joshua Odmark<CIO and Founder, Local Data Exchange>After exiting three startups and building various SaaS products, I've noticed that successful CTOs are those who can bridge the gap between complex technical concepts and business value. Last year, while working with data scientists on our AI initiatives, I realized how important it is to stay hands-on with emerging technologies while also developing your strategic thinking. My advice would be to take on projects that stretch beyond pure engineering - try leading a product launch or diving into customer feedback analysis to understand the full impact of technical decisions.
Joe Davies<CEO, FATJOE>With my experience scaling FATJOE's SEO marketplace, I've learned that technical skills alone aren't enough - you need to understand how technology drives business outcomes. Last year, I pushed myself to spend 30% of my time with our sales and customer success teams, which completely changed how I approached our platform development. My advice is to get your hands dirty in different departments - shadow your marketing folks, join sales calls, and really understand how your technical decisions impact the entire business.
In my years coaching tech leaders, I've noticed that aspiring CTOs often focus too much on technical skills while overlooking crucial people management abilities. Last month, I worked with a brilliant technical director who struggled with team conflicts until we developed his emotional intelligence through role-playing exercises and feedback sessions. I'd strongly recommend investing time in understanding different personality types and communication styles - maybe start by leading a small cross-functional project where you can practice these skills in a lower-stakes environment.
Michael Sumner<Founder and CEO, ScoreDetect.com>When it comes to advancing their careers, I would advise aspiring CTOs to focus on developing a unique blend of technical expertise and soft skills. As someone who has worked with Fortune 100 companies and managed complex software engineering projects, I've learned that being a successful CTO is not just about being a technical genius, but also about being an effective communicator and leader.
One key experience that has been instrumental in my growth as a CTO is learning to balance candor and empathy when providing feedback to team members. I've found that being transparent and honest about areas for improvement, while also showing genuine care for an individual's growth and well-being, can lead to remarkable results. By doing so, I've been able to build high-performing teams that are motivated, engaged, and empowered to take ownership of their work. My advice would be to prioritize developing this skill, as it can make all the difference in driving success and advancing your career as a CTO.
With my experience leading tech teams, I've learned that the most valuable skill for aspiring CTOs isn't just technical expertise - it's being able to translate complex tech concepts into business value for non-technical stakeholders. Last year, I started hosting monthly lunch-and-learns where our tech team presents solutions to business teams, and it's dramatically improved our project buy-in and cross-department collaboration.
During my 15 years in the fast-paced real estate market, I've learned that adaptability and quick problem-solving are absolute game-changers for any tech leader. I'd encourage aspiring CTOs to get hands-on experience with different technologies - like when we had to quickly pivot our property management system during the pandemic, it was my previous experience with various platforms that helped us make the right choice and implement it successfully.
Mike Wall<CEO, EZ Sell Homebuyers>With my background managing large-scale property portfolios, I've learned that aspiring CTOs need to master both people and project management skills, just like how I coordinate multiple renovation teams across my 31 rental properties. I'd suggest focusing on developing your strategic thinking by taking on increasingly complex projects - start small with team leadership roles, then gradually work your way up to department-wide initiatives while staying hands-on enough to understand the technical challenges your team faces.
Patric Edwards<Founder & Principal Software Architect @ Cirrus Bridge, Cirrus Bridge>My advice to aspiring CTOs is to focus on becoming not just a technology expert but a well-rounded business leader. A successful CTO must bridge the gap between technical innovation and business strategy, so cultivating both technical acumen and leadership skills is essential.
Here are key areas to focus on:
Strategic Thinking: Learn to align technology initiatives with business goals. Develop the ability to assess how technological advancements can drive value for the company and its customers.
Communication Skills: As a CTO, you'll need to articulate complex technical concepts to non-technical stakeholders. Practice simplifying technical language and aligning your messaging to the priorities of your audience.
Team Building and Leadership: Invest in people management skills. Building a high-performing, motivated team is a critical aspect of the CTO role. Learn to mentor, delegate, and create an inclusive environment that fosters innovation.
Adaptability and Continuous Learning: Technology evolves rapidly, so staying current is non-negotiable. Be proactive about learning emerging trends and understanding their potential impact.
Hands-on Experience with Scalable Systems: Gaining experience in building or managing scalable, reliable systems prepares you to handle the technical demands of a CTO role in a growing organization.
Finally, seek mentorship from established leaders in the field, as their insights can provide invaluable guidance. By combining technical expertise with strategic vision and leadership capabilities, you position yourself as a compelling candidate for a CTO role.
Justin McKelvey<Founder, SuperDupr>As someone who's steered SuperDupr through periods of significant innovation, I believe aspiring CTOs should emphasize developing an understanding of cross-functional team dynamics. Building and nurturing a diverse team at SuperDupr, where design, strategy, and technology expertise converge, has been pivotal in driving breakthroughs and learning how to leverage each team member's strengths. Focus on team empowerment and collaboration rather than tackling everything solo.
Secondly, prioritize client-focused development. At SuperDupr, customizing digital solutions according to varied client needs has been at the core of our success. When we redesigned Goodnight Law's website, enhancing the visual appeal and integrating automated communication, we saw heightened client satisfaction. Learn to listen and adapt solutions to improve client experiences-this is crucial for any tech role.
Lastly, engage frequently with emergent technologies. This doesn't mean jumping on every tech trend but ensuring that your strategies are informed by current and applicable advancements. We used AI to automate and streamline pricesses at SuperDupr with tangible benefits, like quick launches and cost savings for our clients. Understand how tech can be practically applied to real-world problems to create impactful innovation.Focus on mastering data-driven decision-making. At SuperDupr, using data to refine our processes transformed client outcomes dramatically. For example, by carefully analyzing our client's data, we optimized their marketing strategies, significantly boosting their ROI across various industries.
Another key focus is team building and leadership. I've built a diverse team at SuperDupr committed to innovation and excellence. Cultivating such an environment requires emotional intelligence and the ability to inspire, allowing the team to thrive and innovate. My experience shows that strong leadership and collaborative team dynamics are essential to success.
John Cheng<CEO, PlayAbly.AI>The tech landscape is constantly shifting, and I've found that successful CTOs need to be comfortable with ambiguity and rapid change. In my experience managing various tech teams, the most effective leaders are those who can translate complex technical concepts into business value for stakeholders. I recommend taking on projects that force you out of your comfort zone - maybe lead a technical transformation initiative or volunteer to present technical strategies to business executives.
Praveen Kumar<Founder, Wild Creek Web Studio>I've found that the path to becoming a successful CTO requires a balance between staying hands-on with coding and developing strong leadership abilities to guide your team through challenges. Looking back at my own experience, I wish I'd spent more time early on understanding system architecture and scalability patterns rather than getting caught up in day-to-day coding tasks.
Sheraz Ali<Founder & CEO, HARO Links Builder>One thing that aspiring CTOs looking to advance their careers must note is the importance of creating a strong foundation in technical and business acumen. Technology, though detailed, is understandably important; however, even more crucial is to be aligned with an overall business plan. The dual focus enables aspiring CTOs to make innovative decisions that drive innovation while also supporting the organization's goals.
To reach this position, potential CTOs will need training in very specific skills such as strategic planning, data analysis, and communication skills. Knowledge of new technologies and trends and a good understanding of project management and leadership will further serve them well. Cross-functional experience equips them well with an understanding of how various departments function and how technology can enhance their day-to-day functions.
Supplementing these activities with ongoing, continuous learning via industry conferences, online courses, and networking can further keep skills on point and relevant. In turn, the more aspiring CTOs can develop these skills and experiences, the better qualified they will be to lead strong teams and contribute much to their organizations' success.
Gregory Rozdeba<CEO, Dundas Life>At Dundas Life, I've found that the most valuable skill isn't just technical knowledge - it's being able to translate complex tech concepts into business value for stakeholders and investors. I learned this firsthand while securing our venture capital funding, where explaining our insurtech platform's capabilities in clear, business-focused terms made all the difference.
Shehar Yar<CEO, Software House>One crucial piece of advice I would give to aspiring CTOs is to prioritize building a deep understanding of both technology and business strategy. As a CTO, it's not enough to just be technically proficient. You need to be able to bridge the gap between tech and business goals, ensuring that technology decisions align with the company's overall objectives. Cultivating a strategic mindset alongside technical expertise will set you apart as a leader who can drive innovation and deliver impactful results.
In addition to technical skills, aspiring CTOs should focus on developing strong leadership abilities, such as effective communication and team-building. Leading a tech team requires more than just managing projects; it's about inspiring and empowering your team to innovate and execute. Gaining experience in managing cross-functional teams, understanding product development cycles, and staying adaptable to the ever-changing tech landscape will also provide invaluable insights for any aspiring CTO.
Dhari Alabdulhadi<CTO and Founder, Ubuy New Zealand>Aspiring CTOs should concentrate on developing their technical know-how and leadership abilities. An effective CTO has to understand business strategy and how technology creates value in addition to having extensive technical understanding. To close the gap between stakeholders and technical teams:
Cultivate effective communication abilities.
Get practical experience in project management, scalable system development, and innovation promotion.
Keep up with new developments in technology while developing your emotional intelligence to motivate and guide groups.
In the end, a CTO's influence is determined by their capacity to match technology with organisational objectives and enable their teams to produce outstanding outcomes.
Dr. Kyle Elliott<Founder & Tech Career Coach, CaffeinatedKyle.com>Storytelling skills are critical for CTOs who are looking to advance in their leadership careers. While many technical leaders must convey complex topics to both technical and non-technical audiences, CTOs who want to truly excel must harness the power of storytelling to gain buy-in.
Notably, storytelling can be a difficult skill for CTOs to master, as it often feels contradictory to the right-or-wrong answers they learned in their technical backgrounds. However, leaning into the art of storytelling can set them up for long-term success as they share their ideas and vision with employees, executive peers, investors, and boards.
Lastly, understanding the technology market's dynamics is crucial. At SuperDupr, strategic partnerships with leading tech providers expanded our offerings and diversified our portfolio. Aspiring CTOs should proactively seek out partnerships and be adaptive to market changes to maintain a competitive edge.
