From Hackathon Hacker to SaaS Startup CTO: Lessons from a 3-Year Journey
Three years ago, I was a passionate software engineer who loved spending my weekends at hackathons, furiously coding away alongside other developers and designers to build something cool in 24 caffeine-fueled hours. I never imagined those experiences would be the foundation for my journey to becoming the CTO of a venture-backed SaaS startup with 20 employees.
In this post, I‘ll share an inside look at how I went from participating in hackathons for fun to leading the technical vision and development of a fast-growing software company. I‘ll highlight the challenges I faced at each stage, the valuable lessons I learned along the way, and my advice for other developers considering making the leap into entrepreneurship.
As an engineer, I know how important concrete examples and hard data are, so I‘ll dig into the technical details of our stack and development process, and share some of the key metrics that illustrate our progress. Let‘s dive in!
Hackathons: More than Just Coding for Fun
Like many developers, I started participating in hackathons as a way to learn new technologies, collaborate with other coders, and build exciting, if sometimes impractical, projects. It was a great way to challenge myself and unleash my creativity in a short burst. But I quickly realized that hackathons offer a lot more than just a fun coding experience – they can be a fantastic training ground for entrepreneurship.
In my first few hackathons, my teams and I made a lot of rookie mistakes. We would spend too much time trying to perfect the code and not enough time validating the actual problem we were trying to solve. We would get caught up in technical minutiae and lose sight of the big picture. And we would neglect investing in our final presentation, failing to tell a compelling story to the judges.
The result? We would consistently lose to teams that had a clearer understanding of the target user, the market opportunity, and the value proposition of their project. They may not have had the shiniest tech, but they nailed the fundamentals of pitching a viable business idea. That was an eye-opening lesson.
After a few disappointing finishes, I started to approach hackathons differently. Rather than jumping straight into coding, our team would spend the first few hours of the competition doing customer research and market validation. We interviewed other participants, dug into competitor products, and refined our concept. Only after we had convincing data that we were solving a real problem would we start building.
This approach paid off – we took first place at our next hackathon with a tool that automated a cumbersome process for developers. The judges praised our focus on a clear target user and our compelling demo. Most importantly, the experience gave me the confidence that I could identify a meaningful problem, validate a solution, and execute on an MVP – the core skills needed to found a startup. I was hooked.
From Nights & Weekends to Full Time
After a few more promising hackathon projects, I decided to pursue entrepreneurship more seriously. I teamed up with a few friends to apply to a local startup incubator program. To my surprise and excitement, we were accepted!
Over the next 3 months, we went through a crash course in Lean Startup methodology and B2B SaaS fundamentals. We learned how to:
- Conduct effective customer interviews and synthesize insights
- Define a target market and articulate a clear value proposition
- Identify and test a Minimum Viable Product (MVP)
- Design experiments to validate key business model assumptions
- Create a realistic financial plan and pitch to investors
One of our biggest takeaways was that successful startups are built through a continuous cycle of iteration and experimentation. You have to be willing to put your ideas out there, gather data and feedback, and adapt quickly based on what you learn. Clinging to your original vision in the face of contradictory evidence is a recipe for failure.
We applied this learning by completely pivoting our initial idea based on customer feedback. While our original plan was to build a developer productivity tool, our research revealed that the market was already saturated with similar solutions. However, we uncovered a bigger, more painful problem that companies were facing: managing and scaling cloud infrastructure, especially for Kubernetes deployments.
We decided to focus on building a DevOps automation platform to tackle this opportunity. We prototyped a solution and started testing it with early design partners. The results were promising – users were able to automate routine tasks 5x faster with our platform. We knew we were onto something.
Over the next 6 months, we continued to iterate on the MVP, gathering more feedback and refining the core features. We built a waitlist of eager customers. And we raised a small pre-seed investment to help us make the leap to full-time on the startup. It was an exciting, intense period with many ups and downs, but we believed deeply in the potential impact of our vision.
The Challenges of Scaling
After launching our SaaS platform publicly, we started to gain some early traction, with a few big enterprise customers and a growing number of individual users. But we knew that to fully capitalize on the opportunity, we needed to scale our team and product quickly.
Raising our $3M seed round was a huge milestone that allowed us to build out our engineering, marketing, and sales teams. But it also came with high expectations and pressure to execute. I had to rapidly level up my skills in areas like:
- Technical architecture and systems design
- Engineering team management and development processes
- Product strategy and roadmapping
- Cross-functional leadership and communication
On the technical side, I learned that my experience building isolated projects at hackathons was very different from designing and shipping a production-grade SaaS platform. Scaling our system to handle thousands of users and terabytes of data required careful consideration of factors like:
- Service-oriented architecture to support new feature development
- Horizontal scalability to handle spiky workloads
- Distributed data stores to manage high read/write throughput
- Comprehensive monitoring and automated failure recovery
- Security and compliance for enterprise customers
We decided to standardize on a modern cloud stack, including:
- Kubernetes for container orchestration
- Istio for service mesh and traffic management
- Prometheus and Grafana for metrics and alerting
- ELK stack for log aggregation and analysis
- HashiCorp Vault for secrets management
By leveraging open-source and managed cloud services wherever possible, we were able to focus on building differentiated features and creating customer value. But we also had to be disciplined about:
- Automated testing and continuous integration to maintain quality
- Trunk-based development to support frequent, incremental releases
- Managing technical debt and refactoring proactively
- Baking security and reliability into the development process
Alongside the technical challenges, I discovered that people management and leadership were equally important – and equally challenging. Interviewing, onboarding, and training new engineers was a significant time investment. I had to balance giving clear direction and feedback with empowering individual autonomy and growth. Building a culture of psychological safety, open communication, and continuous improvement was critical.
Over time, a few key principles emerged that helped us scale successfully:
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Hire the best talent and give them hard problems to solve. Smart, driven people are the foundation of any great company.
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Foster a culture of experimentation and learning. Encourage risk-taking and treat failures as opportunities to improve. Celebrate the wins.
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Align everyone behind a shared vision and clear priorities. Communicate the "why" behind decisions and get buy-in.
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Continuously gather customer feedback and let it guide your product roadmap. Don‘t get attached to ideas that aren‘t delivering real value.
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Invest in automation and tooling to maintain developer velocity. Empower engineers to make data-driven architecture decisions.
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Balance short-term execution with long-term technical strategy. Set ambitious goals but adapt based on changing needs.
The Secrets of SaaS Success
Besides building a great product, I learned that there were a few other key drivers of success for a B2B SaaS company:
- Nailing Product-Market Fit:
Perhaps the most important factor was achieving strong product-market fit. This meant having a deep understanding of our target customers, their needs, and their willingness to pay. It required constant experimentation and iteration to find the right set of features that delivered real value.
Some key metrics we tracked obsessively:
- Activation rate: % of signup up who became active users
- Weekly active usage: level of engagement with key product features
- NPS: customer satisfaction and likelihood to recommend
- Logo churn: % of customers who quit each month
Through continuous user research and product analytics, we honed in on the core job-to-be-done for our personas and built the simplest possible workflow to solve it. Some tactics that worked well:
- Interviewing churned customers to diagnose points of friction
- Analyzing heatmaps and user recordings to optimize key flows
- Offering 1:1 onboarding and implementation consulting
- Identifying and building for power users and champions
- Achieving Negative Churn:
Acquiring customers is great, but retaining and growing them is even better. We knew that the most successful SaaS companies had negative revenue churn – their existing customer base was growing faster than churn, without adding any new customers.
To get there, we focused on:
- Building sticky features that increased the switching cost
- Offering incredible customer support to drive loyalty
- Expanding usage within accounts through cross-selling and upselling
- Leveraging a land-and-expand model to grow deal sizes over time
Some of our best performing growth initiatives included:
- Launching an on-demand training platform
- Tiered pricing based on feature and usage-level
- Automated triggered emails to activate free trial users
- In-product guides and walkthroughs for key workflows
- Investing in customer success managers for high-touch onboarding
- Creating Network Effects:
For a SaaS platform like ours, there were powerful network effects that we could harness to create winner-take-most dynamics. By building a large community of customers, we could:
- Accelerate the learning and improvement of our product
- Facilitate the creation and sharing of best practices
- Provide social proof and credibility to new potential customers
- Source high-quality referrals and word-of-mouth
Some of the community-building activities we invested in:
- Launching an online forum and Slack group for customers
- Hosting regional meetups and an annual customer conference
- Sponsoring and speaking at popular industry events
- Publishing thought leadership content on our blog and newsletter
- Contributing to relevant open source projects and standards
Never Stop Learning
If there‘s one thing I can attribute my personal growth and our startup‘s success to, it‘s having a mindset of continuous learning. The skills and knowledge that allowed me to be a productive hackathon participant were just the tip of the iceberg compared to what I needed to lead the development of a venture-scale SaaS company.
Some of my most valuable learning resources have been:
- Online courses & certifications (ex: Linux Academy, A Cloud Guru)
- Technical books and whitepapers (ex: Site Reliability Engineering, Designing Data-Intensive Applications)
- Podcasts (ex: Software Engineering Daily, This Week in Startups)
- Local meetups and workshops (ex: DevOpsDays, CTO School)
- Peer mentors and advisors with domain expertise
- Open source communities (ex: Kubernetes, Istio, Prometheus)
Perhaps more than any specific skillset, the meta-skill of being able to rapidly acquire new knowledge and adapt to a changing environment has been my secret weapon. It‘s what allowed me to:
- Replatform our backend from Rails to Elixir to improve concurrency
- Implement CI/CD best practices to ship changes multiple times per day
- Migrate our data pipeline from batch to streaming for real-time insights
- Learn enough UX design to step in when we were short-staffed
- Develop financial models to forecast our cash flow and runway
Beyond expanding my own capabilities, I believe that one of my most important responsibilities as a technology leader is to create an environment that enables my team to constantly learn and grow as well. Some initiatives that have worked well for us:
- Investing in a substantial learning & development budget for every employee
- Hosting regular internal tech talks and demos to share knowledge
- Offering formal mentorship and career coaching
- Supporting and rewarding open source contributions
- Celebrating productive failures and learnings in blameless post-mortems
No matter how large the company grows, I never want to lose that scrappy hackathon spirit of enthusiastically diving into new domains, collaborating with customers to solve hard problems, and fearlessly embracing the unknown. It‘s what keeps me engaged and fulfilled in my work.
Key Takeaways
For any developers out there who dream of launching your own successful software company, here are a few key pieces of advice, based on my journey:
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Participate in hackathons to build your skillset and test new ideas. Focus on customer validation as much as technical execution.
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Leverage an incubator or accelerator to pressure-test your business model and get access to mentors, investors, and early customers.
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Embrace pivots and iteration. Your first idea probably won‘t be the one that succeeds. Keep talking to users and let the data guide you.
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Pick technologies and architectures that will scale with your business. But don‘t overengineer for problems you don‘t have yet.
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Invest in automated testing, monitoring, and deployment processes early. The upfront cost will pay massive dividends in maintainability and agility.
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Obsess over achieving product-market fit and sustainable growth metrics. Building something people want is more important than building something impressive.
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Hire the best talent you can find and build a culture that enables them to do their best work. Your team is your most valuable asset.
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Foster a community around your product and company. Their evangelism and support will be rocket fuel.
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Never stop learning and expanding your skillset. Encourage your team to do the same. The most successful companies are the most adaptable.
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Enjoy the journey and don‘t forget to celebrate the milestones. Building a company is incredibly hard work, but also incredibly fulfilling.
Eyes Forward
It‘s been a wild ride these past 3 years, going from hacking all night at a folding table to pitching to investors on Sand Hill Road. I‘ve grown more as a leader and technologist than I ever imagined. And I know we‘re still just at the beginning of our company‘s potential.
When I zoom out, I‘m driven by the belief that thoughtful application of technology can solve some of the world‘s biggest problems – and transform people‘s lives for the better in the process. I feel incredibly lucky that I get to wake up every day and work alongside a brilliant team to make that future a reality.
I‘m excited to take our SaaS platform to the next level, expanding into new markets and pushing the boundaries of what‘s possible with DevOps and cloud management. I know there will be many more challenges and learnings ahead, but that‘s part of what makes the journey so exhilarating.
To my fellow developers out there – I encourage you to dream big and take the leap. Start by finding a problem you care deeply about, and validate that others need it solved too. Build, measure, learn, and iterate. Stay close to customers and let them guide your path. Embrace your unique backgrounds and perspectives. And trust that with ingenuity, perseverance, and a bit of luck – you can will your vision into existence.
See you at the next hackathon. Maybe it will change your life too.