Five Years as a Startup CTO: How, Why, and Was It Worth It? Sergey Khaladzinski reflects on his 5-year journey as a CTO at an early-stage startup, sharing insights, challenges, and lessons learned. --- The Beginning Approached with a startup that had no product or team, built unsuccessfully on Salesforce. Early product failed to meet target customer needs, common in "done for you" projects. Sergey took the challenge despite unfamiliarity with Salesforce and fintech, emphasizing a "business-first" approach. Discovered Salesforce development was a niche with limited consultants available. Partnered with a Belarusian agency to assign Salesforce engineers, allowing forward progress. Technical and Business Challenges Initial Salesforce MVP was useful but limited; complex controls and investor concerns spurred need for own platform. Full rewrite was infeasible; chose a hybrid approach: Retained Salesforce frontend familiar to financial clients. Redirected storage layer to proprietary APIs (“ninja move”). Faced work overload deciding to leave corporate stability and join startup full-time after MVP secured initial capital. Relocated to Denver to work closely with the team and gain alignment. Team Building and Technology Choices Learned early hires must be experienced, hands-on leads to prevent micromanagement. Team structure: Platform, Backend, Frontend, QA, Design. Platform: AWS, Docker, Kubernetes. Backend: Golang (with some internal debate), also experimented with Rails for CRUD projects. Frontend: React ecosystem, kept simple to avoid complexity. QA: Initially underestimated but became critical for saving time and improving confidence in releases. Design: Transitioned from Sketch to Figma; great designers solve problems, organize well, communicate clearly, and advocate effectively to stakeholders. Leadership Philosophy Create and preserve an environment enabling the team to excel. Shift from giving orders to asking questions. Focus on solving real business problems and maintaining open communication. Encourage transparency and continuous improvement. Current Achievements Team of 20+ skilled engineers. Effective change management process bridging business and tech. Continuous delivery pipeline for reliable software releases. Own SaaS B2B platform replacing Salesforce MVP with expanded features. Automated SOC2 compliance framework. Extensive end-to-end test suite enabling confident, frequent releases. Upcoming B2C mobile-first payments product poised for market entry. Personal Reflections & Lessons Learned Cherishes the opportunity to live fully, balancing work and family through changes. Accepts constant change as inherent in life and startups. Key takeaways (not exhaustive): Have financial reserves before jumping in. Expect longer timelines for traction or exit. Document your journey to track progress. Live in the present; every day is a blessing. Build a team early; two people is one, one is none. Ask more questions than giving orders. Understand real business problems before coding solutions. Ownership and legal paperwork matter; review carefully. Be proactive and trust your intuition. Give credit and take blame gracefully. Optimize for remote-first communication; favor public channels. Ensure payroll is timely and reliable. Seek help and network if stuck. Know your runway and milestones. Over-communicate and be transparent during tough times. Record meeting outcomes for clarity. Don’t fear hiring smart people. Consider remote/offshore hiring early. Maintain hobbies for balance. Beware misleading interviews; prioritize actual output. Take care of your health. Future Plans Stabilized enough to take on fractional CTO roles for new projects. Offers technical leadership to help others move from 0 to 1. Invites referrals for leadership