Senior Fractional CTO / Technical Advisor for SaaS Oversight (Ongoing)
Upwork

Remoto
•2 weeks ago
•No application
About
The Role I’m seeking a senior Fractional CTO / Technical Advisor to oversee the technical development and architectural integrity of a SaaS platform undergoing a strategic relaunch. This is a high-touch, ongoing engagement centered on: Technical oversight AWS architecture and security review Vendor accountability Disaster Recovery validation High-level architectural judgment Ensuring long-term scalability and reliability You will work directly with a non-technical founder who values candor, clarity, and expertise. You will be empowered to push back, challenge assumptions, and steer the technology in the right direction. The Challenge An offshore development team is actively building and enhancing the platform. I need a senior leader who can: Evaluate and challenge architectural decisions Audit AWS infrastructure, configuration, and security posture Assess and improve Disaster Recovery planning (documentation provided) Review code quality, deployment processes, and development discipline Validate timelines and technical feasibility Identify risk areas early and provide corrective guidance Communicate directly with the offshore team as needed Translate technical complexities into clear business-aligned recommendations This role requires someone who can confidently say: “Here is the problem, here is why it matters, and here is the correct solution.” ⭐ Optional Participation / Profit-Sharing (For the Right Fit) While hourly compensation is provided, I am also open to offering participation tied to platform success for the right senior advisor who becomes an essential part of our long-term technical leadership. Options may include: Performance-based profit-sharing Advisory-level equity Milestone-based bonuses Participation in long-term upside as the platform scales This is entirely optional and would be discussed only after a successful working relationship is established. It is a bonus, not a substitute for compensation. Responsibilities Initial (First 30–60 Days) Review Disaster Recovery documentation Assess current architecture, AWS usage, and implementation patterns Evaluate codebase quality and development processes Identify weaknesses, risks, or missing components Recommend oversight cadence and monthly engagement level Ongoing Regular interaction with offshore developers Validation of technical decisions and system architecture Review of releases, deployments, and infrastructure updates Oversight of security, performance, and scaling best practices Monitoring development velocity and quality Advising the founder in plain English Being assertive and direct when something needs attention What You Bring Required Senior-level background: CTO, VP Engineering, Principal Architect, or equivalent Strong AWS expertise: EC2, RDS, IAM, VPC, S3, CloudFront, Lambda, backups, monitoring Clear understanding of SaaS architecture and multi-tenant systems Experience overseeing offshore developers Direct, honest, and confident communication style Ability to translate business goals into technical strategy Flexibility to work hours that overlap with U.S. Eastern Time Ideal Experience stepping into mid-build or pre-launch SaaS platforms Background in DevOps, security, performance tuning, and disaster recovery Enjoys the fractional advisory model Comfortable offering strong opinions backed by reasoning Engagement Structure Ongoing fractional role Hourly engagement preferred to start Hourly rate range: $75–$125/hr (depending on experience) Hours/month determined after your initial assessment Founder works late evenings and weekends (EST); flexibility helpful Potential for a hybrid structure (hourly + participation) after trust is established About the Founder (Without Company Names) I am a long-established founder with decades of experience building and scaling businesses in a competitive industry. My background includes pioneering behavioral and motivational strategies that have shaped modern recruitment communication. I’m non-technical but decisive, collaborative, and direct. I value logic, clarity, honesty, and expertise. When something isn’t right, I want to know immediately — and I want to understand why. You will be my senior technical partner — ensuring the platform is built securely, correctly, and future-proof. To Apply (Required Screening Questions) Please answer the following in your proposal: Describe your most relevant CTO/VP Engineering/SaaS architecture experience. Provide an example of a platform you oversaw and the key challenges you solved. Detail your hands-on experience with AWS services listed above. How do you evaluate a codebase and architecture you didn’t originally design? Tell me about a time you had to disagree strongly with a founder or executive — how did you handle it? What hours are you available relative to U.S. Eastern Time? What hourly rate do you propose within the $75–$125/hr range? How many hours/month do you believe are appropriate for this role? Do you have experience overseeing offshore development teams? Next Steps If selected, I will provide: Disaster Recovery documentation A live product demo Background on current architecture and systems Developer introductions Roadmap and technical priorities This is a compelling opportunity for a senior technical leader who enjoys meaningful oversight, strategic impact, and the chance to help shape a differentiated SaaS platform during a pivotal relaunch stage.





