CTO, New Venture: Cloud Architecture AI Agent

The cloud computing market is exploding, yet most companies are struggling with the shift. CIOs are rushing to control cloud costs, DevOps teams are stretched thin, deployments are manual and cloud providers just don’t make life easy with their tooling.

Diagram is building an AI Cloud Architect that intelligently designs and scalably provisions tailored cloud architectures, ensuring companies get the best performance and cost-efficiency right from the start. We are providing enterprises with the ability to easily become cloud-native and say goodbye to manual setups, slow deployments and cost overruns. 

Backed by Diagram Ventures, this venture will have the capital, network and strategic support needed to scale into a high-potential venture-backed company. Diagram has significantly de-risked this venture with product-market fit, technical risks and market landscape verified. As a technical advisor, you’ll be playing a pivotal role in shaping the technology of this venture. 

This is a unique opportunity for a seasoned technologist to provide strategic insights, help shape the technical roadmap, and advise on the execution of a breakthrough AI-driven platform while retaining the opportunity to transition to a founder role.

As a Fractional CTO, you will provide technical and strategic guidance to help bring the venture from idea to launch. Your role will involve advising on the architecture, AI/ML strategies, and cloud infrastructure decisions necessary to build a scalable and resilient platform. Your deep technical expertise will support critical decisions around platform development while also ensuring the venture is leveraging best practices in cloud automation, AI technology, and DevOps.

You will collaborate closely with Diagram Ventures, offering insight and counsel on scaling the platform, building the AI Agent and integrating with cloud providers. 

• Strategic Technical Guidance: Provide high-level guidance on the venture’s technical direction and product roadmap, ensuring alignment with the company’s long-term vision and customer feedback.
• Technical Architecture and Development: Drive the design and implementation choices of the venture’s platform, ensuring it is built with scalability, resilience, and performance in mind. 
• AI-Driven Infrastructure Automation: Advise on the development of the platform's AI algorithms and automation capabilities, ensuring seamless generation of infrastructure-as-code (IaC) for multi-cloud environments with intelligent recommendations for cloud cost optimization, performance, and scalability.
• Team Building and Leadership: Advise on building a high-performing technical team, including recruitment, retention, and professional development of early hires across software engineering, AI/ML, cloud infrastructure, and DevOps profiles. Bringing your experience to cultivate a culture of innovation, ownership, and technical excellence.
• Cloud Provider Integrations: Advise on integrations with cloud providers (AWS, Azure, GCP), ensuring that the platform is compatible with multiple providers and leverages the best features of each
• Technical Risk Management: Help identify and mitigate potential technical risks, including scalability issues, security vulnerabilities, and performance bottlenecks. Advise on best practices for secure coding, reliability, and disaster recovery.
• Innovation and Continuous Improvement: Continuously review the latest technologies and trends to identify opportunities to enhance the venture’s product offerings, improve the user experience, and ensure it remains at the cutting edge of cloud automation and AI technology.
• Collaboration with Stakeholders: Engage with the CEO, investors, and stakeholders to align technology with business objectives. Actively solicit feedback and explore opportunities where technology can provide a competitive advantage.

• Proven Technical Leadership: Demonstrated experience in providing technical leadership. Track record of identifying and hiring top talent, evidence of followership, developing and leading high-performance teams
• 0 to 1 Product Building Capabilities: Proven track record of building product roadmaps based on user feedback and developing platforms with strong UI/UX, excellent performance and resilience.
• Cloud Infrastructure Expertise: Strong background in cloud computing, including designing scalable architectures on AWS, Azure, GCP, or similar environments. Experience with infrastructure-as-code (IaC) and cloud automation tools like Terraform and Kubernetes. Experience with CI/CD platforms like Backstage, Spinnaker and Harness is a plus. 
• AI/ML Knowledge: Hands-on experience with AI/ML technologies, particularly with LLMs and recommendation engines.
• Technical Architecture Oversight: Deep understanding of technical architecture, cloud ecosystems, and the ability to evaluate and recommend the right technology stacks and solutions for long-term scalability.
• Risk and Security Awareness: Expertise in identifying and mitigating technical risks, including security vulnerabilities and performance bottlenecks. Familiarity with secure coding practices and compliance in cloud environments.
• Strong Communication Skills: Ability to clearly communicate complex technical concepts to both technical and non-technical stakeholders. Experience working with leadership teams, investors, and boards is a plus.

Montreal, Toronto or Remote across North America

About Diagram

Diagram is a venture studio that builds new technology businesses from inception with $350M AUM and 25 companies launched since 2016. Our portfolio companies are the result of a marriage between rigorously de-risked ideas, experienced founders and the capital and operational resources they need to grow and scale.

Applying at Diagram

We appreciate your interest in working with us; however, only those applicants selected for interviews will be contacted. Diagram Ventures’ team may reach out to you about other possible opportunities you may be a fit for. We launch new ventures in ClimateTech, FinTech and AI each year and are continually excited to connect with founders and top talent who want to join us and our portfolio companies.