Hands-on CTO | Python, Django, AWS, Security & AI

About Jane

Jane is a technology platform serving Israel’s regulated medical cannabis ecosystem. Our systems connect patients, pharmacies, producers and distributors, and support ordering, inventory, operational workflows and integrations with sensitive external systems.

We operate in a highly regulated environment under a Ministry of Health license. Security, reliability, data protection and operational discipline are fundamental requirements, not afterthoughts.

We are looking for a full-time, hands-on CTO / Head of Engineering to take overall responsibility for Jane’s technology organization.

This is a leadership role for someone who can set technical direction, lead and develop an engineering team, and remain sufficiently hands-on to review architecture, investigate critical production issues and contribute code when needed.

You will own engineering execution, architecture, cloud infrastructure, DevOps, security engineering, AI adoption and technical readiness for strict regulatory requirements. You will work closely with management, product, external security professionals and the CISO.

This is not a role for a solo firefighter. Your responsibility is to build a capable team, reliable systems and clear engineering processes that do not depend on one individual.

• Lead, mentor and manage a distributed engineering team.
• Translate business and product priorities into realistic technical roadmaps.
• Establish delivery standards, ownership, estimation and accountability.
• Own the architecture of our Python/Django platform and critical integrations.
• Remain hands-on through architecture reviews, code reviews and critical implementation.
• Own AWS architecture, environments, CI/CD, containers, observability, backups and disaster recovery.
• Establish secure development practices, access controls, vulnerability management and incident-response procedures.
• Coordinate technical security and compliance work with the CISO and external professionals.
• Ensure safe separation of production, staging, development and sandbox environments.
• Improve system performance, reliability and cloud cost efficiency.
• Build an effective testing strategy across unit, integration and end-to-end testing.
• Evaluate and implement LLM-based capabilities where they provide real business value.
• Establish appropriate controls for LLM quality, privacy, security, latency and cost.
• Recruit and develop additional engineers as the company grows.
• Communicate technical risks, trade-offs and progress clearly to management.

Within the first six months, we expect:

• Clear ownership and an actionable engineering roadmap.
• Improved delivery predictability and code-review standards.
• Documented architecture, environments and operational procedures.
• Reduced production and security risk.
• Tested backup, recovery and incident-response processes.
• Stronger CI/CD, automated testing and observability.
• A development team that operates with greater independence and accountability.
• Measurable progress toward Ministry of Health and CISO requirements.

• Typically 7+ years of professional software engineering experience.
• Strong production experience with Python and Django.
• At least 2 years leading engineers or owning engineering execution.
• Demonstrated ownership of production systems and cloud infrastructure.
• Strong AWS, Docker, CI/CD, networking, IAM and database knowledge.
• Experience with observability, incident response, backup and disaster recovery.
• Practical application-security knowledge, including secure SDLC, OWASP principles, SAST/DAST and secrets management.
• Ability to design scalable systems and make pragmatic architectural decisions.
• Proven ability to mentor developers, delegate effectively and maintain engineering standards.
• Strong written and spoken English.
• Excellent communication with technical and non-technical stakeholders.

• Experience in regulated, healthcare, fintech or sensitive-data environments.
• Experience working with external CISO or security-audit teams.
• Infrastructure as Code experience.
• PostgreSQL performance and data architecture experience.
• Modern frontend experience.
• Experience building production LLM systems, including evaluation, retrieval, tool use and privacy controls.
• Experience with government APIs, payment systems or complex B2B integrations.

• Full-time position.
• Remote work.
• Background verification is required due to the sensitivity of the systems and data.
• Availability date is flexible for the right candidate.

To apply, please send your CV and, optionally, a GitHub profile or examples of relevant work to [email protected].