Head of Software EngineeringAskEddy is an AI-powered booking platform building the next generation of intelligent travel and experience discovery. We combine AI, automation, and technology to help users discover, plan, and book activities through a seamless digital experience.
We are looking for a highly capable technology leader to take ownership of the company's engineering function, AI strategy, platform architecture, infrastructure, cybersecurity, and technical innovation.
This role reports directly to the Founder & CEO and is intended for someone who wants to build, lead, and continuously improve a modern technology platform while helping shape the future direction of the business.
The successful candidate will lead the company's technology function, providing technical leadership across engineering, AI, platform architecture, cloud infrastructure, and cybersecurity. This role is responsible for ensuring the platform remains scalable, secure, innovative, and aligned with the company's long-term objectives.
What You Will Own
- Engineering strategy and long-term technical roadmap
- AI strategy, adoption, experimentation, and implementation
- Platform architecture and system scalability
- Cloud infrastructure, reliability, and performance
- Cybersecurity, risk management, and technical governance
- Technical due diligence and technology decision-making
- Management and oversight of external software development partners
- Future engineering team design, hiring, and leadership
- AI automation initiatives and agent-based systems across the business
Key Responsibilities
- Define and maintain the company's technology architecture
- Lead technical planning and prioritization alongside the Founder
- Identify opportunities to leverage AI across products, operations, and internal workflows
- Monitor global AI developments and evaluate emerging technologies
- Design and oversee the company's long-term AI strategy, including AI-powered automation, internal AI systems, and future agent-based products
- Identify, evaluate, implement, and manage AI agents across the business to improve productivity, automation, customer experience, engineering workflows, operations, sales, marketing, finance, and support functions
- Review technical solutions, architecture decisions, and engineering standards
- Ensure platform stability, security, and operational readiness
- Oversee infrastructure, deployment processes, monitoring, and disaster recovery planning
- Establish development standards, documentation, and engineering best practices
- Evaluate and implement tools, systems, and integrations that improve scalability and efficiency
- Support future fundraising, technical due diligence, and investor discussions when required
- Build the foundations for an internal engineering organization as the company growsWhat Makes This Role Interesting
- Direct collaboration with the Founder & CEO on technology strategy, AI initiatives, product direction, and long-term technical planning
- High level of ownership and decision-making authority
- Ability to influence both business and technology strategy
- Exposure to AI, booking technology, automation, cloud infrastructure, and cybersecurity
- Opportunity to build and shape a technology function from an early stage
- Clear path toward a future CTO position based on performance and business growth
What We're Looking For
- 10–15+ years of software engineering experience
- Strong background in software architecture and distributed systems
- Experience building or scaling SaaS, booking, travel-tech, fintech, marketplace, or transaction-based platforms
- Strong knowledge of cloud platforms such as AWS
- Experience working with modern AI technologies, large language models, and AI-powered products
- Demonstrated experience implementing AI, automation, agentic workflows, or AI-powered systems within products, engineering teams, or business operations
- Solid understanding of cybersecurity principles and secure software development
- Experience managing engineering vendors, agencies, or technical teams
- Strong commercial awareness and ability to align technology decisions with business goals
- Excellent communication and leadership skills
- Hands-on approach with the ability to move between strategy and executionThis Role Is Ideal For Someone Who
- Enjoys solvinWahs g complex technical and business problems
- Stays current with global AI and technology trends
- Thinks beyond software development and understands how technology drives business growth
- Wants to build, scale, and continuously improve a modern technology platform
- Is motivated by ownership, responsibility, and long-term impact.
- Recruitment agencies and third parties — please do not apply.
