Head of Technology

Summary

Join The Points Guy as their visionary Head of Technology, leading the engineering organization into its next chapter. You will shape the tech roadmap, integrate AI into all aspects of the business, and cultivate a resilient, agile, and empowered engineering culture. Collaborate with senior leadership to align technology with business objectives, foster cross-functional teamwork, and deliver exceptional digital experiences. This role demands a leader who combines deep technical expertise with entrepreneurial drive, leveraging technology for lasting consumer impact and organizational growth. If you are passionate about rewards, travel, and the transformative power of AI in consumer products, this is an ideal opportunity.

Requirements

• 10+ years of engineering leadership, with a strong track record of building high-performing, mission-aligned teams
• Proven experience delivering AI-enabled consumer products or platforms
• Minimum of 5 years in senior tech leadership roles; experience scaling or transforming engineering orgs
• Deep experience managing managers and setting up engineering management systems
• Demonstrated history of rapid, high-quality delivery in agile environments
• Strong grasp of modern engineering practices, tooling, and quality standards
• Skilled at aligning technical execution with business outcomes
• Able to think both short-term and long-term — delivering today while building for tomorrow
• Effective at collaborating across disciplines including product, editorial, and revenue functions
• Strong communicator and empathetic stakeholder manager

Responsibilities

• Architect and execute a modern, scalable technology roadmap
• Champion innovation through thoughtful evaluation and integration of emerging technologies
• Lead AI strategy and execution across content internal systems, and consumer-facing products
• Build AI-powered features such as recommendation engines, personalization layers, and editorial workflow tools
• Attract, inspire, and grow top-tier engineering talent
• Establish clear career pathways, robust mentorship, and an inclusive, high-performing engineering culture
• Drive seamless partnership with Product, Content, Design, and Revenue teams to deliver cross-functional value
• Ensure tech priorities are deeply aligned with TPG’s business strategy and consumer goals
• Own technical architecture, cloud strategy, platform security, and infrastructure resilience
• Instill best practices in DevOps, QA, release management, and agile delivery

Benefits

• Health Insurance Coverage (medical, dental, and vision)
• Life Insurance
• Short and Long-Term Disability Insurance
• Flexible Spending Accounts
• Paid Time Off
• Holiday Pay
• 401(k) with match
• Employee Assistance Program
• Paid Parental Bonding Benefit Program