Overview:

At The Points Guy, we are charting the future of travel guidance through innovation, personalization, and cutting-edge technology. As we expand our capabilities and evolve our consumer products, we’re searching for a visionary Head of Technology to lead our engineering organization into its next chapter.

This isn’t just another tech leadership role — you will shape our tech roadmap, embed AI into everything we do, and build a resilient, agile, and empowered engineering culture.

You’ll work hand-in-hand with our senior leadership team to align technology with business outcomes, foster deep cross-functional collaboration, and deliver world-class digital experiences that delight our audience and amplify our brand.

This is a rare opportunity for a leader who blends deep technical expertise with entrepreneurial energy — someone who sees technology as a lever for lasting consumer impact and organizational scale.

If you’re passionate about rewards, travel, and the power of AI to redefine consumer products, we’d love to talk.

What You’ll Do:

• Technology Strategy & Execution: Architect and execute a modern, scalable technology roadmap. Champion innovation through thoughtful evaluation and integration of emerging technologies. 
• AI & Innovation Leadership:  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.
• Team Development: Attract, inspire, and grow top-tier engineering talent. Establish clear career pathways, robust mentorship, and an inclusive, high-performing engineering culture.
• Collaboration at Scale: 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.
• Operational Rigor: Own technical architecture, cloud strategy, platform security, and infrastructure resilience. Instill best practices in DevOps, QA, release management, and agile delivery.

What We’re Looking For:

• Experience: 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.
• Leadership: 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.
• Executional Excellence: Demonstrated history of rapid, high-quality delivery in agile environments. Strong grasp of modern engineering practices, tooling, and quality standards.
• Strategic Acumen: Skilled at aligning technical execution with business outcomes. Able to think both short-term and long-term — delivering today while building for tomorrow.
• Cross-functional Mindset: Effective at collaborating across disciplines including product, editorial, and revenue functions. Strong communicator and empathetic stakeholder manager.

Additionally, the following benefits are provided by Red Ventures, subject to eligibility requirements.

• 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

Who We Are:

Founded in 2000, Red Ventures (RV) is home to a diverse portfolio of industry-leading brands and businesses, strategic partnerships and proprietary technology – including Bankrate, Lonely Planet, The Points Guy, BestColleges and more. Together, RV helps millions of people worldwide make life’s most important decisions, accelerates digital adaptation, and innovates the online consumer experience by improving every step of the consumer journey – from first discovery of information, throughout the decision-making process, to transactions. Headquartered south of Charlotte, NC, Red Ventures employs thousands of people across the US and Puerto Rico, with international offices in the UK and Brazil. For more information, visit https://redventures.com and follow @RedVentures on social platforms.

At Red Ventures, we believe diverse, inclusive teams are better. To help you better understand our core values and beliefs, we encourage you to watch this brief YouTube video: Our Belief Statements. This will give you insight into the principles that guide our work and our commitment to fostering an inclusive environment.

We offer competitive salaries and a comprehensive benefits program for full-time employees, including medical, dental and vision coverage, paid time off, life insurance, disability coverage, employee assistance program, 401(k) plan and a paid parental leave program.

Red Ventures is an equal opportunity employer that does not discriminate against any employee or applicant because of race, creed, color, religion, gender, sexual orientation, gender identity/expression, national origin, disability, age, genetic information, veteran status, marital status, pregnancy or any other basis protected by law. Employment at Red Ventures is based solely on a person's merit and qualifications. 

We are committed to providing equal employment opportunities to qualified individuals with disabilities. This includes providing reasonable accommodation where appropriate. Should you require a reasonable accommodation to apply or participate in the job application or interview process, please contact accommodation@redventures.com. 

If you are based in California, we encourage you to read this important information for California residents linked here.

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