Chief Technology Officer

Reporting to: Chief Executive Officer

Location: Boston, MA (Hybrid)

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Position Summary

Grand Circle Corporation is the leader in international travel, adventure, and discovery for Americans aged 50+. Headquartered in Boston, MA, with 35 offices globally, over two million Americans have traveled with our award-winning brands:

Grand Circle Cruise Line
Overseas Adventure Travel
Grand Circle Travel

We are seeking a visionary Chief Technology Officer (CTO) to join our executive leadership team and lead the company’s global technology strategy. The CTO will help shape and execute a five-year technology roadmap that advances our goal of becoming a leader in real-time personalized relationship marketing.

This leader will bridge business and technology, deploying resources strategically to support the company’s mission, lead enterprise-wide transformation, and drive cross-channel digital capabilities. The CTO will oversee a global team responsible for engineering, infrastructure, project management and delivery, data science, enterprise applications, and information security, ensuring our platforms and data infrastructure support seamless traveler experiences across all channels.

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Key Responsibilities

Technology Strategy & Leadership

Develop and execute the company’s technology strategy aligned with business goals and long-term growth.
Partner with executive leadership to translate the company’s strategic roadmap into scalable technology solutions.
Identify and implement emerging technologies that improve customer engagement, operational efficiency, and business performance.

Digital Transformation & Innovation

Lead modernization of legacy systems and platforms, including customer booking and reservation systems.
Drive the expansion of web and digital capabilities to enhance the customer journey and enable personalization.

Technology Operations

Direct enterprise technology operations including applications, infrastructure, data management, cybersecurity, and network systems.
Oversee development, design, and deployment of new applications and enhancements to existing systems.
Ensure data integrity, security, backup, and disaster recovery capabilities across the organization.

Artificial Intelligence

Own the AI strategy and roadmap.
Leverage AI and advanced analytics to improve customer insights, marketing performance, and service delivery, particularly in call center operations.
Leverage AI as a force multiplier for engineering output and data analysis.
Lead company-wide AI enablement and adoption.

Team & Organizational Leadership

Lead and develop a global team of approximately 85 professionals across engineering, infrastructure, enterprise applications, data science, and security functions.
Build a high-performing technology organization that promotes accountability, collaboration, and innovation.
Establish best-in-class development processes, tools, and frameworks to enable scalability and operational excellence.

Strategic Partnerships & Governance

Manage technology budgets, vendor relationships, and major technology contracts.
Evaluate new systems and technologies to ensure alignment with enterprise architecture and business priorities.
Provide strategic counsel to executive leadership on technology investments, risks, and opportunities.

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Qualifications

Experience & Expertise

15+ years of progressive leadership experience in software engineering or technology organizations, including senior executive roles.
Proven success leading enterprise-wide technology transformation initiatives.
Experience designing and operating large-scale, high-transaction, mission-critical platforms.
Strong background in modern software development methodologies such as Agile and Continuous Delivery.
Experience leveraging data and digital technologies to support marketing, customer experience, and revenue growth.

Leadership & Collaboration

Demonstrated ability to build and lead high-performing teams in global and distributed environments.
Strong executive presence and ability to partner with senior leaders across business and technology functions.
Exceptional communication, collaboration, and problem-solving skills.

Core Competencies

Strategic thinking and innovation
Operational excellence and execution
Team leadership and talent development
Change management and transformation leadership

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Total Rewards

The base salary range for this role is $350,000 – $425,000 annually for employees based in Boston, MA. Final compensation may vary and will be determined based on relevant experience, skills, internal equity, and geographic location.

In addition to base pay, this role is eligible for an annual incentive bonus and first-class benefits, which include:

Health & wellness: Comprehensive and heavily subsidized medical, dental, and vision plans, plus on-site gym access, holistic wellness sessions, and group fitness classes.
Time for you: Substantial Paid Time Off (PTO) and 11 paid holidays, including Juneteenth, Memorial Day, and Labor Day – plus Summer Fridays. Extensive parental leave with up to 12–16 weeks paid leave at 100% base salary.
Travel more, spend less: 50% off our trips for you and a companion, 25% for additional immediate family members, and exclusive quarterly associate travel deals.
Your future, secured: 401(k) with company match, life insurance, and disability coverage.
Continuous growth: Tuition assistance for professional and personal development, opportunities for professional growth through overseas travel, and access to Pinnacle Leadership & Team Development.
Extra perks: Commuter benefits, FSA options, pet insurance, home & auto discounts, and paid volunteer time off.

To learn more, please visit:

www.gct.com | www.oattravel.com | www.grandcirclefoundation.org

Please let Grand Circle Corporation know that you found this role at ctojobshq.com as a way to support us, so we can keep providing you with great CTO job opportunities.

Chief Technology Officer

About the Role

Compensation

About Grand Circle Corporation

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