Chief Technology Officer

Chief Technology Officer

Reporting to: Chief Executive Officer

Location: Boston, MA (Hybrid).

Open to exceptional candidates anywhere. Relocation support available.

Position Summary

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

We are looking for a CTO who has been living and breathing AI since the day ChatGPT launched. Someone who didn’t wait for permission to start experimenting. Someone who has already built things, broken things, shipped things, and learned from all of it. Someone who can walk into a room of 900 associates and make them believe that AI is not a threat to their careers but the biggest unlock of their professional lives.

This is not a traditional CTO role where you sit in the back office managing infrastructure tickets. Technology at GCC is a strategic growth engine. We have four major infrastructure projects in flight (CMS migration, data warehouse, telephony modernization, PCI compliance), a marketing technology stack to build out, and an AI transformation to develop and lead across the entire company. You will own all of it.

You will be the CEO’s partner in driving AI adoption and transformation across every department, not just your own. You’ll set the pace, set the tone, and be the role model for what it looks like when a leader uses AI every day to make better decisions faster. Your team will be approximately 85 people across engineering, infrastructure, project management, data science, enterprise applications, and security. But your influence will reach all 900+ associates worldwide.

Key Responsibilities

AI Transformation & Culture

• Own the AI strategy, roadmap, and sequencing. Know what needs to land in what order. Infrastructure before automation. Data before personalization. Foundation before flash.
• Be the company’s AI leader. Not just for your team. For every team. Partner with the CEO to make AI adoption a company-wide priority with measurable goals tied to individual performance.
• Build and lead an AI Council. Find the internal champions in every department, give them a platform, and let them pull their peers forward. This is grassroots culture change, not top-down mandates.
• Create structured AI learning programs: dedicated weekly training time, certification paths (Anthropic Academy, Microsoft, etc.), department-level hackathons, and a culture where people demo what they’ve built and give each other permission to try.
• Establish AI usage metrics and reporting. Track adoption rates, efficiency gains, and ROI. Make the data visible. Make it a little competitive. Show people what’s possible.
• Design and deploy AI agents to automate repetitive operational tasks, with a focus on reducing SG&A per passenger as the company scales to 160,000 passengers.
• Leverage AI as a force multiplier for engineering output, data analysis, call center operations (real-time coaching, chatbots, self-service), and marketing performance.

Technology Strategy & Infrastructure

• Develop and execute a five-year technology roadmap aligned with the company’s growth targets and its ambition to become a leader in real-time personalized relationship marketing.
• Own delivery of in-flight infrastructure projects: Optimizely CMS migration, Snowflake data warehouse, NiCE telephony upgrade, and PCI compliance. These are the foundation. They must land before everything else can scale.
• Lead modernization of legacy systems and platforms, including customer booking and reservation systems, with online booking as a near-term unlock.

Marketing Technology & Personalization

• Own or closely partner on the marketing technology stack: CMS, CDP, marketing automation, personalization engines, analytics. This is how the company will deliver on its promise of personalized traveler experiences across every channel.
• Drive the expansion of web and digital capabilities in support of the website redesign and the shift toward data-driven, AI-optimized customer acquisition and retention.

Technology Operations

• Direct enterprise technology operations including applications, infrastructure, data management, cybersecurity, and network systems across 35 global offices.
• 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.

Team Leadership & Change Management

• Lead and develop a global team of approximately 85 professionals across engineering, infrastructure, enterprise applications, data science, and security.
• Build a high-performing technology organization where accountability, speed, and experimentation are the defaults.
• Drive change management across a globally distributed workforce with varying levels of technical comfort, including tenured teams in operations and engineering. This takes patience, empathy, and persistence. You are not just managing engineers. You are leading a cultural shift.
• Establish development processes, tools, and frameworks that let your team ship faster and with more confidence.

Strategic Partnerships & Governance

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

What We’re Looking For

Experience & Expertise

• 15+ years of progressive leadership in software engineering or technology organizations, including senior executive roles.
• Proven track record leading enterprise-wide technology transformation. Not just planning it. Delivering it.
• Hands-on AI experience since at least 2023. You’ve deployed AI tools, built AI workflows, set AI adoption goals, tracked usage metrics, and measured real efficiency gains. You’re not learning this on the job. You’ve already done it.
• Track record of driving technology culture change across large organizations. You’ve built internal champions, run learning programs, and moved skeptics to believers. You know this takes 12+ months and you’ve done it before.
• Direct experience with marketing technology platforms (CMS, CDP, marketing automation, personalization engines) and the ability to evaluate, integrate, and optimize a modern MarTech stack.
• Experience designing and operating large-scale, high-transaction, mission-critical platforms.
• Strong background in modern software development methodologies (Agile, Continuous Delivery) and AI-augmented engineering workflows (Copilot, Claude Code, or similar).
• Experience leveraging data and digital technologies to support marketing, customer experience, and revenue growth.

Leadership & Communication

• You can get up in front of a crowd and get people excited about the future. This is not optional. The CTO at GCC is the face of technology transformation for the entire company.
• Demonstrated ability to build and lead high-performing teams in global, distributed environments across multiple time zones.
• Strong executive presence and the ability to partner with senior leaders across business and technology functions. You’re not just the tech person in the room. You’re a business leader who happens to run technology.
• Exceptional communication and collaboration skills. You can translate complex technical concepts into plain language that motivates action.

Core Competencies

• AI strategy, adoption, and enterprise-wide enablement
• Strategic thinking and the ability to sequence a complex, multi-year technology and AI roadmap
• Operational excellence and execution
• Team leadership and talent development
• Change management and transformation leadership

Bonus Points

• You follow the AI space obsessively. You know who the key voices are. You know what shipped last week. You have opinions about it.
• You’ve built or contributed to internal AI communities, newsletters, or knowledge-sharing programs at a previous company.
• You’ve worked in travel, hospitality, consumer services, or another industry where the customer experience is the product.
• You’ve led AI transformation at a company with a workforce that skews older or less technical. You know the soft-skills challenge is harder than the technical one.

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 based on 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 PTO, 11 paid holidays (including Juneteenth, Memorial Day, and Labor Day), Summer Fridays, and up to 12-16 weeks paid parental 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 growth through overseas travel, and direct access to Pinnacle Leadership & Team Development
• Extra perks: Commuter benefits, FSA options, pet insurance, home & auto discounts, and paid volunteer time off
• Relocation: For the right candidate, we will provide a competitive relocation package to Boston, MA

To learn more, please visit our websites at www.gct.com, www.oattravel.com and www.grandcirclefoundation.org.