Senior Full Stack Developer (AI Software)
Reporting To : Director, Digital Experience
Location: Toronto, Canada
Term : Full-Time
Overview
Job Overview
As a Senior Full Stack Developer (AI Software) at Butterfield & Robinson, you will lead the design, development, and delivery of our AI-powered trip planning platform—one of the most strategically significant technology initiatives in the company’s history. This is a senior individual contributor role with leadership responsibility: you will serve as the primary technology owner of the AI trip planning tool, reporting directly to either the CEO or the Director, Digital Experience, and working closely with executive stakeholders to translate B&R’s unparalleled trip expertise into an intelligent, scalable digital product.
You will partner closely with the CEO, Director of Digital Experience, and cross-functional stakeholders to architect and build a system that understands B&R’s unique trip lifecycle (itineraries, traveler preferences, supplier relationships, pricing, and operational workflows) and surfaces that knowledge in ways that delight clients and accelerate the sales process.
This role requires both the technical depth to build complex AI and data systems and the communication skills to hold your own in senior director- and C-suite-level conversations about product direction, model performance, and architectural trade-offs.
Responsibilities
Key Responsibilities
AI Trip Planning Tool – Ownership & Development
- Own the full technical lifecycle of the B&R AI Trip Planning Tool: architecture, development, evaluation, iteration, and deployment.
- Design and implement LLM-powered features that encode B&R’s institutional knowledge of trip planning, traveler segmentation, and destination expertise.
- Build robust data pipelines to ingest, clean, and structure B&R’s fragmented trip data (itineraries, pricing, supplier info, historical bookings) into a unified, queryable foundation.
- Develop and maintain integrations with B&R’s evolving systems landscape
- Implement evaluation frameworks and feedback loops to continuously improve model accuracy, relevance, and business alignment.
- Proactively identify and address data quality issues, scalability constraints, and emerging risks in the AI system.
Data Architecture & Integration
- Lead the data organization sprint required to make B&R’s existing data AI-ready by designing schemas, migrating content, and establishing data governance practices.
- Architect and build APIs that expose AI capabilities to internal tools, the B&R website, and future client-facing surfaces.
- Manage integrations with third-party AI providers, vector databases, and cloud infrastructure relevant to the AI stack.
- Ensure data security, privacy compliance, and responsible AI practices across all system components.
Executive Partnership & Stakeholder Collaboration
- Serve as the primary day-to-day technology owner of AI project(s), reporting to the CEO or Director, Digital Experience, and providing clear, candid updates on progress, blockers, and trade-offs.
- Translate high-level business goals—trip conversion, client satisfaction, planner efficiency—into well-scoped technical features and measurable outcomes.
- Communicate technical complexity clearly to non-technical stakeholders, including trade-offs between build speed, cost, and quality.
Organization-Wide Collaboration
This role is a connective tissue position. The AI trip planning tool will only succeed if it reflects how B&R actually operates—and that requires deep, ongoing collaboration across every part of the business. You will be expected to build relationships across the organization and treat internal subject matter experts as co-authors of the product.
Sales: Partner closely with the Sales team to understand how trip recommendations are built, how client preferences are captured, and where an AI layer can accelerate the journey from enquiry to booking. The tool must map to real sales workflows, not a simplified version of them.
Operations & Trip Planning: Embed with the Operations team to learn the end-to-end logistics of how a B&R trip comes together (ie. supplier relationships, guide assignments, ground operations, contingency planning) and encode that knowledge into the AI system.
Marketing: Collaborate with Marketing on how the AI tool surfaces to clients and supports campaign goals, conversion optimization, and brand storytelling across digital touchpoints.
Finance & Pricing: Work with Finance to understand how trip pricing, margin structures, and packaging logic should inform recommendations and outputs.
Leadership: Maintain a standing cadence with executive stakeholders to align on priorities, surface blockers, and report on tool performance and business impact.
Whole organization: Proactively seek out institutional knowledge wherever it lives (ie. in long-tenured team members, historical trip files, supplier contacts, and operational playbooks) and treat that knowledge as the raw material the AI is built on.
Engineering Standards & Delivery
- Lead code reviews, uphold development standards, and champion engineering best practices.
- Contribute to the broader Digital Experience team’s technical roadmap from an AI and data platform perspective.
- Actively participate in Agile ceremonies and collaborate with the Agile Project Coordinator on scoping and delivery planning.
- Where applicable, mentor junior developers on AI tooling, prompt engineering, and data pipeline best practices.
Required Skills & Abilities
- Strategic and independent thinker who can balance big-picture architecture with precise execution.
- Strong leadership presence with the ability to influence technical direction and elevate those around you.
- Exceptional analytical and problem-solving abilities, with a track record of navigating ambiguity effectively.
- Intellectually curious energized by the challenge of teaching a machine to think like a luxury travel expert.
- High attention to detail and a commitment to delivering polished, production-quality work.
- Excellent written and verbal communication skills, with the ability to articulate technical concepts clearly to both technical and non-technical stakeholders.
- Ability to manage competing priorities and deliver high-quality outcomes in a fast-paced environment.
- Deep appreciation for a global, creative, and collaborative work culture.
- Professional, discreet, and accountable.
Required Experience & Qualifications
- 5+ years of professional full stack development experience, with demonstrated end-to-end ownership of complex software products.
- Hands-on experience building, fine-tuning, or deploying LLM-powered applications—including retrieval-augmented generation (RAG), prompt engineering, and agentic workflows.
- Expert-level proficiency in Python and/or Node.js, with strong command of RESTful API design, integration, and maintenance.
- Experience with agentic coding tools (Claude Code, Codex, v0, Cursor, etc.) and AI-accelerated development workflows.
- Strong data engineering experience: ETL pipelines, schema design, data cleaning, and working with fragmented or legacy data systems.
- Proficiency in SQL and relational databases; experience with vector databases (e.g. Pinecone, pgvector, Weaviate) considered a strong asset.
- Experience integrating with modern CRM and ERP systems (HubSpot, Salesforce, or similar); familiarity with Sugati a plus.
- Demonstrated experience with front-end development in React and/or Next.js—sufficient to collaborate on client-facing surfaces and web integrations.
- Proven experience with CI/CD pipelines, cloud infrastructure (AWS, GCP, or Azure), and modern DevOps practices.
- Strong command of version control workflows (Git) and experience collaborating across multi-developer teams.
- Experience managing projects with multiple developers contributing asynchronously.
- Demonstrated experience working within Agile/Scrum environments, including sprint-based delivery.
- Bachelor’s degree in Engineering, Computer Science, Information Systems, Mathematics, Physics, or a related discipline—or equivalent practical experience.
Additional Notes
Compensation Range: $110,000-$140,000
This job is an existing vacancy.
We use automated tools, including artificial intelligence, to assist with the initial screening of applications. All hiring decisions are ultimately made by a human reviewer.
Butterfield & Robinson is an equal opportunity employer committed to creating a diverse and inclusive environment. We consider qualified applicants regardless of race, colour, religion, gender, national origin, sexual orientation, age, citizenship, disability, or gender identity. Accommodations are available on request for candidates taking part in all aspects of the selection process.
How To Apply
To apply, please send a cover letter and resume by email to: employment@butterfield.com