With millions of diners, 70,000+ restaurant partners and 25+ years of experience, OpenTable, part of Booking Holdings, Inc. (NASDAQ: BKNG), is an industry leader with a passion for helping restaurants thrive. Our world-class technology empowers restaurants to focus on what matters most – their team, their guests, and their bottom line – while enabling diners to discover and book the perfect restaurant for every occasion. 

Every employee at OpenTable has a tangible impact on what we do and how we do it. You’ll also be part of a global team and its portfolio of metasearch brands. Hospitality is all about taking care of others, and it defines our culture.

About the Job

Reporting to the Sr. Director, Global Revenue Strategy, Analytics & Operations, this role sits at the intersection of business strategy and applied AI, building end-to-end AI-powered solutions, workflow automations, and intelligent data systems across OpenTable.

This role will work cross-functionally with strategy, sales, and operations teams to understand how the business actually operates, identify friction points, and build production-ready AI applications, such as agents, RAG pipelines, and automated action triggers, that drive revenue and operational efficiency. Rather than simply executing technical specs, this role is expected to proactively identify where AI can create impact, drawing on a deep understanding of the business alongside strong technical execution.

The Applied AI Engineer, Business Solutions combines business acumen with software and data engineering skills to solve high-impact problems through AI. This position requires excellent communication, strong analytical ability, and a resourceful problem-solver comfortable taking ownership of solutions from concept through deployment.

Responsibilities

• Business-first problem discovery: Partner with strategy, sales, and operations stakeholders to understand how their workflows function, and proactively identify opportunities where AI-driven solutions can create impact.
• AI & automation development: Build, test, and deploy custom AI applications — including LLM integrations, retrieval-augmented generation (RAG), agentic workflows, and automated system triggers — that optimize daily operations.
• System integration & data architecture: Connect AI models and microservices with internal databases (Snowflake), APIs, and third-party tools to automate manual business processes.
• Process optimization: Identify recurring manual tasks and operational bottlenecks across revenue teams, and design automations that reduce friction and accelerate decision-making.
• Testing & quality control: Implement evaluation frameworks and monitoring to ensure AI tools produce reliable, accurate, and secure outputs aligned with company data policies.
• Continuous learning: Stay current on AI frameworks, APIs, and automation technologies, evaluating new tools to enhance the team's capabilities.
• Stakeholder communication: Clearly articulate technical concepts, workflow logic, and project outcomes to non-technical business partners and team leaders.

Minimum Qualifications

• 5+ years in software engineering, data engineering, or applied AI roles, with a track record of building tools or automations that solve real business problems. 
• Bachelor's or Master's degree in Computer Science, Software Engineering, Data Science, Information Systems, or a related quantitative field. 
• Ability to learn a business domain deeply, ask the right questions, and independently identify where AI or automation can create meaningful impact. 
• Hands-on experience with modern AI APIs and frameworks (OpenAI/Anthropic APIs, LangChain, LlamaIndex, vector databases, or agentic automation workflows). 
• Strong proficiency in Python (for building tools, API integrations, and data processing) and SQL (Snowflake or other relational/cloud data warehouses). 
• Familiarity with Git, API design, data orchestration tools (e.g., Airflow or similar), and basic software deployment practices. 
• Excellent written and verbal communication skills, with a track record of working effectively across technical and non-technical teams. 
• Proactive, curious, and adaptable — willing to learn new technologies and take ownership of projects end-to-end. 

Benefits and Perks

• Work from (almost) anywhere for up to 20 days per year
• Focus on mental health and well-being:
• Company-paid therapy sessions through SpringHealth
• Company-paid subscription to Headspace
• Annual company-wide week off a year - the whole team fully recharges (and returns without a pile-up of work!)
• Paid parental leave
• Generous paid vacation + time off for your birthday
• Paid volunteer time
• Focus on your career growth:
• Development Dollars
• Leadership development
• Access to thousands of on-demand e-learnings
• Travel Discounts
• Employee Resource Groups
• 20 days of paid time off
• Private health and dental insurance
• Life and Disability insurance

The best connections happen face-to-face, whether you’re sitting down to dinner or having coffee with a coworker. That’s why OpenTable has adopted a hybrid workplace model. This role aligns with that approach, with an expectation of coming into the office two days a week—giving employees the best of both worlds: in-person collaboration and flexibility.

The expected range of compensation for this position based in Toronto, Canada, including commission and/or bonuses, is $110,000 - $123,000 CAD. There are a variety of factors that go into determining a compensation range, including but not limited to external market benchmark data, geographic location, and years of experience sought/required.

We offer a competitive base salary and benefits including: health benefits; flexible spending account; retirement benefits; life insurance; paid time off (including PTO, paid sick leave, medical leave, bereavement leave, floating holidays and paid holidays); and parental leave benefits. This role is eligible to be considered for an annual bonus and equity grant.

Work Environment & Flexibility

At OpenTable, we pride ourselves on fostering a global and dynamic work environment. As a team member with us, you will benefit from a schedule tailored to accommodate a global workforce operating across multiple time zones. While the majority of your responsibilities may align with conventional business hours, there will be instances where you are expected to manage communications - via calls, Slack messages, or emails - outside of regular working hours to effectively collaborate with international colleagues, respond to restaurant partners, and/or address urgent matters. OpenTable will always abide by and consider local laws and regulations.

Inclusion

We’re committed to creating a workplace where everyone feels they belong and can thrive. We know the best ideas come when we bring different voices to the table, so we're building a team as dynamic as the diners and restaurants we serve—and fostering a culture where everyone feels welcome to be themselves.

If you need accommodations during the application or interview process, or on the job, we’re here to support you. Please reach out to your recruiter to request any accommodations.

#LI-Hybrid