Onboarding Specialist (Remote)

With millions of diners, 60,000+ 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

As an Onboarding Specialist, you are the face of OpenTable for our new restaurant partners, ensuring they transition from a signed contract to a fully optimized, live operation. Using a consultative approach and leveraging modern AI-assisted tools, you lead the end-to-end implementation process, configuring our suite of applications, managing technical setups, and delivering high-impact training. Your goal is to empower hospitality professionals to maximize their revenue and efficiency from day one, acting as an independent owner of the customer’s initial success.

Responsibilities

• End-to-End Implementation: Own the full onboarding lifecycle for a high volume of restaurant partners, guiding them from initial sale through software configuration to a successful go-live.
• Consultative Configuration: Analyze unique restaurant business needs to customize OpenTable Core and Basic applications, ensuring the system is optimized for their specific floor plans and guest flow.
• AI-Driven Efficiency: Utilize internal AI assistants and automation tools to streamline data entry, generate customized training outlines, and reduce manual administrative tasks, increasing your capacity for high-touch consulting.
• Expert Training Delivery: Conduct engaging remote training sessions for key restaurant staff, translating technical features into actionable operational wins using phone and online tools.
• Project Pipeline Management: Independently manage a dynamic queue of implementations, balancing speed and quality to consistently meet or exceed time-to-onboard benchmarks.
• Technical Integration: Coordinate with restaurant staff and third-party providers to deploy the OpenTable booking widget and ensure seamless digital connectivity.
• Cross-Functional Collaboration: Partner with Sales, Customer Success, Customer Support, and Billing teams to proactively resolve roadblocks and eliminate customer difficulties during the transition.
• Process Evolution: Identify trends in the onboarding journey and contribute ideas to refine global program content, scheduling workflows, and implementation playbooks.

Minimum Qualifications

• 4–5 years of professional experience, specifically in implementation, customer success, or a high-level hospitality management role.
• Experience or proficiency in using AI tools (e.g., LLMs, automated workflow tools) to enhance productivity and work quality.
• Demonstrated experience training non-technical customers on software or technical products.
• Strong proficiency in remote collaboration tools (e.g., Zoom, Salesforce, or equivalent CRM).
• Good phone skills and tele-presence required for effective training and implementation.

Preferred Qualifications

• Bachelor’s degree, university degree, or equivalent practical/professional certification.
• Direct experience working in a restaurant environment (Manager, Maitre D', or Lead Host).
• Experience with web-based integrations or widget deployments.
• Experience with software implementation, SaaS platforms, or POS (Point of Sale) systems.

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 expected range of compensation for this position based in Toronto, Canada, including commission and/or bonuses, is $72,000-$82,000 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.

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.