Onboarding Specialist

About OpenTable

OpenTable, part of Booking Holdings, serves millions of diners and more than 60,000 restaurant partners worldwide. With over 25 years in the industry, the company builds technology that helps restaurants run smoothly, serve guests better, and improve their business outcomes. The organization operates with a strong hospitality mindset and values the impact each employee has on customers and the broader team.

Role Overview

In this role, you will represent OpenTable to newly signed restaurant partners and guide them from contract signature through configuration, training, and launch. You will use a consultative approach, supported by AI-enabled tools, to manage the implementation process, set up the product correctly, and help partners become fully operational as quickly and effectively as possible. The position calls for someone who can work independently, own the customer’s early success, and help restaurant teams gain value from the platform right away.

Key Responsibilities

• Take ownership of the complete onboarding process for a large number of restaurant partners, from post-sale setup through a successful go-live.
• Assess each restaurant’s needs and tailor OpenTable Core and Basic configurations to fit their floor plans, guest movement, and operating style.
• Use internal AI assistants and automation features to reduce repetitive work, speed up data handling, and create customized training materials.
• Lead remote training sessions for restaurant staff and explain product functionality in practical, operational terms using phone and online communication tools.
• Prioritize and manage a busy implementation queue while balancing speed, accuracy, and target onboarding timelines.
• Work with restaurants and external providers to install and activate the booking widget and other technical integrations.
• Collaborate across Sales, Customer Success, Customer Support, and Billing to remove blockers and resolve issues during the handoff period.
• Spot recurring patterns in the onboarding journey and contribute suggestions to improve global content, scheduling processes, and implementation guides.

Minimum Qualifications

• 4 to 5 years of professional experience in implementation, customer success, or a senior hospitality management position.
• Ability to use AI tools such as LLMs or automated workflow systems to improve productivity and output quality.
• Proven ability to train non-technical users on software or other technical solutions.
• Strong comfort using remote collaboration platforms such as Zoom and CRM systems such as Salesforce or similar tools.
• Confident phone communication and virtual presence for training and implementation conversations.

Preferred Background

• A bachelor’s degree, university degree, or an equivalent professional certification is preferred.
• Previous work experience in a restaurant environment, such as a manager, maitre d', or lead host, is an advantage.
• Experience with web integrations or widget deployment is helpful.
• Background in software implementation, SaaS products, or POS systems is preferred.

Benefits and Perks

• Option to work from almost anywhere for up to 20 days each year.
• Company-paid therapy through SpringHealth and a paid Headspace subscription.
• An annual company-wide shutdown week that gives the entire team time to fully recharge.
• Paid parental leave.
• Generous vacation allowance plus time off on your birthday.
• Paid volunteer time.
• Development Dollars, leadership development, and access to a large library of on-demand e-learning.
• Travel discounts and employee resource groups.
• 20 days of paid time off.
• Private health and dental coverage.
• Life and disability insurance.
• Additional benefits include a health benefits package, flexible spending account, retirement benefits, paid sick leave, medical leave, bereavement leave, floating holidays, paid holidays, and parental leave benefits.
• This position is eligible for an annual bonus.

Compensation

The estimated pay range for this role in Toronto, Canada is CAD 72,000 to CAD 82,000, with commission and/or bonuses included in the stated range.

Work Environment and Flexibility

This role supports a global team across multiple time zones. Most work will follow normal business hours, but there may be occasions when you need to communicate outside regular hours by phone, Slack, or email to coordinate with international colleagues, restaurant partners, or urgent matters. Scheduling and local labor laws will be respected.

Inclusion and Accommodations

OpenTable is committed to creating an inclusive workplace where people can bring their full selves to work and feel a sense of belonging. If accommodations are needed during the hiring process or in the role itself, support is available through the recruiter.