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. This posting is for an existing vacancy.

About the Job

OpenTable is seeking a highly organized and motivated Associate Counsel, Commercial to join our legal team in Toronto, Canada, in a hybrid capacity (2 days/week in-office). In this role, you will draft, negotiate, and review a diverse suite of commercial contracts across multiple jurisdictions. Working closely with internal business teams, external stakeholders, and colleagues across Booking Holdings, you will support strategic business objectives while proactively managing and mitigating legal risk. This position offers an exciting opportunity to drive key product and vendor initiatives in a fast-paced, collaborative environment.

Responsibilities

• Draft, review, and negotiate a broad spectrum of international commercial agreements, including partner, vendor, SaaS, service agreements, non-disclosure agreements,  real estate leases, and other ancillary agreements.
• Develop and maintain contracting playbooks, workflows, and optimized legal processes, including enabling business teams to self-serve on routine legal matters.
• Deliver practical legal advice on commercial product initiatives, payment-related matters, and customer support inquiries.
• Assess and communicate legal and business risks effectively, offering strategic solutions and actionable mitigation tactics.
• Advise on contractual disputes and guide cross-functional teams toward efficient, favorable resolutions.
• Collaborate seamlessly with cross-functional business units, global procurement, external stakeholders, and global legal counterparts across Booking Holdings.

Minimum Qualifications

• J.D. or equivalent degree from an accredited law school, with active bar admission and good standing in at least one state or province.
• Minimum 3 years of experience drafting, redlining, and negotiating commercial contracts across multiple jurisdictions, including the United States.
• Strong attention to detail, demonstrated experience applying standard playbooks, spotting critical issues, assessing risk, and executing sound decisions under tight deadlines.
• Proven track record of managing multiple legal matters independently and adapting effectively to changing business priorities.
• Strong written and verbal communication skills, with a collaborative approach to partnering across cross-functional teams.
• Collaborative mindset, excellent judgment, high integrity, strong interpersonal skills, and a “can-do” attitude.

Preferred Qualifications

• Prior in-house legal experience.
• Prior experience utilizing contract lifecycle management (CLM) platforms and document management tools.
• Fluency or working proficiency in additional languages to support global commercial operations.
• Demonstrated openness and adaptability to expanding expertise into new or emerging areas of law.

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 $145,000-$155,000 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.

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