Head of Customer Success

About Sadie 

Sadie is transforming how restaurants engage with their customers using AI-powered voice technology. Our intelligent voice agent, Sadie, answers phone calls 24/7 to take bookings, manage reservations, answer FAQs, promote specials, and drive upsells—all without putting pressure on front-of-house staff. Sadie integrates with the world’s leading booking engines and POS systems to deliver a seamless guest experience and operational efficiency. 

We’re live in over 1,000 restaurants across Canada, the US, UK, Germany, and Australia — and we’re just getting started. 

About the Role

As Customer Success Lead, you will own the end-to-end customer journey for Sadie’s restaurant partners—from onboarding through long-term adoption and success. You’ll ensure customers not only launch smoothly, but continue to see meaningful value from Sadie’s Voice AI over time.

This role goes beyond implementation. You’ll act as a trusted advisor post–go-live, guiding customers through adoption, performance optimization, and ongoing engagement. You’ll work cross-functionally with Sales, Implementation, Support, and Product to remove friction, strengthen relationships, and drive retention and expansion.

This is an ideal role for someone who thrives on ownership, communication, and building strong customer partnerships in a fast-growing SaaS environment.

What You’ll Do

• Own customer onboarding and early success: Serve as the primary point of contact for new customers from kickoff through go-live, ensuring a smooth and efficient onboarding experience.
• Lead implementation coordination: Manage account setup, integrations with booking and POS systems, and configuration of Sadie’s voice features.
• Enable customers for long-term success: Deliver virtual onboarding sessions and training to restaurant managers and staff, ensuring confidence and readiness at launch.
• Drive adoption post–go-live: Monitor usage and performance, proactively identifying risks, opportunities, and optimization areas.
• Be a strategic partner: Act as the trusted advisor for customers after implementation, guiding best practices and helping them maximize value from Sadie.
• Collaborate cross-functionally: Partner with Sales, Support, and Product to ensure seamless handoffs, aligned communication, and a consistent customer experience.
• Track success metrics: Manage onboarding timelines, customer health indicators, and go-live milestones to ensure strong outcomes.
• Improve processes: Document customer insights, common challenges, and feedback to inform product improvements and scalable success playbooks.

What You Bring

• 2–4+ years of experience in Customer Success, Onboarding, or Implementation within SaaS, hospitality tech, or a related industry.
• Strong relationship-building skills and the ability to communicate clearly with a range of stakeholders.
• Excellent organizational skills with the ability to manage multiple customers and priorities simultaneously.
• A proactive, problem-solving mindset with comfort navigating technical concepts and integrations.
• Familiarity with restaurant operations, booking systems, or POS platforms is a strong plus.
• Experience owning customer outcomes (adoption, retention, satisfaction) beyond initial setup.

Why You’ll Love Working Here

• Be part of a fast-scaling AI company transforming the hospitality experience.
• High-ownership role with real impact on customer outcomes and retention.
• Collaborative, customer-first culture that values initiative and continuous improvement.
• Flexible, remote-first work environment.
• Competitive compensation and benefits.

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