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Head of Customer Success
full-timeToronto

Summary

Location

Toronto

Type

full-time

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About this role

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.

#Sadie

Other facts

Tech stack
Customer Success,Onboarding,Implementation,Relationship Building,Organizational Skills,Problem Solving,Technical Concepts,Restaurant Operations,Booking Systems,POS Platforms,Adoption,Retention,Satisfaction

About Valsoft Corporation

As a leading player in vertical market software (VMS), Valsoft combines industry expertise with a unique buy-and-hold investment philosophy, managing a growing portfolio of companies that benefit from decentralized leadership and operational autonomy. We actively support our businesses, guiding them in their growth and evolution into market leaders.

Headquartered in Montreal with a global presence, Valsoft is committed to building a legacy of excellence by prioritizing sustainable growth and operational efficiency. Our long-term vision, driven by entrepreneurial spirit and disciplined execution, ensures we create lasting value for our portfolio companies, their customers, and the industries they serve. For more information, visit valsoftcorp.com.

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En tant qu'acteur de premier plan dans le domaine des logiciels pour marchés verticaux (LMV), Valsoft allie expertise sectorielle et une philosophie d'investissement unique axée sur l'acquisition et la conservation. Nous gérons un portefeuille croissant d'entreprises qui bénéficient d'un leadership décentralisé et d'une autonomie opérationnelle. Nous soutenons activement nos entreprises en les accompagnant dans leur croissance et leur évolution en leaders de leur secteur.

Basée à Montréal et présente à l'échelle mondiale, Valsoft s'engage à bâtir un héritage d'excellence en priorisant la croissance durable et l'efficacité opérationnelle. Notre vision à long terme, portée par un esprit entrepreneurial et une exécution rigoureuse, nous permet de créer une valeur durable pour nos entreprises, leurs clients et les industries qu'elles desservent. Pour plus d'informations, visitez valsoftcorp.com.

Team size: 1,001-5,000 employees
LinkedIn: Visit
Industry: Financial Services

What you'll do

  • Own the end-to-end customer journey for Sadie’s restaurant partners, ensuring smooth onboarding and long-term success. Act as a trusted advisor post-go-live, guiding customers through adoption and performance optimization.

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Frequently Asked Questions

What does a Head of Customer Success do at Valsoft Corporation?

As a Head of Customer Success at Valsoft Corporation, you will: own the end-to-end customer journey for Sadie’s restaurant partners, ensuring smooth onboarding and long-term success. Act as a trusted advisor post-go-live, guiding customers through adoption and performance optimization..

Why join Valsoft Corporation as a Head of Customer Success?

Valsoft Corporation is a leading Financial Services company.

Is the Head of Customer Success position at Valsoft Corporation remote?

The Head of Customer Success position at Valsoft Corporation is based in Toronto, Canada. Contact the company through Clera for specific work arrangement details.

How do I apply for the Head of Customer Success position at Valsoft Corporation?

You can apply for the Head of Customer Success position at Valsoft Corporation directly through Clera. Click the "Apply Now" button above to start your application. Clera's AI-powered platform will help match your profile with this opportunity and guide you through the application process. You can also learn more about Valsoft Corporation on their website.