Head of Customer Success
Valsoft Corporation
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
- ...Role Overview & Key Responsibilities: As Head of Customer Success, you will build, lead, and scale the Customer Success function at Mortgage Automator. You will serve as a strategic partner across Product, Sales, Onboarding, Support, and Marketing, working cross-functionally...SuggestedLong term contractInternship
- ...startups in 2025 , 2024 and 2023 , Float is customer-obsessed, passionate and entrepreneurial,... ...all team members feel ownership in our success. Our Product Float is Canada's complete... ...About the Role We’re looking for a Head of Customer Success to join Float and be a...SuggestedLong term contractFull timeWork at office
- ...Role Type: Full-Time Work Location: Remote (Toronto, Canada) Reports to: Head of Customer Success Work Authorization: Candidates must have legal authorization to work in Canada at the time of hire. CWILL is not able to provide visa sponsorship at this time. About...SuggestedFull timeInternshipRemote work
$100k per year
...Guide new clients through onboarding, ensuring they are set up for success and confident in using Mortgage Automator to its full potential.... ...clients maximize their use of the platform and contributing to Customer Lifetime Value (CLTV). Proactively monitor client accounts to...SuggestedLong term contractWork at officeRemote workFlexible hours- ...Phylo is looking for a customer-oriented team player to own the post-sales experience for our most strategic enterprise accounts, and help us figure out what great customer success looks like at an early-stage company. This is a hands-on role for someone who moves fast, thrives...SuggestedLong term contractFull timeInternshipWork at office
$30k per year
...sells, supports, and re-engages customers across the entire journey.... ...own intelligent agent and every customer feels understood. Join us to... ...The Enterprise Customer Success team at Gorgias works with our... ...New York City, reporting to the Head of Customer Experience. What...RemplacementFull timeInternshipImmediate startShift work$160k - $189k per year
...The Director, Customer Success is a senior leadership role responsible for driving retention, expansion, and long‑term customer value across a strategic Enterprise portfolio of B2B SaaS customers. This role owns excellence in execution—translating strategy into outcomes...Long term contractPermanent employmentFull timeWork at officeFlexible hours$80k per year
...At Achievers, we believe recognition fuels performance, and our customers rely on us to help them build workplaces where people truly thrive. As a Customer Success Manager I, you’ll be at the heart of that mission, owning the strategy and long-term success of some of our most...Long term contractPermanent employmentFull timeContract workWork at officeFlexible hours- ...companies and top-rated startups in 2025 , 2024 and 2023 , Float is customer-obsessed, passionate and entrepreneurial, with a team that... ...making decentralized so that all team members feel ownership in our success. Our Product Float is Canada's complete business finance...Long term contractFull timeInternshipWork at office
- ...have opened this role to remote candidates as an exception to our standard policy. The Adventure Ahead As our Manager of Customer Success, you will step into a pivotal leadership role directly reporting to the Vice President of Customer Success. You will lead, inspire...Full timeFor contractorsWork at officeRemote workWorldwide3 days per week
- ...Temporary Customer Success Lead (maternity leave coverage) Remote – Canada Contract / Fixed-term (March 2026 – February 2027) About Circuit Circuit Virtual Tours is a SaaS platform helping colleges and universities create immersive, accessible virtual campus experiences...Long term contractContract workTemporary workFixed term contractRemote workFlexible hours
$85k - $95k per year
...Management Software brand in the world. Serving over 8,000 customers globally, processing more than 125 million orders per year, and... ...by Forbes Advisor. How you'll make an impact: As a Customer Success Manager at Cin7, you’ll be the strategic partner helping our...Long term contractFull time- ...for them. As a fast-growing SaaS company, we serve over 4,000 customers across 140 countries, helping more than 9 million users enhance... ...how businesses operate globally. We are seeking a Customer Success Manager to join our team and support some of our largest global...Long term contractFull time
- ...powered maintenance and asset management platform, serving 13,000+ customers including Duracell, Shell, Cintas, and Brenntag. We raised $... ...match. We are currently seeking a talented and motivated Customer Success Manager to join our team. Job Summary As a Customer...Full timeImmediate start
- ...Marsello helps over 2,000 brands around the world build stronger customer relationships through personalized loyalty marketing. We're growing fast, and we're looking for a Customer Success Manager based in Toronto to join our global team spread across New Zealand, Canada,...Full timeRemote work
- ...Job Description The Customer Success Manager will be a critical member of our Canadian team at Sodales Solutions and ensure that the company’s vision of delivering innovative, high-quality SaaS solutions is successfully adopted by our customers. As a key customer-facing...Long term contractFull timeImmediate start
$50k - $60k per year
...TouchBistro helps restaurants run better — and our Customer Success team makes sure every customer gets the most out of their investment. As a Customer Success Specialist, you’ll work directly with restaurant owners and operators to ensure they’re set up for success: proactively...Full timeInternshipFlexible hoursShift work- ...shaping healthcare's next era. Ready for the challenge? Job Summary We're seeking a strategic and relationship-focused Customer Success Manager with 3-5 years of experience to manage our portfolio of mid-market healthcare organisations. In this role, you'll own 20-...Full time
- ...collaboration drives the best products, services and values to customers. And the market agrees with us. Enable is a rapidly... ...us revolutionize the entire supply chain experience. As a Customer Success Manager, Enterprise, you will be assigned to work with some of...Full timeInternshipLocal area
$84k - $105k per year
...As a Customer Success Manager, you will be crucial in ensuring our customers achieve their desired outcomes with our products/services. You will be our customers' primary point of contact, responsible for creating raving Tipalti fans by building and maintaining strong, long...Full timeWork at officeFlexible hours- ...The Director, Customer Success is a senior leadership role responsible for driving retention, expansion, and long‑term customer value across a strategic Enterprise portfolio of B2B SaaS customers. This role owns excellence in execution—translating strategy into outcomes...Long term contractPermanent employmentFull time
- ...mission to make a real impact - for our customers, our team, and the world around us. We believe... ...into remarkable outcomes. Showing Customer Empathy ❤️ You bring humble confidence... ...announce that we are looking for a Customer Success Specialist to join our team at Levitate....Full time
$75k - $85k per year
...As a Customer Success Manager at Lone Wolf, you will own the ongoing success of a portfolio of customers and help them achieve meaningful business outcomes through our solutions. You will serve as a trusted advisor, customer advocate, and internal orchestrator across the...Full time- ...podcasts. Over the past five years, we’ve cultivated a devoted customer base of over 1,000 corporate and accounting firms across North America... ...to hear from you! Reporting to our Sr. Manager of Customer Success, the Customer Success Associate will be responsible for the...Full timeWork at officeRemote workFlexible hours
- ...POSITION DESCRIPTION POSITION: Customer Success Manager REPORTS TO: Manager, Customer Success Cority is the global enterprise EHS software provider creating industry-leading technology to empower those who transform the way the world works. For over 35 years, Cority...Full timeContract work
- ...has quickly led to big wins, including: Driving 100+ paying customers under 12 months of launching Partnering with industry... ...excellence in its craft, apply. The Role We're looking for a Customer Success Associate to own our start-up customer base and serve as the...Full timeWork at office3 days per week
$64k - $74k per year
...We are looking for a Customer Success Associate to join our team in Toronto! As a Customer Success Associate you will be responsible for driving strategy for the Achievers recognition and engagement platform while continuously driving value for our customers. You will play...Long term contractFull timeContract work$78k - $105k per year
...achieve the best results by doing things together. And that successful leaders need to adopt a curious and collaborative mindset in... ...billion people listen, learn and work better together. As a Customer Success Manager, you will help our customers to make Mentimeter become...Long term contractFull timeTemporary workWork at office3 days per week- ...we are looking for flexible go-getters who welcome the challenge of meeting the needs of a growing business. We are building the Customer Success program to help drive FacilityOS's growth forward. We are looking for a rockstar Customer Success Manager who will manage, retain...Full timeWork at officeFlexible hours
$52k - $55k per year
.... We welcome talented individuals to explore rewarding career opportunities across our diverse teams. Job Summary The Customer Success Representative (CSR) is responsible for managing customer accounts, processing orders accurately, and providing exceptional service...Full time
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to Head of Customer Success. Be the first to apply!
