Customer Success Manager, AI Enablement

Job Title: Customer Success Manager - AI Enablement

Location: Saskatoon

The Customer Success Manager, AI Enablement exists to own and optimize the self-serve partner cohort — a segment served primarily by Vendasta’s AI Employees. This role acts as the first human point of contact for new partners, bridging the gap between initial configuration and the AI-driven success layer.

About the Job

This role is responsible for conducting Configuration Calls that establish platform setup and AI Employee activation before handoff to the AI-driven success layer. Beyond onboarding, the CSM is accountable for the performance, configuration, and continuous improvement of the AI Employees (Vector, etc.) deployed as the frontline success layer. This role requires translating partner health signals into AI tuning decisions, escalating edge cases that require human intervention, and driving NRR within the self-serve cohort.

Your Impact

• Partner Onboarding: Conduct structured Configuration Calls to establish setup, document partner context, and set expectations for the AI-driven model.
• AI Employee Ownership: Configure, deploy, and optimize AI personas, knowledge bases, and escalation logic while monitoring interaction quality and resolution rates.
• Cohort Health & Retention: Monitor health scores across the self-serve book, executing human-touch interventions for high-risk accounts to maintain NRR above 100%.
• Workflow Design: Build and iterate on AI-powered playbooks, including onboarding sequences and proactive check-in cadences.
• Cross-Functional Advocacy: Synthesize partner feedback and AI data into product recommendations, serving as an internal subject matter expert on AI Employee capabilities.

What You Bring to the Table

• 3–5 years in Customer Success, Account Management, or equivalent client-facing SaaS role.
• Bachelor’s degree in Business, Communications, Computer Science, or related discipline.
• Hands-on experience configuring AI agents or AI-powered tools (e.g., Vendasta AI Workforce, Intercom Fin, Drift AI) in a business context.
• Proficiency in prompt engineering to govern AI behavior, tone, and knowledge retrieval.
• Ability to communicate clearly and effectively in written and verbal formats.
• Working knowledge of LLMs and how to assess AI output quality and identify gaps.
• Strong knowledge of Customer Success frameworks, including Success Planning and health scoring.
• Systems-thinking mindset with the ability to design scalable AI-powered workflows.
• Data literacy and the ability to interpret reports from CRM and AI performance dashboards.

About Vendasta

We help businesses get more customers. And keep them. We’re on a mission to build the most trusted AI-powered platform for small businesses and the partners who support them. At Vendasta, you’ll be part of something ambitious: helping bring AI transformation to local businesses at scale. As a team member, you’ll enjoy:

• Competitive health benefits, flex time, and annual work-from-anywhere options
• Equity opportunities and a chance to directly shape our AI future
• A vibrant workplace culture that embraces experimentation, thought leadership, and continuous learning
• A place where building AI isn’t just a buzzword, it’s the core of everything we do

Perks

Join the Vendasta family, where your growth, adaptability, and long-term career trajectory are our top priorities. We’re building for a rapidly changing, AI-powered world, and we’re committed to helping our people learn, evolve, and lead through it. At Vendasta, you’ll work alongside driven, curious teammates in a culture rooted in Drive, Innovation, Respect, and Agility, solving meaningful problems that shape the future of local business. We invest deeply in your development through continuous learning opportunities, hands-on exposure to emerging technologies, in-house training, education reimbursement, and leadership development programs designed to help you grow as the world evolves. We support this growth with flexibility, wellness benefits, and an environment that trusts you to do your best work - whether that’s learning something new, taking on bigger challenges, or building the next chapter of your career. At Vendasta, you’re not just keeping up with change. You’re growing with it.

Discover your potential. Build something that matters.

Help us lead the AI revolution from right here in Saskatoon.