About Bask HealthBask is the best Telehealth platform on the market. Our mission is to empower entrepreneurs and businesses to launch a DTC telemedicine company quickly and easily, abstracting away the complexities of the industry into an easy-to-use platform. With hundreds of features to meet the unique needs of Telehealth, we put all the tools in our customers' hands for success.

We are a rapidly growing startup, and we work with care and intention to create a high-performance company with the following in mind: Intuition, Then Data. We're a data-driven company. We start with our instincts and then use data to validate our decisions and improve.

Customer-Obsession. We are obsessed with helping all our customers launch multi-billion-dollar companies with ease. We accomplish this by knowing our customers incredibly well and finding ways to make their businesses better.

About the RoleClient Success at Bask Health is AI-first and customer-obsessed. We're looking for an AI-Native Client Success Manager who takes full ownership of client relationships and uses AI as an essential part of their everyday workflow. In this role, you'll manage client accounts from onboarding through renewals and expansion, helping entrepreneurs launch and grow their Telehealth businesses on the Bask platform.

You'll use AI tools to research client needs, troubleshoot challenges, improve processes, and identify opportunities to deliver a better client experience. We're looking for someone who is comfortable experimenting with new technologies, thinks independently, and knows how to combine AI-driven efficiency with genuine human relationships. Build solid relationships with Bask clients and help them successfully launch and grow their businesses.





Use AI tools and large language models (LLMs) to research client needs, structure problems, draft communications, and improve day-to-day workflows. Develop AI-assisted workflows and automations to streamline onboarding, account management, follow-ups, and troubleshooting. Help clients launch medications and identify opportunities to expand their product offerings.

Monitor client health, platform usage, and engagement metrics to identify potential churn risks and growth opportunities. Develop proactive strategies to improve client adoption, retention, and overall account performance. Deliver platform demonstrations, answer technical questions, and recommend creative ways for clients to get more value from Bask.

Use client data and measurable outcomes to evaluate the effectiveness of AI-assisted processes and client success initiatives. Validate AI-generated recommendations through research, testing, and client feedback before implementation. Document and share successful AI prompts, automations, and repeatable workflows with the Client Success team.

Work Weekends. 5+ years of experience in Customer Success, Account Management, or Client Services within a SaaS organization.

Experience in e-commerce, ideally supporting DTC brands, online merchants, or e-commerce technology platforms.

Experience managing large or enterprise-sized client portfolios.



Demonstrated hands‑on experience using AI tools such as ChatGPT, Claude, Gemini, or similar LLMs to improve professional workflows.

Experience creating, implementing, or improving AI-assisted processes, automations, or repeatable workflows. Ability to provide real examples of how you've used AI to solve problems, improve efficiency, or deliver measurable business results. Strong understanding of client onboarding, adoption, retention, renewals, and account expansion.

Experience using client engagement data and performance metrics to identify risks and growth opportunities. Ability to independently research problems, evaluate AI-generated information and turn findings into practical solutions. Good judgment when handling sensitive client information and using AI tools in accordance with company privacy and security requirements.

A creative problem solver who takes initiative and is comfortable navigating unfamiliar challenges. Strong organizational skills and the ability to manage multiple client accounts and priorities.

How We Work

With AIAt Bask Health, AI isn't an occasional productivity tool. It's part of how we approach problems, make decisions, and support our clients. Start with AI when researching, organizing information, and exploring solutions.

Use independent judgment to verify AI-generated recommendations before putting them into practice. Measure the effectiveness of AI-assisted workflows and continuously refine them based on results. Experiment with new AI tools and approaches.

The ideal candidate doesn't need to be an AI engineer, but should be someone who naturally looks for ways to use AI to work smarter and deliver better results #

📌 Ai-Native Client Success Manager (Winnipeg)
🏢 Bask Health
📍 Winnipeg