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Enterprise Customer Success Specialist

Job in Winnipeg, Manitoba, Canada
Listing for: AirMason, Inc
Full Time position
Listed on 2026-10-11
Job specializations:
  • Customer Service/HelpDesk
    Customer Success Management
Job Description & How to Apply Below
Air Mason is redefining how companies build, manage, and scale their employee experience through modern, interactive handbooks and compliance-driven workflows.
Our platform combines thoughtful design, powerful automation, and AI-driven capabilities to help organizations stay compliant, communicate clearly, and create better employee experiences m fast-growing startups to complex, multi-state enterprises, Air Mason enables teams to simplify compliance while delivering a polished, on-brand experience for their workforce.
As we continue to evolve our platform and expand into more intelligent, AI-powered solutions, Customer Success plays a critical role in ensuring our customers not only adopt Air Mason, but also fully realize its long-term value.
About the Role  As an Enterprise Customer Success Specialist, you will own the success of Air Mason’s most strategic and complex customer relationships. You will act as a trusted advisor to enterprise stakeholders, ensuring customers successfully implement, adopt, and realize measurable value from the Air Mason platform.
This is a highly cross-functional role, partnering closely with Sales, Product, Design, and Engineering to deliver seamless implementations, drive adoption, and identify opportunities for growth and expansion.
You will be responsible not just for supporting customers, but for proactively guiding them toward long-term success, retention, and partnership with Air Mason.

Key Responsibilities  Customer Success & Engagement   Act as a trusted advisor to customers, deeply understanding their goals, challenges, and evolving needs
Demonstrate strong user empathy and expertise in the lifecycle of a customer issue or request; you are able to read between the lines, identify root needs, and drive toward clear, effective resolutions
Maintain crisp, thoughtful, and detail-oriented communication across all channels (email, Slack, calls, etc.)
Proactively guide customers in adopting new features and understanding complex concepts in a simple, actionable way
Monitor customer health, engagement, and usage trends, and take proactive steps to improve adoption and satisfaction
Identify and mitigate risks early, ensuring a consistently high-quality customer experience
Post-Launch Success & Adoption   Partner with the Technical Onboarding team to ensure a smooth transition from implementation to ongoing success
Gain deep context on each customer’s implementation, goals, and configuration
Continue momentum post-launch by reinforcing training, adoption, and engagement strategies
Deliver ongoing enablement, including advanced use cases, new feature education, and optimization guidance
Own the enterprise renewal processes to ensure high retention across accounts
Identify expansion opportunities, including additional use cases, features, or business units
Partner with Sales on upsell and cross-sell opportunities within existing accounts
Mitigate churn risk through proactive engagement and issue resolution
Technical Coordination & Problem Solving   Triage and manage technical questions, working closely with Engineering and Product teams
Translate customer needs into clear technical requirements and actionable insights
Navigate ambiguity and complex problem-solving across technical and non-technical stakeholders
Customer Insights & Product Influence   Advocate for the customer internally by sharing feedback, trends, and feature requests
Identify recurring friction points and opportunities to improve the product or customer experience
Partner with Product to inform roadmap priorities based on enterprise needs
How You Work   You lead with empathy and curiosity, taking time to deeply understand customer needs rather than reacting at a surface level
You communicate clearly and…
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