This role involves managing a book of around 20 of Ashby’s largest enterprise customers, worth over $2m in total ARR, focused on driving product adoption and customer health rather than renewals or upsells. You’ll become a deep product expert, tailor configurations, craft training, and work closely with stakeholders across Sales, Marketing, Product, and Operations to help shape a growing Strategic customer success motion. Ashby is looking for at least five years of customer success experience in B2B SaaS, ideally supporting complex, highly configurable products through implementation and adoption. Strong communication skills, comfort with ambiguity, attention to detail, and cross-functional collaboration are significant. Prior recruiting or hiring experience is a plus but not required. This is a full-time position open to candidates based in Canada or the USA, working remotely. The interview process includes a recruiter call, hiring manager interview, take-home exercise, and a multi-part panel interview. Applicant tracking systems sit between most online applications and the hiring manager. If your resume hasn't been looked at with that in mind lately, it's worth a second opinion.

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📌 Strategic Customer Success Manager – Americas Ashby (Winnipeg)
🏢 HelpfulRemote
📍 Winnipeg