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Senior Customer Success Manager

Draftwise
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Hybrid (New York, NY; Chicago, IL; Toronto, ON; Remote (US))$150k - $190kFull-timePosted 11mo ago

About the role

Contract and negotiation AI built for lawyers. Senior Customer Success Manager responsible for onboarding, adoption, reducing churn, and acting as the voice of customers to inform product improvements.

Responsibilities

  • Onboard customers and drive platform adoption
  • Reduce churn and ensure customers realize value from the DraftWise platform
  • Act as voice of users, collecting feedback and proposing new product features
  • Design scalable customer success operations and determine tools to support growing customer base
  • Own initiatives related to customer success and potentially shape company processes and culture while collaborating with a small, flexible team

Qualifications

  • 6+ years in customer-facing SaaS roles
  • Exceptional communication skills with an emphasis on building trust
  • Proven track record of driving customer engagement, retention, and expansion
  • Experience designing software training and analyzing cohort retention
  • Interest in the legal industry or language analytics

Skills

Required:Customer success managementCommunication
Nice to have:Training design and cohort analysisData analytics and reporting

Benefits

  • Flexible remote work - with a hybrid option if desired
  • Equity plan
  • Competitive salary
  • Private medical care
  • New laptop and a work-from-home stipend for necessary accessories
  • Generous PTO / sick leave
  • Opportunity to lead our company as we disrupt the legal world
Last updated Sep 23, 2026. Interested? Apply on the company site.
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About Draftwise

Contract and negotiation AI built for lawyers

Draftwise is redefining contract work for lawyers with AI that streamlines drafting, review, and negotiation. Draftwise empowers lawyers with intelligent, data-driven tools that use a firm’s own knowledge base—drawing from past deals, preferred language, and internal guidance to improve the entire contract workflow—from first draft to signed deal.

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