Senior Customer Success Manager (Chicago)

DraftWise; Chicago (IL); Remote; USD 80,000 - 120,000; Full time

Job summary

DraftWise is seeking a Senior Customer Success Manager to enhance customer engagement and retention for their innovative legal knowledge platform. This role involves onboarding, driving adoption, and gathering feedback to improve product offerings. Join a fully remote team with a focus on collaboration and high-quality work, backed by leading venture capital.

Benefits

Flexible remote work with hybrid options

Equity plan

Competitive salary

Private medical care

Work-from-home stipend and new laptop

Generous PTO and sick leave

Opportunity to impact the legal industry

Qualifications

• 6+ years in customer-facing SaaS roles.
• Proven success in driving customer engagement and retention.
• Experience in designing software training and analyzing cohort retention.

Responsibilities

• Ensure customers achieve desired outcomes and realize platform value.
• Onboard customers and drive adoption.
• Gather user feedback to inform product development.

Skills

Communication

Customer Engagement

Adaptability

Data Analytics

Job description

Senior Customer Success Manager (Chicago)

Join to apply for the Senior Customer Success Manager (Chicago) role at DraftWise.

DraftWise is building an innovative knowledge platform for the legal industry. Our core product unlocks access to historic legal contracts negotiated by firms for their clients. We leverage data management, machine learning, and language analytics to help lawyers and legal professionals write better, safer contracts.

Our founding team includes former Palantir and Google engineers and an experienced lawyer from a top global law firm. We are a fully remote company with options to cowork in major North American and European cities. We hire globally, valuing respect, collaboration, and high-quality work. Backed by Y-Combinator, Index Ventures, and leading VC funds, we serve top-tier clients worldwide and are experiencing rapid growth.

As a Senior Customer Success Manager, you will ensure our customers achieve their desired outcomes and realize the full value of our platform. Your responsibilities include onboarding, driving adoption, reducing churn, and gathering user feedback to inform product development. You will help design scalable operations and support our expanding customer base, with broad ownership of initiatives and the opportunity to influence company culture.

What We Value

• Strong communication skills in an open environment
• Building trust through constructive feedback
• Ability to work independently and make decisions
• Adaptability in a dynamic environment

About You

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

Preferred Skills

• Experience in scaling company processes early-stage
• Legaltech industry experience
• Upselling skills for new features and products
• Interest in product management and UX design
• Data analytics and reporting proficiency

What We Offer

• Flexible remote work with hybrid options
• Equity plan
• Competitive salary
• Private medical care
• Work-from-home stipend and new laptop
• Generous PTO and sick leave
• Opportunity to impact the legal industry

Job Details

• Seniority level: Mid-Senior level
• Employment type: Full-time
• Job function: Other
• Industry: Software Development