About the Role

As a Senior Customer Success Manager at Draftwise, you will own client relationships end to end, from onboarding and adoption through retention and expansion. You will be the person helping lawyers and legal teams understand and unlock the full power of AI in their day-to-day work, turning curiosity about the technology into deep, sustained usage that delivers real outcomes for their clients.

Your primary focus is driving meaningful engagement and measurable value for every customer in your portfolio: accelerating adoption of AI-powered workflows, deepening usage across practice groups and matter types, and ensuring lawyers at your firms become committed advocates for the product.

You will serve as the voice of your users across the organization, translating their feedback into product insights and partnering directly with our product team to shape what we build next. As we scale rapidly, you will also help design the systems and processes that let us deliver this level of partnership to more customers over time.

This is a high-ownership role on a small, fast-moving team working on one of the most consequential technology shifts in the legal industry. You will have the autonomy to shape how we work, the opportunity to build something from the ground up, and the satisfaction of seeing your customers win with AI.

What We Value

• Strong communication skills and a genuine commitment to transparency
• The ability to work independently and make sound decisions with minimal direction
• A collaborative mindset and low-ego approach to cross-functional work
• Comfort operating in a dynamic environment where priorities evolve
• Genuine curiosity about AI and how it can transform the way professionals work

About You

We're looking for someone who has:

• Exceptional communication and relationship-building skills, with a track record of earning trust at senior stakeholder levels
• Proven ability to drive engagement, retention, and expansion in a B2B SaaS environment
• Experience owning net revenue retention and expansion metrics for a defined book of business
• Passion for seeing customers succeed and turning satisfied users into vocal advocates for AI-powered tools
• Experience managing large-scale software rollouts in complex organizational environments, ideally involving AI or technically sophisticated products
• Experience designing training programs that help non-technical users build confidence with new technology
• Comfort with data: pulling reports, tracking health metrics, and translating numbers into action
• Enthusiasm for AI and a desire to stay close to a fast-moving product
• Interest in the legal industry or language analytics
• 5+ years in a customer-facing SaaS role

It's also great if you have:

• Experience in legaltech or working with law firms
• Hands-on experience with AI tools, whether in a professional or personal context
• Experience designing scalable CS processes at an early-stage or high-growth company
• A track record of identifying and executing upsell and expansion opportunities

What We Offer

• Flexible, fully remote work with optional co-working in major cities
• Competitive salary with meaningful equity at Series A, in a company at the center of the AI moment in legal
• Private medical care
• New laptop and home office stipend
• Generous PTO and sick leave