About Draftwise
Draftwise is at the forefront of AI in the legal industry, building a secure knowledge platform that helps lawyers at elite law firms draft, negotiate, and review contracts faster and with an edge over their competitors. Our core product unlocks for the first time the years of historic legal contracts that firms have negotiated for their clients, combining the latest in machine learning, language analytics, and generative AI to help legal professionals work smarter and write better, safer contracts.
A few reasons to join Draftwise:
Our core offering has achieved product-market fit, proven by partnerships with leading Vault 10, Magic Circle, and Am Law 100 firms
Our founding team is composed of former Palantir and Google engineers alongside an experienced lawyer from a top global law firm
We recently raised $20M in our Series A, backed by Y-Combinator and Index Ventures
We are fully remote, with co-working options in major US and European cities
We are at the cutting edge of applied AI in legal, building tools that are genuinely changing how lawyers work
Our users love what we build, and the best is still ahead of us
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
Skills Required
- 5+ years in a customer-facing SaaS role
- 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
- Experience managing large-scale software rollouts in complex organizational environments
- Experience designing training programs that help non-technical users adopt new technology
- Comfort with data: pulling reports, tracking health metrics, and translating numbers into action
- Exceptional communication and relationship-building skills with senior stakeholders
- Ability to work independently and make sound decisions with minimal direction
- Genuine curiosity about AI and enthusiasm for AI-powered products
- Interest in the legal industry or language analytics
- Experience in legaltech or working with law firms
- Hands-on experience with AI tools
- Experience designing scalable CS processes at an early-stage or high-growth company
- Track record of identifying and executing upsell and expansion opportunities
