Customer Success Lead US - Wexler

Pear VC•New York, NY

37d

About The Position

The litigation landscape is changing forever thanks to generative AI. Customer Success is driving this change. We're looking for an experienced, entrepreneurial Customer Success Lead with a demonstrated commercial record to join as our founding US hire and help drive how America's top law firms adopt, scale, and win with Wexler's platform for expert litigators. As the founding Customer Success lead for Wexler in the United States, you will be our boots on the ground with AmLaw 100 firms and Fortune 500 legal departments, overseeing the full client lifecycle, onboarding, training, adoption, renewal and expansion, ensuring every firm sees measurable value from the start. You will build trusted, long-term relationships with partners and senior associates, running regular health checks and strategic reviews, while proactively monitoring usage analytics, resolving issues and funnelling product feedback to Engineering. Your remit includes creating best-practice playbooks and knowledge-base content that scale expertise across our user community, and protecting and growing revenue by accurately forecasting renewals, identifying upsell opportunities and negotiating commercial terms that align with client outcomes. Beyond traditional CS duties, you will become Wexler’s in-house litigation specialist. You’ll guide fee-earners through complex workflows and make them experts in Wexler’s product, covering all of their day-to-day responsibilities and feeding back your insights to product. As our first US hire and founding Customer Success lead in North America, you'll have the unique opportunity to establish our entire US market presence from scratch, working directly with the CEO and Co-Founder to build the client engagement strategy, market relationships, and operational playbooks that will scale with our explosive US growth trajectory.

Requirements

3-5 years in Customer Success, Account Management, or Sales with enterprise B2B software, particularly complex technical products that require deep user adoption. Legal tech or professional services experience is a strong plus.
Proven ability to drive usage-based revenue growth through expansion within existing accounts, with a track record of growing client relationships from thousands to hundreds of thousands in ARR.
Commercial acumen and deal-closing skills. You're identifying opportunities, building business cases, and negotiating expansions with sophisticated procurement teams.
Experience with professional services clients - lawyers, consultants, accountants, or other expert users who demand precision and have complex, high-stakes workflows.
Technical curiosity and learning agility; you can quickly understand how AI models work, what makes document processing effective, and how to troubleshoot when things go wrong.
Executive presence and communication skills; you can hold your own in partner meetings while also being hands-on with implementation teams reviewing millions of documents.
Data-driven mindset with a focus on usage metrics, processing volumes, and ROI calculations rather than traditional SaaS vanity metrics.
Startup mentality - you're excited by ambiguity, rapid iteration, and the opportunity to build something from the ground up in a category-defining market.
AI enthusiasm - you're genuinely excited about the potential of AI to transform professional services
New York-based and willing to travel - You'll work closely with our London team but own the US customer base independently, with regular travel to client sites and occasional trips to London for team alignment.

Responsibilities

Become the trusted litigation AI expert for our clients, working directly with partners, associates, and corporate legal teams to maximise their document processing and case strategy capabilities. Your focus will be driving measurable usage growth that translates directly to revenue expansion.
Build our US market presence from the ground up as Wexler's first American team member, establishing relationships with elite US law firms and becoming the face of Wexler across the Atlantic.
Manage accounts and renewals across our customer base, focusing on driving Net Revenue Retention, ensuring no churn and maximising enterprise value.
Drive document volume and usage growth across your client portfolio of elite law firms and Fortune500 corporate legal teams, focusing on expanding Wexler adoption into new matters and practice areas.
Master complex legal workflows to guide clients through sophisticated implementations, from initial case setup to advanced fact extraction across millions of documents.
Become a litigation strategy consultant, working alongside legal teams to identify high-impact use cases where our AI can uncover case-winning facts and dramatically reduce document review time.
Own commercial expansion within accounts by identifying new matters, practice groups, and office locations where Wexler can drive results, then negotiating usage-based pricing expansions.
Build deep relationships with key stakeholders across both law firm partnerships and corporate legal departments, understanding their dispute resolution strategies and budget cycles.
Analyse usage patterns and case outcomes to demonstrate ROI through concrete metrics like time savings, document processing efficiency, and case success rates.
Partner closely with our technical teams to ensure client feedback shapes our AI capabilities, particularly around the nuances of different litigation types and jurisdictions.
Pioneer our customer engagement methodology as we scale our client base from dozens to hundreds of the world's most demanding legal organisations.