Customer Success Lead at Pear Vc

ABOUT THE ROLE The litigation landscape is changing forever thanks to generative AI. Customer Success is at the centre of this shift. We are looking for an ambitious, commercially minded Customer Success Lead to join our growing London team as the second Customer Success hire, helping the world’s top law firms on both sides of the Atlantic adopt, scale, and win with Wexler’s platform for expert litigators. This is a high-impact role for someone who wants to grow quickly. You will work directly with our Head of Customer Success, CEO, and Co-Founder to manage strategic client relationships, drive adoption, and help build the foundations of a world-class CS function. You will own key customer accounts across the full lifecycle onboarding, training, adoption, renewal, and expansion ensuring every client sees measurable value from day one. You will become a trusted advisor to partners, associates, and litigation teams, helping them integrate Wexler into critical workflows and uncover new opportunities for impact. As employee number two in Customer Success, you will play a major role in shaping how we scale customer engagement, refine processes, and build a best-in-class experience for elite legal clients. WHAT YOU WILL DO You will be central to the company's growth, by becoming a trusted partner for our customers, helping them maximise Wexler’s value across their organisations. At this stage, Customer Success has an exciting wide scope, including: Managing portfolio of strategic accounts across leading law firms and in-house legal teams, across the customer lifecycle with direct ownership of adoption, retention and growth metrics. Driving product usage and expansion by identifying new matters, teams, and offices where Wexler can deliver results. Building trusted client relationships with partners, associates, innovation teams, and operations stakeholders. Finding innovative ways to engage our customers with events, workshops and tailored sessions. Spot customer health and usage trends early by understanding usage data, customer feedback, and commercial insights. Master complex litigation workflows so you can advise customers on best practices and strategic use cases. Partner closely with Product and Engineering to surface customer feedback, resolve issues quickly, and influence roadmap priorities. Help build the CS playbook by improving processes, templates, enablement materials, and customer success strategy as we scale. WHAT YOU BRING You understand that litigation AI is changing how elite legal professionals approach their highest-stakes work, and that earning their trust takes more than a good demo. You enjoy working with smart, demanding customers and thrive in environments where depth and results matter. We are looking for: 2–5 years of experience in a client-facing role: customer success, account management, consulting, or something adjacent, in B2B SaaS or a high-performance client-facing environment. We care less about the exact title and more about whether you have owned relationships, navigated complexity, and been accountable for outcomes. You communicate clearly and calibrate well. Writing to a senior litigation partner is different from briefing your own leadership team, which is different from checking in with an associate who is stuck. You know how to adjust and you know when to listen more than you talk. You can read data and turn it into a story. Usage dashboards, adoption trends, credit consumption patterns: you should be able to look at a set of numbers and know what they mean for a client relationship, a renewal conversation, or a growth opportunity. You do not need to be an analyst, but you do need to be fluent. You are comfortable with technology and genuinely curious about it. You can pick up a new product quickly, understand how it works under the surface, and demo it confidently to someone who is not easily impressed. You do not need an engineering background, but you do need to be the kind of person who wants to understand the "how" and not just the "what." You are comfortable with ambiguity. This role sits at the intersection of relationship management, commercial strategy, and product expertise, in a company that is still building its playbook. Experience with law firms or legal teams is a plus but not a requirement. What matters more is that you are willing to learn the domain deeply - litigation workflows, how disputes actually run, what lawyers care about - because that knowledge is what makes you credible with clients and useful to your colleagues. London-based and office-focused. We work from WeWork Aldwych 4 days per week, and in-person collaboration is core to our culture. WHAT WE OFFER At Wexler, you will work directly with some of the world’s best litigation teams on problems that genuinely matter. You will join early enough to have real ownership, visibility, and influence, while learning fast in a high-performing environment. As the second Customer Success hire, you will have a front-row seat in building the function, with significant room to grow into senior leadership as the company scales. We offer a competitive salary, meaningful equity in a rapidly growing company, huge autonomy and ownership, budget for learning and professional growth, and bi-annual team retreats.