Head of Customer Success

DeepJudge•,

2d•$350,000 - $400,000

About The Position

DeepJudge is seeking a Head of Customer Success to rebuild and lead the post-sale engine for AI-native products. This role involves owning Gross Revenue Retention (GRR), Net Revenue Retention (NRR), and expansion Annual Recurring Revenue (ARR). The ideal candidate will be a first-principles operator who has personally managed these metrics, built and evolved post-sale motions in fast-moving environments, and possesses the judgment to design and execute the AI-native version. The role requires customer obsession, a focus on building relationships with sophisticated buyers, systems thinking, and high standards. The Head of Customer Success will work closely with the implementation team and the CRO to ensure a seamless customer experience and drive value realization.

Requirements

Personally owned GRR, NRR, and expansion ARR.
Experience building and evolving post-sale motions in fast-moving environments.
Customer obsession.
Ability to hire people better than oneself and set high standards.
Experience building relationships with sophisticated buyers.
Systems thinking approach.
High standards, direct communication, humility, and a bias for action.
Legally authorized to work in the United States.
Experience leading customer success teams.
Experience in designing and implementing post-sale strategies for enterprise SaaS.

Nice To Haves

Experience in the legal tech industry.
Experience with AI-native products.

Responsibilities

Own and influence GRR, NRR, and expansion ARR.
Lead customer implementations alongside the team, acting as an expert on product, adoption, and value realization.
Develop training materials, change management playbooks, and executive value stories.
Personally own marquee customer relationships, acting as a key point of contact and shaping customer value realization.
Partner with the implementation team to ensure customers land real use cases, integrated data, and embedded workflows on schedule.
Design and install an AI-native post-sale motion, evolving adoption, renewal, and expansion strategies.
Double the Customer Success Manager (CSM) team size, hiring and developing Tier-1 operators.
Build and run a Customer Advisory Board with marquee customers.
Embed customer health scoring and early-warning systems.
Build the foundation of a repeatable post-sale system, including methodology, RACI, cadence, scorecards, and AI-powered tooling.
Operate as one revenue team with no silos, ensuring tight coordination between Sales, Customer Success, and Implementation.