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Lead Customer Success Manager

Job in Waukegan, Lake County, Illinois, 60087, USA
Listing for: PowerToFly
Full Time position
Listed on 2026-09-12
Job specializations:
  • Business
    Change Management, Client Relationship Management
  • Management
    Change Management, Client Relationship Management
Salary/Wage Range or Industry Benchmark: 100000 - 150000 USD Yearly USD 100000.00 150000.00 YEAR
Job Description & How to Apply Below

Posting Type

Remote/Hybrid

Job Overview

The Lead Customer Success Manager operates at the intersection of strategic customer consulting and internal team leadership. This role owns a portfolio of Premier Tier (PSP) accounts, which are the highest-value, most complex relationships in the business. This role also serves as a methodology leader, coaching resource, and execution standard-setter for the broader CSM team. The Lead CSM is accountable, not only for their own portfolio outcomes, but for the quality of AI adoption, change-management practice, and domain expertise that CSMs in their orbit deliver.

This role shapes what excellence looks like.

Job Description and Requirements
  • Deliver the full Premier Tier value proposition: orchestrate the PSP catalogue, coordinate the account team(TAM, Adoption Services, Executive Sponsor), and own the customer's overall success program quality.

  • Own customer health; make building the renewal business case a daily motion.

  • Lead ROI Summaries, benchmarking reports, and executive-level Business Reviews that quantify impact and connect to customer C-suite priorities.

  • Build VO champion relationships; deliver referenceable outcomes that Marketing and Sales leverage — and holdself accountable to referenceable account targets.

Lead AI Adoption and Change Management at the Highest Level
  • Serve as the team's AI adoption and change-management exemplar: lead customers through comprehensiveai

    Rworkflow integration, advising on governance, defensibility, and how to transform legal practice.

  • Own the conversation with GCs, senior partners, and legal ops leaders on what AI means for their team, their workflows, and theirriskposture. Be the person customers trust to co-design AI-governed legal workflows.

  • Use generative AI tools to accelerate success planning, VO creation, and customer prep,and model what this looks like for peers.

  • Build repeatable AI adoption and change-management playbooks for your segment; contribute to the team's Tier 1methodology.

Serve as a Methodology Leader and Internal Multiplier
  • Own at least one department-level initiative per year with measurable business impact (e.g., AIadoptionplaybook development, Tier 1methodology, change-management framework).

  • Train and coach CSMs on VO quality, Tier 1 adoption, AI governance conversations, exec engagement, and success planning; serve as the practical expert peers go to before escalating to management.

  • Represent the CSM function in cross-functional forums, product councils, or Sales alignment meetings; bring a documented customer perspective that shapes decisions.

Execute with Executive Credibility and Commercial Awareness
  • Maintain C-suite relationships across PSP accounts; be recognized by customer executives as a strategic peer and change-management advisor

  • Partner with AEs and Sales leadership as a peer: bring account intelligence, surface growth signals, and co-develop expansion strategies,whilemaintainingthe trusted advisor boundary.

  • Anticipate and navigate complex stakeholder environments, including multi-entity global structures and political dynamics, without escalation dependency.

What We're Looking For
  • 7-10 years in Customer Success, Consulting, or Strategic Account Management with demonstrable ownership of enterprise or premier-tier relationships

  • Track recordof driving measurable outcomes across complex, multi-stakeholder accounts at the executive level

  • Proven ability to develop teammethodology, playbooks, or enablement assets that improve peer performance

  • C-suite credibility: able to lead exec-level conversations, challenge assumptions constructively, and influence strategic decisions

  • Deep AI fluency: able to advise customers onai Radoption strategy, AI governance, workflow defensibility, and the business case for AI-enabled legal practice transformation

  • Change-management leadership: able to help customers build internal consensus, navigate resistance, and measure adoption by outcomes.

  • Commercial awareness: understandsrenewal dynamics, growth signals, and how to support Sales without overstepping role boundaries

Required
  • Deepexpertisein legal technology, eDiscovery, litigation operations, or a compliance-regulated environment. This role advises GCs and senior partners; domain credibility is non-negotiable

Preferred
  • Background in legal practice, litigation support, or legal operations; the ability to speak as a peer to senior legal professionals

  • Experience owning Premier or paid success programs with defined SLAs and commercial accountability

  • Gainsight…

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