Customer Success Manager Job at UserFirst Software Inc., Cambridge, MA

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  • UserFirst Software Inc.
  • Cambridge, MA

Job Description

Customer Success Manager II (CSM II)Level: Mid-Level Individual ContributorReports to: Head of Customer ExperienceLocation: Remote (Hybrid optional Boise, ID)Status: Full-Time, ExemptRole SummaryThe Customer Success Manager II is a mid-level role responsible for managing a defined portfolio of customer accounts across multiple lifecycle stages. This position is best suited for someone with prior experience owning account relationships and revenue outcomes. CSM IIs serve as the primary point of accountability for onboarding, value realization, retention, and expansion within their assigned book of business.Youll operate with a high degree of autonomyleading lifecycle strategy, commercial planning, customer engagement, and internal coordination. In addition to direct customer outcomes, youll also contribute to CX team development through mentorship, process improvements, and cross-functional collaboration. This is a fully revenue-responsible role with defined metrics for retention and growth.Key ResponsibilitiesCustomer Relationship Leadership: Build and maintain strong relationships across your accounts. Understand each customers business model, goals, and use case with LeanLaw. Lead check-ins, business reviews, and ongoing value conversations. Develop success plans that evolve over time.Onboarding & Change Management: Deliver structured, high-impact onboarding for new customers with minimal oversight. Tailor workflows based on firm structure and complexity. Guide clients through product adoption, internal change management, and value realization.Renewal Management & Retention: Own renewal forecasting and execution. Identify risk early, maintain accurate pipeline data, and drive retention conversations grounded in usage and business impact. Draft renewal agreements in collaboration with leadership.Expansion & Commercial Execution: Proactively identify and scope growth opportunitiessuch as user expansion, feature upgrades, or new departments. Present value-aligned recommendations, then collaborate with Sales or CX leadership to close.Lifecycle Strategy: Build and maintain structured lifecycle engagement strategies for your accounts. Coordinate success planning, check-in cadences, education, and value delivery with internal teams as needed.Issue Management & Escalation: Handle product issues and escalations with independence. Use internal systems (FIN, ProductBoard) to resolve issues before escalating. Contribute structured feedback to Product to help inform roadmap decisions.Documentation & Forecasting: Maintain full, real-time documentation of account activity, health indicators, opportunity signals, and renewal status in HubSpot. Ensure data is accurate and compliant with CX team SOPs.Team Contribution & Peer Enablement: Support junior team members through mentoring, shared accounts, and best practice sharing. Contribute to playbook updates, tool improvements, and process design.Key Metrics & Performance ExpectationsLogo Retention: 92% in assigned bookNet Revenue Retention (NRR): 100% quarterly averageExpansion Revenue: $6K$10K influenced per quarter (stretch target: $10K; targets may evolve based on business growth and team maturity)Renewal Forecast Accuracy: 10% within a 60-day forecast windowTime to First Value (TTV): 30 days from onboarding startCRM Hygiene: 100% activity logging and lifecycle tracking in HubSpotEscalation Quality: 5% escalations that bypass triage or processPortfolio Coverage: 100% accounts contacted within past 30 daysQualifications Required:35 years in a Customer Success, Account Management, or similar client-facing roleProven ability to independently manage a portfolio with renewal and expansion responsibilityStrong written and verbal communication skills, including with executivesOperational discipline and fluency in CRM systems (e.g., HubSpot, Salesforce)Familiarity with SaaS lifecycle models, success metrics, and adoption patternsAbility to work in an early stage, rapidly changing startup environment driven by self-guided learningPreferred:Experience with law firms, financial workflows, or billing/accounting softwareWorking knowledge of QuickBooks Online or LeanLaw integrationsPrior contributions to internal process improvement, documentation, or peer enablementCareer PathwaysCSM IIs may grow into one of two tracks based on performance, leadership, and impact:Senior Customer Success Manager (CSM III): Strategic account ownership, executive alignment, and team leadershipSpecialized CX Roles: Onboarding operations, enablement, program management, or cross-functional ownershipProgression is based on consistent outcomes, peer leadership, ability to drive scalable impact, and business success.Compensation & BenefitsBase Salary: $70,000$85,000 (based on experience and location)Benefits: Medical, dental, vision insurance; 401(k) with company match; generous PTO and paid holidaysWork Style: Remote-first with flexible scheduling; hybrid optional in BoiseIncentive Planning: LeanLaw is actively exploring future performance-based compensation models for customer-facing rolesAbout LeanLawLeanLaw helps law firms modernize their financial operations through intuitive, integrated legal billing software. Our Customer Experience team plays a critical role in client success, revenue growth, and product adoption. We believe in structured ownership, proactive engagement, and enabling our customers to drive long-term value.The Application Process Please submit your resume and cover letter. ResumeCover LetterWhich includes answers to the following questions:LeanLaws CX team is shifting from a service/support model to a revenue-owning Customer Success model. Based on your experience, what are the biggest mindset or behavior changes required to succeed in this kind of environment?Youre managing a book of 30+ accounts. Two accounts are suddenly at risk: one is underutilizing the product and unresponsive; the other is actively engaged but considering a competitor. How would you prioritize your time and what steps would you take with each?Our internal expectation is full CRM hygiene and process discipline100% logging, lifecycle stage tracking, and renewal forecasting. How do you ensure your systems stay updated in real time while maintaining meaningful customer engagement?Tell us about a time when you were solely responsible for driving a customer outcome across multiple internal stakeholders. How did you ensure follow-through on dependencies, and how did you track progress to completion?Salary ExpectationsWe will reach out to a shortlist of candidates for an initial interview to learn more about you. If you are a great fit, we will invite you for a panel discussion so you can meet the LeanLaw team and discover how we work.
recblid bqlmx8b6bc4scbpafbgkp0nflkl5e3

UserFirst Software Inc.

Job Tags

Full time, Flexible hours, Shift work,

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