Senior Customer Success Manager-Strategic/Enterprise Team

linksquaresinc; Boston (MA); Hybrid; USD 90,000 - 125,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

401k with company match

Equity awards

Flexible paid time off

Parental leave

Life and disability insurance

Job summary

LinkSquares, a Boston-based AI-powered CLM SaaS leader, seeks a Sr. Customer Success Manager (Strategic/Enterprise) to guide customers from onboarding to renewal. You will blend relationship-building, problem-solving, and growth tactics to boost retention and revenue.

In this highly visible role, you will own strategic partnerships, manage renewals, and identify upsell opportunities while collaborating with Product, Support, and Sales to maximize customer value.

Qualifications

• 5+ years handling renewals, upsells and cross-sells in SaaS.
• Ability to build strategic relationships at multiple levels.
• Experience with Salesforce, Gong.io, Outreach and Catalyst.
• Highly organized, process-oriented with target-driven mindset.

Responsibilities

• Strategic partnership: develop customized success plans driving value.
• Relationship management: primary contact for portfolio with strategy calls and proactive outreach.
• Retention & growth: manage renewals and identify upsell opportunities to expand product usage.
• Cross-functional advocacy: connect customers with Product, Support, and Sales teams.
• Value realization: educate customers on product updates and best practices.

Skills

Relationship-building

Negotiation

Strategic relationships

Organized & process-driven

Tools

Salesforce

Gong.io

Outreach

Catalyst

Job description

About the company

LinkSquares is a Boston-based, AI-powered CLM SaaS leader trusted by organizations like DraftKings, Manscaped, and Vivid Seats. We automate the contracting process for legal, finance, and HR teams, helping them save time, cut costs, and improve business outcomes. For more information, visit linksquares.com .

About the team

Join our Customer Experience organization, a detail-oriented and financially driven team dedicated to driving long-term value and growth. The Account Management team sits at the heart of our net retention strategy, transforming product usage data into strategic opportunities. We are a collaborative group that works closely with Marketing, Legal, and CS to navigate complex negotiations and ensure our customers-like TIME and Peregrine Hospitality-achieve their positive business outcomes.

About the role

As a Sr. Customer Success Manager (CSM)-Strategic/Enterprise , you will serve as the primary guide and strategic partner for our customers throughout their entire lifecycle. From onboarding through renewal, you will help customers unlock the full potential of our AI-powered platform to achieve their unique business goals. This is a highly visible role where you will blend relationship-building, creative problem-solving, and a growth-oriented mindset to directly impact LinkSquares' retention and revenue goals.

Responsibilities

• Strategic Partnership: Understand customer goals and collaborate on customized success plans that drive measurable business value through the LinkSquares platform.
• Relationship Management: Act as the primary point of contact for your portfolio, developing strong connections with key stakeholders through regular strategy calls and proactive outreach.
• Retention & Growth: Manage the renewal process for your designated accounts while proactively identifying upsell and cross-sell opportunities that introduce new features and drive additional value.
• Cross-Functional Advocacy: Connect customers with the right internal and external resources to resolve inquiries smoothly, collaborating closely with Product, Support, and Sales teams.
• Value Realization: Continuously educate customers on product updates and best practices, ensuring deep adoption and alignment with their evolving operational needs.

Requirements

• 5+ years of proven experience handling and negotiating renewals, upsells, and cross-sells in a high-performance SaaS environment.
• Ability to build strategic relationships at various levels, both internally and externally.
• Experience with Salesforce, Gong.io, Outreach, and Catalyst (or similar CRM/CS tools).
• Must be highly organized, process-oriented, and capable of working to strict targets and deadlines.

Compensation and benefits

Compensation for this role includes an annual base salary between $90,000 to $125,000. On-target commissions for this role range between $13,000 to $18,500 annually, with an opportunity to earn more than the on-target commission by exceeding targets. LinkSquares takes into consideration a number of factors when determining an employee's starting salary, including work location, job-related skills, and relevant education, experience and training.

Candidates are eligible to participate in the company's benefit programs.

LinkSquares' benefits include but are not limited to

• medical
• dental
• vision insurance
• 401k retirement plan with a company match
• equity awards (a new hire grant, along with opportunities for additional awards throughout your tenure)
• flexible paid time off
• generous parental leave
• life and disability insurances and more

Equal Opportunity Statement

LinkSquares is an Equal Opportunity Employer and does not discriminate based on any legally protected characteristics.