Senior Customer Success Manager-Strategic/Enterprise Team

MassMutual Ventures; Boston (MA); On-site; USD 90,000 - 125,000; Full time

Benefits offered by this job

Medical, dental & vision insurance

401k with company match

Equity awards

Generous paid time off & parentalleave

Job summary

LinkSquares is a Boston-based, AI-powered CLM SaaS leader seeking a Sr. Customer Success Manager (CSM) - Strategic/Enterprise to guide customers from onboarding to renewal and drive retention and revenue.

You will blend relationship-building, problem-solving, and a growth mindset to deliver measurable value on the LinkSquares platform. You will manage strategic relationships, execute renewal and upsell strategies, and collaborate with Product, Support, and Sales to resolve inquiries and drive

Qualifications

• 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.

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.

Skills

Strategic relationship-building

Negotiation

Customer success

Goal-oriented

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 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. The recruiter assigned to this role will share more information about the specific compensation and benefit details associated with this role during the hiring process.

Candidates are eligible to participate in the company’s benefit programs. LinkSquares’ benefits include but are not limited to medical, dental, and 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.

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