Renewals Specialist - OpenSesame

About OpenSesame

OpenSesame is the trusted partner for Workforce Reinvention in the age of AI. OpenSesame delivers integrated software, curated and customizable content, and expert services—embedded into existing learning, HR, and work systems—to help organizations expand their human+AI potential and thrive through change.

About the Team

Our Customer Success Managers (CSMs) are dedicated partners to our customers, working closely with them to understand their training goals and ensure OpenSesame delivers meaningful results. They provide ongoing guidance, recommend the right solutions, and help customers maximize the value of their learning programs.

Through thoughtful engagement and strong relationship-building, the CSM team drives utilization, supports strategic initiatives, and helps customers maintain momentum with OpenSesame. Their impact is reflected in renewals, account growth, reduced churn, and consistently high customer satisfaction.

About the Job

As a Renewals Specialist, you’ll be the engine powering our customer retention and expansion efforts. Partnering closely with our Customer Success Managers, you’ll drive the entire renewal cycle—from developing pricing strategy and leading negotiations to crafting proposals, generating quotes, sending Sales Orders, closing opportunities, and completing RFPs.

We’re looking for a proactive, experienced Procurement, Vendor Management, Account Management, or Sales professional with strong negotiation skills, who will work with CSMs to prove the value delivered to our customers and drive the contract renewal process.

30/60/90/120 Day Expectations

In Your First 30 Days:

• Gain a deep understanding of how OpenSesame Customer Success Managers operate and how renewals support the overall customer journey.
• Build strong working relationships with internal and cross-functional teams, including Sales, Finance, and Legal.
• Become proficient in CPQ/SFDC and the systems that support the renewals process.
• Generate quotes and Sales Orders and begin closing opportunities with guidance.
• Confidently articulate the value of OpenSesame products and services during internal and customer conversations.

In Your First 60 Days:

• Actively engage with customers and internal stakeholders to manage assigned renewals.
• Begin crafting pricing proposals in collaboration with CSMs and proactively resolve roadblocks to ensure on-time renewals.
• Review customer usage metrics and clearly articulate value delivered to reinforce renewal justification.
• Complete RFPs in our internal tool in partnership with CSMs.
• Forecast and begin closing upcoming renewals while identifying early upsell opportunities.

In 90 Days:

• Fully own the renewals and upsell lifecycle—from outreach to negotiation to close—for SMB and mid-market customers.
• Diagnose renewal risks, lead negotiation calls with Procurement teams, and collaborate with CSMs on enterprise opportunities.
• Confidently manage the renewals pipeline, ensuring continuous and accurate forecasting.
• Drive customer retention and expansion by contributing to a streamlined, customer-centered renewal strategy.

In 120 Days:

• Take over full management of enterprise renewals.
• Build strong cross-functional partnerships with Customer Success, Sales, Finance, and Legal to support seamless renewal and contract processes.
• Maintain accurate, up-to-date records of activities, opportunities, and forecasts in Salesforce on a daily basis.
• Demonstrate a solid grasp of customer needs, market dynamics, and expansion opportunities to further strengthen retention and revenue growth.

Working with AI at OpenSesame

Every team at OpenSesame works with AI tools daily as standard practice. You'll build fluency with hands-on training and clear guardrails to experiment responsibly. AI amplifies your creativity and judgment rather than replacing them.

Location & Travel Requirements

• Position can be based anywhere in the US (Remote-First).
• Requires up to 15 days of travel per year for company meetings and offsites.

Compensation & Benefits

• Base Salary: $100,000 USD
• Benefits:
  • Comprehensive medical, dental, and vision coverage
  • Flexible PTO
  • 401(k) matching
  • Incentive stock options
  • Volunteer time off
  • Employee Resource Groups
  • Professional development program with dedicated annual time off for learning