Remote Renewals Specialist: Retention & Upsell Pro

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. Our Customer Success Managers 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. 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. We’re looking for proven examples from your career that show you can do this job, that you’ve built systems, driven alignment, and created impact at scale. When you look back a year from now, you’ll know you’ve made OpenSesame better, faster, and stronger because of your impact. Although it should go without saying (but it doesn’t), OpenSesame is an equal opportunity employer and we strive to create a welcoming, inclusive environment that celebrates diversity. We use AI. For real. Every team at OpenSesame works with AI tools daily, not as a buzzword, but as practice. You'll build fluency that most companies are still talking about adopting, with hands-on training and clear guardrails to experiment responsibly. AI amplifies your creativity and judgment. It doesn't replace them. The skills you build here travel with you. Location : This position can be based anywhere in the US. We operate as a remote-first company and invest in all-company in-person meetings several times a year. Performance Driven : We're looking for self-starters with a track record of delivering excellent results, but we're highly selective about who we hire. We don't focus on typical job requirements; instead, we're interested in specific examples from your past experiences. All positions can be based anywhere in the US, and require up to 15 days of travel per year, with senior management and leadership teams requiring up to 35 days. Compensation: The base salary for this role will be $100,000 USD.We carefully consider a wide range of compensation factors, relying on market data to determine compensation and consider your specific job family, background, skills, and experience. We prioritize pay transparency, fairness, and equity to create a positive and inclusive work environment, regularly reviewing our compensation practices to align with our values and goals. Benefits: Benefits include comprehensive medical, dental, and vision coverage, flexible PTO, 401(k) matching, incentive stock options, volunteer time off, Employee Resource Groups, and a generous professional development program with dedicated annual time off for learning and growth. Equal Employment Opportunity : OpenSesame is an Equal Employment Opportunity and Affirmative Action employer that values and welcomes diversity. We do not discriminate on the basis of various legally protected characteristics, including criminal history, and strive to provide reasonable accommodations to qualified individuals with disabilities. We prioritize safety and security and may use your information accordingly, and you can contact us for assistance or accommodations during the job application process. Pay Transparency : At OpenSesame, we prioritize pay transparency, fairness, and equity to create a positive and inclusive work environment, regularly reviewing our compensation practices to align with our values and goals. We provide competitive and fair compensation to our employees based on their skills, experience, and performance. CPRA (California Candidates): When you submit your application, OpenSesame may collect and use your personal information in accordance with our privacy policy and the CPRA. This may include personal details and employment history, and will only be used for employment-related purposes. We may share this information with third-party service providers, but we will not sell it to third parties. If you have any questions or concerns, please contact us, and for more information on your rights under the CPRA, refer to our privacy policy or the California Attorney General's website. We Care About Your Security: We’ve been made aware of a phishing scam involving individuals impersonating OpenSesame recruiters. All legitimate communication from our team will come from @opensesame.com email addresses. If you receive a suspicious message, please contact us directly at View email address on click.appcast.io . Your security matters to us — thank you for staying vigilant Create a Job Alert Interested in building your career at OpenSesame? Get future opportunities sent straight to your email. Accepted file types: pdf, doc, docx, txt, rtf Enter manually Accepted file types: pdf, doc, docx, txt, rtf LinkedIn Profile * Website Do you currently require or will you need sponsorship for employment visa status now or in the future? * Select... Which best describes your experience managing customer renewals? * Select... Which best describes your experience negotiating with Procurement, Vendor Management, or similar customer stakeholders? * Select... Which customer segments have you managed renewals for? * Select... What was the typical annual contract value (ACV) you renewed? * Select... Which best describes your experience managing a renewal or sales pipeline and forecast? * Select... Tell us briefly about a renewal or customer negotiation you personally led. What did you own, how did you approach the negotiation, and what was the outcome? * We use Greenhouse’s AI-powered Talent Matching tool to compare your application against our job requirements. #J-18808-Ljbffr OpenSesame