15Five is the AI-powered performance management platform built for business impact. 15Five’s AI-powered all-in-one people management system is easy to use, delivers effortless insights, and enables managers to lead with impact so that companies and their people can thrive. Within the flow of work, HR leaders are empowered with data-driven insights and recommendations while managers are transformed into change-makers, accelerating engagement, performance, and retention. 15Five combines generative AI, custom analytics, and human-centered principles within a complete platform, including 360° performance reviews, engagement surveys, goal tracking, manager coaching and training, and ongoing feedback tools like guided 1-on-1s and check-ins. A career at 15Five is the chance to have high impact in a fast paced, remote startup environment that operates with focus, urgency, and accountability. Every role and every hire meaningfully impacts our trajectory. We’re a high-performance, high-purpose team that gives you the chance to Build the Future of Work . We run on High Standards and High Support — holding a high bar for results, ownership, clarity, and disciplined execution, while investing in manager enablement, skill development, and whole-person care. We are committed to a No B.S. environment, meaning we anchor ourselves in truth, course-correct in real time, and expect people to lean into direct conversations. We are focused on ensuring every 15Fiver can Work in the Future and that starts with proactively using AI across all aspects of your role to increase leverage, speed, and impact. If you're energized by a fast pace, high standards, and high accountability for yourself and others, you'll thrive here and we encourage you to apply. The Renewal Specialist protects and stabilizes retention across a high-volume portfolio of primarily unowned and scaled accounts, ensuring predictable renewal execution through a risk-prioritized, data-driven system. By leveraging AI-enabled insights, automation, and targeted outreach, the Renewal Specialist proactively identifies churn risk, leads negotiations, manages stakeholder relationships, and ensures customers are renewal-ready by reinforcing realized value and positioning them for continued success and outcomes with the platform. Areas of Focus Retention Performance Proactive Risk-Based Renewal Prioritization Commercial & Negotiation Excellence Trusted Executive & Stakeholder Engagement Forecast Accuracy & Operational Discipline Responsibilities Own end-to-end renewal execution across the prioritized unowned portfolio, including outreach, negotiation, contracting, and forecast management, supported by AI and automation Lead renewal readiness conversations with executive stakeholders to ensure alignment on continued platform adoption and outcomes Monitor and act on risk signals to proactively mitigate churn risk Execute targeted engagement strategies across risk tiers, balancing scaled automation with strategic human intervention where risk warrants Escalate at-risk accounts early and orchestrate internal cross-functional resources to drive retention outcomes Maintain disciplined CRM hygiene, renewal stage progression, and forecasting accuracy Continuously provide feedback to improve risk signals, automation workflows, and renewal playbooks Required Experience & Competencies Demonstrated success managing high-volume renewal or commercial portfolios, including contract negotiation and retention ownership Genuinely love the craft of sales! Strong executive presence and negotiation capability, with the ability to lead commercially complex renewal discussions Proven ability to prioritize effectively using data and risk indicators in fast-paced, high-volume environments Ability to orchestrate cross-functional internal resources to resolve customer risks and stabilize renewal outcomes Experience leveraging automation, AI-driven tools, and modern GTM systems to scale customer engagement Adaptability in dynamic, fast-changing environments, navigating ambiguity while maintaining execution consistency Thrives in startup environments, energized by building, scaling, and shaping long-term company potential Sample Week in the Life Monday: Review renewal risk priority reports and dashboards, conduct targeted outreach to newly flagged at-risk customers, customer calls and prepare renewal readiness plans for upcoming renewal conversations later in the week Tuesday: Renewal & Expansion Team weekly meeting, lead renewal alignment calls with key stakeholders and executive buyers, update renewal stages and forecasting inputs Wednesday: Weekly enablement session, Strategic Account Management team office hours, coaching 1:1 with manager, review recent product releases Thursday: Customer calls, collaborate with cross-functional teams to stabilize high-risk accounts, escalate accounts requiring leadership involvement to accelerate renewal progress, 1:1 with the Customer Sales Specialist on identified upside potential Friday: Renewal 1:1 with manager, customer calls, team Deal Walk, review performance metrics, and lock forecasting for the week ahead Schedule & Work Location This is a full-time, salaried exempt position. The typical work week will be Monday through Friday, between the hours of 8:00 am and 6:00 pm (flexible), working an expected 40+ hours/week. Ability to accommodate early-morning or after-hours meetings minimum 4 days a week is a must due to support efforts across various time zones. This role reports to our Head of Renewals & Expansion We offer amazing benefits that align with our values and culture at 15Five. Your Health & Wellbeing Medical, dental, vision with 15Five cost subsidy Employer paid Short-Term, Long-Term Disability, and Term LifeFamily planning support with enhanced medical plans and consultation programs Inclusive Benefits Stipend Access to mental health and wellness resources Your Life Flexible Time Off Program Generous paid leave for new parents Military leave Paid Company Holidays Sabbatical Program Your Future 401K with 4% Matching after 6 months Your Work Life Remote work Work with experts in leadership, culture, and personal development For more information see: Our Mission, Vision, & Values - https://www.15five.com/about Our People and Culture - https://www.15five.com/about/careers Our Personal & Professional Development Resources - https://www.15five.com/resources/content-library Reading over the role description and feeling like you don’t check every box? That’s okay; if you think you have what it takes but don’t necessarily meet all the criteria, please apply—you could be exactly who we are looking for! 15Five follows equitable hiring practices. Our compensation programs are designed to attract, motivate, and retain talented employees who are highly engaged, high performing, and have an exceptional impact on the business and our customers. The salary range displayed on each job posting reflects the target for new hire salaries for the role across all US locations. Within the range, individual pay is determined by budget allocated for the role and additional factors, including job-related competencies and skills, experience, and relevant education or training. Please note that the compensation details listed in US job postings do not reflect added total compensation including equity or benefits. In compliance with federal law, all persons hired will be required to verify identity and eligibility to work in the United States and to complete the required employment eligibility verification document form upon hire.