Renewal Specialist - 15Five

Job Title: Renewal Specialist
Job Location: US, Remote
Job Listing URL: https://jobs.lever.co/15five/22a4bb44-66c7-4238-82cb-eb6fe1fc41c7
Job Description: 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