15Five is the performance management platform that creates effective managers, highly engaged employees, and top-performing organizations. Backed by 500 Global.
About the role
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. Found on 1752vc Careers, the job board for startup and VC roles.
What they're looking for
- 3–5+ years in support operations, CX operations, knowledge management, or conversational AI operations, with hands-on ownership of a production AI agent (Intercom Fin strongly preferred, Ada, Forethought, Decagon, or similar also relevant)
- A proven content engineer: customer-facing help content you owned end to end, plus taxonomy, content verification workflows, structured authoring, and writing for AI retrieval, not just human readers
- An experimenter's method: hypothesize, test small, measure, then scale. Comfortable with AI-assisted workflows as a daily practice
- Strong analytical habits: you can trace a wrong AI answer through retrieval, content, and product behavior to root cause, and you show your work
- Collaboration as a first-class skill: you raise concerns early, directly, and through agreed channels, you disagree openly, commit fully, and treat peers' domains with the respect you expect for yours
- You build systems, not dependencies: your instinct when you become the only person who can do something is to document it and train a second
More about this role
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...
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