15Five Benefits Overview

Serve as a technical sales partner for mid-market and enterprise accounts. Lead strategic deal support, tailored product demonstrations, HRIS integration architecture, API and SFTP scoping, proof-of-concept configuration, security questionnaire responses, and technical closing. Create sales enablement content, provide market intelligence, influence product direction, and translate HR requirements into technical solutions. Collaborate closely with Account Executives while using tools such as Postman, Salesforce, Gong, and AI platforms.

Own the day-to-day operation and quality of the customer-facing AI support agent, Help Center knowledge base, and AI feedback loop. Manage content taxonomy, verification, retrieval readiness, prompt and behavior tuning, escalation design, failure triage, launch readiness, runbooks, and operational continuity. Measure automation quality, knowledge-gap closure, escalation precision, operability, and partner trust while documenting systems and training backups.

Own and improve 15Five’s AWS and Kubernetes infrastructure, databases, CI/CD pipelines, observability, reliability, disaster recovery, security operations, and AI platform. The role includes incident leadership, on-call participation, infrastructure automation with Terraform and Ansible, PostgreSQL administration, access and secrets management, compliance support, and cross-functional project delivery. This remote position requires strong ownership, communication, and the ability to independently deliver infrastructure, security, reliability, and AI governance initiatives.