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.
15Five's customer support runs on an AI-native operating model: our AI agent (Fin) resolves routine customer questions, AI assistance lives inside every support tier, and a closed-loop content system turns every wrong or missing AI answer into a published fix. The AI Support Manager role operates that system; the percentages under What You'll Own are approximate shares of time. You own the day-to-day performance of our customer-facing AI agent, the Help Center content it draws from, which you own end to end, and the feedback loop that makes both better every week.
This is an operator role with clear boundaries, real authority inside them, and a defined escalation path for everything outside them. You will be the expert on how our support AI behaves and why. You will not be a lone hero: the role is built around documented runbooks, a shared intake queue, and a named second for every critical system. What You'll Own
• Fin/AI agent operations (25%): our customer-facing AI agent resolves routine questions correctly and the quality-adjusted automation rate holds or improves month over month. Owns resolution quality, deflection with quality gates, topic configuration, prompt and behavior tuning, and escalation-to-human design.
• Help Center content ownership (40%): accuracy and AI-readiness of the Help Center as the shared knowledge layer feeding customer self-service and every AI surface. This role is the owner of every published article, where ownership means accountability for every published word, not typing them: AI drafts, this role structures, verifies, and publishes. Owns the taxonomy, article templates, and AI-retrieval writing standards, the Guru collections, the drafting pipeline, and the verify-and-publish workflow with Tier 1. Nothing ships to the knowledge layer without passing this role’s quality bar.
• The content flywheel (20%): every detected wrong or missing AI answer becomes a published fix. Triage AI-failure reports from the shared intake queue, trace each to root cause (retrieval failure, content defect, or product-truth gap), route product-truth gaps to their owner, and report gap-closure velocity.
• Launch readiness (10%): no release ships without its support content ready. Hold the support seat in release planning and prepare Help Center articles, Fin topics, and frontline teams before go-live.
• Operability (5%): no single point of failure. Maintain the runbooks, configuration documentation, and measurement baselines, and keep a trained second for every critical system. Documentation is part of done.
Where This Role Sits
- This role is the support side of a larger AI ecosystem. It works best when the seams are clean, so here is who owns what around it:
• R&D owns the AI knowledge-base architecture and the in-product AI (Amaya) knowledge stores, with a separate role scoped to that work. This role is their closest consumer: it keeps the knowledge layer they read from accurate and feeds architecture gaps back to them.
• Leadership owns org-wide AI-native strategy and internal AI consolidation. This role informs those calls with ground truth from the operation.
• Support tier leads own ticketing platform administration and support workflows. This role designs the AI handoffs that land in them.
• This role owns the Guru collections and keeps them accurate and AI-ready, since Guru's AI answers from them.
• New cross-team AI initiatives start with your manager, so they get prioritized before work begins.
How Success Is Measured
• Quality-adjusted automation rate: AI resolutions with no human takeover, no negative feedback, no reopen.
• Knowledge gap closure rate: speed from detected wrong/missing answer to published fix, weighted by impact. Top articles are proactively owned and current, not just reactively fixed.
• Escalation precision: when the AI hands off to a human, it lands in the right place with full context.
• Operability: every critical system has current runbooks and a functioning second; no single point of failure.
• Partner trust: tier leads, content, and product partners would say this function makes their work easier.
What We'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.
Working Style
This role touches systems that many teams depend on, which makes judgment about scope as important as technical skill. The people who thrive in it:
- check in before investing significant time in adjacent work,
- surface risks to their manager as crisp recommendations rather than broad escalations, and
- measure their impact by outcomes the team ships together rather than by territory.
We are explicit about this because the role's leverage is real: operated with focus and trust to deliver meaningful impact.
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.
