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Olive Systems

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Customer Success Manager & AI Trainer (US Remote)

Anywhere
full-time
Posted 7/28/2025
Verified Source
Key Skills:
Customer Success
AI prompt design and optimization
SaaS onboarding and support
Cross-functional collaboration
Enterprise account management
AI tools and automation platforms

Compensation

Salary Range

$70K - 120K a year

Responsibilities

Lead customer onboarding and success for AI-powered SaaS products, optimize AI agent behavior, and drive customer retention and growth.

Requirements

2-4 years in customer success or client-facing SaaS roles, experience with enterprise onboarding, strong communication skills, and comfort with AI tools.

Full Description

Location: (USA Remote) | Full-Time Hiring for: Quack AI Via: 5Candidates About the Company At 5Candidates, we help cutting-edge startups scale with top talent. We’re currently hiring a Customer Success Manager & AI Trainer (NYC) on behalf of Quack AI — a fast-growing, venture-backed startup trusted by global companies like Yotpo, Artlist, Notable, and Rentman. Quack is building the next operating system for customer support teams. They’re well-funded, shipping fast, and building AI-powered products that customers genuinely love. About Quack Quack is led by a founding team with 6+ years of experience across multiple ventures. Headquartered in Tel Aviv, the team works closely with U.S. customers, and the CEO frequently travels to New York. The company is backed by leading investors and operators from California and New York, offering a unique opportunity to grow within a globally connected network. They value clear communication, deep focus, simplicity, and full ownership across everything they do. About the Role We’re hiring a sharp, detail-obsessed Customer Success Manager & AI Trainer to lead successful customer onboarding, optimize LLM prompt behavior, and ensure outstanding delivery of Quack’s AI Copilot and Agentic products. You’ll work cross-functionally with customers, product teams, and LLMs to drive adoption, retention, and measurable business impact — while directly shaping how Quack’s AI agents speak, behave, and evolve. What You’ll Do Customer Success & Onboarding • Own the full implementation process for new customers from kickoff to go-live • Build tailored success plans based on customer goals and workflows • Lead onboarding and training sessions for customer teams • Monitor account health and proactively flag risks AI Training & Optimization • Design and refine LLM prompts, blocks, and flows for each customer • Test, QA, and optimize behavior directly within the Quack Brain • Use real-world conversation data to continuously improve agent performance • Collaborate with Product and Engineering to explore automation opportunities Strategic Growth • Identify and pitch expansion opportunities (new channels, seats, or use cases) • Convert learnings into repeatable playbooks and internal documentation • Turn real usage into customer stories, feedback, and insights What We’re Looking For • 2–4 years of experience in Customer Success, Support Ops, or a client-facing SaaS role • Proven track record of onboarding and supporting enterprise accounts • Excellent attention to detail and structured thinking • Strong communication skills — especially with execs and cross-functional teams • Comfortable working with AI tools, prompts, and automation platforms Bonus Points • Hands-on experience writing or optimizing AI prompts • Familiarity with tools like Intercom, Zendesk, Notion, HubSpot, and Slack • Background in customer support, B2B SaaS, or LLM-based products • Ability to manage multiple projects with tight deadlines Job Type: Full-time Work Location: Remote

This job posting was last updated on 7/30/2025

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