[Hiring] AI Client Success Manager @OuterBox

Role Description

OuterBox is seeking an AI Client Success Manager to own the client experience across our growing AI service line. This role sits in the AI team and is responsible for ensuring clients get real, measurable value from their AI engagements, from onboarding through long-term adoption and expansion.

This is a client-facing role for someone who is genuinely fluent in AI, not as a buzzword, but as a daily working tool. You will guide clients through implementations, document outcomes, build internal workflow proof points, and serve as the trusted expert clients call when they want to do more.

Hard line into the AI Director. Dotted line into Sales leadership to support cross-sell and upsell opportunities within the existing client base. Roughly 80% of the role is client success, AI delivery, and internal transformation work; 20% is supporting expansion conversations alongside the sales team.

What You Get To Do Every Day:

• Serve as the primary point of contact for clients across active AI engagements, owning the relationship from onboarding through ongoing success.
• Guide clients through AI implementations, ensuring they understand what has been built, how to use it, and how to get more value from it over time.
• Monitor client health across AI engagements and proactively surface opportunities to improve adoption, expand usage, or address gaps before they become churn risks.
• Document client outcomes and workflow wins, including time saved, quality improvements, and efficiency gains, and translate those results into clear reporting for clients and internal stakeholders.
• Partner with the AI team on delivery handoffs, staying involved post-sale to ensure alignment between what was scoped and what gets built.
• Build and maintain a library of onboarding materials, training guides, and success playbooks inside OBxChat so the client experience scales consistently.
• Act as an internal AI adoption resource, identifying power users across client organizations and helping teams move from basic usage to higher-value applications.
• Stay current on AI model capabilities, emerging tools, and competitive positioning, and translate that knowledge into practical guidance for clients.
• Support the sales team on expansion conversations within the existing client base, bringing client context and usage data to identify cross-sell and upsell opportunities.
• Contribute to pre-sales narratives for qualified AI opportunities, drawing on client success stories and documented proof points to strengthen the pitch.
• Measure and report on AI service line performance, including client retention, expansion revenue, and engagement health.
• Other duties, as assigned.

Qualifications

• 3–7 years of experience in a digital agency, MarTech, SaaS, or AI consulting, with a track record of scoping or selling complex technical services.
• Genuine, daily fluency with AI tools. Can prompt effectively, build basic agents, and understand the practical capabilities and limits of current models.
• Comfortable leading conversations with VP- and C-level stakeholders. Confident, plain-spoken, earns trust quickly without relying on jargon.
• Demonstrated ability to translate business pain points and data into a clear narrative — this is the hardest skill to train and the most important one we’re hiring for.
• Understanding of digital marketing service delivery and what it takes to scope, build, and ship. Protects the delivery team from bad handoffs.
• Experience with AI platforms and tools such as Claude, ChatGPT, or similar, including working knowledge of API-based implementations, agent frameworks, or workflow automation (N8N, Zapier, Make, or equivalent).
• Familiarity with digital marketing analytics (GA4, Ahrefs, or similar) and the ability to use data to build a client-facing growth narrative.
• Strong organizational skills with the ability to manage multiple scoping conversations and client engagements simultaneously.
• Agency experience preferred. Comfort operating in a fast-moving environment where the product is still being built.

Requirements

• Fast-paced, dynamic environment. May be required to work outside of regular office hours to resolve issues or complete projects.
• This is a remote-eligible role with periodic travel expectations.
• Travel up to 20% of time may be required to OuterBox offices, team meetings, or client offices.

Benefits

• Cohesive Culture + Good Humor + Combined Skills = Awesome Results
• At OuterBox, we’re here to thrive together — not simply survive.
• Salary Description: $80,000 – $95,000
• Team-centric work culture rooted in trust, respect, accountability, appreciation, fun, and collaboration.
• Awarded as a Top Workplace for three years running in 2022–2024 by The Plain Dealer & Cleveland.com.