Customer Success Manager (AI)

TL;DR

Customer Success Manager (AI): Owns a portfolio of customers, ensuring they achieve specific, measurable outcomes from Siena's AI agents, with an accent on automation, conversion rates, and CX quality. Focus on diagnosing performance issues, leading improvement plans, and translating customer goals into concrete success plans.

Location: Remote (North America - East Coast, specifically Boston, Miami, New York, North Carolina, Philadelphia, Toronto, and Washington)

Company

Siena is the first intelligence layer for customer experience, building an operating system of AI agents that learn, remember, and act across every customer touchpoint.

What you will do

• Own customer outcomes from post-onboarding through long-term success.
• Diagnose performance issues and lead improvement plans, ensuring accountability with clear owners and timelines.
• Master product features, common use cases, and integration capabilities, explaining technical concepts to non-technical stakeholders.
• Engage confidently with senior stakeholders, identify expansion opportunities, and quantify customer ROI.
• Lead cross-functional execution by turning vague customer problems into clear problem statements and execution plans.
• Educate and enable customers through training sessions, content creation, and strategy workshops.

Requirements

• 3+ years in Customer Success Management, account management, or client-facing strategic roles with complex software solutions.
• Proven track record with customer service technology platforms or e-commerce ecosystems.
• Experience in the AI/ML space, particularly conversational AI or automation platforms.
• Hands-on prompt engineering experience with the ability to optimize AI responses and train conversation flows.
• Comfort with API integrations, conversation flow design, and business intelligence tools.
• Thrive in fast-paced startup environments with evolving priorities and ambiguous challenges.

Culture & Benefits

• Make a meaningful impact directly shaping the product and company.
• Join a globally distributed team working at the bleeding edge of CX and AI.
• Opportunity for equity or stock grants.
• Access a learning budget and premium AI accounts (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable).
• Be part of building something new and tackling unsolved problems, redefining customer experience.
• Work with curious, customer-obsessed colleagues who take ownership and give direct feedback.