Strategic Customer Success Manager

Summary

Join Siena, a company building enterprise empathic AI Agents, as a Customer Success Manager. You will serve as a trusted advisor to clients, driving platform adoption and optimization. Responsibilities include strategic growth and optimization, technical excellence and product mastery, customer education and enablement, relationship management and communication, process development and cross-functional leadership, and acting as the voice of the customer. You will need 3+ years of experience in customer success management or related fields, strong technical aptitude, and experience with AI/ML, particularly conversational AI or automation platforms. Preferred qualifications include experience scaling customer success teams and expertise in e-commerce operations. Siena offers competitive compensation, flexible time off, a learning budget, and a fully remote, globally distributed team environment.

Requirements

• 3+ years in Customer Success Management, account management, or client-facing strategic roles with more technical and complex software solutions
• Proven track record with customer service technology platforms or e-commerce ecosystems
• Strong technical aptitude with ability to configure complex automations and troubleshoot AI workflows
• Demonstrated ability to drive customer growth, retention, and expansion through data-driven insights
• Experience in AI/ML space, particularly conversational AI or automation platforms
• Hands-on prompt engineering experience with ability to optimize AI responses, train conversation flows, and refine model outputs
• Experience analyzing usage patterns, competitive landscapes, and translating data into actionable strategies
• Comfort with API integrations, conversation flow design, and business intelligence tools
• Self-directed professional who asks for help when needed and brings solutions rather than just raising issues
• Thrives in fast-paced startup environments with evolving priorities and ambiguous challenges
• Strong self-awareness of personal strengths and weaknesses with commitment to continuous learning

Responsibilities

• Own the complete growth and optimization journey for existing customers, fresh from onboarding through expansion
• Configure complex automations and provide best practice recommendations during live strategy sessions
• Analyze usage patterns and trends to identify actionable insights that drive business impact
• Leverage client data and industry benchmarks to challenge assumptions and demonstrate value
• Document client outcomes and translate them into clear success plans with tracked priorities
• Proactively identify obstacles, issues, and expansion opportunities while maintaining focus on company objectives
• Master all product features, common use cases, and integration capabilities
• Perform advanced troubleshooting and resolve complex technical challenges
• Consistently demonstrate new features to clients and tailor product updates based on specific needs
• Understand complex business processes and competitive landscape dynamics
• Lead strategic discussions and training sessions with key stakeholders
• Create customer-facing content, training materials, and improve existing documentation
• Design and facilitate strategy sessions, workshops, and webinars showcasing advanced use cases
• Engage actively in our private Slack community as a thought leader and trusted resource
• Develop strong stakeholder relationships and manage escalations effectively
• Consistently engage key decision-makers to drive strategic initiatives
• Present insights and recommendations confidently to C-level executives
• Maintain calmness during crises and adapt communication style to different audiences
• Build foundational processes and playbooks that scale the Customer Success function
• Participate in cross-functional projects and develop strong internal partnerships
• Implement best practices and drive efficiency improvements across customer operations
• Mentor team members and influence others' professional growth
• Serve as primary conduit between customers and product team, capturing feedback and pain points
• Investigate root causes, challenge assumptions, and explore new opportunities
• Anticipate customer challenges and provide proactive solutions based on deep understanding

Preferred Qualifications

• Background training, mentoring, or scaling customer success teams in high-growth environments
• Deep expertise in e-commerce operations, customer journey optimization, or omnichannel support
• Previous experience at high-growth SaaS companies serving enterprise or mid-market clients
• Track record of participating in cross-functional projects and driving team success initiatives

Benefits

• Make a real impact. Your work directly shapes our product and company
• A Voice that matters. In a small team, every perspective counts—yours included
• Working at Siena. We are a fully remote, globally distributed team working at the bleeding edge of CX and generative AI
• Competitive compensation. Great salary plus the opportunity for equity or stock grants
• Flexible time off. Take at least 15 days—more if you need it
• A Learning budget. If you're growing, so are we
• The thrill of building something new. Join us at a stage where your contributions matter most
• Tackling meaningful challenges. We’re redefining how work gets done through AI