Strategic Customer Success Manager

About Siena

Siena is building enterprise empathic AI Agents powered by reasoning-adept LLMs. Siena is the first AI Agent of its kind, designed to integrate with existing systems and interact with customers across multiple channels from a single, unified platform.

If you're excited about the intersection of human-to-machine communication and want to be part of a team driving innovation and making a real impact in automating agentic workflows, join us on our mission to revolutionize customer experience through empathetic AI.

Our AI-First Philosophy

At Siena, AI isn't just a tool—it’s embedded in our DNA. We believe that leveraging AI-first workflows empowers individuals to work smarter, faster, and more creatively. Our team embraces AI-powered augmentation in everything we do, from research to execution, making us more efficient and innovative every day.

About the Role

We're seeking a Customer Success Manager who will serve as a trusted advisor to our clients, driving continuous growth in platform adoption and optimization. You'll proactively identify expansion opportunities, guide customers through advanced use cases, and ensure they're maximizing ROI from Siena's AI-powered customer service solutions.

What You'll Do

Strategic Growth & Optimization:

• 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

Technical Excellence & Product Mastery:

• 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

Customer Education & Enablement:

• 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

Relationship Management & Communication:

• 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

Process Development & Cross-Functional Leadership:

• 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

Voice of Customer & Strategic Insight:

• 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

Experience & Background:

• 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

Technical & Analytical Competencies:

• 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

Mindset & Approach:

• 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

Highly Valued 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

Why Join Us

We’re a startup, so no fancy offices or corporate fluff. But here’s what we do offer:

• 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.

Our values

We’re not about corporate jargon—here’s what truly matters to us:

• Curiosity and creativity: You always seek new knowledge, ask questions, and explore different perspectives to deepen your understanding.

• Customer empathy: You are driven by our customers’ success. You see needs they can’t articulate.

• Resilience: You bounce back from setbacks, adapt to change, and thrive in the face of challenges.

• Ownership and autonomy: When things break, you fix first, explain later.

• Relationships: You create bonds with your colleagues - building trust and sharing success.

• Craft and speed: You balance vision with pragmatism. Your standards pull everyone higher.

• Open and direct: You share and receive feedback. You are open about what’s working and what not.

AI-First Tooling

To ensure you stay at the cutting edge of AI-driven work, we provide:

• Perplexity Pro account

• ChatGPT Pro account

• Claude Pro account

• Quarterly budget for experimenting with new AI tools

• A culture that encourages AI experimentation and adoption

We encourage our team to explore and integrate AI tools into their workflows, allowing them to maximize efficiency and innovation in their roles.

At Siena, we’re not just looking for people who can do a job. We’re looking for people who want to break boundaries, create the future, and reshape industries. If that’s you, we look forward to your application.

Siena provides equal employment opportunities to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, genetics, sexual orientation, gender identity, or gender expression. We are committed to a diverse and inclusive workforce and welcome people from all backgrounds, experiences, perspectives, and abilities.