Implementation 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:

As an Implementation Manager, your mission is to get new customers up and running on the Siena platform — efficiently, confidently, and excitedly. You’ll be the face of Siena during the most critical phase of our customer relationship: the implementation. This means guiding new users through onboarding, translating their SOPs into AI-powered automations, and ensuring they become self-sufficient experts on our platform.

We’re looking for an entrepreneurial mindset, a fearless attitude, and a passion for excellence in onboarding new clients onto our product. Our team not only takes pride in our work but also in the way we do it. You must be capable of successfully implementing new business while ensuring a high degree of client satisfaction. You'll work with medium to large-sized organizations, with no limit on the complexity or feature/functionality usage of the client.

What You'll Do

• Customer Onboarding

  Own and manage onboarding projects from kickoff through go-live (typically 4–6 weeks), working cross-functionally with Sales, Customer Success, Product, and Managed Services.

• Client Management

  Build relationships with stakeholders in order to proactively identify and mitigate any implementation risks

• Training & Enablement

  Train customer teams — from frontline AI Managers to busy executives — on Siena’s platform: how to draft automation instructions (prompts), QA automated responses, trigger actions, and leverage insights and analytics.

• AI Prompt Engineering & Testing

  Help customers convert their complex SOPs into high-quality automation instructions and conduct thorough testing and validation before go-live

• Technical Scoping & Implementation

  Partner with the Solutions Engineering team to scope complex technical solutions and the implementation of custom app integrations, requiring knowledge of how APIs function

• Product & Process Feedback

  Systematically collect customer feedback to improve the implementation process and contribute to the product roadmap based on implementation insights

• Project Management & Change Management

  Track milestones, call out blockers, and keep all stakeholders — internal and external — aligned and accountable while managing organizational change and adoption challenges within customer teams

• Content & Materials Development

  Maintain and create self-serve onboarding materials, including training decks, automation templates, help guides, and implementation playbooks.

You'll Work Closely With

• Customer Success (you live here)

• Sales (for smooth handoffs)

• Managed Services (for ongoing support or white-glove onboarding)

• Product and Engineering (for feature gaps or custom integrations)

What You Should Know

• How to explain complex systems to non-technical users

• How prompting works for LLMs and the basics of AI QA

• How APIs and app integrations work in the real world of e-commerce

• How to be effective in startup chaos: document as you go, forgive gaps, and ship forward

Who You Are

• Have 3+ years of experience in onboarding, implementation, CSM, or CX operations in a B2B SaaS environment

• Have used tools like Shopify, Zendesk, Gorgias, Kustomer, or similar

• Love teaching others and know how to pace training sessions for both power users and execs

• Are organized as hell, juggling multiple projects and timelines without letting balls drop

• Are comfortable in fast-moving, scrappy environments where not everything is perfectly documented

• Can hold your own in a Zoom room full of C-level execs — and then hop into a screen share to troubleshoot a broken automation

• Are a self-starter who can move forward with minimal guidance and prioritize ruthlessly

Please Don’t Apply If You...

• Expect every process to be polished and every tool perfectly set up

• Need a lot of structure to operate

• Don’t enjoy teaching or running 1:1 sessions

• Are easily frustrated by ambiguity or fast iteration cycles

• Think startup scrappiness = incompetence

What Success Looks Like

• 1 month: You’ve mastered the platform, understand common customer use cases, and can draft and QA automations confidently

• 3 months: You’ve led 2–3 successful implementations from start to finish and your customers are graduating from onboarding

• 6 months: You’re maintaining and improving our self-serve onboarding content, helping newer IMs, and contributing to scalable processes

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.