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:

The Customer Automation Engineer will be responsible for AI prompt engineering, automation setup, custom API integrations, quality assurance, and project/change management to drive customer success and internal efficiency. This role will report to the Manager of Partner and Implementation Services. The ideal candidate has experience in prompt engineering, various AI tools, and API integrations.

In this role, you’ll work closely with cross-functional teams – including Customer Success, Sales, Managed Services, and Product & Engineering – to align automation initiatives with both customer goals and product capabilities. By collaborating across departments, you’ll help ensure a unified approach and drive successful outcomes for our customers.

What You’ll Do

AI Prompt Engineering & Testing:
- Translate complex customer SOPs into agentic workflows.
- Conduct thorough agent testing and validation.
Proactive Automation Leadership:
- Identify and implement automation opportunities across all customer touchpoints.
- Actively monitor for inefficiencies and propose automatable solutions.
Project Management:
- Complete tasks on schedule and communicate updates to internal and external stakeholders.
Quality Assurance:
- Review and test automated conversations to ensure accuracy and reliability.
Technical Integrations:
- Build and configure automation workflows, including API integrations and workflow orchestration.
- Ensure all integrations are properly tested.
Feature Enablement Focus:
- Translate Siena’s feature roadmap into real customer value through effective implementation of new features.

Who You Are

You have 2+ years of experience in technical onboarding, implementation, CSM, or CX operations in a B2B SaaS environment.
You have a customer-centric mindset and a strong desire to improve customer experiences through technology.
You are passionate about AI-driven automation and eager to continuously learn and adopt new tools and approaches. Proficiency with ChatGPT, Claude, and other LLMs for research, documentation, and workflow optimization.
Experience in AI prompt engineering.
Strong API development and integration skills (preferred).
Proficiency with automation tools like Zapier and Gumloop.
Experience with tools like Cursor AI for prototyping.
Quality assurance/testing experience, especially in conversational AI.
Project and change management experience.
You are detail-oriented and quality-driven, able to critically test and validate solutions to ensure reliability.
You are a self-motivated team player who can effectively collaborate across departments and also tackle projects independently.
Excellent communication and stakeholder management skills.
Creative problem-solving skills, with the ability to craft custom workarounds when standard automation isn't possible.
You thrive in a fast-paced startup environment and adapt quickly to change.

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 managed 2-3 successful customer implementations from and completed 1-2 custom API integrations
6 months: You’re improving our approach to building automations and creating best practices.

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.

Siena

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