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.

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.

About the Role

As VP of Sales at Siena AI, you’ll own our revenue engine—driving sales strategy, building a high-velocity pipeline, and scaling a category-defining AI company. You’ll work cross-functionally to refine pricing, messaging, and the customer journey, ensuring Siena’s AI transforms how businesses engage with their customers.

What You’ll Do

Develop and execute a scalable sales strategy to drive predictable revenue growth.
Build and manage a high-velocity pipeline, optimizing conversion rates and deal execution.
Lead and mentor a top-tier sales team in a fast-moving AI-driven environment.
Collaborate with Marketing, Product, and Customer Success to refine go-to-market strategies.
Strengthen relationships with key enterprise and mid-market clients to drive long-term value.
Be a force multiplier—driving thought leadership, collaboration, and continuous growth.

Who You Are

Proven Sales Leader – 7+ years of SaaS sales experience, ideally in AI, automation, or commerce tech.
Track Record of Exceeding Targets – Demonstrated success in scaling revenue and leading high-growth teams.
Strategic & Hands-On – Able to develop strategy while also closing deals and driving execution.
Customer-Centric Mindset – Deep understanding of enterprise & mid-market sales cycles, with a consultative approach.
Builder Mentality – Experience establishing sales playbooks, processes, and GTM motions from the ground up.
Tech-Savvy & Data-Driven – Comfortable with CRM tools (e.g., HubSpot, Salesforce, etc), analytics, and automation tools.

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.
Work your way. Whether it’s from home, a coffee shop, or a moon base—if you're productive, we’re happy.
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.

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.

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VP of Sales

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