VP of Sales

Position Overview

• Location Type: Remote
• Employment Type: Full-Time
• Salary: (Salary not provided)

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.

About Siena

Siena values:

• 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.

Responsibilities

• 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.

Requirements

• Experience: 7+ years of SaaS sales experience, ideally in AI, automation, or commerce tech.
• Track Record: Demonstrated success in scaling revenue and leading high-growth teams.
• Skills:
  • 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.

Application Instructions

(Application instructions not provided in the original job description)

Company Information

(Company information not provided in the original job description)