Account Executive - Toronto - Siena AI

Description

Overview

Meet Siena. Siena is the first intelligence layer for customer experience. We're creating an operating system of AI agents that learn, remember, and act across every customer touchpoint—from support conversations to shopping experiences to voice and social media interactions.

Siena doesn't just automate support; it powers shopping agents, builds persistent customer memory, generates actionable business insights, and creates empathetic interactions that feel human. We're transforming how businesses understand and connect with their customers, turning every interaction into intelligence that makes the next one better.

The Team

We're a small, distributed team that punches way above our weight. Every person here has outsized impact because we've built leverage into everything we do. This philosophy makes us faster and, frankly, more fun to work with. If you're excited about building something that doesn't exist yet, keep reading. We're building agents that don't just respond to customers—they remember them, learn from every interaction, and connect experiences across channels.

About The Role

As an Account Executive, you'll be on the front lines of Siena's growth, closing high-value enterprise deals and bringing AI-driven automation to the world's top brands. This role is built for a hunter, someone who thrives in prospecting, navigating complex sales cycles, and turning cold leads into long-term partnerships. If you have experience selling into enterprise CX, or AI-driven automation, this is an opportunity to shape the future with Siena.

While we\'ve listed a few preferred locations, we\'re flexible as the role is remote. What matters most is your ability to overlap with EST hours and join us in NYC from time to time for in-person collaboration.

What You'll Do

• Own the full sales cycle from prospecting to close, targeting enterprise accounts.
• Build and maintain strong relationships with senior decision-makers in CX, digital transformation, and operations.
• Develop strategic outbound motions to break into top accounts and expand Siena's footprint.
• Manage complex, multi-stakeholder sales cycles with a consultative and value-driven approach.
• Work closely with marketing, sales development, and solutions engineering to refine our go-to-market strategy.
• Drive adoption of Siena's AI solutions by aligning our capabilities with customer pain points and business outcomes.
• Consistently exceed quota and revenue targets, contributing to Siena's high-growth trajectory.
• Leverage AI tools to scale prospecting, research, and deal preparation.
• Build and maintain custom AI workflows for account intelligence, objection handling, and competitive analysis.

Who You Are

• 5+ years of experience in enterprise SaaS sales, ideally in AI, CX, automation technology.
• Proven success in hunting new business and closing six- and seven-figure deals.
• Skilled in multi-threading enterprise sales cycles and navigating complex organizations.
• Deep understanding of enterprise customer experience, digital transformation, and automation trends.
• Highly strategic and data-driven, leveraging insights to optimize deal execution.
• Comfortable working in a fast-moving startup environment where adaptability and ownership are key.
• Power-user of AI tools with proven ability to build custom agents/prompts that enhance sales productivity.
• Comfort with rapidly evolving AI landscape by staying current on AI capabilities and applying them to sales motion.

Bonus Points

• Experience selling AI, automation, or workflow intelligence products.
• Established relationships within executives, CX, eCommerce, or BPOs.
• Experience selling enterprise and multi-product software.

Why Siena?

• Meaningful impact. Your work directly shapes our product and company.
• Globally distributed team working at the bleeding edge of CX and AI.
• Great salary plus the opportunity for equity or stock grants.
• 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.
• AI-fluency. Make AI your second nature.
• Tackle unsolved problems. We're redefining how customer experience will look like in the next decades.

Our values

The people who thrive here are curious, customer-obsessed, and take ownership without being asked. They fix problems first and explain later. They\'re direct about feedback—both giving and receiving it—because they care more about getting things right than being polite. They maintain high standards while moving at startup speed, and they build real relationships with teammates because they know that\'s how great work gets done. When things get tough, they adapt and keep pushing forward.

Our approach to AI

The people who thrive here treat AI like a natural extension of themselves. They\'ve built their own ecosystem of agents—some for research, others for debugging, writing, analysis, or writing code. They know which AI works best for what problem.

Everyone gets premium accounts (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable) plus a quarterly budget for new tools. But the magic happens in how we share knowledge. Demo days where someone shows off a clever workflows. Slack threads about which model handles a specific use case better. Learning from each other\'s AI workflows.

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.