Siena AI

Head of Sales

Siena AI Toronto, Ontario, Canada

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.

Some of our values

  • We put customers first: We work hard to understand our customers. We try to put ourselves in their position and do more than they expect.
  • We're direct and honest: We believe in straightforward, truthful communication. We say what we think, clearly and respectfully.
  • We try new things: We're not afraid to do things differently if it means finding better solutions.
  • We step up: When we see a chance to make a difference, we take it. We trust ourselves to decide and take responsibility for what happens.
  • We keep improving: We're always looking for ways to do better and be better at what we do.
  • We're quick on our feet: We adapt to changes and challenges. We see them as chances to learn and grow.
  • We stay curious: We ask questions and explore new ideas. What we learn helps us keep growing.
  • We own it: We're all owners here. We take charge, make the call, and own the outcome.

The Role:

As the Director of Sales, you'll shape our sales team, strategy and collaborate with our founders, customer success and product teams closely. You'll drive our revenue growth and market penetration while building and guiding a top-notch sales team.

What You'll Do:

  • Be the driving force behind our sales team, setting ambitious targets and ensuring we hit them consistently.
  • Develop and execute sales strategies that align with our company's vision and goals.
  • Foster an environment where excellence, continuous improvement, and teamwork are the norms.
  • Ensure our sales processes are optimized and that the team operates efficiently and effectively.
  • Work with various departments to ensure our sales strategies are integrated and support overall business objectives.
  • Build and maintain strong relationships with customers, ensuring high levels of satisfaction and retention.
  • Attract, hire, and nurture top sales talent to build a world-class team.

Who You Are:

  • You have 8 years of a solid track record of hitting revenue targets and scaling sales teams in CX, AI, ecommerce or related industries.
  • You excel in setting up and optimizing sales processes, with a deep understanding of CRM systems and pipeline management.
  • You have impeccable communication skills, able to clearly articulate your vision and influence cross-functionally.
  • You see the big picture while being obsessed with details, ensuring every aspect of our sales strategy is executed flawlessly.
  • You are passionate about sales, customer relationships, and creating exceptional customer experiences.
  • You thrive in dynamic environments and can balance short-term needs with long-term strategic goals.

You Shouldn't Apply If:

  • You find fast changes and uncertainty uncomfortable – we often need to think on our feet and adapt quickly.
  • Working closely with the company's founders and being involved in key decisions sounds overwhelming to you.
  • You only want to focus on big ideas and prefer not to get involved in the day-to-day work – this role is hands-on.
  • The idea of leading a new team through rapid growth and the ups and downs that come with it doesn't excite you.

Benefits

  • Flexible work location: At Siena you have the flexibility to work from wherever you're most productive and inspired — be it your home office or a your favorite local workspace.
  • Flexible hours: We believe in giving you the autonomy to design your workday in a way that fits your life and maximizes your productivity.
  • Competitive compensation: We offer competitive salaries and equity packages because we believe in rewarding your contributions to our shared success.
  • Generous PTO: With unlimited paid time off and a minimum of 15 days off per year, you'll have ample opportunity to recharge, travel, or pursue your passions outside of work.
  • Learning & development budget: We provide an annual stipend for you to continue growing professionally and personally. We're committed to investing in your growth and development.

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 (EEO) 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.

  • Seniority level

    Director
  • Employment type

    Full-time
  • Job function

    Sales and Business Development
  • Industries

    Technology, Information and Internet

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