Head of Sales

About us

At Siena we are revolutionizing the customer service industry with the world's first autonomous AI customer service agents. We are a remote-first startup that's passionate about enabling machines to engage in delightful and empathic conversations. Siena is the first of its kind, designed to work out-of-the-box to interact with customers across all channels from a single platform.

If you're excited about AI and the intersection of human-to-machine communications, and want to be part of a team who is driving innovation and making a real impact, then come join us in pushing the boundaries of AI and CX.

Some of our values

  • Customer First: It's not just about solving issues or closing deals. We're in the business of understanding our customers so well that we can anticipate their needs and blow their minds.
  • Straight Talk: Communication isn't just a checkbox for us—it's our operating system. We say what we mean, mean what we say, and have no hidden agendas or sugar-coating..
  • Question & Disrupt: We do things that have never been done before—not for the sake of being different but for being radically better.
  • Act with Agency: We don't wait for permission or perfect conditions. We evaluate the situation, make our best call, and go for it.
  • Raise the Bar: We're not just meeting standards, we're aiming for setting them.
  • Fast & Fearless: We move quickly but thoughtfully, and view mistakes and failures as stepping stones, not setbacks.
  • Driven by Curiosity, Fueled by Growth: We ask the questions no one else is asking, dive deep, and come out the other side better for it.
  • Synergy Over Solo: We value collaboration over individual achievement. When we work together, we're unstoppable. We're not just co-workers; we're co-creators.

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.


🏠 The flexibility to work from anywhere. Even if it's just from the comfort of your own bed (because let's face it, who doesn't love a good WFH situation?)

🌞 Flexible working hours. Because who said you can't design your day on your terms?

💸  Competitive salary and stock options. We offer highly competitive salaries and equity, because we're building this together.

🌴 Unlimited PTO. With unlimited paid time off and a minimum of 15 days off per year, you'll have plenty of time to explore the world (or just your couch).

📖 Growth stipend. An annual budget to continue learning and expanding your horizons. It's like getting a raise without having to ask for it. We invest in you, so you can continue to invest in yourself.

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.

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