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Account Executive (Remote)


New York, Toronto, Boston

At Siena, we are building the world's first autonomous customer service platform, leveraging artificial intelligence to enable machines to engage in useful and empathic conversations. Our platform is the first of its kind, designed to work out-of-the-box to effectively solve customer problems across all digital channels.

Our self-service, autonomous CX platform uses advanced natural language processing techniques to communicate with customers in a natural tone and promptly answer questions, while also utilizing conversation redirecting algorithms to develop a human + AI operating model. As a result, companies see a significant reduction in ticket backlogs, a marked improvement in customer experience, improved ability to manage unpredictable conversation volumes, and an increase in agent capacity to handle high empathy cases.

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

Team and culture:

  • Product-driven. We're on a mission to building a best-in-class product that will power millions of brands.
  • Ownership. We do meaningful work and we own it 100%. We share wins with the team and take individual responsibility when things don't pan out. It takes courage to take responsibility even in the face of failure. Be an owner and you'll thrive here.
  • Autonomy. We have the ability to unblock ourselves, search for answers before asking for help, and make reasonable decisions within our scope without seeking consensus from others.
  • Customer-first. We understand our customers and optimize to build the best product for them.
  • Impact. We take our work seriously. We’re a small squad on a mission to change ecommerce for the better.
  • Open & thoughtful communication. We prefer an async way of working with a focus on deep work vs. endless meetings and politics.

About the role:

As Siena’s first Account Executive, you will be responsible for building the foundation of our sales department. This includes identifying and securing new business opportunities, setting up sales processes and strategies, selecting and implementing sales tools, and achieving sales targets.

What you'll be doing:

  • Sales Infrastructure Setup: Define and set up the sales process, including lead qualification, proposal development, negotiation tactics, and closing strategies.
  • Sales Tools Selection: Evaluate and implement sales tools like CRM software to manage and streamline the sales process.
  • Business Development: Identify, qualify, and secure business opportunities by establishing contact and developing relationships with prospects.
  • Customer Relationship Management: Nurture relationships with potential clients and maintain existing client relationships.
  • Customer Success. Support clients for as long as it is needed post-closing.
  • Sales Targets: Set, meet, and exceed monthly, quarterly, and annual sales targets.
  • Product Knowledge: Develop and maintain an extensive understanding of our product suite to effectively communicate the value and benefits to potential clients.
  • Market Insight: Maintain knowledge of market trends, competitive landscape, and customer needs to inform sales strategies.
  • Reporting: Provide accurate and timely sales forecasts and reports to the management team.

Join the team if you:

  • Have 3+ years proven experience as an Account Executive or similar role, preferably in a SaaS startup.
  • Have experience setting up sales processes and selecting sales tools.
  • Have a strong understanding of sales principles and ability to deliver excellent customer experience.
  • Have excellent communication, negotiation, and interpersonal skills.
  • Are self-motivated and driven to succeed with minimal supervision.

Impress us even further:

  • You hit consistent achievement or overachievement of sales targets.
  • Excellent organisational skills, with the ability to simultaneously manage multiple projects and stakeholders.
  • Self-starter with a high level of initiative and a ‘can do’ attitude.


  • 🏠 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 salaries, smaller egos. We offer highly competitive salaries and equity, because we're building this together.
  • 🌴 Time off? More like time on. 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).
  • 📖 "Edu-tainment" budget - 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 AI, 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 redefine the world of B2B SaaS. 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.

Siena AI is the first-of-its-kind autonomous customer service platform designed for commerce. We combine human empathy with advanced LLM-powered automation to redefine how brands like K18, Kitsch, and Simple Modern engage with their customers.

3 jobs
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