VP, Engineering

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.

Why should you be part of Siena AI's success story?

Join us in our journey to connect brands with AI, offering seamless service experiences. Having just closed our seed round led by world-class investors, there's no better time to become part of our story.

Get ready to:

  • Lead a multifaceted engineering team, collaborating closely with Product, Design, and QA to build our AI platform.
  • Recruit a world-class engineering team, scaling from small groups to a larger, well defined function.
  • Oversee the R&D efforts in building the next-generation of AI agents for customer-facing teams.
  • Establish and improve on development processes to meet rapid growth demands.
  • Cultivate a culture of excellence, ensuring our roadmap is developed effectively, always prioritizing our customers' experience.

The expertise you’ll bring to your new team:

  • 15+ years of software engineering, with a minimum of 10 years in leadership roles.
  • Mastery of modern software development, with a strong background in AI and cloud services.
  • Adept in agile methodologies and passionate about building scalable, customer-focused SaaS solutions.

You're the leader we're looking for if you:

  • Excel in scaling engineering teams and fostering a collaborative remote-first culture.
  • Are autonomous, owning your initiatives while contributing positively to our team culture.
  • Communicate effectively, collaborating with diverse groups to solve complex problems.
  • Embrace challenges with optimism and a balanced, business-oriented approach to product development.
  • Prioritize customer impact, ensuring your work significantly advances our service quality.

Extra accolades for:

  • Experience with 24/7 SaaS operations.
  • Proficiency in serverless architectures on major cloud platforms.
  • Hands-on experience with TypeScript and distributed team leadership.

Total Rewards:

  • Competitive compensation, including equity in a fast-growing startup.
  • Customizable tech setup to suit your workflow.
  • Flexible work location – home, coworking spaces, or wherever inspires 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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