Head of Engineering

Join to apply for the Head of Engineering role at Siena AI.

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.

We empower ships, generate actionable business insights, and create empathetic interactions that feel human.

About The Role

As Head of Engineering you set the technical vision for the first intelligence layer in customer experience—AI pipelines, evaluations, integrations, and multi‑agent orchestration. Your job is to decide where we build, what we buy, and how we scale.

You shape Siena’s technical strategy, influence product direction, build the culture, and operate as a peer to product, design, and revenue leadership. You still prototype with modern AI tools on weekends because that’s who you are.

Responsibilities

• Set technical roadmap aligned to business goals—make build vs buy decisions at company level.
• Double our engineering team over 12–18 months—design team structures, develop leaders, coach and set an example for agentic coding.
• Stay hands‑on with AI tools—write prototypes, review critical PRs, ship experiments, maintain technical credibility.
• Operate cross‑functionally—partner with product, design, and revenue as peer, shape company strategy.
• Drive velocity at scale—ship weekly, cut scope based on learning, rally teams through ambiguity.
• Build culture that attracts top talent—create momentum through energy, establish scalable practices.

Qualifications

• Scaled engineering teams to 30+ successfully.
• Can code using AI tools such as Cursor, Claude, Codex, Lovable, v0.
• Deep technical depth and AI‑native fluency.
• Comfortable engaging customers—join enterprise calls, understand technical pain, build executive trust.
• High agency—take bets, shape direction proactively.
• Led teams that shipped regularly at scale.
• Made strategic technical decisions that shaped company direction.
• Developed multiple leaders from ICs.
• Maintained velocity during high growth.
• Experience with conversational AI, event‑driven systems, LLM applications, CX platforms, e‑commerce, API integrations.
• Zooms from strategy to debugging fluidly.
• Bring infectious energy and a positive culture‑building mindset.
• Startup DNA—comfortable with ambiguity, moves fast.

Why Siena?

• Meaningful impact—your work directly shapes our product and company.
• Globally distributed team at the bleeding edge of CX and AI.
• Competitive salary plus equity or stock grants.
• Learning budget—grow with us.
• The thrill of building something new; contributions matter at this stage.
• AI fluency—make AI your second nature.
• Opportunity to tackle unsolved problems—help redefine customer experience for the future.

Our Values

We thrive on curiosity, customer obsession, and ownership. We fix problems first, explain later. We give and receive direct feedback, focus on getting things right over politeness. We maintain high standards while moving fast, and build real relationships with teammates.

Our Approach to AI

We treat AI as a natural extension of ourselves. Each of us builds personal AI ecosystems—research, debugging, writing, analysis, code. We know which AI works best for which problem.

Everyone gets premium AI accounts (Chat
GPT, Claude, Perplexity Pro, Cursor, Lovable) and a quarterly budget for new tools. Knowledge sharing happens in demo days, Slack threads, and learning sessions.

We seek 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.