Head of Engineering (AI)

TL;DR

Head of Engineering (AI): Setting the technical vision for the first intelligence layer in customer experience, focusing on AI pipelines, integrations, and multi-agent orchestration. Focus on scaling teams, shaping technical strategy, and maintaining hands-on coding with AI tools.

Company

Siena is the first intelligence layer for customer experience, creating an operating system of AI agents that enhance customer interactions.

What you will do

• 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 be an example for what's possible with 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/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 practices that scale

Requirements

• You've scaled teams to 30+ successfully
• You still code building using AI tools like Cursor, Claude Code, Codex, Lovable, v0
• You have technical depth with AI-native fluency
• You're comfortable with customers—join enterprise calls, understand their technical pain, earn trust at exec level
• You have high agency—take bets, shape direction proactively
• You've led teams that shipped regularly at scale