Head of Engineering

October 18

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Siena AI

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Artificial Intelligence • eCommerce • SaaS

Siena AI is an advanced autonomous customer service platform designed for commerce, integrating human empathy with AI to enhance customer experience. By handling over 80% of daily customer interactions, Siena AI helps companies streamline support while maintaining a consistent, empathetic brand voice across multiple channels. Siena provides real-time, omnichannel management and leverages powerful AI models for cognitive reasoning and multilingual support, transforming customer service into a strategically automated, revenue-driving function. The platform supports various integrations, allowing seamless deployment across modern commerce tools and communication channels for improved customer satisfaction and engagement.

11 - 50 employees

🤖 Artificial Intelligence

🛍️ eCommerce

☁️ SaaS

📋 Description

• 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. • You've made technical decisions that shaped company direction. • You've developed multiple leaders from ICs. • You've maintained velocity during high growth. • You've built with relevant technology: conversational AI, event-driven systems, LLM applications, CX platforms, e-commerce, API integrations. • You zoom from strategy to debugging fluidly. • You bring infectious energy, positive culture builder mindset. • You have startup DNA—comfortable with ambiguity, move fast.

🏖️ Benefits

• Great salary plus the opportunity for equity or stock grants. • Learning budget. If you're growing, so are we. • The thrill of building something new. Join us at a stage where your contributions matter most.