Siena AI · 1 month ago
Head of Engineering
United States
Full-time
Remote
Director/ExecutiveSiena AI is creating an operating system of AI agents that enhance customer experience across various touchpoints. As the Head of Engineering, you will set the technical vision for AI pipelines and integrations while scaling the engineering team and shaping the company's technical strategy.
Artificial Intelligence (AI)E-CommerceEnterprise SoftwareMachine LearningSoftware
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 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
Qualification
Required
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.
Everyone gets premium accounts (ChatGPT, Claude, Perplexity Pro, Cursor, Lovable) plus a quarterly budget for new tools.
Company
Siena AI
Siena AI is the creator of an autonomous chat platform that aims to blend human empathy and intelligent automation.
Founded in 2022
11-50 employees
Funding
Current Stage
Early StageTotal Funding
$11.05MKey Investors
Sierra VenturesGapMinder VC
2024-09-01Seed· $6M
2023-11-16Seed· $4.7M
2020-09-28Pre Seed· $0.35M
Leadership Team
Andrei Negrau
ceo, founder
Recent News
2025-08-19
2025-07-02
2025-07-02
Company data provided by crunchbase