[Remote] Head of Engineering at Siena AI

Warsaw, Masovian Voivodeship, Poland

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Not SpecifiedCompensation

Expert & Leadership (9+ years)Experience Level

Full TimeJob Type

UnknownVisa

Artificial Intelligence, Customer ExperienceIndustries

Requirements

Scaled teams to 30+ successfully
Still code using AI tools like Cursor, Claude Code, Codex, Lovable, v0
Technical depth with AI-native fluency
Comfortable with customers—join enterprise calls, understand their technical pain, earn trust at exec level
High agency—take bets, shape direction proactively
Led teams that shipped regularly at scale
Made technical decisions that shaped company direction
Developed multiple leaders from ICs
Maintained velocity during high growth
Built with relevant technology: conversational AI, event-driven systems, LLM applications, CX platforms, e-commerce, API integrations
Zoom from strategy to debugging fluidly
Bring infectious energy, positive culture builder mindset
Startup DNA—comfortable with ambiguity, move fast

Responsibilities

Set technical roadmap aligned to business goals—make build vs buy decisions at company level
Double 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

Skills

Key technologies and capabilities for this role

AI PipelinesAI EvalsIntegrationsMulti-Agent OrchestrationSystem ArchitectureTechnical LeadershipTeam ScalingCursorClaude

Questions & Answers

Common questions about this position

Is this position remote?

Yes, the position is fully remote.

What salary or compensation is offered for the Head of Engineering role?

This information is not specified in the job description.

What key experiences are required for this role?

Candidates must have scaled teams to 30+ successfully, stayed hands-on coding with AI tools like Cursor and Claude Code, and possess technical depth with AI-native fluency.

What is the company culture like at Siena AI?

Siena AI has a small, distributed team that punches above its weight, with every person having outsized impact due to built-in leverage, making it faster and more fun.

What makes a strong candidate for Head of Engineering?

A strong candidate has high agency, infectious energy, experience scaling teams to 30+, remains deeply technical with AI tools, and can operate from board strategy to debugging production.

Siena AI

Autonomous AI customer service platform for e-commerce

About Siena AI

Siena AI offers an autonomous customer service platform tailored for the commerce sector, enabling businesses to implement AI-driven support with ease. The platform integrates with existing help desk systems, allowing merchants and brands in the e-commerce market to provide timely and accurate customer service. Siena's technology utilizes advanced models from OpenAI, delivering human-like responses and cognitive reasoning capabilities. The company operates on a subscription-based model, offering various service tiers that cater to different business needs, including features like smart routing and the Siena Copilot for human agents. A key differentiator for Siena is its commitment to data security; it does not train its models on client data, ensuring the protection of sensitive information. The goal of Siena AI is to enhance customer support efficiency and accuracy for e-commerce businesses while maintaining a strong focus on privacy.

San Francisco, CaliforniaHeadquarters

2023Year Founded

$4.6MTotal Funding

SEEDCompany Stage

Enterprise Software, Cybersecurity, AI & Machine LearningIndustries

11-50Employees

Benefits

Remote Work Options

Paid Vacation

Stock Options

Company Equity

Professional Development Budget

Risks

Increased competition from companies like Discover Financial Services using generative AI.

Dependency on external partners like LTVplus for technological advancements.

New AI-driven platforms in Eastern Europe may challenge Siena AI's market position.

Differentiation

Siena AI combines human empathy with intelligent automation for customer service.

The platform integrates seamlessly with existing help desk systems for easy deployment.

Siena AI prioritizes data security by not using client data for model training.

Upsides

Siena AI raised $4.7M to develop empathic AI customer service agents.

Partnership with LTVplus enhances customer service through empathic AI.

Subscription-based model ensures steady revenue and scalable customer service operations.

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