Founding Engineer: AI-Driven Automation & Scalable Systems

a16z-speedrun

Austin (TX)

On-site

USD 180,000 - 240,000

Full time

14 days+

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Job summary

Maestro is seeking a Founding Engineer to build and scale the systems powering our AI-enabled travel platform in Austin, working directly with the Founder and cross-functional partners. This role blends engineering, product, and operations to translate real-world friction into reliable software, shipping automation and AI tooling that expands team capacity and improves member experiences.

As an early member, you will help move from high-touch manual work to scalable solutions and shape how we

Responsibilities

Ship, debug, and improve production code across the stack - backend, APIs, and AI systems
Integrate and operationalize AI workflows (LLMs, orchestration, APIs, automation) that are stable, understandable, and trusted internally
Translate ambiguous product and ops needs into working software
Prioritize based on measurable business impact, in partnership with product
Make pragmatic tradeoffs between speed, quality, and scalability
Instrument what you build and track performance in real usage
Reduce manual, human-heavy workflows through thoughtful automation
Collaborate closely with our offshore engineering team - sharing context, reviewing work, and unblocking one another to keep delivery moving across time zones
Ship core AI workflows and integrations that are stable and adopted internally
Measurably reduce manual, repetitive operational work through automation
Establish reliability in the systems the team depends on daily
Ship consistently, with fewer blockers and surprises
Create systems that scale as membership grows