Founding Engineer

a16z-speedrun; Austin (TX); On-site; USD 180,000 - 240,000; Full time

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

Job description

We are hiring a Founding Engineer to build and scale the systems that power Maestro - in person, in Austin.

This role sits at the intersection of engineering, product, and operations. You will work directly with the Founder and partner closely with Product and Ops to translate real-world operational friction into reliable, AI-enabled software.

This is not a ticket-taking role. This is a builder role.

You will be responsible for shipping the automation, tooling, and AI systems that increase team capacity and improve member experience - and driving them to launch and adoption.

Mission

Maestro is building a high-touch, AI-enabled travel platform for high-net-worth members. We combine human expertise with automation and intelligent systems to deliver exceptional travel experiences - while building operational leverage that allows us to scale sustainably.

As a Founding Engineer, your mission is to turn AI and engineering effort into reliable, scalable systems that actually get used and reduce human work.

We are early, fast-moving, and intentional about who we hire. Every person we bring in meaningfully shapes the company.

The Multiplier Effect

At Maestro, we don't hire to redistribute work; we hire to create exponential leverage. Every hire must bring a unique superpower - whether that's technical judgment, systems thinking, or the ability to solve ambiguous problems under pressure. As a founding engineer, your code is the leverage: the systems you build should let the team do dramatically more without growing headcount linearly.

What You'll Do

• 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

You will help us move from "high-touch but manual" to "high-touch and scalable."

We hire for outcomes, not activities. In your first 3-6 months, you will:

• 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

The Maestro Core (Universal Competencies)

Regardless of the role, every Maestro team member must embody:

• High Agency: You find a way over, under, or through obstacles without waiting for permission.

• Execution Velocity: You move work forward with momentum and intentionality.

• Judgment: You make smart tradeoffs under uncertainty.

• Human-Centered Conduct: You treat people like people, even under high pressure.

• Ownership: You act like it's yours—without being told.

Are You a Stage Fit?

We are an early-stage, high-growth company. This means we value slope over pedigree.

We need productive challengers who:

• Have thrived in ambiguity and incomplete inputs before - not just tolerated it.

• Start by doing, not delegating - there are no "pure managers" here.

• Optimize for leverage before elegance, and ship "good enough" systems that are reliable and adopted.