Founding Engineer

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.
• Admit uncertainty and ask for help early to protect team velocity.
• Take initiative without waiting for perfect clarity.
• Care about building durable systems, not just shipping features.

Qualifications
Required Experience

• 4+ years building and shipping production software (full-stack or backend-leaning)
• Strong technical judgment across backend, APIs, and modern web
• Hands-on ability to ship, debug, and improve code independently
• Comfort making speed / quality / scalability tradeoffs at an early stage
• Demonstrated ownership of outcomes (not just shipping features)

Strongly Preferred

• Experience building or integrating AI-enabled products (LLMs, orchestration, AI agents, automation, ML systems)
• Experience increasing operational leverage (reducing manual work, improving capacity)
• Experience building internal tools, operational systems, or workflow automation
• Experience working collaboratively with distributed or offshore engineering teams
• Experience in high-touch service environments (marketplaces, travel, fintech, concierge, logistics, etc.)
• Comfort with metrics, instrumentation, and reliability practices
• AI-first workflow - you actively use AI to increase your own and the team's efficiency

Work Model

• In-person / hybrid role, based in Austin, TX (minimum 3 days/week in-office).
• In-person collaboration is core to how we work and learn as a team.

Compensation & Growth

• Competitive salary based on experience, plus meaningful founding-level equity.
• Equity is structured to align long-term ownership with company growth.
• Significant room to grow scope and technical leadership as the company scales.
• Significant opportunity for impact and cross-functional exposure as the company grows.

Why Join Maestro?

• Founding-Level Ownership from Day One - This is not a feature-factory role. You'll own core systems and technical decisions from the start, and directly influence company direction as one of our earliest engineers.
• Build at the Inflection Point - We have paying members, real revenue streams, and strong early signal - but we're still small enough for your work to materially shape the company.
• AI Applied to Real Problems - We use AI as infrastructure - embedded into workflows that increase advisor capacity and improve high-stakes decision-making. This isn't demo AI. It's AI that moves metrics.
• High-Agency, High-Talent Team - We hire for superpowers. We move fast. We disagree without being disagreeable. You'll work alongside people who take ownership and expect the same.
• Path to Senior Leadership - This role has meaningful scope and the opportunity to grow into broader technical or engineering leadership as the company scales.
• Human-Centered Product - We're not building abstract SaaS. We're helping real people plan meaningful travel experiences - where trust, judgment, and service matter.
• Early-Stage Upside - Competitive compensation with meaningful equity. If we execute well, you share in the value created.
• In-Person Builder Energy (Austin-Based) - We believe early-stage velocity benefits from being in the room. Tight feedback loops. Fast iteration. Real collaboration.