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.