Maestro Ai

The way code gets written has changed more in the last year than in the previous twenty. Maestro is the platform engineering leaders use to navigate this transition — helping teams adopt AI deliberately, hold their craft to a higher standard, and turn the moment into a durable advantage instead of a missed one.

As an early-stage, venture-backed startup, joining our team means you’ll play a critical role in shaping our product and company culture. You’ll have the opportunity to design and deliver customer-facing features, address critical customer issues, and contribute to our technical and operational foundations from day one. We are a Seattle-based company, biased toward in-person collaboration, but open to fully remote for the right candidates.

The role

As a Founding Account Executive at Maestro, you’ll be responsible for:

• Own pipeline end-to-end: prospecting, qualification, discovery, demo, negotiation, and close.
• Run demos with engineering leaders, VPEs, and CTOs — alongside the founders. Tell the Maestro story in a way that lands with skeptical, sharp buyers.
• Partner with founders on every meaningful deal. We sell as a team in the early innings, and the closer the AE is to the founders, the faster we learn.
• Carry feedback from the field back into product. The best early AEs aren’t order-takers — they’re the sharpest signal product has about what to build next.
• Build the playbook. The messaging that lands, the objections we keep hearing, the ICP that’s actually closing — document it well enough that the next AE we hire can run it.
• Hit your number. Then beat it.
• Land the next wave of design-partner customers and turn them into reference accounts that pull others in.
• Stand up the first repeatable outbound motion: who we go after, what we say, what works.
• Crack the enterprise pricing conversation: what engineering leaders will actually pay for visibility into how their teams use AI.
• Build the GTM rituals — pipeline reviews, win/loss analysis, deal desk — that we’ll scale into a real sales org.

If this is you, let’s talk:

• 4+ years closing technical SaaS, ideally selling to engineering leadership (VPEs, CTOs, Heads of Platform).
• Track record as a top performer at an early-stage startup. We’re looking for someone who built territory from zero, not someone who inherited it.
• Genuine curiosity about engineering and AI. You don’t need to write code, but you do need to be able to hold an unbluffable conversation with a CTO about how their team uses Claude Code.
• Hunter mentality. Outbound doesn’t scare you; it energizes you.
• Disciplined with the CRM and the forecast. Pipeline hygiene isn’t admin — it’s how you sleep at night.
• Comfortable being wrong in public, in front of founders, and changing your mind fast.
• You’ve been a founding AE before
• Experience selling developer tools, dev infrastructure, or engineering analytics
• Based in Seattle

Compensation

Base salary $120,000–$160,000 plus variable, with OTE $220,000–$280,000. Generous early-employee equity and benefits. Final offer depends on skills and experience. Equity at this stage is a real part of the package, not a footnote.

How to apply

If you’re interested in this role, please say hello and send us your résumé at careers@getmaestro.ai . We read every application.

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