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Calibrate Group AI

Senior Technical Lead

remote / Posted
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We're hiring our founding technical hire — a Senior Technical Lead who will own the entire technical vision and execution. This is a co-builder role, not a cog-in-machine role.
What You'll Own:
  • Designing and building custom AI implementations for SMB clients — from discovery through deployment
  • Integrations across the platforms our clients already use (Toast, Square, Mindbody, QuickBooks, HubSpot)
  • Our AI tooling stack (Claude API, Make.com, Clay) and the internal systems that power delivery
  • Ongoing maintenance, optimization, and evolution of client AI systems
  • Client-facing portal and delivery infrastructure
  • Technical hiring as we scale
What We're Looking For:
  • 8+ years of engineering experience shipping real SaaS products
  • AI-native workflow: Cursor, Claude API, Make.com are daily tools, not experiments
  • Led a small team. You think in business outcomes, not just code
  • Former founding engineer or technical co-founder is a strong signal
  • Comfortable with ambiguity. You build the plane while flying it.
Compensation:
  • $160,000 - $200,000 base salary
  • 4.5% equity (founding-level)
  • Fully remote, US-based
How to Apply: Send your background, what you've built, and why this role fits to [email protected]

How does that feel? Once you're happy with it I'll update everything — Wellfound live posting, the Battle Kit doc, and the email to Josh.

We're hiring our founding technical hire — a Senior Technical Lead who will own the entire technical vision and execution. This is a co-builder role, not a cog-in-machine role.
This is an application-layer engineering role. You'll be building AI-powered tools that solve real business problems for real operators — not managing GPU clusters, optimizing inference pipelines, or scaling cloud infrastructure. If you get more excited connecting QuickBooks to an AI agent that saves a business owner 10 hours a week than you do tuning Kubernetes configs, keep reading.


Please mention the word **EFFECTIVENESS** and tag RMTI4LjE0MC45MS4xNzE= when applying to show you read the job post completely (#RMTI4LjE0MC45MS4xNzE=). This is a beta feature to avoid spam applicants. Companies can search these words to find applicants that read this and see they're human.