Senior Technical Lead

Remote

Requirements

Designing and building custom AI implementations for SMB clients â 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
AI-native workflow: Cursor, Claude API, Make.com are daily tools, not experiments
Fully remote, US-based How to Apply: Â Send your background, what you've built, and why this role fits toÂ josh@calibrategroup.ai How does that feel? Once you're happy with it I'll update everything â Wellfound live posting, the Battle Kit doc, and the email to Josh.
You'll be building AI-powered tools that solve real business problems for real operators â 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.
This is a beta feature to avoid spam applicants.

We're hiring our founding technical hire â 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:
Comfortable with ambiguity. You build the plane while flying it. Compensation:
$160,000 - $200,000 base salary
4.5% equity (founding-level)
We're hiring our founding technical hire â 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.