Senior Technical Lead

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 josh@calibrategroup.ai

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.