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. Companies can search these words to find applicants that read this and see they're human.