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-buil

Responsibilities

• Design and build custom AI implementations for SMB clients from discovery through deployment
• Manage integrations across client platforms (Toast, Square, Mindbody, QuickBooks, HubSpot)
• Own the AI tooling stack (Claude API, Make.com, Clay) and internal delivery systems
• Provide ongoing maintenance, optimization, and evolution of client AI systems
• Build and maintain client-facing portal and delivery infrastructure
• Lead technical hiring as the company scales

Requirements

• 8+ years of engineering experience shipping real SaaS products
• AI-native workflow proficiency with Cursor, Claude API, and Make.com as daily tools
• Experience leading a small team
• Ability to think in business outcomes, not just code
• Comfort with ambiguity and building while executing

Preferred Qualifications

• Former founding engineer or technical co-founder experience

• $160,000 - $200,000 base salary
• 4.5% equity at founding level
• Fully remote
• US-based