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 deploymentIntegrations 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 deliveryOngoing maintenance, optimization, and evolution of client AI systemsClient-facing portal and delivery infrastructureTechnical hiring as we scaleWhat We're Looking For:8+ years of engineering experience shipping real SaaS productsAI-native workflow: Cursor, Claude API, Make.com are daily tools, not experimentsLed a small team. You think in business outcomes, not just codeFormer founding engineer or technical co-founder is a strong signalComfortable with ambiguity. You build the plane while flying it.Compensation:$160,000 - $200,000 base salary4.5% equity (founding-level)Fully remote, US-basedHow to Apply: Send your background, what you've built, and why this role fits to josh@calibrategroup.aiHow 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 RODguMTk4Ljk5LjE0Mw== when applying to show you read the job post completely (#RODguMTk4Ljk5LjE0Mw==). 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.

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 deploymentIntegrations 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 deliveryOngoing maintenance, optimization, and evolution of client AI systemsClient-facing portal and delivery infrastructureTechnical hiring as we scaleWhat We're Looking For:8+ years of engineering experience shipping real SaaS productsAI-native workflow: Cursor, Claude API, Make.com are daily tools, not experimentsLed a small team. You think in business outcomes, not just codeFormer founding engineer or technical co-founder is a strong signalComfortable with ambiguity. You build the plane while flying it.Compensation:$160,000 - $200,000 base salary4.5% equity (founding-level)Fully remote, US-basedHow to Apply: Send your background, what you've built, and why this role fits to josh@calibrategroup.aiHow 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 RODguMTk4Ljk5LjE0Mw== when applying to show you read the job post completely (#RODguMTk4Ljk5LjE0Mw==). 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.