Senior Technical Lead

Calibrate Group AI

FULLY_REMOTE

FULL_TIME

Remote

Posted Apr 21, 2026

Description

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:

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
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: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.

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.
This is an application-layer engineering role. 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.

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.

Interview Prep Guide

AI-generated

Preparation Strategy

To prepare for this role, focus on reviewing your experience with AI-native workflows, application-layer engineering, and building AI-powered tools. Practice discussing your approach to designing and building custom AI implementations, integrating them with existing platforms, and maintaining and optimizing client AI systems. Be prepared to talk about your experience leading a team, thinking in business outcomes, and handling ambiguity. Additionally, review the company's goals and vision, and prepare to discuss how your skills and experience align with them.

Likely Interview Rounds

1. Technical~60 min
What to prep: Review your experience with AI-native workflows, specifically with tools like Claude API, Make.com, and Clay. Be prepared to discuss your approach to designing and building custom AI implementations and integrating them with existing platforms.
- How would you design an AI-powered tool to solve a real business problem for an SMB client?
- Can you walk me through your experience with integrating AI implementations with existing platforms like QuickBooks or HubSpot?
- How do you approach ongoing maintenance and optimization of client AI systems?
2. Behavioral~60 min
What to prep: Prepare examples of your experience leading a team, thinking in business outcomes, and handling ambiguity. Review your approach to technical hiring and be ready to discuss your strategy.
- Can you describe your experience leading a small team and how you think in business outcomes?
- How do you handle ambiguity in a technical role, and can you give an example from your past experience?
- How do you approach technical hiring as a team scales?
3. Final~90 min
What to prep: Review the company's goals and vision, and prepare to discuss how your skills and experience align with them. Be ready to talk about your experience with application-layer engineering and building AI-powered tools.
- How do you see yourself contributing to the technical vision and execution of Calibrate Group AI?
- Can you describe your experience with application-layer engineering and building AI-powered tools?
- How do you prioritize your work and manage your time in a fully remote environment?

Most Likely Questions

How do you stay current with the latest developments in AI and machine learning?
Can you describe your experience with cloud-based platforms and tools?
How do you approach problem-solving in a technical role?
Can you walk me through your experience with agile development methodologies?
How do you handle conflicting priorities and tight deadlines in a technical role?

Common Pitfalls

Lack of experience with AI-native workflows and tools
Inability to think in business outcomes and prioritize work accordingly
Insufficient experience with application-layer engineering and building AI-powered tools
Poor communication skills and inability to work effectively in a fully remote environment

Free Prep Resources

• LeetCode
• System Design Primer (GitHub: donnemartin)
• NeetCode
• Claude API documentation
• Make.com documentation

Salary Negotiation Tips

Given the salary range of $160,000 - $200,000, be prepared to negotiate based on your experience and qualifications. Consider highlighting your experience with AI-native workflows, application-layer engineering, and building AI-powered tools, as well as your ability to think in business outcomes and lead a team. Be sure to also discuss your expectations for equity and other benefits.

Preparing interview guide...

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About Calibrate Group AI

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Senior Technical Lead

Description

Tags

Interview Prep Guide

Preparation Strategy

Likely Interview Rounds

Most Likely Questions

Common Pitfalls

Free Prep Resources

Salary Negotiation Tips

Apply for this Position

About Calibrate Group AI

Job Stats

Hiring Across Borders?

Get Paid in USD/EUR

Interview Prep Guide

Preparation Strategy

Likely Interview Rounds

Most Likely Questions

Common Pitfalls

Free Prep Resources

Salary Negotiation Tips