About the role

Headquarters: Florida
URL: http://Calibrategroup.ai

About the Role:

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.

What You'll Own

AI-powered diagnostic and recommendation engine — our core client acquisition tool

Integrations with SMB platforms (Toast, Square, Mindbody, QuickBooks, HubSpot)

AI agent stack (Claude API, Make.com, Clay) for client implementations

Client-facing portal for ongoing optimization and reporting

Technical hiring as we scale toward $3M+ revenue

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

Bonus: experience in consulting, agencies, or client-facing technical work

To apply: https://weworkremotely.com/remote-jobs/calibrate-group-ai-senior-technical-lead

Interview prep

Walk in with sharper answers.

Use this as a quick practice sheet before you speak with the employer.

Role

Technology & IT Accounting API integration CRM Data Analysis Remote Collaboration remote

Likely questions

Tell us about work you have done that is close to the Senior Technical Lead role.
How would you approach your first 30 days at Calibrate Group AI?
Which of Accounting, API integration and CRM have you used recently, and what did it help you achieve?
Describe a time you solved a problem without waiting to be told exactly what to do.
How do you stay organised and communicate clearly when working remotely?

Prepare before the call

A recent example that proves your experience with Accounting, API integration and CRM.
One short story with a problem, your action, and the result.
Two examples that show the strengths listed on your CV.
A clear reason why this role and company interest you.
Your availability, preferred work style, and salary expectations.

Ask them

What would success look like in the first 90 days?
What are the main problems this hire should help solve?
How does the team give feedback and measure good work?
What does a normal working week look like for this role?

Practice line

I am interested in the Senior Technical Lead role because I can bring practical experience in Accounting, API integration and CRM, learn the team quickly, and contribute to the outcomes Calibrate Group AI needs from this hire.

Senior Technical Lead

About the role

Walk in with sharper answers.

Likely questions

Prepare before the call

Ask them

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