Senior Technical Lead
Calibrate Group AI · Posted 2026-04-20
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
What this role looks like for a working parent
Calibrate Group AI is hiring a Senior Technical Lead on a fully remote basis from Anywhere in the World. Below we've reframed the listing through the FlexCareers lens — what this job actually means if your day is bracketed by a school run, a nap window, or a caregiving block.
Why we surfaced this role
- Remote role suitable for a flexible, school-hours schedule with async communication
How a parent might shape the day
Most of the candidates we hear from in this category split their week into two or three deep-work blocks: an early-morning window before the household wakes, a midday block during nap or school hours, and a short evening sweep for asynchronous responses. A role like Senior Technical Lead typically rewards focused output over hours-at-desk, which is exactly the trade working parents want.
Questions to ask in the interview
- What does a "core hours" overlap look like across time zones?
- Is the team genuinely async, or is async a synonym for "ping me on Slack"?
- How are deadlines and on-call expectations handled around school holidays?
- What does parental leave and return-to-work look like at Calibrate Group AI?
- Are there meeting-free days or focus blocks already on the team's calendar?
Before you apply
Read the full description below carefully. Calibrate Group AI owns the application process — clicking Apply for this role takes you directly to their listing. FlexCareers does not collect applications, take a placement fee, or sit between you and the employer. We surface the role; you do the work.