Senior Technical Lead
at Calibrate Group AI · Florida
About this 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
Why we flagged this for parents & caregivers
FlexCareers scored this listing 50/100 on parent-friendliness based on the language the employer used in their own posting. We did not see explicit parent-friendly keywords (async, part-time, flexible hours, parental leave) — but the role is fully remote, which is the baseline filter for inclusion on FlexCareers. Read the application page closely and ask about parental leave, expected meeting hours, and core overlap windows during your first conversation. Employers who answer those questions clearly are usually the ones who'll respect the boundaries later.
Questions worth asking before you apply
- What are the required core hours of overlap, and which timezone are they in?
- How is on-call or after-hours coverage handled?
- What does parental leave actually look like — duration, pay, ramp back?
- What's the expected response time on Slack / chat outside of meetings?
- How does the team handle a sick kid day or a school pickup window?