Fractional CTO for Insurance Automation

Get Logan Inc is a fast-growing US trucking insurance brokerage serving 10,000+ fleets across the US. We are building our automation backbone to replace manual workflows with smart, reliable systems. We are looking for a hands-on Fractional CTO / Technical Lead who can help us design and implement our automation roadmap. The Mission You will own and execute our automation roadmap, one workflow at a time: 1. COI Automation — First 30 Days Automate the Certificate of Insurance request process, including intake, document generation, and delivery. 2. Client Follow-Up Automation Build automation for renewal reminders, pipeline touchpoints, and status updates. 3. Quoting Workflow Automation Automate data collection, carrier submissions, and tracking. Each automation cascade must result in a working system that our team actually uses daily — not just a prototype. What You'll Do Audit our current workflows across our agency management systems, CRM, email, and spreadsheets. Design the automation architecture. Build and launch automations using APIs, integrations, no-code/low-code tools, and custom scripts where appropriate. Advise the founder on technology decisions in clear, non-technical language. Document everything you build so our team can operate the systems independently. Evaluate and select tools/vendors for AMS, e-signature, email automation, and AI-assisted workflows. What We're Looking For 5+ years of experience building business automation, integrations, or internal tools. Insurance, logistics, or fintech experience is a strong plus. Hands-on technical experience — you write code, configure tools, and ship working solutions. Strong experience with REST APIs and webhooks. Experience with Zapier, Make, n8n, and similar automation platforms. Python or a similar programming language. Ability to work independently for 10–15 focused hours per week. Strong written communication and proactive weekly updates. Paid Test Project Before the contract begins, we will run a paid one-week test project ($300–$500). The task will be to automate one real workflow end-to-end, for example: COI request intake → document generation → email delivery The test will be performed in a test environment only. No production systems or credentials will be provided until the contract stage. Pass criteria: working automation, proper documentation, and delivery on time. What We Offer Direct access to the founder — decisions can be made quickly. Real business volume: your systems will be used by 30+ people daily. Milestone bonuses and rate growth with each successful automation cascade. Long-term opportunity to grow into a lead technical role as the automation platform scales. Important: We are looking for someone who builds and ships, not someone who only provides advice. We also expect proactive written communication and weekly progress updates. How to apply: Please do not send a long cover letter. Send us exactly 3 sentences: -One automation you built that you are proud of. -The technology stack you would choose for this project. -Your available start date.