Fractional CTO — Technology Stack Audit & Zendesk Evaluation

We are a growth-stage, multi-entity home services company operating across Northern California with a team of 60+ and three business entities under common ownership. We are seeking an experienced fractional CTO to conduct an audit of our current technology stack, beginning with an immediate evaluation of our Zendesk implementation, and to provide a clear, actionable technology roadmap going forward. Scope of work Phase 1 — Zendesk evaluation (immediate priority) • Assess our current Zendesk configuration against our operational needs • Evaluate the ticketing system's effectiveness for a CSR team handling inbound calls, texts, and emails • Compare Zendesk against alternative platforms (e.g., Dialpad) for our specific use case • Deliver a clear recommendation: optimize current Zendesk setup or migrate to an alternative Phase 2 — Full technology stack audit • Inventory and assess all current technology platforms, integrations, and contractors • Evaluate how systems interconnect and identify gaps, redundancies, and risks • Review code ownership, documentation standards, and contractor deliverable controls • Provide a prioritized technology roadmap aligned with our growth objectives Requirements • Demonstrated Zendesk expertise — configuration, administration, and platform evaluation • Experience auditing technology stacks for growing service businesses, including CRMs that are industry specific • Ability to assess contractor deliverables, code ownership, and documentation standards • Clear, non-technical communication style — findings must be presentable to a non-technical CEO • Project-based engagement with structured deliverables, not open-ended retainer • Available for an initial scoping call within one week Deliverables • Written Zendesk assessment with a clear optimize vs. migrate recommendation • Full technology stack inventory and risk assessment • Prioritized technology roadmap with cost and timeline estimates • Executive summary suitable for CEO review We are a growing company with an expanding technology footprint. Beyond this initial engagement, we are hoping to find the right person who could grow with us as an ongoing trusted advisor as our needs evolve.