Fractional Chief Technology Officer (CTO)

Learntastic is a fast-growing online education platform delivering accredited continuing education, professional certification, and compliance training (including CPR/AED, First Aid, ACLS, PALS, HIPAA, and industry-specific CE) to individual learners and corporate/group accounts across healthcare, education, and other regulated industries. We're scaling our LMS, e-commerce, and subscription infrastructure to serve a rapidly growing base of individual and enterprise customers. We're looking for a hands-on Fractional CTO to own our technical strategy and execution as we scale from a course-purchase platform into a broader subscription, package, and corporate-account ecosystem, at a commitment of ~20 hours per week. You'll partner closely with Product, Design, and the executive team to translate business goals — checkout optimization, subscription models, corporate dashboards, vendor integrations — into reliable, scalable systems. This is a builder-operator role: even at a fractional commitment, you'll be expected to stay closely involved in architecture decisions, code quality, and day-to-day delivery with the engineering team — prioritizing your time toward the highest-impact work each week. What You'll Do: Own the technical roadmap for our LMS, e-commerce/checkout, and corporate account systems, aligning engineering priorities with product and business goals Write and review code directly — this is a hands-on role, not purely managerial Lead and scale multiple engineering functions, including backend development, frontend development, QA, and automation/DevOps teams Oversee our Laravel/PHP-based platform, ensuring clean architecture, maintainability, and scalability as the product grows Manage cloud infrastructure on AWS, including servers, deployment, monitoring, security, and cost efficiency Drive our A/B testing program end-to-end — infrastructure, test design collaboration with Product, and reliable tracking/reporting of results Own conversion rate optimization, including reducing credit card and cart abandonment, and identifying and resolving tracking/analytics issues Identify and implement automation opportunities, both for internal operations (support, admin workflows) and customer-facing features Explore and integrate LLM/AI capabilities where they can improve the platform — automation, personalization, internal tooling, or customer support Oversee platform reliability and performance, ensuring uptime and speed across the customer-facing site, corporate/group admin dashboards, and backend LMS Lead website security and compliance certifications (e.g., SOC 2), and ensure ongoing compliance as we scale Oversee customer-facing customization and portal development, including corporate/group admin portals and account-specific configurations Manage vendor and third-party integrations, including payment processors, BNPL providers, course content vendors, and compliance/accreditation systems Establish data infrastructure to support better reporting on customer behavior, course completion, subscription retention, and A/B test outcomes Own technology budgeting and forecasting, including infrastructure costs, tooling, and headcount planning Partner directly with executive leadership — collaborating closely with the CPO, CMO, CRO, and CEO to align technology strategy with product, marketing, and revenue goals Contribute to overall company strategy, not just technology strategy — working alongside the CEO, CPO, CMO, and CRO on business priorities, growth planning, and how technology decisions support broader company direction What We're Looking For: 15+ years of software engineering experience, with 5+ years in a senior technical leadership role (CTO, VP of Technology, or equivalent) Proven experience scaling e-commerce, subscription, or LMS platforms — EdTech experience strongly preferred Hands-on coding ability — comfortable reviewing and contributing to code, not just managing from a distance Experience managing multiple technical functions: backend, frontend, QA, and automation/DevOps teams Strong hands-on expertise with Laravel/PHP architecture and modern web application development Experience with AWS and cloud infrastructure — server management, deployment pipelines, scaling, and cost optimization Proven track record running A/B testing programs, including infrastructure setup, experiment design, and results tracking Experience improving conversion rates and reducing cart/credit card abandonment, backed by solid analytics/tracking practices Experience leading organizations through security/compliance certifications such as SOC 2 Experience building customer-facing customization and portal solutions (e.g., corporate or multi-tenant account portals) Experience building or integrating automation (workflows, internal tooling, CI/CD, or business-process automation) Familiarity with LLM/AI integration (e.g., building AI-powered features, automation, or internal tooling using large language models) Experience with payment systems, checkout flow optimization, and/or BNPL integrations Experience with budgeting and forecasting for technology spend and headcount Strong communication and collaboration skills — proven experience partnering with CPO, CMO, CRO, and CEO-level stakeholders to align technology with business strategy Experience with corporate/multi-tenant account systems (admin dashboards, sub-admins, group management) is a strong plus Experience in healthcare compliance or regulated-industry software is a plus What Success Looks Like: A stable, scalable checkout architecture with measurable improvements in conversion rate and reduced cart/payment abandonment A high-functioning engineering organization (dev, QA, automation) with clear processes and strong delivery velocity Reduced technical debt and improved platform performance across individual and corporate account experiences Achieved or maintained key security/compliance certifications (e.g., SOC 2) Technology budget and forecasting that supports growth without surprises Strong working relationship with the executive team (CPO, CMO, CRO, CEO), enabling fast, aligned decision-making on pricing, packaging, and platform priorities Compensation & Logistics: Engagement type: Part-time / Fractional — approximately 20 hours per week Location: Remote Budget: $5,000/month