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

Powered by JazzHR