[Hiring] Fractional Chief Technology Officer @Learntastic

Role Description

Learntastic is 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 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.

Qualifications

• 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.