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

Originally posted on Himalayas