CTO / Technical Architect at OSI Engineering

Job description

Apply Now Share Industry: eLearning Contract : No Direct Hire: Yes Job Type: Full Time Location: Miami, Florida Telecommute: No Salary/Wage: 200,000 To $350,000 Per Year Travel Required: TBD Job Description: Join a leading eLearning company that is seeking a hands-on CTO / Platform Architect to lead the greenfield buildout of a unified, AI-native learning platform. Summary: This person will own the technical vision and architecture, consolidate multiple legacy platforms into one scalable ecosystem, establish the company’s AI-native engineering strategy, and build a small, high-caliber engineering team. This is not a traditional migration or modernization project. The team is replacing its existing technology stack and rebuilding its learning ecosystem from the ground up into a single platform. The person in this role will report directly to the CEO and partnering closely with executive leadership, this person will define the technology stack, make foundational architecture decisions, personally contribute to core platform development, hire senior engineers, and establish an agentic-first engineering culture. This is a highly technical leadership role for someone who can operate as both a builder and architect. The ideal candidate should think like a technical founder, remain actively involved in engineering, challenge assumptions, translate business objectives into technical strategy, and build a high-autonomy organization capable of delivering quickly without sacrificing scalability, security, or quality. Key Responsibilities: • Own the greenfield platform architecture: Define and lead the buildout of a unified, AI-native learning platform that consolidates multiple products into one scalable ecosystem. • Set the technical strategy: Select the technology stack, architecture patterns, platform roadmap, engineering standards, and foundational technical decisions required to support long-term scalability, security, performance, and maintainability. • Build core platform capabilities: Architect and contribute to foundational services, including APIs, authentication, API gateways, shared services, integration layers, unified data structures, microservices, and cloud infrastructure. • Lead AI-native engineering: Establish agentic engineering workflows, AI-assisted development practices, automated review and testing loops, CI/CD, infrastructure as code, and the tooling required to accelerate high-quality delivery. • Integrate enterprise systems: Design reliable integration frameworks across CRM, ERP, billing, payments, subscriptions, accounting, and other business-critical systems such as Salesforce, NetSuite, Zuora, and Yuno. • Build and lead a lean senior team: Hire, mentor, and organize a small group of high-autonomy engineers who can own architecture, implementation, testing, deployment, and delivery with limited traditional project management or quality assurance support. • Partner with executive leadership: Work directly with the CEO, Product, and business leaders to translate business goals into technical strategy, execution plans, investment priorities, timelines, and risk tradeoffs. • Own technology and vendor decisions: Evaluate AI services, cloud platforms, engineering frameworks, developer tools, and technical vendors with a focus on capability, cost efficiency, scalability, and long-term fit. • Establish a strong local engineering presence: Work from either Medellín or Madrid and collaborate closely with leadership and team members to build a highly aligned, execution-focused engineering organization. Requirements: • Hands-on senior technical leadership experience, ideally as a CTO, Technical Architect, VP of Engineering, Head of Engineering, Founding Engineer, first technical hire, or similar role. • Proven experience designing and shipping scalable production software in lean, fast-moving, or ambiguous environments. • Experience owning greenfield platform architecture, including technology stack selection, architectural standards, shared services, APIs, integrations, distributed systems, or microservices. • Strong cloud architecture experience, preferably AWS, with practical experience across modern infrastructure, DevOps, CI/CD, infrastructure as code, automated testing, deployment automation, and release quality. • Experience integrating enterprise systems across areas such as CRM, ERP, accounting, billing, subscriptions, payments, or other business-critical workflows. • Practical experience using AI-assisted development tools and establishing AI-native or agentic engineering workflows. • Ability to personally contribute to foundational software development while leading architecture, technical reviews, and engineering execution. • Experience hiring, mentoring, and leading senior engineers in a high-autonomy environment. • Strong product and business judgment, with the ability to translate strategic objectives into technical scope, sequencing, risks, and execution plans. • Clear communication skills with technical teams, Product leaders, executive leadership, and business stakeholders. • Professional fluency in English. • Spanish proficiency is required, ideally at a conversational or intermediate level or higher. • Must be based in or willing to relocate to Miami, FL. Preferred Experience: • Experience with EdTech, LMS platforms, online learning, consumer education, or digital learning products. • Experience developing unified platforms that support multiple products, brands, user segments, or geographies. • Experience with child-safe environments, COPPA, GDPR-K, or similar privacy and compliance requirements. • Experience with AI tutors, personalization engines, LLM orchestration, model routing, AI-native platforms, or agentic frameworks. • Prior experience as a startup CTO, Founding Engineer, first technical hire, or early technical leader in a founder-led or high-growth environment. • Experience building both customer-facing products and internal operational tools. • Evidence of a strong builder mindset through personal projects, open-source contributions, AI experimentation, or visible technical craftsmanship. • GCP or Azure experience may be considered when supported by strong cloud architecture fundamentals. Location: • The location for this role is Miami, FL. • Candidates located elsewhere may be considered only if they are willing and able to relocate. • Remote work from another city or country is not available for this position. Contact Information: Damion Contreras 408.550.2800 x123 Manage Consent To provide the best experiences, we use technologies like cookies to store and/or access device information. Consenting to these technologies will allow us to process data such as browsing behavior or unique IDs on this site. Not consenting or withdrawing consent, may adversely affect certain features and functions. Functional Functional Always active The technical storage or access is strictly necessary for the legitimate purpose of enabling the use of a specific service explicitly requested by the subscriber or user, or for the sole purpose of carrying out the transmission of a communication over an electronic communications network. 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Requirements

Must-haves

Industry: eLearning
Contract : No
Direct Hire: Yes
Job Type: Full Time
Location: Miami, Florida
Telecommute: No
200,000 To $350,000 Per Year
Travel Required: TBD
Join a leading eLearning company that is seeking a hands-on CTO / Platform Architect to lead the greenfield buildout of a unified, AI-native learning platform.
Own the greenfield platform architecture: Define and lead the buildout of a unified, AI-native learning platform that consolidates multiple products into one scalable ecosystem.
Integrate enterprise systems: Design reliable integration frameworks across CRM, ERP, billing, payments, subscriptions, accounting, and other business-critical systems such as Salesforce, NetSuite, Zuora, and Yuno.
Partner with executive leadership: Work directly with the CEO, Product, and business leaders to translate business goals into technical strategy, execution plans, investment priorities, timelines, and risk tradeoffs.
Own technology and vendor decisions: Evaluate AI services, cloud platforms, engineering frameworks, developer tools, and technical vendors with a focus on capability, cost efficiency, scalability, and long-term fit.
Establish a strong local engineering presence: Work from either Medellín or Madrid and collaborate closely with leadership and team members to build a highly aligned, execution-focused engineering organization.
Hands-on senior technical leadership experience, ideally as a CTO, Technical Architect, VP of Engineering, Head of Engineering, Founding Engineer, first technical hire, or similar role.
Proven experience designing and shipping scalable production software in lean, fast-moving, or ambiguous environments.

Nice-to-haves

Experience with EdTech, LMS platforms, online learning, consumer education, or digital learning products.
Experience developing unified platforms that support multiple products, brands, user segments, or geographies.
Experience with child-safe environments, COPPA, GDPR-K, or similar privacy and compliance requirements.
Experience with AI tutors, personalization engines, LLM orchestration, model routing, AI-native platforms, or agentic frameworks.
Prior experience as a startup CTO, Founding Engineer, first technical hire, or early technical leader in a founder-led or high-growth environment.
Experience building both customer-facing products and internal operational tools.
Evidence of a strong builder mindset through personal projects, open-source contributions, AI experimentation, or visible technical craftsmanship.
GCP or Azure experience may be considered when supported by strong cloud architecture fundamentals.

Application prep

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aiapici/cdawsllmgcpazure

Platform: careers-html
Effort: medium

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