Chief Technology & AI Platform Leader

Stride, Inc.; Tallahassee (FL); On-site; USD 132,000 - 195,000; Full time

Benefits offered by this job

Health benefits

Retirement contributions

Paid time off

Job summary

Stride, Inc. is seeking a Head of Technology to lead Tallo's engineering and technology organization, guiding the team, setting technical direction, and partnering with Product, Data, Marketing, and leadership to translate strategy into execution.

This is a working leadership role reporting to the CEO. The leader will own the engineering structure, architecture, and platform health, while steering AI/ML initiatives and cross‑functional collaboration with the parent company.

Qualifications

• Extensive software engineering leadership across multi‑team organizations.
• Proven track record hiring and developing engineering leaders.
• Strong experience with modern cloud-based architectures, DevOps, and distributed systems.
• Experience shipping data-driven or AI-enabled features.
• Excellent communication and executive collaboration skills.

Responsibilities

• Lead and grow an existing engineering team, setting clear ownership and metrics.
• Define and evolve platform architecture and technical standards.
• Partner with Product, Data, Marketing, and leadership to translate strategy into execution.
• Oversee safety, security, and compliance across technology.
• Drive AI/ML strategy and data partnerships.

Skills

Software engineering leadership

Engineering management

Cloud architectures

DevOps practices

Distributed systems

AI/ML strategy

Security & compliance

Data collaboration

Stakeholder communication

Hiring and coaching

Job description

Stride, Inc. is seeking a Head of Technology to lead Tallo's engineering and technology organization, guiding the team, setting technical direction, and partnering with Product, Data, Marketing, and leadership to translate strategy into execution.

This is a working leadership role reporting to the CEO. The leader will own the engineering structure, architecture, and platform health, while steering AI/ML initiatives and cross‑functional collaboration with the parent company.