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OnStak is seeking an innovative, strategic, and hands-on Chief Technology Officer (CTO) to lead the company’s technology vision and execution. The CTO will play a critical role in shaping OnStak’s technology strategy, building a high-performing engineering organization, and ensuring that our technology platform can scale with the company’s growth.
This is a leadership role for someone who combines strong technical expertise with business judgment, product thinking, and the ability to turn ambitious ideas into reliable, scalable technology.

The Opportunity

As CTO, you will own the overall technology direction of OnStak. You will work closely with the CEO and leadership team to translate business objectives into a clear technology roadmap while fostering a culture of innovation, accountability, security, and continuous improvement.
You will be responsible for both strategic technology leadership and execution, from architecture and infrastructure to engineering processes, cybersecurity, data, and future technology initiatives.

• Develop and execute OnStak’s long-term technology strategy in alignment with company goals.
• Lead the architecture, development, deployment, and ongoing improvement of OnStak’s technology platforms and products.
• Build, mentor, and lead a world-class engineering and technology organization.
• Establish scalable engineering practices, development standards, and technical processes.
• Partner closely with the CEO, product, operations, and other business leaders to prioritize technology investments and initiatives.
• Evaluate emerging technologies and determine how they can create competitive advantages for OnStak.
• Ensure systems are scalable, reliable, secure, and designed for long-term growth.
• Oversee cybersecurity, data protection, infrastructure, cloud strategy, and technology risk management.
• Establish and monitor technical KPIs, engineering performance metrics, and system reliability standards.
• Manage technology budgets, vendors, partners, and third-party platforms.
• Develop and maintain a clear technology roadmap with measurable milestones.
• Ensure technical decisions balance speed, quality, scalability, security, and cost.
• Promote automation, innovation, and continuous improvement across the technology organization.
• Serve as a senior technology representative for OnStak with customers, partners, investors, and other stakeholders when appropriate.
• Stay current with advances in AI, cloud computing, software architecture, cybersecurity, data platforms, and other technologies relevant to OnStak’s business.

Qualifications

• 10+ years of progressive experience in software engineering, technology, product development, or related fields.
• Significant experience leading engineering or technology teams, preferably in a high-growth or technology-driven company.
• Proven experience designing and scaling complex technology platforms.
• Strong understanding of modern software architecture, cloud infrastructure, APIs, databases, cybersecurity, and DevOps.
• Experience recruiting, developing, and retaining high-performing technical teams.
• Strong business acumen and the ability to connect technology investments to measurable business outcomes.
• Excellent communication and leadership skills.
• Demonstrated ability to operate strategically while remaining close enough to the technology to make informed technical decisions.
• Experience managing technology budgets and external technology partners.
• Bachelor’s degree in Computer Science, Engineering, Information Technology, or a related field preferred; equivalent experience will be considered.

Leadership Qualities

The ideal CTO for OnStak is:

• Strategic: Able to create a technology vision that supports long-term business growth.
• Innovative: Constantly looking for better ways to use technology to solve meaningful problems.
• Hands-On: Comfortable diving into architecture, systems, and technical decisions when needed.
• Business-Minded: Understands that technology exists to create customer and business value.
• People-Focused: Builds strong teams and develops future technology leaders.
• Decisive: Makes thoughtful decisions quickly and takes ownership of outcomes.
• Security-Conscious: Treats reliability, privacy, and security as fundamental parts of the technology strategy.
• Collaborative: Works effectively across departments and communicates complex technical concepts clearly.

What Success Looks Like

Within the first 12–18 months, the CTO will be expected to:

• Establish a clear and scalable technology strategy for OnStak.
• Build and strengthen the engineering organization.
• Develop a prioritized technology and product roadmap.
• Improve platform reliability, scalability, security, and performance.
• Establish strong engineering processes and measurable technical KPIs.
• Identify opportunities to use automation and emerging technologies to accelerate growth.
• Create a technology culture focused on innovation, ownership, quality, and execution.
• Position OnStak’s technology platform for sustained long-term growth.

Why Join OnStak?

This is an opportunity to have an foundational impact on the future of OnStak. The CTO will have significant influence over the company’s technology, product capabilities, engineering culture, and growth strategy.
If you are an experienced technology leader who wants to build something meaningful, lead talented teams, and help shape the future of a growing company, we would love to hear from you.
OnStak is an equal opportunity employer committed to building a diverse, inclusive, and innovative workplace.