Director, Office of the CTO

About hireworks

hireworks is building a community of top talent in key international markets by unlocking unparalleled access to positions at leading U.S. based companies. As your employer, hireworks will ensure you have a seamless interview, onboarding, and employee experience - providing ongoing support and resources along the way. Established in 2023, hireworks is forging corp-to-corp relationships with leading U.S. based organizations looking to grow their teams with best-in-class talent around the world. Working with hireworks means unlocking access to a network of local peers and mentors and career opportunities through our client network.

About Our client

A leading provider of innovative software and services to K-12 schools and educational institutions worldwide. Their mission is to empower schools to transform education through technology. They believe in the power of education to shape the future, and are committed to helping schools prepare students for success and make a positive impact on the world.

Position Overview

We are seeking a Director to serve as a senior technical leader and strategic partner to our client’s CTO and the broader engineering organization. This individual will work across engineering teams and initiatives, taking ownership of complex, high-impact challenges, developing clear recommendations, and driving them through resolution. Our client is entering a significant period of technology transformation, including a major platform rebuild and the continued evolution of its engineering processes and organization. With several critical initiatives underway simultaneously, this role will provide additional senior technical leadership, helping teams navigate architectural decisions, technical challenges, vendor relationships, and key transformation efforts. The scope of this position is intentionally broad. Depending on the needs of the organization, this individual may evaluate why a critical initiative has stalled and establish a path forward, partner with vendors on architectural decisions, investigate customer-impacting incidents and proposed solutions, or advise engineering leaders as they navigate complex technical and organizational challenges. The ideal candidate combines deep technical experience with broad architectural judgment, strong problem-solving skills, and the ability to lead through influence rather than direct authority. They are comfortable stepping into unfamiliar situations, quickly identifying what matters most, developing a well-informed point of view, and turning ambiguity into a practical plan of action.

Key Responsibilities

• Serve as a senior technical advisor to the CTO, providing clear, well-supported recommendations on complex engineering, architecture, operational, and organizational challenges.
• Take ownership of high-impact technical initiatives and problems that span multiple teams, driving alignment, decisions, and execution through resolution.
• Quickly assess unfamiliar systems, codebases, teams, initiatives, and vendor relationships to identify key issues, risks, dependencies, and potential solutions.
• Evaluate complex architectural decisions and technical trade-offs, including legacy modernization, platform strategy, vendor solutions, scalability, and long-term maintainability.
• Lead through influence, building credibility and alignment with senior engineers, engineering directors, vendors, and cross-functional stakeholders without relying on direct reporting authority.
• Conduct and guide technical root-cause analysis of complex software, platform, and customer-impacting incidents to ensure proposed solutions address underlying issues.
• Partner with engineering directors and emerging leaders, providing technical guidance, mentorship, and practical support as they navigate unfamiliar or particularly challenging situations.
• Navigate complex legacy environments pragmatically, balancing modernization goals with business priorities, budget constraints, technical risk, and existing vendor engagements
• Turn loosely defined problems into structured plans by identifying priorities, evaluating trade-offs, establishing clear recommendations, and defining practical next steps.
• Recognize when additional expertise or information is required and engage the appropriate technical or business stakeholders to inform decisions.

Required Qualifications

• 10+ years of progressive technical experience, including experience at the Principal Engineer, Staff Engineer, Technical Architect,technical consulting, or equivalent senior technical leadership level.
• Extensive experience within startup, scale-up, or fast-moving technology environments, working closely with core technologies and cross-functional teams.
• Demonstrated ability to operate without direct authority and drive alignment and technical execution across multiple engineering teams.
• Strong architectural judgment with experience evaluating complex system designs, modernizing legacy platforms, and assessing third-party or vendor solutions.
• Deep technical problem-solving and root-cause analysis skills, with the ability to investigate complex operational or software incidents and evaluate both immediate and long-term solutions.
• Proven ability to operate effectively amid ambiguity and rapidly shifting priorities, structure undefined problems, and take end-to-end ownership through resolution.
• Strong executive-level communication skills with the ability to translate complex technical issues into clear recommendations, risks, trade-offs, and decisions.
• Strategic partner and mentor mindset, with the ability to advise engineering directors and emerging leaders on complex technical and organizational challenges.

Preferred Qualifications

• Experience within B2B SaaS, EdTech, or other complex software/platform environments.
• Experience supporting significant platform modernization or transformation initiatives.
• Experience partnering with external technology vendors on architecture, implementation, or platform strategy.

Benefits:

hireworks is cultivating a growing community of top talent across LATAM. In addition to unlocking access to positions at top tier U.S. based companies, we offer a variety of benefits to enhance your experience:

• Competitive Pay - compensation that reflects your experience and accomplishments
• Remote Flexibility - work from anywhere within your home country (Brazil, Colombia or Argentina)
• Paid Time Off - ample vacation days to rest and recharge
• Public Holidays - local federal holidays are fully paid days off