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Head of Technology

"Stride

Remote · US$132k – $195k

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About this role

Job Description The Head of Technology leads Tallo’s engineering and technology organization, developing and supporting the existing team and growing the structures and systems that power a career platform serving early talent. This leader manages engineering managers (currently 2 roles) who lead software engineering and QA teams, sets the technical direction for the platform, and partners closely with Product, Data, Marketing, and company leadership to translate strategy into execution. This is one of the most important roles in the organization.

The Head of Technology is accountable for the structure and health of the engineering organization, the soundness of Tallo’s technical architecture, delivery against the product roadmap, and the long-term evolution of the platform, including where and how AI and machine learning create real product value. This is a working leadership role. The person in this seat earns trust through direct engagement with the team, not from the sidelines. This role reports to the Chief Executive Officer. HOW WE WORK: This leader builds an engineering organization that lives Tallo’s core values: we craft systems over individual heroics, we choose outcomes for users over internal comfort, we prioritize ruthlessly over pleasing everyone, and we offer effective help over artificial harmony. These values work together as one operating system, and we count on them most when decisions are hard. Everything this role builds, from team structure to architecture to where we invest in AI, ties back to our three company goals: Engagement, Outcomes, and Growth.

ESSENTIAL FUNCTIONS: Reasonable accommodations may be made to enable individuals with disabilities to perform the essential duties. Organization & People Leadership • Take over an existing engineering team and develop and support it, building a culture that crafts durable systems over individual heroics and holds itself accountable to user outcomes. • Own the structure of the engineering organization, evolving it from where it is today and growing it as the product and roadmap require. • Set clear expectations for the engineering manager role, including how EMs partner with product managers and the staff engineer. • Hire exceptionally well across the engineering organization, and onboard and coach engineering managers with the context and support they need to lead well. • Identify the strongest technical leaders on the team, including the lead architect, staff engineer, and senior developers, and empower them with the trust and scope to increase their impact. • Establish engineer leveling and development paths so engineers at Tallo have a clear picture of growth and how to get there. • Make it clear to every member of the engineering team how they’re doing and how they can increase their impact. • Set clear standards for engineering quality, ownership, and accountability at each level.

Systems, Process & Engineering Culture • Own and continuously improve core engineering practices: sprint cadence, code review standards, and release process. • Own quality assurance, setting the standards and practices that make sure what Tallo ships works and holds up. • Define how technical authority and people and delivery authority work together across the staff engineer and engineering managers. • Champion agile, iterative ways of working grounded in a shared understanding of user goals. • Keep engineering work connected to user outcomes and product goals, not just feature delivery, so teams understand why they’re building what they build. • Guide the platform and enablement team on balancing cross-cutting feature work (auth, notifications, shared components) with maintenance and infrastructure work (tech debt, CI/CD, environment improvements), keeping platform priorities aligned to what feature squads need. • Set the model for mobile native engineering that best serves the product and team.

Architecture & Technical Direction • Set and evolve technical architecture and standards across the platform, ensuring solutions are secure, performant, scalable, and sound. • Prioritize ruthlessly across short-term feature delivery and long-term technical investment, including identifying and addressing technical debt to reduce risk. • Influence build versus buy decisions, vendor partnerships, and long-term platform investments.

Safety, Security & Compliance • Own safety and security for technology, making sure the platform protects its users and their data by design. • Work with Operations and other teams on compliance, given Tallo’s young user base and the regulatory expectations that come with it. • Own the technology relationship with the parent company (Stride), meeting its security, compliance, and reporting requirements while keeping Tallo moving.

Data Partnership • Partner with the data and data science team on the direction of the function and the technical decisions that shape it. • Collaborate on data architecture that powers Tallo’s metrics framework, product analytics, and reporting, making sure it’s sound and scalable. • Work with data science on methodology and prioritization, connecting the work to product and business questions. • Partner on data quality standards and monitoring, and help shape and hire for the data engineering roles the team needs.

Marketing & Operations Partnership • Partner with Marketing on ongoing SEO, organic search, and platform performance work that drives growth. • Work with Operations and cross-functional teams to make sure engineering supports the systems and workflows the business runs on. • Bring engineering into business conversations early so technology decisions support how the company operates and grows.

Product Partnership & Roadmap Delivery • Partner with the principal PM, head of insights lab, and product managers on roadmap priorities, sequencing, and capacity planning. • Ensure engineering teams have the context to make good tradeoff decisions, including not just what to build, bu

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