Head of Technology

Job Description Tallo builds bridges between talent and opportunity. We help individuals ages 13 to 30 explore and discover careers, learn and earn valuable credentials, and ultimately get a job and build a better life. Our vision is to be the co-pilot that helps people move from career uncertainty to confident action, with the tools and connections for lasting success. We don’t rely on luck. We build the machine that makes opportunity inevitable. We do it by building scalable systems over one-off heroics, prioritizing ruthlessly what matters, and staying obsessively focused on user outcomes. SUMMARY: 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 who lead software engineering and QA teams, and also directly manages strategic individuals and some engineers, 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. Promote a culture of skills-based hiring within engineering, prioritizing measurable technical competence and proven ability over traditional educational credentials. 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 & Shipping User Outcomes Partner with the principal PM, head of insights lab, and product managers to turn user problems into shipped, iterative work, adjusting priorities as the team validates what’s actually moving. Ensure engineering teams have the context to make good tradeoff decisions, including not just what to build, but why it matters and what success looks like. Connect every engineering effort to Tallo’s company goals of Engagement, Outcomes, and Growth, and to the metrics that track progress against them. Identify and clear blockers to delivery across teams, including dependencies, requirements, resourcing, and cross-team coordination. AI / ML Strategy Evaluate realistic AI and ML use cases given Tallo’s data, user base, and product goals, including matching, recommendations, career path prediction, skills inference, and content personalization. Recommend where Tallo should and should not focus on AI and ML, framed around Engagement, Outcomes, and Growth, and distinguish what can be done in the near term from what requires more mature data infrastructure. Advise on tooling and infrastructure decisions for ML work, including model hosting, experimentation, and evaluation, building a foundation that scales as the landscape changes. Leadership & Cross-Functional Influence Report to the CEO with close day-to-day partnership with the Principal PM on priorities, roadmap alignment, and strategic context, and regular collaboration with Marketing and Data. Communicate complex technical concepts clearly to non-technical audiences and represent technology in executive forums, giving visibility into progress, risks, capacity, and investment tradeoffs. Communicate regularly with leadership on progress, priorities, and emerging opportunities, and raise issues early. Choose effective help over artificial harmony when hard things need saying. Build a strong working partnership across Tallo and its parent company (Stride). Establish and track engineering metrics that actually measure value, such as delivery throughput, quality, reliability, and team health, and use the data to improve outcomes. SUPERVISORY RESPONSIBILITIES: Directly supervises 5 - 8 Full-time Equivalent (FTE) regular employees and/or contractors, including engineering managers who manage software engineering and QA teams. Carries out supervisory responsibilities in accordance with the organization's policies and applicable laws. Responsibilities include interviewing, hiring, and training employees; planning, assigning, and directing work; appraising performance; rewarding and disciplining employees; addressing complaints and resolving problems. MINIMUM REQUIRED QUALIFICATIONS: Ten (10) years of experience in software engineering and senior leadership of multi-team organizations or related work. An exceptional hirer who consistently identifies, attracts, and lands strong engineers and engineering leaders, and builds teams that raise the bar. Proven experience leading engineering managers and building team structures, leveling frameworks, and operating models. A track record of identifying and empowering strong technical leaders, giving them the scope to grow their impact. Demonstrated success building and scaling engineering organizations in high-growth environments. Strong background in modern cloud-based architectures, DevOps practices, and distributed systems. Track record of shipping customer-facing product capabilities, including data-driven or AI-enabled features, into production. Experience owning quality assurance and the standards and practices that keep what a team ships reliable. Ownership mindset for technology safety and security, with experience building secure systems and meeting compliance requirements, ideally for sensitive or young user populations. Experience partnering with data and data science functions, including data architecture and analytics. Excellent people leadership skills, including coaching managers, building performance cultures, and developing technical leaders. Strong strategic thinking paired with a hands-on execution orientation. Comfortable working directly with the team rather than leading from a distance. Outstanding written and verbal communication skills with the ability to influence at the executive level. Ability to clear required background checks. CERTIFICATES AND LICENSES: None required. COMPENSATION & BENEFITS: Stride, Inc. considers a person’s education, experience, and qualifications, as well as the position’s work location, expected quality and quantity of work, required travel (if any), external market and internal value when determining a new employee’s salary level. Salaries will differ based on these factors, the position’s level and expected contribution, and the employee’s benefits elections. Offers will typically be in the bottom half of the range. We anticipate the salary range to be $132,365-$195,000. Eligible employees may receive a bonus. This salary is not guaranteed, as an individual’s compensation can vary based on several factors. These factors include, but are not limited to, geographic location, experience, training, education, and local market conditions. Stride offers a robust benefits package for eligible employees that can include health benefits, retirement contributions, and paid time off. WORK ENVIRONMENT: The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. This position is virtual and open to residents of the 50 states and D.C. The above job is not intended to be an all-inclusive list of duties and standards of the position. Incumbents will follow any other instructions, and perform any other related duties, as assigned by their supervisor. All employment is “at-will” as governed by the law of the state where the employee works. It is further understood that the “at-will” nature of employment is one aspect of employment that cannot be changed except in writing and signed by an authorized officer. Job Type Regular The above job is not intended to be an all-inclusive list of duties and standards of the position. Incumbents will follow any other instructions, and perform any other related duties, as assigned by their supervisor. All employment is “at-will” as governed by the law of the state where the employee works. It is further understood that the “at-will” nature of employment is one aspect of employment that cannot be changed except in writing and signed by an authorized officer. If you are a job seeker with a disability and require a reasonable accommodation to apply for one of our jobs, you can request the appropriate accommodation by contacting View email address on click.appcast.io. Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities Stride, Inc. is an equal opportunity employer. Applicants receive consideration for employment based on merit without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability or protected veteran status, or any other basis prohibited by federal, state, or local law. Stride, Inc. complies with all legally required affirmative action obligations. Applicants will not be discriminated against because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant. Tallo enables young talent to discover and explore career options, take courses, earn valuable certifications, and get a job that helps them build a better life. Everyone has a skill, interest, or ability that someone else is looking for. Tallo makes the connection.