Technology Planning & Implementation Lead

Thanks for your interest in Success Academy! Running a large, fast-growing, and high-performing network of public charter schools takes a village - families, children, teachers, staff and faculty, advocates, and supporters alike. We are growing fast in New York and expanding to Florida, and we would love to welcome you to our community! We work tirelessly every day to ensure children have access to a fun, rigorous, whole-child education regardless of zip code or economic status. When you join SA, you play a part in giving every student who walks through our doors a fair shot at reaching his or her potential.

We are looking for a Technology Planning & Implementation Lead to own the implementation of one of Success Academy's most consequential technology initiatives: the full replacement of our academic technology stack with an integrated ecosystem of Canvas, Learnosity, and a new Content Management System serving 20,000+ scholars across our network.

This role reports to the Head of Educational Technologies and sits at the center of a complex, multi-year program. This person owns the implementation: the pilot, the release process, the coordination across workstreams, and the organizational work that determines whether the technology actually lands. They will partner closely with our Leader of Schooling Systems, who will own the technical design, architecture, and build, as well as our Schooling and Education Institute teams, who own the learning design and educational outcomes. 

At its core, this role is an integration function. The program involves a set of forces that do not automatically align — what the business wants, what the technology can do, and what teachers and scholars need. This person's job is to understand all of those forces deeply and hold them in tension productively. That requires genuine curiosity. This person needs to actively seek out the perspective of teachers, school leaders, and business stakeholders, not just at the start of the project, but continuously, and use what they learn to keep the program grounded in reality as it evolves. This person must be comfortable stepping into gaps, picking up what isn't being owned, and doing whatever the program needs without waiting for clarity that may not come. 

The right candidate has led complex implementations before, thrives in ambiguous environments, and measures themselves by outcomes rather than the tidiness of their scope.

What You'll Own

Integration Across Business, Technology, and Constraints

• Develop and maintain a complete, current picture of the program across all its dimensions

• Serve as the connective tissue between technical, operational, and school-based stakeholders, ensuring that decisions made in any one of those contexts account for the constraints and realities of the others

• Surface conflicts early and drive those conflicts to resolution before they become problems

• Represent the overall goals and constraints of the program in every room, ensuring that no workstream optimizes for itself at the expense of the whole

Voice of the Customer and the Business

• Actively and continuously seek out the perspective of teachers, school leaders, and business stakeholders throughout the program 

• Synthesize what you hear into insight that is actually useful

• Bring that insight into planning conversations, pilot design, release sequencing, and stakeholder communications, ensuring the program stays grounded in how real users experience the technology, not just how it performs in design

Pilot Design and Release Management

• Own the design and execution of all pilots prior to full migration: define the sample, set success criteria, manage the process end to end, and translate findings into a clear recommendation for rollout

• Own the release management process for the full implementation: the sequencing of feature releases, readiness criteria, and the coordination required to bring each phase to launch

• Ensure each release reflects what has been learned from the previous one, and that lessons are captured, shared, and applied

Program Coordination and Momentum

• Own the coordination machinery for the academic tech migration: workstream tracking, milestone management, risk identification, decision documentation, and cross-functional communication

• Run the communication cadence that keeps the Head of Educational Technologies, senior leadership, and key stakeholders oriented 

• Maintain momentum across a long, multi-stakeholder program

School Adoption and Change Management

• Partner with the Schooling and EI teams on the strategy for school-facing adoption: how the new tools get introduced to teachers and school leaders, how training is structured, how readiness is assessed, and how problems surface and get resolved

• Own release readiness on the school-facing side: confirm that schools and operational processes are ready before each phase goes live

• Ensure that the pace and structure of the rollout reflect what you are hearing from schools — adjusting the approach when adoption patterns suggest the plan needs to change

What We're Looking For

This list of must-haves is short, but the bar is high. We would rather hire someone with excellent instincts and limited sector experience than someone with years in education technology who cannot move fast, make decisions, or operate without structure.

Non-Negotiables

• You are a natural integrator: you instinctively pull together information from disparate sources, find the tensions, and work to resolve them before they become problems

• You are deeply curious about how things actually work: you seek out the perspective of end users and business stakeholders not because it is on a checklist, but because you genuinely want to understand what they are experiencing

• You have owned outcomes in complex, cross-functional environments

• You have startup or high-growth experience and know what it means to operate without institutional scaffolding or clean swim lanes

• You are a strong enough communicator to write a tight executive memo, run a sharp meeting, present to skeptical senior stakeholders, and have hard conversations when they are needed

• You are politically intelligent: you read rooms accurately, understand what people actually care about, and navigate competing interests without losing momentum

• You are a self-starter who identifies what needs to happen and does it

Core Competencies We Hire For

We evaluate every candidate against five attributes that predict success at Success Academy, regardless of role:

• Critical Thinking. You get to the bottom of problems quickly and rigorously. You don't accept the first explanation, you interrogate assumptions, and you can distinguish between what's true and what's merely plausible.

• Communication. You write with clarity and economy, and you're effective in person. You know that real communication means understanding your audience's perspective well enough to actually move them, not just transmit information at them.

• Entrepreneurial Drive. You take full ownership of your outcomes. You are assertive about removing obstacles, you don't wait to be told what to do next, and you measure yourself by results rather than effort.

• Resilience. You receive hard feedback and use it as fuel rather than a reason to disengage. You hold yourself to a high standard, and when someone raises the bar, your instinct is to rise to it.

• Curiosity. You want to understand how things actually work, from the systems you're building to the teachers and scholars at the end of the chain. You trace your work through to its real-world impact and care about the details and edge cases you find along the way.

Strong Candidates Will Also Have

• 8–12 years of total professional experience, with at least 4–5 years owning complex cross-functional implementations with real organizational stakes

• Demonstrated experience as an integrator across technical, business, and user-facing workstreams: someone who has held the whole picture and used it to drive better decisions across all three

• Experience working at the intersection of technology and business operations: not as an engineer, but as someone who has worked closely with technical teams, understands system constraints, and has successfully translated between technical and non-technical stakeholders

• A track record of actively seeking out and incorporating end-user feedback

• A background in high-growth or fast-moving organizations — media, publishing, content platforms, EdTech, or adjacent consumer technology industries are particularly relevant

• Experience in K–12 education is a plus, but explicitly not a requirement; what matters more is experience delivering complex programs to end users at scale in organizations that move fast and expect a lot

Success Academy Charter Schools is an equal opportunity employer and actively encourages applications from people of all backgrounds. Compensation is competitive and commensurate with experience. Success Academy offers a full benefits program and opportunities for professional growth.

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We are an equal opportunity employer and value diversity at our organization. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We actively seek applications from people of all backgrounds to strengthen our community and the perspectives needed to flourish in a multicultural world. Success Academy offers a full benefits program and opportunities for professional growth.

Success Academy Charter Schools does not offer employment-based immigration sponsorship.