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 — a…