Technology Planning & Implementation Lead

Success Academy Charter Schools•New York, NY

9d•$160,000 - $180,000•Hybrid

About The Position

Success Academy is seeking a Technology Planning & Implementation Lead to manage a significant technology initiative: the replacement of their academic technology stack with an integrated ecosystem including Canvas, Learnosity, and a new Content Management System. This role will oversee the implementation for over 20,000 students across their network, reporting to the Head of Educational Technologies. The position is central to a multi-year program, focusing on the pilot, release process, cross-workstream coordination, and ensuring the technology's successful adoption. The Lead will collaborate with the Leader of Schooling Systems (technical design and architecture) and the Schooling and Education Institute teams (learning design and educational outcomes). The core function of this role is integration, balancing business needs, technological capabilities, and the requirements of teachers and students. This requires deep understanding of all aspects, active engagement with stakeholders, and the ability to navigate ambiguity and drive outcomes in a fast-paced environment.

Requirements

Natural integrator: instinctively pulls together information, identifies tensions, and resolves them.
Deep curiosity about how things work: seeks out end-user and business stakeholder perspectives.
Proven experience owning outcomes in complex, cross-functional environments.
Experience in startup or high-growth environments, comfortable operating without institutional scaffolding or clear swim lanes.
Strong communication skills: ability to write executive memos, run meetings, present to stakeholders, and have difficult conversations.
Political intelligence: ability to read rooms, understand stakeholder priorities, and navigate competing interests.
Self-starter: identifies needs and takes action without being told.
Critical Thinking: ability to quickly and rigorously get to the bottom of problems, interrogate assumptions, and distinguish truth from plausibility.
Communication: clarity and economy in writing, effectiveness in person, ability to move audiences.
Entrepreneurial Drive: full ownership of outcomes, assertiveness in removing obstacles, results-oriented.
Resilience: ability to receive and use hard feedback, high personal standards.
Curiosity: desire to understand systems and real-world impact, attention to detail and edge cases.

Nice To Haves

8–12 years of total professional experience.
At least 4–5 years owning complex cross-functional implementations with significant organizational stakes.
Demonstrated experience integrating technical, business, and user-facing workstreams.
Experience at the intersection of technology and business operations, working closely with technical teams and translating between technical and non-technical stakeholders.
Track record of actively seeking and incorporating end-user feedback.
Background in high-growth or fast-moving organizations (media, publishing, content platforms, EdTech, or adjacent consumer technology industries).
Experience in K–12 education (explicitly not a requirement, but a plus).

Responsibilities

Develop and maintain a comprehensive understanding of the program across all dimensions.
Act as the liaison between technical, operational, and school-based stakeholders, ensuring decisions consider interdependencies.
Identify and resolve conflicts proactively.
Represent program goals and constraints to prevent workstream optimization at the expense of the whole.
Continuously gather and synthesize perspectives from teachers, school leaders, and business stakeholders.
Incorporate user insights into planning, pilot design, release sequencing, and communications.
Own the design and execution of all pilots, including defining samples, setting success criteria, managing the process, and making rollout recommendations.
Manage the release process for full implementation, including sequencing, readiness criteria, and launch coordination.
Ensure each release incorporates lessons learned from previous ones.
Oversee program coordination, including workstream tracking, milestone management, risk identification, decision documentation, and cross-functional communication.
Manage communication cadences for senior leadership and key stakeholders.
Maintain program momentum across a multi-stakeholder initiative.
Partner on the strategy for school-facing adoption, including tool introduction, training, readiness assessment, and problem resolution.
Confirm school and operational readiness before each phase goes live.
Adjust rollout plans based on school feedback and adoption patterns.