VP, Software Engineering

95 Percent Group is looking for a VP of Software Engineering to lead the software engineering organization. You will lead the unification of multiple platforms — including recently acquired products — into one modern architecture, build an AI-first, agile, global engineering organization, and help drive the organizational transformation to the Product Operating Model. You will get close to customers to understand their problems, then turn that understanding into technology that drives real value.

You will lead as an engineer first — and scale your impact by growing the people and systems around you — with genuine empathy for the teachers and classrooms we serve.

• Own the technical strategy and roadmap to unify multiple products into a single platform, utilizing generative AI technologies, cloud-native architecture, and modern integration patterns.
• Increase velocity, throughput and quality from the engineering teams by embedding AI-assisted development tools into the engineering workflow, and partner with Product Management to identify where AI creates real value for our customers.
• Build and scale a high-performing, global, agile engineering organization and co-lead (with the VP, Product Management) the organization's shift to the Product Operating Model, built around cross-functional teams with accountability for outcomes.
• Build a deep bench of engineering leaders through mentorship, growth and succession planning, ensuring leadership continuity as the organization continues to scale.
• Drive operational excellence by establishing a data first approach to metrics (DORA metrics, cycle time, quality, adoption, business outcomes) in all areas of engineering, to prove the operating model and development efforts are working and driving value for our customers.
• Own the reliability of the platform in production — uptime, SLAs, incident management, and on-call practices — ensuring the platforms are available, secure and performant.
• Make architecture, build-vs-buy, and infrastructure decisions needed to modernize the platform for scale, security, reliability, and speed of iteration.
• Partner closely with VP, Product Management team to build and maintain the roadmap, ensuring all priorities map to real customer and business needs.
• Define and maintain data privacy and responsible – AI guardrails in partnership with Security, Legal, and IT.
• Represent engineering in company-wide strategic planning, M&A technical diligence, and company-wide updates on strategy; report on engineering health, roadmap progress, and platform modernization to the ET on a regular cadence.
• Partner closely with Customer Experience and Support to ensure our customers have the support they need when they need it.
• Manage engineering budget, vendor and tooling decisions, and workforce planning responsibly.

• Bachelor's degree in Computer Science, Engineering, or a related field, or equivalent experience.
• 15+ years in software engineering with 8+ years in senior engineering leadership positions, owning a full, global engineering organization.
• Experience building and leading globally distributed engineering teams across multiple time zones.
• Direct experience leading an organization through adoption of Product Operating Model or an equivalent shift from project-based to outcome-based ways of working.
• Deep fluency in Agile/Scrum at scale.
• A track record of consolidating or modernizing multiple platforms into one, through re-architecture, re-platforming, or post-acquisition integration.
• Familiarity with accessibility standards and experience building compliant, inclusive software for K-12 or similar markets
• Demonstrated experience building an AI-first engineering culture, including use of AI coding tools and delivery of AI/ML-powered product features.
• Strong technical background sufficient to be credible on architecture, cloud infrastructure, data, and security decisions.
• Excellent communication skills and the presence to operate and work with the Executive team.

• Experience in K-12 education technology, ideally with products used directly by classroom teachers and elementary (K-5) students.
• Experience operating inside a…