Vice President Software Engineering Jobs in Chicago, IL

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 private-equity-backed or growth-stage company.
• Familiarity with the science of reading, structured literacy, or evidence-based instructional design.
• We offer hybrid and fully remote roles depending on the position and where candidates live
• Laptop and any necessary equipment to perform the duties required
• Monthly technology stipend
• BCBS Medical and Vision with employee premiums
• FREE basic life insurance policy and short and long-term disability programs
• 401k with generous company match and immediate vesting
• PTO policy that starts accruing upon hire up to a maximum level based on tenure and does not expire
• 16 Holidays – 9 designated days, 3 Floaters and a Winter Closure between Christmas and New Year
• 1 Paid Volunteer Day annually
• Donate a PTO Day program for colleagues in need
• 3 Weeks Paid Parental Leave after 12-months of employment for birth, adoption or foster placement
• Discretionary Bonus Eligible

95 Percent Group is a leader in literacy intervention instruction for pre‑K through grade 8 across the U.S. The company offers professional development training for teachers and administrators as well as print and online products to assist teachers with helping students who struggle with reading. 95 Percent Group's comprehensive educational consulting, professional development, diagnostic assessments, and instructional materials help schools deliver intervention instruction that consistently and significantly increase reading achievement.

The company was founded in 2005 and is based in Lincolnshire, IL (northwest suburban Chicago). Its customers are primarily school districts across the U.S., and they are served by consultants who travel for on‑site training as well as through online training. The company has over 30 employees, with about half based in Chicago and half located in other states.

95 Percent Group has a fully engaged and highly committed leadership team who cares deeply about our mission. We've hired the best from inside and outside the industry. This is a tremendous opportunity to join a company positioned for continued significant growth. An added plus is knowing that what you're doing every day is making a significant difference in children's lives. Come work with a group of smart, fun, passionate professionals who value creativity, innovation, and making an impact.

95 Percent Group, LLC is an equal opportunity employer and will consider all applications without regards to race, sex, age, color, religion, national origin, veteran status disability, sexual orientation, gender identity, genetic information or any characteristic protected by law.