Training & Quality Assurance Manager

About Odyssey: K-12 education is one of the most consequential determinants of a child’s future — and many families have had limited ability to shape how and where their child learns. Education Savings Account (ESA) programs are changing that. One of the fastest-growing public education initiatives in the U.S., they give states the ability to put education funding directly in the hands of families, who can then choose the learning experiences that best fit their child — from schools and tutors to therapy, curriculum, and technology. But once these policies are signed into law, states face an enormous operational challenge. They must stand up entirely new programs, manage the secure and compliant flow of public funds, approve and monitor thousands of vendors, support families at scale, and prevent fraud — all while delivering a high-quality user experience. That’s where Odyssey comes in. We partner with state agencies to design, launch, and operate ESA and school chocie programs on their behalf. We provide the technology, program operations, vendor ecosystem, and family experience that make these programs actually work in the real world. Today, we operate across 10 states, and our platform powers programs serving 250,000+ students and over $2B in annual education funding — and we’re just getting started. Most recently, we launched the Texas Education Savings Account (EFA) program — the biggest day-one ESA launch in the country — which has already received nearly 200,000 applications. It’s the kind of moment that captures exactly what we’re building toward: programs that work at scale, from day one, when it matters most. We’re backed by respected investors, including a16z and Tusk Venture Partners, and we’re building the team that will take us to the next stage. Odyssey sits at the intersection of GovTech, EdTech, and FinTech. We are a public-sector operator, a technology company, and a program delivery partner all at once. The work we do is civic infrastructure — it determines whether families can access life-changing educational opportunities. WHY THIS WORK IS DIFFERENT We’re in the weeds with state partners, internally with our product teams, and turning ambiguous policy into real systems that families depend on. This means building a platform that meets each state’s configuration needs while being flexible enough to support all customers. We are not building be-spoke software! If you want a highly structured environment, this will feel uncomfortable. If you want ownership, speed, and problems that actually matter, you’ll feel right at home. ABOUT THE ROLE We’re looking for a Training & Quality Assurance Manager to lead the training, quality assurance, and knowledge management functions within Odyssey’s Support organization. This role will be responsible for ensuring our Support teams have the knowledge, skills, tools, and feedback they need to consistently deliver accurate and high-quality experiences to parents, schools, and vendors. You’ll oversee our Training and Quality Assurance & Knowledge team while establishing the strategy, standards, and operating rhythms that allow these functions to scale as Odyssey grows. This is a highly cross-functional and hands-on leadership role. You’ll work closely with Support leadership and partners across Product, Operations, Program, and other teams to understand what is changing, identify where performance or knowledge gaps exist, and ensure those changes are translated into effective training, documentation, and quality standards. Most importantly, you’ll connect quality insights to action. When QA, CSAT, escalations, or operational data identify an opportunity, you’ll determine the root cause and develop the right response—whether that means additional training, improved documentation, process changes, coaching, or clearer expectations. WHAT YOU’LL DO Training & Enablement - Own the overall training and enablement strategy for Odyssey’s Support organization. - Lead the development and continuous improvement of new-hire onboarding, ongoing education, upskilling, leadership training, and change-management programs. - Ensure training programs are engaging, scalable, and tied to measurable performance outcomes. - Partner with Support leadership to identify skill and knowledge gaps and develop targeted learning plans. - Establish readiness standards and assessments to ensure specialists are prepared before supporting customers independently. - Build Train-the-Trainer programs that enable Support leaders to reinforce learning consistently across their teams. - Ensure teams are prepared for new program launches, policy changes, product releases, and major operational changes. Quality Assurance & Customer Experience - Develop and own Odyssey Support’s quality assurance strategy, standards, scorecards, and calibration process. - Establish consistent quality expectations across Parent, School, and Vendor Support. - Analyze QA results, CSAT, escalations, contact drivers, and other customer experience data to identify trends and opportunities. - Translate quality insights into actionable coaching, training, documentation, or process improvements. - Partner with Support leaders to ensure quality findings result in measurable performance improvement. - Establish regular reporting that gives Support leadership visibility into quality trends, knowledge gaps, and areas of risk. - Identify systemic issues rather than focusing solely on individual specialist performance. Knowledge Management & Documentation - Own the strategy and governance for Support knowledge management, including SOPs, FAQs, internal documentation, and customer-facing help content. - Ensure documentation remains accurate and current as policies, products, and processes change. - Establish standards for how knowledge is created, reviewed, approved, communicated, and maintained. - Partner cross-functionally to translate complex program and product requirements into clear, actionable guidance for Support teams. - Identify opportunities to improve self-service for both Support Specialists and customers. People Leadership - Directly manage and develop the Training Associate and Quality Assurance & Knowledge Associate. - Set clear goals, priorities, and performance expectations for both functions. - Provide ongoing coaching and professional development while creating opportunities for team members to grow their skills and ownership. - Build scalable processes and operating rhythms that allow the team to proactively identify opportunities rather than simply react to requests. - Prioritize work based on customer impact, operational risk, and business needs. ABOUT YOU - Experience leading training, quality assurance, enablement, knowledge management, or similar functions within a customer support or operations environment. - Previous people-management experience with a demonstrated ability to coach, develop, and hold team members accountable. - Strong understanding of contact center operations and how training, QA, knowledge management, and performance management work together. - Experience developing QA programs, scorecards, calibration processes, or quality standards. - Experience building or managing new-hire and ongoing training programs. - Strong analytical mindset with the ability to use QA results, CSAT, operational metrics, and customer feedback to identify trends and root causes. - Excellent written and verbal communication skills with the ability to simplify complex information for different audiences. - Strong project-management and organizational skills with the ability to manage multiple priorities in a fast-moving environment. - Comfortable working through ambiguity and building processes where structure may not yet exist. - Able to balance strategy with execution—you’re comfortable setting the direction while also jumping in and doing the work when needed. - Strong cross-functional partner who can influence without direct authority and confidently push back when necessary. - Proactive and curious, with a natural tendency to investigate why something is happening rather than simply treating the symptom. - Passionate about developing people and creating consistently excellent customer experiences. Our Commitment to Equal Opportunity Employment: Odyssey is an equal opportunity employer. Reasonable accommodations are available upon request.