Director of Customer Success, Operations

About OpenEd At OpenEd, we’re opening the world to every learner. With over 100,000 students served and growing rapidly, families trust us as a partner to the most precious thing in their lives, their children. Our vision: a future where education is no longer constrained by geography, rigid models, or outdated systems. Our mission: to give every student customized, world-class education and resources, empowering families and opening millions of doors for learners across the country. Our Culture (The Foundation of Everything We Do) Culture at OpenEd is intentional. It’s defined by what we promote—and what we tolerate. Our latest eNPS (employee net promoter score) of 76 places OpenEd in the top .1% of technology companies. Our values aren't just words; they are non-negotiable principles that guide every decision: Customer First – Obsessed with delivering value; we fight tirelessly for our learners and families. Hard Choices, Easy Life – Face challenges directly, swiftly, and transparently. I Did > We Should – Action over theory; bring experiments, not just opinions. Learn Out Loud – Share your growth openly; feedback is a gift, ego is the enemy. Prioritize Ruthlessly – Excellence in the few critical areas over mediocrity everywhere. Fast AND World Class – Speed doesn’t compromise quality. Strong Opinions, Weakly Held – Advocate passionately, adjust readily. Make Others Famous – Elevate your colleagues, partners, and community. We're currently accepting applications from those living in: AR, AZ, CO, FL, GA, ID, IN, IL, IO, KS, MA, MD, MN, MO, MT, NC, NM, NV, NY, OH, OK, OR, RI, SC, TN, TX, UT, VA, WA, WI, WV. About the Role The Director of Customer Success, Operations is the right-hand operational partner to the VP of Success. They are the person who drives the division’s biggest initiatives from planning through execution. You are the connective tissue across all five Success functions (Enrollment Advisors, Family Success Managers, Support, Processing, and Program Communications), driving the division’s biggest initiatives from planning through execution and keeping teams aligned align the way. You’ll own project management, cross-functional coordination, inspection cadences, and documentation so the VP can focus on strategy, executive relationships, and long-term division direction. You’ll dig directly into CRM and data to understand performance, identify trends and breakdowns, surface actionable insights, and build solutions that improve how the team works. This is not a coordination-only role. We’re looking for an analytical, technically capable execution machine who can move between strategy and the details, diagnose what isn’t working, build or drive the solution, and make sure initiatives actually cross the finish line. Own end-to-end project management for major division initiatives — assessments, interventions, enrollment, launches, and whatever comes next. Build and maintain project plans, timelines, and milestones, surfacing risks and blockers before they become fire drills. Track progress against quarterly OKRs and division goals, keeping the VP and function leads informed without requiring constant check-ins. Own the operating cadence for the Success division, including KPI reviews, initiative inspection, and regular reporting that gives leaders a clear view of performance, risks, and where action is needed. Dig directly into CRM and operational data to build ad hoc reporting, investigate performance gaps, identify trends and root causes, and surface actionable insights and recommendations. Build and ship operational solutions beyond identifying gaps. Serve as the primary point of coordination across Enrollment Advisors, Family Success Managers, Support, Processing, and Program Communications. Represent Success priorities in cross-functional meetings when the VP can’t attend, accurately carrying both the priorities and the reasoning behind them. Build and maintain SOP documentation across division workflows so processes are repeatable and not dependent on institutional knowledge held by one person. Drive initiatives through implementation, not just planning — including rolling up your sleeves on execution details when that’s what the work requires. Own follow-through on action items from leadership meetings and SLT commitments, closing gaps in process or ownership before they stall an initiative. Your Immediate Impact Fully ramped on the division’s current major initiatives and independently driving at least one to completion within your first 60 days. A documented project tracking system and reporting cadence stood up and running for every active initiative. A clear inspection cadence established for the division’s most important KPIs, with performance gaps understood and action plans in place. Questions are answered faster and performance gaps are surfaced proactively through hands-on use of the division’s systems, CRM data, and ad hoc reporting. Working relationships established with all five function leads and key cross-functional partners. A visible reduction in the number of items requiring the VP’s direct, hands-on involvement. First set of SOPs published for the division’s highest-impact initiatives, with a standard format others can follow. Risks and dependencies on in-flight initiatives identified, owned, and communicated. There are no surprises at the deadline. Success Metrics: On-time delivery of division initiatives against quarterly OKRs and committed milestones. 100% of active initiatives have a documented plan, a named owner, and current milestone tracking. Division KPIs have clear reporting and inspection cadences, with variances understood and action plans in place. Operational issues and opportunities are proactively surfaced through data and inspection before they become escalations or missed targets. Insights translate into shipped improvements to workflows, systems, processes, or customer experience, not just recommendations. Measurable reduction in VP hours spent on project execution versus strategy and executive work. SOP coverage across core division workflows, kept current as processes change. Fewer single points of failure — critical processes documented and transferable as the division scales. Who You Are: 4+ years in program/project management, operations, or a similar execution-focused role, ideally in a fast-scaling or multi-workstream environment. Demonstrated ability to manage multiple concurrent, cross-functional initiatives without dropping details. Highly analytical and comfortable using data to inspect performance, diagnose problems, and make decisions. Technically comfortable working directly in CRM and operational systems, building reports and dashboards, and learning new tools quickly. A strong written communicator, particularly for SOP and process documentation that other people can actually use. Comfortable operating with ambiguity and taking ownership without heavy oversight. Skilled at driving accountability across teams you don’t manage — influence, not authority. Experience partnering with Product, Engineering, or similar technical teams on prioritization is a plus. Education, edtech, or high-growth startup experience is a plus, but not required. This Role Will Excite You IF: You’re an execution machine. You’d rather close the gap than write a ticket about it. You see a KPI moving in the wrong direction and immediately want to understand why. You’re equally comfortable presenting the story behind the data to a leader and getting into the system yourself to figure out what’s happening. You like building the fix, not just recommending one. You get genuine satisfaction from turning a messy, multi-team initiative into a plan people actually follow. You want to be the connective tissue across five functions rather than heads-down in one. You’d rather be measured on what shipped than on meetings attended Ambiguity energizes you, and choosing the few things that matter most comes naturally You want your work to reach 100,000+ students and the families who trust us with them You like making other people’s teams run better and getting them the credit for it Team & Autonomy: You’ll work across all five Success functions — Enrollment Advisors, Family Success Managers, Support Operations, Processing, and Program Communications — plus close partnership with cross-functional teams to drive initiatives forward. High autonomy: you’ll set the tracking systems, cadences, and documentation standards for the division rather than inheriting them. This is an individual contributor leadership role — no direct reports at hire; your impact comes through influence, ownership, and follow-through. Fully remote, with the flexibility and work-life balance that comes with a distributed team. Expect to move between altitudes: leadership-level planning one hour, hands-on execution details the next. Reporting Line: Reports directly to the VP, Success. Company Benefits: Competitive salary and 401k plan + company matching opportunities. Comprehensive Health Benefits: Health insurance package including medical, dental, vision, life, critical illness, accident, STD/LTD, HSA, and FSA with dependent care. Flexible Work Arrangement: We’re a fully remote workforce that emphasizes a healthy work-life balance by allowing some autonomy in work hours. Generous Paid Time Off policy, enabling you to recharge, spend quality time with loved ones, and pursue personal interests outside of work. Supportive Team Environment: Join a supportive and collaborative team environment where your contributions are valued, and teamwork is encouraged, fostering a culture of success and mutual respect. EEO Statement OpenEd is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. OpenEd participates in E-Verify.