[Hiring] Director of Customer Success, Operations @OpenEd

Role Description

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 along the way.

• 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.

Qualifications

• 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.

Requirements

• 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.

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.