Director of Customer Success, Operations

About the Role

The Director of Customer Success, Operations is the right-hand operational partner to the VP of Success. This individual drives the division’s biggest initiatives from planning through execution. They are the connective tissue across all five Success functions (Enrollment Advisors, Family Success Managers, Support, Processing, and Program Communications), ensuring alignment and execution of major initiatives. This role owns project management, cross-functional coordination, inspection cadences, and documentation, allowing the VP to focus on strategy and long-term direction.

The individual will 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 an analytical, technically capable execution role that moves between strategy and details, diagnoses issues, and ensures initiatives cross the finish line.

• Own end-to-end project management for major division initiatives — assessments, interventions, enrollment, launches, and more.
• Build and maintain project plans, timelines, and milestones, surfacing risks and blockers proactively.
• Track progress against quarterly OKRs and division goals, keeping leaders informed without constant check-ins.
• Own the operating cadence for the Success division, including KPI reviews, initiative inspection, and regular reporting.
• Dig into CRM and operational data to build ad hoc reporting, investigate performance gaps, and surface actionable insights.
• 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.
• Build and maintain SOP documentation across division workflows to ensure repeatable processes.
• Drive initiatives through implementation, including hands-on execution when needed.
• Own follow-through on action items from leadership meetings and SLT commitments.

Your Immediate Impact

• Fully ramped on the division’s current major initiatives and independently driving at least one to completion within the first 60 days.
• A documented project tracking system and reporting cadence 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.
• Faster answers and proactive surfacing of performance gaps through hands-on use of systems and data.
• 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 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 — 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 proactively surfaced through data and inspection before they escalate.
• Insights translate into shipped improvements to workflows, systems, processes, or customer experience.
• 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.

Requirements

• 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 others can use.
• Comfortable operating with ambiguity and taking ownership without heavy oversight.
• Skilled at driving accountability across teams not managed directly — 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 who prefers closing gaps over writing tickets.
• You see a KPI moving in the wrong direction and immediately want to understand why.
• You’re equally comfortable presenting data insights to leaders and digging into systems to diagnose issues.
• You like building fixes, not just recommending them.
• You get satisfaction from turning messy, multi-team initiatives into plans 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 prioritizing what matters most comes naturally.
• You want your work to impact 100,000+ students and their families.
• You enjoy making other teams run better and giving them 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.
• This is an individual contributor leadership role — no direct reports at hire; impact comes through influence and ownership.
• Fully remote, with flexibility and work-life balance in a distributed team.
• Expect to move between altitudes: leadership-level planning one hour, hands-on execution details the next.

Reports directly to the VP, Success.

Benefits

• Competitive salary and 401k plan with company matching.
• Comprehensive health benefits: medical, dental, vision, life, critical illness, accident, STD/LTD, HSA, and FSA with dependent care.
• Flexible work arrangement: fully remote workforce with autonomy in work hours.
• Generous paid time off policy.
• Supportive and collaborative team environment where contributions are valued.

Available to candidates residing in: AR, AZ, CO, FL, GA, ID, IN, IL, IA, KS, MA, MD, MN, MO, MT, NC, NM, NV, NY, OH, OK, OR, RI, SC, TN, TX, UT, VA, WA, WI, WV.