[CG] Head of Fulfillment & Student Success - 19011, Cape Town

Position:  Head of Fulfillment & Student Success
Working Hours: Full-Time │Monday - Friday │9:00 am - 6:00 pm EST
Search Location: Latin America, South Africa, Canada, and the United States
Salary:  6000 - 7000 USD /month │Latin America - South Africa
:  USA / Canada /UK
Incentives:  Performance-based incentives tied to revenue/margin targets
Perks & Benefits:  Work Device Provided - Can begin within 2–4 weeks of receiving an offer.
:  The Final Salary Offer depends on the client’s decision, interview results, and experience

About the Role:

We are seeking a Head of Fulfillment & Student Success to own and optimize the post-sale client journey within a high-growth B2C coaching and outcomes-driven education business. This leader

will be responsible for fulfillment quality, student retention, refunds, dispute management, and

operational excellence while ensuring students achieve measurable outcomes.

Role Responsibilities:

• Own end-to-end fulfillment and student success operations from onboarding through outcomes.
• Drive retention, reduce churn, and manage refunds, disputes, and chargeback resolution.
• Take accountability for Trustpilot and review management initiatives and improve customer
• sentiment metrics.
• Lead, manage, and scale freelance/contractor coaches and instructors.
• Monitor program performance and implement systems to improve delivery quality and outcomes.
• Handle escalations directly and make difficult people decisions including performance
• improvement plans (PIPs) and termination decisions.
• Partner with leadership while maintaining ownership of post-sale business metrics

Requirements:

• 5–10 years of experience in B2C coaching, bootcamps, or high-ticket online education businesses.
• Background should align with outcomes-driven companies similar to Pathrise, Interview Kickstart, HyperionDev, BloomTech, Springboard, On Deck, or similar models.
• Proven ownership of refund rates, chargeback/dispute handling, retention metrics, and review management.
• Ability to discuss measurable impact and metrics improved in prior roles.
• Experience leading freelance/contractor coaches or instructors (not only traditional W-2 academic teams).
• Strong overlap with US business hours; US or UK timezone strongly preferred.
• Comfortable independently handling performance management decisions
• Can begin within 2–3 weeks of receiving an offer.
• Must have no non-compete / restraint clauses or contractual restrictions for a seamless transition

NOTE: We prioritize the processing of one application at a time. If you have applied for multiple job openings within our organization, we kindly request that you direct any update inquiries to the team responsible for handling your initial application.