Head of Sales and Retention (remote)

TripleTen • Boston, MA

7h • Remote

About The Position

TripleTen is an award-winning online school in the technology bootcamp space. Our mission is to help people transform their lives and succeed in tech. We offer flexible learning, career mentorship, resume and portfolio support — and we proudly maintain an 87% job placement rate across our Web Development, QA, Data Analytics, and Data Science programs.

We’re looking for a Head of Retention for LATAM, who will be responsible for student retention and for leading three core teams: Onboarding, Refunds, and Success. Your goal will be to build a scalable, predictable retention system that increases student engagement and reduces churn.

You will work closely with the Product team to improve the student journey, strengthen retention touchpoints, and implement initiatives that drive measurable impact.

We’re seeking a leader with strong commercial experience, who can translate business goals into effective operational processes. The ideal candidate can evaluate performance through data, make strategic decisions quickly, and guide teams through both day-to-day operations and long-term improvements.

Requirements

• 5+ years in retention/sales with 3+ years managing teams of 5+ people
• Direct ownership of churn/retention metrics with documented results (e.g., reduced churn X% to Y%)
• Experience building retention strategy or transforming existing operations
• Deep understanding of retention mechanics: churn rate, cohort analysis, LTV, NRR
• Comfortable with analytics tools (Tableau or similar)
• Revenue-first mindset: thinks in ROI, unit economics, not just satisfaction
• Hands-on execution: builds playbooks, scripts, and can handle retention calls personally
• Strategic thinking + bias for action (test and learn approach)
• Influence without authority (cross-functional collaboration)
• English fluent
• Willing to working in the LATAM timezone

Nice To Haves

• EdTech, online education, or subscription B2C experience
• Spanish or Portuguese language
• 1+ years tenure in previous roles

Responsibilities

• Own retention metrics and build strategy
• Direct accountability for monthly churn, cohort retention curves, NRR, and LTV
• Build retention strategy based on cohort analysis and customer journey mapping
• Identify drop-off points (currently 15% churn months 1-2, 10% months 4-5) and design interventions
• Build retention operations
• Create retention playbooks: scripts, objection handling, intervention workflows
• Establish processes from at-risk signals to actions (automated + manual touchpoints)
• A/B test retention tactics and systematically measure results
• Lead the team
• Manage onboarding lead, retention lead, and success team
• Structure work with clear functional splits and coordination
• Design KPI frameworks and compensation aligned with retention goals
• Drive commercial prioritization
• Segment students by LTV and design differentiated retention approaches
• Calculate ROI before launching initiatives; allocate budget based on expected impact
• Make trade-offs: when to fight for retention, when to let go
• Cross-functional collaboration
• Influence Product roadmap with retention insights
• Partner with Curriculum to improve learning experience
• Sync with Marketing/Sales on student expectations

Benefits

• Competitive compensation.
• Full-time remote contract with a flexible schedule.
• Direct ownership of critical business metrics affecting revenue and student satisfaction.
• High autonomy to build and optimize operational systems from the ground up.
• Resources including budgeting authority, dedicated analytics support, and access to the CRM team.
• Fully remote collaboration alongside an experienced, global professional team.

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed
• Number of Employees: 1,001-5,000 employees