Retention, Lifecycle & CRM Specialist (Freelance)

Overview

You're running retention and lifecycle marketing for a tutoring marketplace that connects students (ages 8-18) with tutors. You'll be deep in HubSpot building automated email/SMS flows, analyzing cohort retention data, and running experiments to reduce churn and increase referrals. This is a freelance role at an 11-person startup, so you'll own this function completely with minimal oversight.

Role Snapshot

Company Context

Stage: Early-stage startup (exact funding unknown, but 11 employees suggests pre-seed or seed)

Size: 11 employees

Growth: Hiring for specialized freelance roles indicates they're beyond initial PMF and scaling retention operations

Market Position: Operating in crowded tutoring market competing with platforms like Wyzant, Varsity Tutors, Chegg - differentiation through AI/data-driven matching

GTM Reality

Customer Base:

• Primary: Parents of students ages 8-18
• Secondary: Students themselves (especially older teens)
• Tutors as a second-side marketplace consideration

Growth Levers:

• Student/parent retention (reducing churn between sessions/semesters)
• Tutor retention and engagement
• Referral programs (parent-to-parent, student-to-student)
• Win-back campaigns for inactive users

Current State: Small team means CRM infrastructure is probably functional but not optimized. You'll be the first person focused purely on lifecycle, so expect to inherit some technical debt and manual processes.

Competitive Landscape

Main Competitors: Wyzant, Varsity Tutors, Chegg Tutors, local tutoring centers, independent tutors

How They Differentiate: AI-driven matching, personalized learning approach, data-informed tutor recommendations

Common Objections: Price vs. cheaper alternatives, commitment concerns, platform vs. direct tutor relationship

Win Themes: Better tutor matching, data-driven progress tracking, comprehensive support system

What You'll Actually Do

Time Breakdown

HubSpot Workflow Building (35%) | Data Analysis (25%) | Campaign Execution (25%) | Strategy/Planning (15%)

Key Activities

• HubSpot Workflow Optimization: Build and refine automated email/SMS sequences for onboarding, session reminders, re-engagement, and referral prompts. Debug broken automations, optimize send times, write copy, set up A/B tests.
• Retention Analysis: Pull cohort reports to understand where students drop off (after first session, after 5 sessions, seasonal gaps). Identify patterns in churn and create targeted campaigns to address them.
• Win-Back Campaigns: Design and run campaigns to re-activate parents/students who haven't booked in 30/60/90 days. Test different messaging angles (new tutors available, subject-specific help, seasonal exam prep).
• Referral Program Management: Build and track referral incentives, create automated referral request flows, optimize referral landing pages and tracking codes.
• Cross-Functional Coordination: Work with founder/CEO on strategic priorities, coordinate with whoever handles tutor operations on supply-side engagement, potentially align with whoever does acquisition marketing.

The Honest Reality

What's Hard

• Limited resources: 11-person startup means no marketing team, probably minimal design support, tight budget for tools/experiments. You're building with what you have.
• B2C complexity: Parents make buying decisions but students are end users. Mixed communication preferences (email vs SMS vs WhatsApp), seasonal patterns (summer slump, exam season spikes), sensitivity to pricing.
• Data limitations: Small team likely means data isn't perfectly clean. You'll spend time cleaning lists, fixing attribution, reconciling HubSpot with whatever billing system they use.
• Freelance scope creep: As the retention expert, you might get pulled into adjacent stuff like customer support templating, NPS surveys, or product feedback loops that aren't strictly your job.
• Two-sided marketplace: You're not just retaining students - tutor retention matters too. That doubles the complexity of your lifecycle work.

What Success Looks Like

• Retention improvement: Move 60-day or 90-day student retention rate up by 10-15 percentage points within 6 months
• Reactivation volume: X number of previously churned students re-engaged per month through win-back campaigns
• Referral growth: Referral-driven new student acquisitions increase by Y% quarter-over-quarter
• Operational efficiency: All manual retention touchpoints automated into HubSpot workflows, reducing founder time spent on follow-ups

Who You're Working With

Primary Stakeholder:

• Florian Zandbergen (Founder/CEO) - Sets strategic priorities, approves major campaigns, final say on budget/tools

Cross-Functional Partners:

• Whoever manages tutor operations (coordination on supply-side engagement)
• Potential customer support person (feedback loop on why customers churn)
• Whoever handles acquisition (alignment on messaging, handoff from acquisition to activation)

End Users:

• Parents making purchase decisions (primary communication target)
• Students using the service (secondary communication, especially teens)
• Tutors (engagement/retention to ensure supply)

Requirements

• 3+ years hands-on experience building lifecycle marketing programs, ideally in B2C subscription or marketplace businesses
• Deep HubSpot expertise - workflow automation, list segmentation, reporting, A/B testing, integration management
• Strong analytical skills - comfortable pulling retention cohorts, calculating LTV, identifying drop-off points, sizing campaign opportunities
• Experience with win-back and re-engagement campaigns specifically, not just nurture sequences
• Bias toward action - you test and iterate quickly rather than planning for months
• Comfortable working independently with minimal oversight in a freelance capacity
• Bonus: Experience with two-sided marketplace dynamics or education/tutoring industry
• Bonus: Familiarity with referral program mechanics and tracking