
Cherry Assistant

Cherry Assistant
About the job Operations & Tech Support VA
This is an exciting opportunity to join a fast-growing online membership and coaching brand that empowers female entrepreneurs and creators. The CEO is a visionary, neurodivergent founder who thrives on big ideas, fast execution, and high-quality community experiences.
We’re looking for a Operations & Tech Support VA to anchor the backend of the business — managing automations, tools, membership workflows, and light community support. This is a behind-the-scenes integrator role where you’ll ensure the systems run smoothly so the brand can scale with clarity and excellence.
Key Responsibilities:
Backend Systems & Tech (75%)
Manage and troubleshoot automations (Zapier)
Maintain and optimize Airtable tracking systems
Oversee Thrivecart checkouts, upsells, and memberships
QA email automations in Flodesk
Monitor Stripe and implement failed payment recovery workflows
Ensure healthy integration across all platforms (Zapier, Airtable, Thrivecart, Stripe, Flodesk, Circle.so)
Spot bugs or bottlenecks and recommend improvements
Member Operations & Light Community Support (10%)
Onboard new members (automations + personal touch)
Manage cancellations, billing queries, and support
Post discussion prompts and updates in the community (Circle.so)
Celebrate wins, highlight members, and encourage participation
Data & Reporting (15%)
Pull monthly reports on churn, payment success, and user feedback
Track community engagement and identify trends
Present clear recommendations for optimization
Required Qualifications:
2+ years experience as a Tech VA, Online Business Manager, or Operations VA
Prior experience in online coaching, education, or membership-based brands
Fluent in English (C1+), friendly and emotionally intelligent communication
Self-managed and detail-oriented with strong problem-solving ability
Proven ability to support fast-paced, creative founders
Preferred Qualifications:
Experience working with neurodivergent or ADHD entrepreneurs
Past work with 6- or 7-figure online brands
Familiarity with building out and documenting SOPs
Background in data reporting or performance optimization
Required Skills & Tools
Thrivecart (required)
Flodesk (email marketing)
Zapier (automations)
Airtable (data and task tracking)
Stripe (payments)
Google Drive / Docs
Circle.so (preferred, or willingness to learn quickly)
Loom & Telegram (for internal communication)
Schedule & Hours
10–15 hours per week (scaling to 20 hours)
Must have at least 4 hours overlap with UK business hours (9 AM – 5 PM UK time)
Fully remote
Monday to Friday only (no weekends)
4-week trial (onboarding not included in retainer)
Annual raises and performance-based bonuses
US Holidays Paid Time Off
Why This Job?
US holidays off + no weekend work
Fully remote & flexible
Work directly with an inspiring, creative founder
Make a meaningful impact on a growing brand with a mission
High autonomy and trust-based relationship
Learn behind the scenes of a high-level coaching business
Gain experience managing top-tier tools and systems used by online businesses in the US and UK markets
💜 To Apply:
Please submit:
A 3–4 min Loom video introducing yourself and sharing why you’re excited about this role
Examples of systems/automations/workflows you’ve built or maintained
Your resume/CV or portfolio
Operations & Tech Support VA
Business Consulting and Services