Head of Customer Retention

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Legacy Farmer

WebsiteLinkedInAll Job Openings

1 - 10 employees

Founded 2019

💼 Consulting

🌾 Agriculture

📚 Education

💰 $2M Seed Round - Legacy Farmer on 2023-11

Consulting • Agriculture • Education

Legacy Farmer is a membership and training platform that helps family farms achieve financial mastery, operational organization, and generational business growth. It offers immersive training curriculum, expert-led coaching, strategic playbooks, community support, and farmer-focused software/tools to track borrowing power, balance sheets, and cash flow, plus guidance on banking, bookkeeping, team structure, and long-term planning.

📋 Description

• Own gross and net revenue retention (NRR/GRR), define metrics, build dashboards, and present outcomes monthly to leadership • Lead and assess the Customer Success team • Define career paths, hire, and coach or exit team members where standards are not met • Own, instrument, and map onboarding, adoption, renewal, expansion, and win-back • Establish and enforce written service standards, response times, proactive outreach, and save plays • Partner with the VP of Coaching to align coaching delivery with retention playbooks under one scoreboard • Raise the standard of customer service and value across the Customer Success and Coaching departments

🎯 Requirements

• Must be located in the US with Central-time overlap • Proven track record leading customer success or retention at a B2B SaaS or coaching/services company with $5M+ ARR • Demonstrated experience owning NRR and driving measurable improvements in retention metrics • Experience managing Customer Success in a hybrid software plus services/coaching business model preferred • Familiarity or quick adaptability to the agricultural industry and farm operator mindset preferred • Data and metrics-driven approach focused on NRR/GRR • Ability to raise performance standards with clarity and accountability while respecting established team relationships • Ability to build repeatable playbooks, health scores, escalation paths, and QBR cadences • Fluency in SaaS adoption metrics and human coaching/service dynamics • Respectful, humble, and able to connect authentically with faith-and-family-driven farm families • A 2-minute introductory video explaining fit for the role is required • Participation in E-Verify

🏖️ Benefits

• Performance bonus tied directly to retention outcomes • Health Reimbursement Program • 401(k) participation • Flexible Time Off • Paid Company Holidays • Up to $500 annual home office and wellness reimbursement