Head of Customer Retention

Legacy Farmer is always looking for growth-oriented, high-performance people ready to deliver amazing results for our clients and team.

Who We Are

At Legacy Farmer, we are committed to helping Farmers Master their Finances and Build a Great Business that will Thrive for multiple generations in the future. Our work matters here and we will do whatever is required to accomplish our mission of helping the great people in this industry.

Legacy Farmer is the financial operating system for American family farms. We combine built-for-ag software (Farmer Metrics) with ag finance coaching delivered by a team of ~44 people. Our customers aren't logos on a slide, they're farm families betting their operation, and their kids' future, on the numbers we help them see clearly. We're building toward 2,000 farm operations served and $100M ARR.

About the Role

The Mission:

• Own gross and net revenue retention (NRR/GRR), defining metrics, building dashboards, and presenting outcomes monthly to leadership.
• Lead and assess the CS team, define career paths, hire, and coach or exit where standards aren't met.
• Own, instrument, and map the customer journey including onboarding, adoption, renewal, expansion, and win-back so farm families feel value within 30 days.
• Establish and enforce written service standards, response times, proactive outreach, and save plays.
• Work shoulder to shoulder with the VP of Coaching to align coaching delivery with retention playbooks under one scoreboard.

Ideal Candidate

• Data & Metrics-Driven: Focuses on measurable retention metrics (NRR/GRR) rather than vague customer satisfaction concepts.
• High-Standard Leader: Raises performance standards with clarity and accountability while respecting established team relationships.
• System Builder: Builds repeatable playbooks, health scores, escalation paths, and QBR cadences.
• Hybrid Model Adaptable: Fluent in both SaaS adoption metrics and human coaching/service dynamics.
• Relatable & Values-Aligned: Respectful, humble, and able to connect authentically with faith-and-family-driven farm families.

Requirements

• Must be located in the US (Remote with Central-time overlap).
• Proven track record leading customer success or retention at a B2B SaaS or coaching/services company ($5M+ ARR).
• Demonstrated experience taking ownership of NRR and driving measurable improvements in retention metrics.

Preferred Qualifications

• Experience managing Customer Success in a hybrid software + services/coaching business model.
• Familiarity or quick adaptability to the agricultural industry and farm operator mindset.

A 2-minute video introducing yourself and explaining why you’re a great fit for this role will be required to be considered for this role.

Pay

Salary: $90,000 - $120,000 base + performance bonus tied directly to retention outcomes. The final salary offered will be determined by the candidate’s relevant skills, experience, and geographic location.

Benefits

• Healthcare: Health Reimbursement Program
• Retirement: 401(k) participation
• Time Off: Flexible Time Off plus Paid Company Holidays
• Remote Work Support: Up to $500 annual home office and wellness reimbursement