Head of Customer Retention
About The Position
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 We're raising the standard of what our customers experience, and we're hiring one person to own that. You will step into a business with a working CS function and a strong Coaching department and set a new, higher expectation of service and value across both. The Mission: The Retention Number: Own gross and net revenue retention (NRR/GRR), defining metrics, building dashboards, and presenting outcomes monthly to leadership. Department Leadership: Lead and assess the CS team, define career paths, hire, and coach or exit where standards aren't met. The Customer Journey: Own, instrument, and map onboarding, adoption, renewal, expansion, and win-back so farm families feel value within 30 days. The Standard: Establish and enforce written service standards, response times, proactive outreach, and save plays. Partnership with Coaching: Work shoulder to shoulder with the VP of Coaching to align coaching delivery with retention playbooks under one scoreboard.
Requirements
- Must be located in 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.
Nice To Haves
- Experience managing Customer Success in a hybrid software + services/coaching business model.
- Familiarity or quick adaptability to the agricultural industry and farm operator mindset.
Responsibilities
- 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 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.
Benefits
- Salary: $90 - $120,000 base + performance bonus tied directly to retention outcomes.
- 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
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What This Job Offers
Job Type
Full-time
Career Level
Senior
Education Level
No Education Listed
