Head of Customer Success

Head of Customer Success

Compensation: $175K OTE ($120K–$130K base) + equity

Job Type: Full-time | Remote

Reports to: CEO

Team: Onboarding and Customer Support (globally distributed)

About REsimpli

REsimpli is an all-in-one CRM and operating system built specifically for real estate investors. Our customers run their entire business in one place — marketing, lead management, communication, deal tracking, and closing.

We serve thousands of customers and are at 8-figure ARR. Our mission is to build the system that runs a real estate investor's entire business, powered by AI. As AI becomes the foundation of how our customers operate, helping them adopt it and get real results from it is central to how we grow.

The Role

We're looking for a Head of Customer Success to own every customer's experience after they sign up — and to turn the department into a measurable growth engine rather than a cost center.

You'll lead two teams with distinct but connected missions:

• Onboarding is proactive and outcome-focused. Its goal is to get every new customer set up properly and to first value fast — so they build their business on REsimpli from day one. Their message: "Let's get you set up to succeed with REsimpli."
• Customer Support is reactive and issue-focused, working across chat, email, and live Zoom. When a customer has a question, hits a problem, or needs help with a feature, Support gets them timely, accurate help. Their message: "You have a problem. Let's solve it."

Your job is to make these two teams work as one system. Every support interaction becomes a signal about adoption, risk, and retention. Every customer onboarded properly means fewer problems reach Support — and fewer customers who churn.

What You'll Own

1. Churn Reduction (Primary KPI)

• Own and drive down logo and revenue churn across all customer segments.
• Identify the biggest drivers of churn and prioritize what to fix first.
• Build systems that catch at-risk customers early: health scores, early-warning signals, and save playbooks.

1. Net Revenue Retention & Expansion

• Own NRR and expansion revenue targets.
• Drive adoption of higher-value products, especially our AI offerings.
• Partner with Sales and Marketing to build clear upgrade paths and expansion motions within the existing customer base.

1. Customer Support Excellence

• Ensure customers get fast, accurate, empathetic help with questions, troubleshooting, and feature guidance.
• Own support metrics: first response time, resolution time, CSAT, and ticket trends.
• Coordinate with Product and Engineering on bugs, technical issues, and escalations.
• Reduce ticket volume through better self-service, knowledge base content, and automation.

1. Onboarding, Adoption & Training

• Improve time to first value for new customers.
• Define and enforce activation milestones that predict long-term retention.
• Build proactive training and engagement programs, with AI adoption tracked as a core leading indicator.

1. Team Leadership & Accountability

• Lead, structure, and scale both the Onboarding and Support teams.
• Set clear ownership, KPIs, and performance standards for every role.
• Define handoffs between Onboarding and Support so no customer falls through the cracks.
• Hire, coach, and make hard decisions when needed.

1. Customer Insights → Product Feedback Loop

• Use support trends and churn reasons to answer key questions: Is this issue hurting adoption? Who is at risk? Who needs training? What becomes a retention problem if we don't act?
• Work directly with Product and Engineering to ground roadmap decisions in real customer behavior.

1. Reporting

• Own all department metrics: logo churn, revenue churn, NRR, expansion revenue, activation rates, CSAT, and support performance.
• Deliver weekly insights and recommended actions to the CEO — not just reports.

What Success Looks Like

• Churn decreases consistently month over month.
• NRR improves and becomes a core growth driver.
• AI products are adopted across a large share of the customer base.
• Customers get fast, high-quality support, and recurring issues are fixed at the root.
• The department runs with clear accountability and becomes a predictable revenue engine.

Who You Are

• Proven operator at our stage: you've built and improved customer-facing teams at a growing SaaS company, and you know what works at $10–30M ARR — not just at enterprise scale.
• Leader of both sides: you understand reactive support and proactive onboarding, and how to make them reinforce each other.
• Builder and optimizer: you can fix what's broken and scale what works.
• Numbers-driven: you run your org on metrics, not intuition.
• Highly accountable: you take full ownership of outcomes.

Experience

• 7+ years in Customer Success, Customer Support, Retention, or Account Management, including significant leadership experience. (Required)
• Led teams of 10+ people, with clear evidence you can scale an org as it grows. (Required)
• Proven track record of reducing churn and/or improving NRR. (Required)
• Experience at a $10M–$30M ARR SaaS company. (Preferred; equivalent scope considered)
• Experience with SMB customers or in high-churn environments. (Preferred)
• Experience in real estate, real estate tech, or CRM software. (Bonus)

Compensation

• Base: $120K–$130K
• OTE: $175K, with variable pay tied to churn reduction, NRR growth, and expansion revenue
• Equity: meaningful stake vesting over 4 years, with the range shared early in the interview process

Why This Role Matters

At our stage, growth doesn't come only from new customers. It comes from keeping the customers we have, increasing their lifetime value, and making REsimpli something they can't imagine running their business without. This role is directly accountable for all three.

Work Location: Remote

Pay: $120,000.00 - $130,000.00 per year

Benefits:

• Paid time off
• Parental leave

Application Question(s):

• How many years of relevant customer-facing experience do you have?
• How many people have you directly managed at one time?
• Have you directly owned churn reduction and/or NRR targets?
• Describe the most significant measurable improvement you achieved in customer retention or churn reduction, including the baseline, result, and timeframe.
• Have you led both Customer Onboarding and Customer Support teams?
• Do you have experience working in real estate, real estate technology, or CRM software?

Work Location: Remote