Head of Customer Success

Capitalize is transforming the $6 trillion commercial real estate (CRE) debt market with AI-driven technology that enhances transparency, improves lead quality, and accelerates deal efficiency. We empower capital markets, investment sales, lenders, and investors with the data and technology needed to fuel revenue growth and enable smarter decision-making. Join us in reshaping the future of CRE finance through AI and innovation.

Summary Comp : $90K–$120K base + 20–30% bonus

Location : Preferred in Newport Beach, CA (open to hybrid across LA / OC / San Diego)

Capitalize.io is one of the fastest-growing AI / proptech companies in commercial real estate. We help commercial mortgage brokers, lenders, investment-sales brokers, and CRE investors source new deals using real-time liens, maturities, SREO portfolios, borrower contact data, distress signals, and AI-driven matching. 300+ companies rely on Capitalize today — and we're scaling fast.

We're hiring a high-performing, analytical, PLG-native Head of Customer Success to take full ownership of the customer lifecycle. This person will drive activation, adoption, retention, and expansion across a high-velocity book of SMB and mid-market accounts.

Core Responsibilities Reduce churn by building proactive engagement, renewal, and risk-mitigation processes

Increase adoption via hands-on onboarding, scalable training, and customer education

Drive seat expansion & PQLs by identifying usage gaps and spotting product-qualified signals

Build repeatable playbooks for onboarding, lifecycle management, health scoring, renewals, and QBRs

Work cross-functionally with Product to relay customer feedback and influence roadmap

Partner with Sales to optimize handoffs, expansion workflows, and commercial strategy

Implement systems, dashboards, and analytics to track health, activation, NRR, and usage

Own renewals, churn metrics, customer satisfaction, and lifecycle KPIs

Build and manage onboarding sequences, lifecycle nudges, and automated touchpoints

Improve help center content, documentation, and customer training materials

Handle customer escalations with urgency and professionalism

What We're Looking For 3–6 years in SaaS Customer Success or Account Management

Experience in product-led or hybrid PLG SaaS environments

HubSpot power user (workflows, filters, lifecycle automations, sequences; certified is a plus)

Highly analytical — comfortable using dashboards to identify risk, guide strategy, and optimize retention

Strong process-builder : can create scalable onboarding, lifecycle, and expansion frameworks

Proven examples of improving activation, retention, or expansion

Player-coach mentality — willing to execute while building the long-term CS function

Excellent communication skills; collaborative with Sales, Product, and founders

Industry fit preferred : CRE data, proptech, financial data platforms, or data-heavy SaaS

Preferably located near Newport Beach HQ (hybrid options available across LA / OC / SD)

Competitive Compensation : Base salary with lucrative commission structure.

Professional Development : Opportunities for career growth and advancement.

Work Environment : Collaborative and innovative company culture with a focus on employee well-being and work-life balance.

Capitalize provides equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state, or local laws.

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