Capitalize.io
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.
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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.
#J-18808-Ljbffr