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SupportFinity™

Head of Customer Success

SupportFinity™, Florida, New York, United States

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At 8020REI, you’ll play a key role in shaping the future of data for the real estate investment industry. You’ll have the opportunity to lead customer-centric strategies, work with cutting-edge technologies, and collaborate with a dynamic team passionate about innovation and results.

Role Overview We’re seeking a

results-driven, strategic leader

to take full ownership of our Customer Success function and scale it through our next phase of growth. As

Head of Customer Success , you’ll own the outcomes—driving retention, maximizing customer lifetime value, and turning client success into a growth engine. You’ll lead and grow a team of 7+ CSMs and Operations specialists, build scalable systems, and ensure our clients achieve measurable results with 8020REI. You’ll support our expansion into new verticals, starting with home services, ensuring that CS is built to deliver impact at scale. Reporting to the

COO

and working closely with the

CEO , you’ll contribute to strategic decisions shaping the customer experience and revenue growth.

You’ve been where we’re going: scaling a CS function during rapid growth, building high-performing teams, and owning customer results from onboarding through expansion.

Key Responsibilities

Own retention, expansion, and customer success outcomes, not just processes

Design and execute a scalable CS strategy aligned with business growth and vertical expansion

Build systems and processes to predict risk, prevent churn, and increase customer lifetime value

Lead and grow a high-performing team, setting clear KPIs and ensuring execution against results

Drive operational excellence through CRM optimization, dashboards, playbooks, and team rhythms

Act as the escalation point, ensuring resolution and reinforcing value

Partner closely with Sales and Product to align goals, improve onboarding, and capture feedback loops

Play a key role in launching new verticals, ensuring Customer Success is ready to support expansion

Champion a culture of accountability, ownership, and continuous improvement across the CS team

Qualifications

7+ years in B2B SaaS or data-driven customer success roles, with 3+ years of senior leadership

Demonstrated ability to own and deliver on key outcomes, retention, expansion, and CS-driven revenue

Proven experience scaling CS teams, systems, and results in fast-growing companies

Strong strategic thinking, paired with execution discipline and operational follow-through

Comfortable managing complexity, navigating change, and leading through ambiguity

Excellent communication and leadership skills, with a clear executive presence

Experience working cross-functionally with Product, Sales, and Finance

Bonus: experience supporting GTM for new verticals or client segments

Spanish a plus

Why Join Us At 8020REI, you’ll be at the forefront of shaping our customer success strategy and execution. As the Head of Customer Success, you’ll lead critical initiatives to maximize customer lifetime value and build a world-class CS organization. This role offers autonomy to define processes, drive strategic decisions, and create a scalable foundation that directly impacts growth and market presence.

What We Offer

Competitive Base Compensation

Retention Bonus

Performance Bonus

Flex PTO (up to 26 days per year)

Home Office Upgrade Bonus

Health Bonus

Full-time Remote Work

Opportunity for significant growth and team-building potential

Ongoing support and budget to develop new skills

Join us and revolutionize real estate data. We’d love to hear from you if you’re a visionary leader with a passion for customer success and a drive to build and scale high-performing teams.

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