TheGuarantors is a cutting edge fintech company setting the standard in rent coverage with unrivaled insurance products. With a deep understanding of owner, operator, and renter needs, we believe renters deserve better access to the home of their dreams and operators deserve greater protection and growth opportunities. That’s why we’re leveraging our expertise in real estate and using AI-based technology to help operators qualify renters faster while mitigating the risk of rental income loss. With $5B+ in rent and deposits guaranteed, we work with 9 of the country’s top 10 operators and have been named one of Inc. 5000’s fastest-growing companies, one of Forbes’ Best Startup Employers, and one of Deloitte’s Technology Fast 500.

The Opportunity

The Director of Customer Success Operations plays a critical role in optimizing systems and processes that drive operational efficiency at TheGuarantors. This role is ideal for a systems-oriented leader with deep expertise in HubSpot and Zendesk, and a strong background in SaaS tools and automation. Reporting to the EVP of Underwriting and Customer Success, you will own the department’s tech stack—leading the design, implementation, and enhancement of tools that improve both internal workflows and the customer experience.

Location

This is a remote position.

What you'll do

• Drive operational efficiency and automation efforts across HubSpot, Zendesk, Ada, Aircall, Zapier, and Twilio
• Design and build scalable workflows, automation, ticket routing, analytics dashboards, and system configurations
• Support internal teams in delivering an exceptional customer experience through effective tooling and process optimization
• Analyze cross-functional business processes and data flows to inform systems improvements
• Scope requirements, define project plans, and manage implementation timelines for all systems initiatives
• Oversee rollout and adoption of new technologies, features, and processes
• Serve as the department’s representative in company-wide systems initiatives

What you bring

• Proficiency in REST API design and development, JSON data handling, JavaScript programming, and integration development
• HubSpot Administrator Developer
• Minimum of 4+ years of experience with HubSpot, expertise in building CRM workflows required
• Ability to build for long term, but also able to find efficient short-term means
• Strong analytical and data-driven decision-making skills
• Proven experience collaborating cross-functionally with product, engineering, marketing, and finance
• Experience implementing and supporting GenAI chatbot tools is strongly preferred

Benefits

• Opportunities to make an impact within a fast growing company
• Medical, dental, & vision insurance, beginning day one
• Health savings account with employer contribution
• Flexible spending accounts (healthcare, dependent care, commuter)
• 401(k)
• Generous PTO and paid holidays
• Flexible working hours
• Paid parental leave
• Company sponsored short and long term disability

Base Salary

The base salary range is between $145,000 - $160,000 annually.

Base salary does not include other forms of compensation or benefits. Final offer amounts are determined by multiple factors, including prior experience, expertise, location and current market data and may vary from the range above.

Stay in Touch

Does this role not quite match your skills, but you’re still interested in what we're doing? Stay In Touch to be one of the first to hear about future opportunities!

TheGuarantors is an Equal Opportunity Employer. We celebrate diversity and are committed to an inclusive environment for all.