Customer Success Supervisor 

Be a Leader in Customer Experience and Drive Long Term Retention 

Are you a strategic customer success leader with 3+ years of experience in customer retention while mentoring high performing teammates and driving measurable improvements in customer retention, add-on sales, and customer satisfaction?  Do you excel at balancing hands on leadership with operational excellence across the entire customer lifecycle? Can you transform customer insights into scalable processes while maintaining a customer focused culture and increasing revenue? 

With 46 years of success as an AI powered trading technology pioneer, VantagePoint AI is entering an exciting growth phase, and we need an experienced Customer Success Supervisor to be a leader our customer coaching, customer service, and retention initiatives. 

Why VantagePoint AI? 

• Join a recognized industry leader blending AI driven innovation with financial market expertise. 
• Lead customer success within a close-knit, high-performance team of just under 100 professionals. 
• Experience true work life balance with standard business hours (8:30 AM to 5:30 PM, limited weekends). 
• Receive 100% employer paid healthcare and dental coverage. 
• Thrive in a collaborative, people first culture that values both tradition and forward thinking strategies. 
• Enjoy company sponsored social events, team building retreats, and a modern workspace in Wesley Chapel. 

Your Impact as Customer Success Supervisor

You won't just support customers. You will be a versatile leader who excels across the entire customer journey, from frontline support to strategic retention initiatives. Your ability to flex between hands-on customer service, team mentorship, and cross-functional collaboration will directly impact customer satisfaction, loyalty, and long-term retention while ensuring operational excellence across all customer touchpoints.

Customer Support Excellence & Team Development

• Lead by example in delivering exceptional customer support, actively handling escalations, complex cases, and high-priority customer inquiries
• Support, mentor, and develop team members across customer support, onboarding, and retention functions
• Stay deeply engaged in frontline support activities to maintain expertise, model best practices, and remain connected to evolving customer needs
• Help foster a culture of responsiveness, empathy, problem-solving, and continuous improvement throughout the support organization
• Assist in developing, implementing, and facilitating training programs focused on support quality, product knowledge, and customer communication skills
• Lead coaching sessions to elevate team performance in customer support delivery
• Demonstrate flexibility by seamlessly shifting between customer-facing support work, team mentorship, operational tasks, and strategic projects

Customer Retention & Relationship Management

• Take ownership of retention initiatives by proactively identifying at-risk customers and implementing intervention strategies to prevent churn
• Monitor customer health metrics and support data-driven analysis to predict and address retention risks before they escalate
• Build and maintain strong relationships with key sales stakeholders, serving as a trusted advisor and escalation point for critical issues
• Support retention strategies  designed to improve customer satisfaction and reduce attrition
• Collaborate with cross-functional teams to address customer pain points, resolve recurring issues, and enhance the overall support experience
• Track and analyze retention metrics, onboarding completion rates, time to value, and customer satisfaction scores to identify improvement opportunities
• Help implement proactive outreach programs that strengthen customer relationships and demonstrate ongoing value

Versatile Customer Lifecycle Support

• Support the end-to-end customer journey from initial onboarding through renewal, demonstrating flexibility across all phases of the customer lifecycle
• Help design and optimize support processes, onboarding workflows, and retention touchpoints that drive product adoption and customer satisfaction
• Flex between operational execution and strategic planning to ensure seamless customer experiences at every stage
• Assist in implementing scalable systems and workflows for support ticket management, customer communication, and success operations
• Partner with Sales, Product, and Marketing teams to ensure smooth handoffs, consistent messaging, and alignment on customer goals
• Adapt quickly to shifting priorities, handling everything from urgent customer escalations to long-term process improvement initiatives

Quality Assurance & Support Performance

• Support quality assurance frameworks specifically focused on customer support interactions, response times, and resolution effectiveness
• Monitor and analyze key support performance indicators including CSAT, NPS, first response time, resolution time, ticket volume, and customer satisfaction scores
• Conduct quality reviews of support tickets, calls, and customer interactions to maintain service excellence and identify coaching opportunities
• Use support data and customer feedback to drive continuous improvement in team performance and support delivery
• Assist in delivering insights and reporting to leadership with clear recommendations for enhancing support operations and retention outcomes

Cross-Functional Collaboration & Customer Advocacy

• Serve as a strong Voice of the Customer, championing support feedback and retention insights across the organization
• Collaborate with Product teams to communicate recurring customer issues, feature requests, and support trends that impact retention
• Partner with Sales and Revenue Operations to ensure smooth post-sale transitions and proactive support for new customers
• Work with Marketing to leverage customer success stories, support insights, and retention data for lifecycle campaigns
• Coordinate with leadership to identify support inefficiencies, retention gaps, and opportunities for scalable, customer-centric solutions

What You Bring to the Table

Required Experience & Expertise

• 3+ years of hands-on experience in customer support, customer success, or customer-facing operations
• Proven track record of delivering exceptional customer service while contributing to improved retention, satisfaction metrics, and operational efficiency
• Demonstrated experience supporting and mentoring customer-facing team members in support or success functions
• Strong background in handling customer escalations, resolving complex issues, and managing difficult conversations with professionalism and empathy
• Emerging leadership capabilities with readiness to take on supervisory responsibilities while maintaining active support involvement
• Bachelor's degree in Business, Communications, or related field (or equivalent experience)

Hard Skills

• Deep expertise in customer support best practices, ticketing systems, and support workflows
• Data-driven mindset with experience tracking and reporting on customer support and retention KPIs (CSAT, NPS, churn rate, retention rate, response time, resolution time)
• Strong analytical skills with ability to identify support trends, diagnose retention issues, and implement data-informed solutions
• Proficiency with CRM platforms (Salesforce), customer support tools (Zendesk, Intercom, Freshdesk, or similar), and reporting systems
• Experience with customer journey workflows, support escalation processes, and retention lifecycle strategies
• Familiarity with quality assurance methodologies, support performance management, and customer feedback systems
• Understanding of SaaS business models, subscription metrics, and how support excellence drives revenue retention

Soft Skills & Leadership Qualities

• Customer-first mindset with genuine passion for solving problems, delivering exceptional support, and building lasting relationships
• Exceptional communication skills with ability to handle difficult conversations, de-escalate tense situations, and influence across all levels
• Highly adaptable and versatile with proven ability to flex between hands-on support work, team leadership, strategic projects, and operational tasks
• Empathetic team player who builds trust, fosters collaboration, and supports team performance through coaching and mentorship
• Solution-oriented problem solver with ability to identify root causes of support and retention issues and implement scalable fixes
• Proactive and results-oriented with strong sense of ownership, accountability, and bias toward action
• Resilient and composed under pressure with ability to thrive in a dynamic, fast-paced support environment
• Willingness to roll up sleeves and handle frontline support, escalations, and complex customer issues to stay connected to customer needs and model excellence
• Growth mindset with eagerness to develop leadership skills while maintaining deep customer support expertise

Preferred Skills

• Experience in fintech, financial services, SaaS, or high-growth technology environments with complex support needs
• Background in customer retention programs, churn analysis, or customer health scoring
• Exposure to support automation, customer onboarding tools, or lifecycle communication platforms
• Experience with multiple support channels (email, chat, phone, social media)
• Interest in pursuing certification in customer experience, support management, or quality assurance

Compensation & Benefits

• Competitive base salary commensurate with experience
• 100% employer-paid healthcare and dental coverage
• Generous paid time off (PTO) and paid holidays
• Birthday leave
• Company-inclusive birthday, anniversary, and special achievement celebrations
• Professional development and growth opportunities in support leadership
• Work with cutting-edge A.I. technology in the fintech space
• Off-site company-sponsored events for employees and family members
• A stable and thriving company positioned for long-term growth, regardless of economic conditions

Location & Work Arrangement 

On site employment at our modern offices in Wesley Chapel, FL (Tampa Bay Area) 

Be Part of Something Bigger 

At VantagePoint AI, you won't just manage customer support. You'll be a strategic leader helping independent traders achieve financial freedom by ensuring they receive world class service and support. This is your chance to make a measurable impact at a company that has been revolutionizing trading technology for over 46 years. 

Ready to lead? Apply today and help us write the next chapter in customer success excellence. 

We participate in E-Verify.