About Portside, Inc.

Portside is a leading provider of modern SaaS solutions for the global aviation industry. We serve over 1,200 enterprise customers across business aviation, regional commercial aviation, and aircraft leasing & finance. Our platform helps operators streamline day-to-day operations, enhance data exchange, and leverage powerful analytics.

We are seeking a highly driven, strategic, and results-oriented VP of Customer Support & Success to lead and scale our customer-facing teams. This role requires a sharp, execution-focused leader with a proven track record of building, scaling, and optimizing customer support and success functions in a fast-paced technology startup or similar high-growth environment.

The ideal candidate thrives under pressure, can rapidly assess and improve processes, and operates with the urgency and aggressiveness needed to drive exceptional customer experiences while balancing efficiency and scalability.

Job Summary

The VP of Customer Support & Success will be responsible for customer retention, satisfaction, and operational efficiency. This leader will implement scalable processes, AI-driven support solutions, and customer health metrics while ensuring seamless collaboration between Support, Product, Engineering, Sales, and Accounting.

This role is ideal for someone who moves fast, operates with high accountability, and sets world-class standards for their teams.

Key Responsibilities

Customer Support: Operational Excellence

• Build and scale customer support operations, implementing best practices to improve efficiency and customer experience.
• Develop and enforce support policies and SLAs to ensure high-quality, consistent customer interactions.
• Create, document, and communicate key operational processes for support workflows.
• Deploy, configure, and manage customer support systems and tools.
• Drive AI initiatives, leveraging automation and AI-driven analytics to improve efficiency.
• Define and track key support metrics, ensuring the team meets performance benchmarks and OKRs.
• Manage, train, and mentor the support team, handling escalations and career development.
• Implement knowledge base best practices, optimizing self-service content to reduce ticket volume.
• Facilitate cross-functional coordination between Support, Product, Engineering, Sales, and Accounting to resolve issues efficiently.
• Develop and oversee after-hours support processes to ensure 24/7 customer coverage.

Customer Success: Retention, Growth & Proactive Engagement

• Build and scale customer success operations, ensuring seamless onboarding, adoption, and long-term retention.
• Define and implement a comprehensive customer success strategy to enhance the customer journey from onboarding to expansion.
• Lead the Customer Success team to drive adoption, customer satisfaction, and retention.
• Build strong customer relationships, acting as a trusted advisor to help clients achieve business goals.
• Conduct regular business reviews (QBRs) with customers to align on performance, outcomes, and future opportunities.
• Develop and maintain customer health metrics, tracking NPS, CSAT, retention, and churn rates.
• Champion a customer-first culture, ensuring every interaction strengthens loyalty and retention.
• Drive proactive outreach strategies to maximize customer value.
• Own and optimize renewal processes, including pricing, packaging, and documentation.
• Develop escalation management processes to effectively handle critical customer issues.
• Work closely with cross-functional teams to define the ideal customer journey, value delivery methodology, and operational models.
• Establish and manage key performance indicators (KPIs) for the Customer Success team, including adoption, expansion, and advocacy metrics.

Leadership & Strategic Initiatives

• Build and lead a high-performing global team across Customer Support and Customer Success.
• Establish a data-driven approach, using customer insights to drive decisions.
• Optimize customer segmentation, refining high-touch vs. tech-touch engagement models.
• Ensure alignment between customer-facing teams and internal stakeholders, improving communication and issue resolution.
• Oversee the implementation and continuous improvement of CRM and support tools to enhance operations and insights.
• Develop a robust customer feedback loop, leveraging insights to inform the product roadmap, support processes, and customer experience improvements.

Qualifications

• 3+ years of leadership experience in Customer Success and/or Support.
• Proven track record in building, scaling, and improving customer support and success functions in a fast-paced technology startup or high-growth environment.
• Highly execution-focused, results-driven, and comfortable operating with urgency.
• Experience implementing support automation, AI-driven tools, and customer success platforms.
• Strong expertise in customer health scoring, renewal processes, and escalation management.
• Deep understanding of SaaS pricing models, contract renewals, and customer advocacy programs.
• Exceptional leadership, communication, and cross-functional collaboration skills.
• Ability to analyze data and drive strategic decision-making based on KPIs.
• Experience deploying and managing customer support systems and tools.

What We Offer

• Competitive salary
• Fully remote work
• Generous time off policy
• Health, dental, and vision insurance
• Opportunities for professional development and career advancement.
• Dynamic, collaborative, and fast-growing work environment.