Customer Success Manager, Enterprise

Portside is a leading provider of cloud-based software solutions for the global aviation industry. Our platform powers critical operations across business aviation, regional airlines, and aircraft leasing & finance, helping over 1,000 aviation organizations streamline operations, improve decision-making, and operate more efficiently.

Backed by leading technology investors Vista Equity Partners and Insight Partners, Portside is entering an exciting phase of growth. We are expanding our platform, investing in AI driven innovation, and building a global team focused on shaping the future of aviation technology.

Portside is seeking an experienced Enterprise Customer Success Manager to own a portfolio of large, enterprise, aviation accounts. You will guide each customer through a defined engagement model, from a structured onboarding hand-off through ongoing success and operational reviews, to renewal and expansion, delivering measurable value and building durable executive relationships along the way.

This role partners closely with Sales, the onboarding team, Renewal Specialists, Product, and Marketing to execute a consistent, high-touch engagement motion across the enterprise book. You will run the cadence of reviews and training that keeps each account healthy, surface expansion signals for Sales to close, and use Portside's digital success layer to extend your reach and impact across the portfolio.

The ideal candidate is a seasoned, relationship-driven Customer Success professional who is equally comfortable presenting to C-suite stakeholders and managing the operational rigor of a structured, multi-phase engagement model at enterprise scale.

• Own the end-to-end customer journey for a portfolio of enterprise accounts, executing Portside's defined engagement model across onboarding, cadence, training, reporting, renewal, and expansion.
• Receive and act on structured internal hand-off documentation from Sales; lead the external kickoff meeting and guide each customer through the defined onboarding motion.
• Build and maintain a custom success plan for each account, aligning platform usage to the customer's operational and business goals.
• Run bi-annual or quarterly success reviews and monthly or bi-monthly operational reviews, tailoring cadence to account size, complexity, and risk profile.
• Deliver up to 8 hours of annual training per account through live sessions, webinars, and adoption campaigns to drive platform proficiency and engagement.
• Drive the 180-day renewal outreach cadence in partnership with a dedicated Renewal Specialist, ensuring accurate forecasting and proactive risk mitigation ahead of each renewal date.
• Identify and surface expansion signals using Portside's playbooks, handing qualified opportunities to the Account Executive to close; reinforce expansion through product-led, in-app prompts.
• Leverage Portside's digital success layer, including automated Q  generation, workflow optimization recommendations, product release briefings, and data-triggered journeys, to extend consistent coverage across the portfolio.
• Track usage, health scores, and account analytics to proactively identify at-risk accounts and adjust engagement accordingly.
• Serve as the primary point of contact and executive-level relationship owner for each assigned account.
• Partner with Product and Engineering to relay enterprise customer feedback and influence roadmap priorities.
• Facilitate customer advocacy, including executive references, testimonials, and case studies, in support of new business and expansion motions.
• Maintain accurate account data, health scores, and engagement history in the CRM and customer success platform.
• Represent Portside at industry conferences and customer events as needed.

• 5+ years of SaaS experience in Customer Success, Account Management, or a related enterprise customer-facing role, including direct ownership of strategic or enterprise-tier accounts.
• Demonstrated success managing a defined, multi-phase engagement model or playbook across onboarding, adoption, renewal, and expansion at the enterprise level.
• Strong executive presence, with experience building and maintaining relationships with senior and C-suite stakeholders.
• Proven ability to manage structured cadences (success reviews, operational reviews) across a portfolio of complex accounts.
• Experience partnering with the wider organization to ensure success for your named accounts.
• Strong technical aptitude, including comfort…