Strategic Sales Executive

About Portside

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.

Job Summary

Portside is seeking a Strategic/Enterprise Sales Executive to drive growth across a portfolio of key aviation customers and prospects. This role is responsible for developing executive relationships, identifying expansion opportunities, and positioning Portside as a long-term technology partner across multiple aviation segments, including charter, fractional, corporate flight departments, regional airlines, emergency services, and government operators.

The ideal candidate has a consultative, enterprise-sales mindset and a proven ability to manage complex, multi-stakeholder sales cycles. This role will focus on expanding customer relationships, increasing platform adoption, and driving recurring revenue growth through strategic account planning and solution-based selling.

This position requires travel up to 30% of the time.

Key Responsibilities

• Own and grow a portfolio of strategic/enterprise accounts across charter, fractional, corporate, regional airline, emergency services, and government aviation segments.
• Develop and execute account strategies that drive adoption of the broader Portside platform through cross-sell, upsell, and expansion opportunities.
• Position Portside as a strategic technology partner by aligning solutions to customers' operational, financial, and commercial objectives.
• Build and maintain executive-level relationships with key stakeholders, including C-suite leaders, operations teams, finance organizations, maintenance leaders, flight departments, and IT teams.
• Lead complex sales cycles from opportunity identification through negotiation, contracting, and successful handoff to implementation and customer success teams.
• Collaborate closely with Customer Success, Product, Marketing, and Leadership teams to maximize customer value and long-term account growth.
• Identify opportunities created by mergers, acquisitions, fleet growth, operational changes, and evolving regulatory requirements.
• Maintain a deep understanding of aviation market trends, customer challenges, competitive dynamics, and emerging technology solutions.
• Deliver accurate forecasting, pipeline management, account planning, and territory management while consistently achieving revenue objectives.
• Act as the voice of the customer by providing market intelligence, competitive insights, and product feedback to support Portside's product and go-to-market strategies.
• Leverage CRM, sales intelligence, and AI-assisted tools to improve account planning, prospecting, forecasting, and customer engagement.
• Represent Portside at industry events, conferences, and customer meetings to strengthen relationships and expand market presence.

Qualifications

• 5+ years of experience in enterprise SaaS sales or strategic account management roles.
• Experience selling into aviation, transportation, logistics, financial services, or other complex operational industries is preferred.
• Proven track record of growing existing accounts through expansion, cross-sell, upsell, and strategic relationship management.
• Experience managing complex sales cycles involving multiple stakeholders and executive-level decision-makers.
• Strong consultative selling skills with the ability to align technology solutions to business outcomes.
• Experience developing and executing strategic account plans and territory growth strategies.
• Strong communication, presentation, negotiation, and relationship-building skills.
• Ability to leverage data, analytics, CRM platforms, and AI-assisted tools to drive sales effectiveness and forecasting accuracy.
• Knowledge of business aviation operations, fleet management, flight operations, maintenance, or aviation technology is a strong plus.
• Ability to thrive in a fast-paced, high-growth, and collaborative environment.

What We Offer

• Competitive salary and performance-based commission structure.
• Health, dental, and vision insurance.
• Flexible remote work environment.
• Professional development and career growth opportunities.
• Opportunity to help shape the future of aviation technology at a rapidly growing, market-leading software company.

Portside is an equal-opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.