Strategic Sales Executive

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.