Enterprise Sales Executive

Job Summary Portside is seeking an experienced and results-driven Enterprise Sales Executive to expand our presence in the airline sector. This role is focused on prospecting, selling to, and closing deals with large airlines. The ideal candidate has a deep understanding of airline operations, extensive experience in enterprise software sales, and a proven ability to navigate complex sales cycles with large, global carriers. Travel is required up to 30% of the time for this role.

Key Responsibilities Identify and engage key decision-makers at major airlines, including executives in operations, finance, IT, and commercial strategy. Drive end-to-end sales cycles, from prospecting and initial outreach to contract negotiation and closing multi-million-dollar deals. Sell Portside’s airline solutions, including custom projects spanning the Flight Scheduling and Optimization, Crew Management, and Data Analytics platforms, tailoring demonstrations and proposals to address airlines' operational challenges and efficiency goals. Develop deep relationships with airline stakeholders, ensuring high client satisfaction and long-term partnerships. Collaborate with marketing and product teams to create messaging, sales collateral, and go-to-market strategies for airline solutions. Maintain a pulse on industry trends, competitive offerings, and evolving airline technology needs to position Portside as the leading solution provider. Qualifications Bachelor's degree in Business, Aviation Management, or a related field. Minimum of 3+ years of experience in enterprise sales, with a strong track record of selling to and closing deals with major airlines. Deep understanding of airline operations, scheduling, crew management, and revenue optimization is a must Proven ability to exceed sales targets and manage complex, long sales cycles within the aviation industry. Exceptional communication, negotiation, and presentation skills. Ability to work independently in a remote environment while collaborating effectively with internal teams. What We Offer Competitive base salary with performance-based bonuses. 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. While this role is open to candidates across Canada, unfortunately we are not able to hire in Quebec at this time.