Enterprise Sales Executive

Rippling; Remote; CAD 85,000 - 120,000; Full time

Job summary

A leading SaaS provider in aviation is hiring an Enterprise Sales Executive to enhance its presence in the airline sector. This remote role involves engaging with airline decision-makers, driving sales from prospecting to closing multi-million dollar deals, and selling tailored solutions. Candidates should have at least 3 years of enterprise sales experience within the aviation sector and a strong grasp of airline operations. The package includes competitive salary, bonuses, and comprehensive health benefits.

Benefits

Competitive base salary

Performance-based bonuses

Generous time off policy

Health, dental, and vision insurance

Opportunities for professional development

Qualifications

• 3+ years of experience in enterprise sales with airlines.
• Proven track record of closing multi-million dollar deals.
• Ability to exceed sales targets and manage complex cycles.

Responsibilities

• Engage decision-makers at major airlines.
• Drive end-to-end sales cycles.
• Sell airline solutions tailored to operational challenges.

Skills

Enterprise software sales

Communication skills

Negotiation skills

Presentation skills

Understanding of airline operations

Education

Bachelor's degree in Business or Aviation Management

Job description

Portside is the leading SaaS platform serving the global business aviation industry, providing cutting‑edge solutions for management companies, aircraft owners, and corporate flight departments. Our cloud‑based platform supports seamless data exchange, advanced reporting, and powerful analytics to streamline aviation operations.

With a $55M strategic growth investment in May 2024, we are scaling rapidly. We’re looking for motivated professionals ready to drive growth and take on the challenges of a fast‑paced, innovative environment.

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.