Trip Assist Sales Representative

United States, Remote

Portside ( is a leading provider of modern software solutions for the business aviation industry. Our cloud-based operating system for business and government aviation is designed to support all aspects of flight operations, including flight operations management (Avianis, BART and PFM brands), fleet and crew optimization (Optimizer), data sharing, reporting & analytics (Owner Portal), customer billing (ExpensePulse), crew recruiting (Staffing Marketplace), crew and passenger travel accommodations (TripAssist), and safety management (Baldwin SMS). With 1,000 customers and over 10,000 aircraft on the platform, Portside is the go-to solution for operators of business, government, military, helicopter, charter, fractional and medevac fleets worldwide. We are a team of 150 professionals with a passion for building great products that support one of the most dynamic and rapidly evolving industries.

Seamless internal and external system integrations are at the core of what we do. Our customers use anywhere from 5 to 20 different systems to run their flight operations. Reducing friction by minimizing repetitive data entry is key to the success of our platform. We are looking for a Trip Assist Sales Representative to own the day-to-day execution of our Trip Assist Sales Pipeline. This is a remote position – you will be working closely with the sales team and may be required to travel up to 25% of the time. We will consider candidates with a range of experience and are prepared to train the right person who is smart, ambitious and eager to learn.


  • Manage sales pipeline from lead generation through onboarding.
  • Execute outbound sales strategies to identify and engage potential clients.
  • Manage Salesforce effectively to track leads, opportunities, and sales activities.
  • Effectively communicate product offerings, including product demos, to potential clients.
  • Establish rapport with leads through effective communication and relationship-building.
  • Demonstrate adaptability and problem-solving skills in a fast-paced environment.
  • Collaborate with cross-functional teams to ensure a cohesive approach to sales.
  • Maintain a customer-centric focus throughout the sales process.
  • Demonstrate persistence and resilience in achieving sales targets.
  • Embrace continuous learning to stay updated on industry trends and product knowledge.


  • Product familiarity and knowledge (aviation software, scheduling systems, etc).
  • Salesforce management skills.
  • Proficiency in prospecting tools.
  • Understanding of communication tools and use.
  • Lead qualification expertise.
  • Market research capabilities.
  • Building rapport with clients.
  • Adaptability.
  • Problem-solving skills.
  • Collaboration with team members.


  • Prior experience in the aviation industry, with a particular preference given to part 91 and 135 experience.
  • Proven experience as an SDR or BDR in a similar role.
  • Experience with outbound sales and lead generation.
  • Familiarity with startup or early-stage company culture.
  • Excellent communication and interpersonal skills.
  • Ability to work independently and collaboratively within a team.
  • Results-driven mindset with a focus on achieving sales targets.


  • Competitive salary commensurate with experience plus commission.
  • Full benefits package.

Interested? Email us your cover letter, resume, and linkedin profile to .