Career Opportunities

View our current career openings and apply today!

Why Work at TripStack?

Just a few of the benefits you'll experience when joining the TripStack team

Free Food

Free breakfast, snacks and drinks every day. Weekly free catered lunch.

Choose Your Hardware

Pick your laptop, monitor and desk type. It will be ready for you on your first day.

We Love to Travel

Employees receive great discounts on Flights, Hotels, Car Rentals and All Inclusive Packages for your family and friends


Company Events

Every month or so we get together for fun. Sometimes in the office, and sometimes out at a fun activity after work.

Beautiful Downtown Office

Our downtown Toronto office is stunning with quick access to the TTC and GO.

Competitive Salary & Benefits

We offer a competitive salary and a great benefits package.

Current Career Opportunities

Software (SaaS) Sales Representative

TripStack  is expanding and, as a result, is seeking a skilled Sales Representative who will be responsible for generating and qualifying prospects as well as scheduling and presenting the TripStack product offering. This Sales Development Representative will ensure that the front line of our sales organization is effectively hitting its monthly targets by dealing exclusively with prospects who are properly qualified and are ready to benefit from our platform.


  • Create a go-to-market plan
  • Design and create key sales and marketing initiatives
  • Prepare presentations & proposals and deliver these to potential clients in a timeline manner
  • Create marketing campaigns including email, LinkedIn, etc
  • Achieve designated sales objectives
  • Achieve daily, weekly and monthly activity targets
  • Develop and maintain a pipeline of potential prospects
  • Attend conferences and trade shows to leverage networking opportunities (travel may be required)
  • Expert use of Salesforce CRM (or similar tools)
  • Cultivate relationships with prospects
  • Work closely with TripStack leadership team
  • Proactively share best practices and reports on how to improve our process
  • Understand the offerings of our competitors
  • Act as a liaison between the product and engineering teams
  • Onboard new clients


Skills & Experience

  • Solid understanding of SaaS platforms and highly technical environments
  • Experience selling complex software solutions to executive decision makers
  • Excellent verbal and written skills
  • Exceptional presentation, interpersonal and networking skills
  • Excellent customer service attitude/interpersonal skills, strong ability to quickly and naturally build rapport
  • Superior presentation skills
  • Strong attention to details reinforced by strong work ethic
  • Proven track record exceeding sales targets
  • Highly motivated & self-driven, hunter mentality
  • 5+ years of demonstrable software sales
  • Startup experience a plus
  • Travel industry experiance a plus
  • Bachelor's Degree required

Integration Specialist

We are hiring an Integration Specialist to join the TripStack Customer Experience Team. You will be a key member of the Customer Integration Team, working closely with the Sales and Product teams and report directly to the Director of Product. Your main tasks will include supporting customers who are integrating TripStack products, by providing any technical and business direction that they may require.

If you’re looking for a technical challenge, a motivated team, and the chance to work in a $1.3 trillion industry, search no further.


  • Support all new and existing customer product integrations
  • Develop, implement and review customer integration onboarding and operational procedures and documentation.
  • Acting as a customer advocate with a focus on improving the overall experience.
  • Maintaining a good working knowledge of all customer-facing company products
  • Staying current on all product roadmaps and industry trends.
  • Presenting and demonstrating the value of TripStack products and services to prospective customers.
  • Building long-lasting, mutually beneficial relationships with external contacts and internal departments to create a better customer experience.


  • Degree in Computer Engineering, Business Administration or related field.
  • 5+ years in a technology-driven role.
  • Excellent problem-solving skills.
  • Analytical mindset.
  • Exceptional interpersonal skills.
  • Excellent written and verbal communication skills.
  • Attention to detail.

Software Engineer (TripBuilder Team)

TripStack is looking for a software engineer to join our TripBuilder product team.  The TripBuilder platform analyzes billions of airline route combinations and price points to produce unique flight itineraries at the lowest prices not found online.   Your main responsibilities will be to help build and deliver the TripBuilder platform as part of a team of data engineers, software developers and data scientists.

The ideal candidate is experienced with building solid tested code  and working with a team of like-minded individuals.  We are a dynamic group who value learning, trust, empowerment and teamwork.



  • Build testable products using technologies like Cassandra, Spark, Kafka, Redis, ElasticSearch, and other Big Data related technologies
  • Collaborate with technical leads, developers and key individuals within other functional groups
  • Actively participate in code review and test solutions to ensure it meets best practice specifications
  • Work with data scientists to maximize our products
  • documentation of all processes and code
  • Hands on involvement in the day to day build out of the product as well as through code reviews


  • 3-5 years of software development and deployment experience with at least 2 years of hands-on experience with data-driven applications
  • Experienced in Java, Go, and  Python preferred.
  • Experience working with continuous integration framework, building regression-able code within data world using GitHub, Jenkins and related applications
  • Analytical approach to problem-solving with an ability to work at an abstract level and gain consensus
  • Excellent interpersonal  and communication skills

C# API Developer

We are are looking for C# API developers (Junior to Senior) to join our fast growing team in downtown Toronto.  Our ideal candidate is passionate about development with .NET technologies and has hands on experience with C++, C#, WCF, WCF REST and Microservices.

About you

  • Solid understanding & experience with .NET technologies and a minimum of 2+ years development experience
  • Master of C#
  • Well versed in WCF and WCF REST
  • C++ experience a plus
  • Linux experience a plus
  • AWS experience including EC2, SQS, SNS, Lambda, API Gateway a plus
  • Hands on experience with microservices
  • N-tiered System design
  • Strong background in parallel processing, concurrency and thread management
  • Familiarity with database technologies such as SQL Server, Postgres, NoSQL, etc.
  • Strong problem solving skills
  • Startup experience a plus
  • Team player with strong interpersonal and communication skills

Junior Web Developer

We are always looking for Junior Web Developers to join our downtown Toronto team. Ideal candidates are people who are passionate about web development, love to code and analyze web pages. We will review your submission and contact you if we think there is a fit. We’d love to get back to every person that applies, but we’re only human (for now).

A day in the life:

  • Analyze Low Cost Carrier (LCC) web pages and their structures
  • Analyze the technology being used on a site (jQuery, React, Angular, etc)
  • Evaluate if an LCC is a fit for our platform based on this analysis
  • Build a process to incorporate LCC inventory into our Trip Builder API
  • Jump into existing code and debug
  • Participate in daily stand-up meeting and provide input into the various processes
  • Contribute to projects and initiatives and make the lives of your team easier

About you

  • Love to code
  • Have a strong understanding of  JavaScript, HTML, and CSS
  • experience with C# is a definite asset
  • jQuery knowledge/experience would be a nice-to-have
  • You’re not afraid to speak your mind
  • You’re also ready to learn a lot

Apply for a Career at TripStack