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


Team Trips

Every year we go away and do something fun with the team for a few days. No work just fun.

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

Technical Lead (TripBuilder)

TripStack is looking for a Technical Lead of our TripBuilder product.  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 plan, design, implement and deliver the TripBuilder platform.

The ideal candidate is experienced leading teams and delivering projects in the Big Data space as well as contributing to the leadership team of a high growth startup.


  • Lead, design and implement innovative analytical solution using Hadoop, Spark, Mongo, Redis, ElasticSearch, and other Big Data related technologies
  • Collaborate with technical leads, developers and key individuals within other functional groups
  • Perform detailed analysis of business problems and technical environments and use this in designing quality technical solutions
  • Actively participate in code review and test solutions to ensure it meets best practice specifications
  • Build and foster a high performance engineering culture, mentor team members and provide team with the tools and motivation to make things happen
  • Ensure systems meet business requirements and industry best practices
  • Ensure documentation of all processes
  • Involved in full SDLC and is expected to lead design, development, and CI/CD operations
  • Hands on involvement in the day to day build out of the product as well as through code reviews
  • Coach & mentor a team of developers with of various experience levels



  • 8-10 years of software development and deployment experience with at least 5 years of hands-on experience with Big Data applications (e.g. administration, configuration management, monitoring, debugging, and performance tuning)
  • 5+ years experience building data ingestion pipelines
  • 5+ years of experience working with AWS Cloud platforms, experience with Azure or Google Cloud is also acceptable
  • Hands on experience with the ELK stack (Elastic, Logstash, Kibana)
  • Hands-on development experience using open source big data components such as Hadoop, Hive, Pig, Spark, HBase, Hawk, Oozie, Mahout, Flume, Kafka, ZooKeeper, and Sqoop (or some combination thereof), preferably with Hortonworks distribution
  • Experience working with continuous integration framework, building regression-able code within data world using GitHub, Jenkins and related applications
  • Experience with programming/scripting languages such as Scala/Java/Python/R
  • Analytical approach to problem-solving with an ability to work at an abstract level and gain consensus
  • Excellent interpersonal, leadership and communication skills
  • BSc or MSc in Computer Science or equivalent

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