Come Join our Team!

Tailwind is made up of REAL people, making REAL products, for REAL people. Our team of highly skilled transportation and software industry experts are on a mission to help small to medium sized trucking companies and break-out freight brokerages grow their business, free up their time, and feel the WIND at their back. We don’t stand much on ceremony. We focus on getting things done, and enjoy a laugh or two (or three or four) along the way.


Customer Success Specialist

Location: Delta, BC

Company Overview:

Tailwind Transportation Software, a fast-growing logistics software company, is looking for a Customer Success Specialist to join the team at its head office in North Delta, BC.

Tailwind creates and markets a software-as-a-service transportation management application across North America and around the world, delivering a solution that helps trucking and freight brokerage companies organize and operate their businesses more effectively.

Tailwind offers a competitive salary, along with a benefits package. We promote a balanced work-life environment, supporting employee wellness and strong communities.

Does this sound like a fit for you? Please send us your resume and cover letter outlining why you’d be a great fit for Tailwind.

Job Description:

As a Customer Success Specialist your primary responsibility is to help prospective and current customers achieve success with their Tailwind products and services; resolving customer issues effectively and efficiently.

Duties & Responsibilities:

  • Assist with the onboarding of new customers including doing data imports to prepopulate their systems
  • Responds to all customer inquiries and enters them as cases whether obtained by phone, email or other channels
  • Resolves product or service problems using the Tailwind resolution process
  • Assessing customer issues and escalation of customer cases as appropriate
  • Ensure that all bugs are confirmed, triaged, reported, submitted and tracked effectively
  • Custom training for our customers
  • Respond to customer queries about their billing
  • Maintain accuracy of all documents associated with customer facing activities, internal application and process documentation
  • Write documentation for review and publishing for customer and internal support department use
  • Participate in On-Call Support services on a rotating basis with other Support team members


  • Excellent Customer Service Skills
  • Past experience doing remote telephone and/or chat support
  • Good Tech-Fluency in a Microsoft environment
  • Desire and Ability to Learn
  • SQL familiarity an asset
  • Transportation Industry knowledge an asset

Job Type: Full-time

Salary: $35,000.00 to $40,000.00 /year


  • Customer Service: 2 years (Required)

Does this sound like a fit for you? Please send your resume and cover letter to