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.



Location: Delta, BC

Company Overview

Tailwind Transportation Software, a fast-growing logistics software company, is looking for an experienced Accountant 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 that includes a gym membership to a facility 100 yards away. 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

Reporting to the President and CFO, the Accountant position will be a key contributor in managing accounts payable, accounts receivable and payroll, as well as preparation and analysis of financial statements. This position will assist in the preparation of the annual budget and will be assigned various financial projects and other administrative functions as required.

Duties & Responsibilities

  • Prepare payroll on a semi-monthly basis including commission calculations and payroll deductions
  • Maintain general ledgers and complete monthly bank account reconciliations
  • Prepare financial statements and analysis including monthly and year-end
  • Manage account payable and prepare ELECTRONIC cheque runs (includes GST, PST, HST payments)
  • Assist in managing account receivables
  • Prepare customer invoices
  • Ensure paperwork is matched and filed appropriately
  • Assist in preparing the annual budget and variance analysis
  • Recommend and implement improvements in business processes and internal control procedures
  • Assist in any financial projects that may arise
  • Assist with other admin functions, as required


  • Currently enrolled in the CPA program or currently holds a Diploma or Degree in Accounting
  • Minimum of two years of bookkeeping experience required with two fiscal year ends completed
  • Experience with an accounting software package, ideally Sage Intacct
  • Experience managing payroll in a similar-sized company
  • Extremely proficient with Excel or comparable development experience, great computer skills required
  • Ability to identify and implement accounting appropriate accounting policies
  • Strong sense of customer focus
  • Ability to work effectively within and collaborate with a team
  • Ability to handle stressful situations in a fast-paced working environment
  • Ability to work independently, time manage and prioritize multiple tasks
  • Excellent English verbal and written communication skills
  • Detail-oriented with the ability to problem-solve with relative ease

Job Type: Full-time

Salary: $55,000.00 to $60,000.00 /year


  • bookkeeping: 2 years (Required)


  • CPA (Preferred)

Job Duties:

  • Accounts payable
  • Accounts receivable
  • Payroll
  • Reviewing and maintaining internal controls processes and systems
  • Presenting budgets and reports to upper management

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

Customer Success Specialist

Location: Delta, BC

About Us

Tailwind is an established and growing software company that serves trucking companies and freight brokers. We focus on helping our customers use our software to run their business more efficiently – freeing up their time so they can grow their business and spend time with their families. Tailwind’s success depends on our customers’ success.

The Customer Success Specialist role is essential to us fulfilling that mandate – you are the primary point of contact with our customers.

We are a tightly knit and diverse team who work together to build a strong business and a positive culture.

About You

The most important requirements of the role are:

1) Excellent Customer Service Skills: proven ability to connect with customers over the phone – you must be able to understand how their technical/business issue is impacting their business and lay out a plan for problem resolution.

2) Good Tech-Fluency: the ability to manage multiple technologies (and screens) at a given time (e.g. service desk software, phone, remote connection to customer, help docs in browsers) while assisting the customer.

3) Desire and Ability to Learn: Tailwind software is complex, as are the business cases it supports – we don’t expect folks to know it all, but we do need you to come in with a desire and ability to learn

Experience in the transportation industryis a big plus. Familiarity with SQL is also an asset, but not required.

The Team

We have an exceptional support team – each member with a different specialization. We work closely to resolve customer issues and collaborate to solve both individual and systemic issues. You will have colleagues to mentor you and to escalate issues to. You will have an opportunity to develop your own specialization within the team. Everyone at Tailwind is essential to our success – we all are given opportunities to contribute both working in the business (directly with customers and in day-to-day operations) and on the business (improving systems to help get us to the next level).

The Work

The Customer Success Specialist’s primary responsibility is to help prospective and current customers achieve success with their Tailwind products and services and ultimately in their business. They resolve customer cases and issues effectively and efficiently,

Duties include

  • Customer Issue Resolution
  • Customer Training
  • Customer Success Communication (outbound/inbound calls/emails)
  • Basic internal IT Support
  • Billing Administration
  • Bug Diagnoses and Reporting
  • Documentation writing
  • Custom report specification gathering
  • Record management
  • Participating in on-call support rotation

Job Type: Full-time

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