Come Join our Team!

Director of Operations

Location: Delta, BC

Tailwind Transportation Software, a fast-growing logistics software company, is looking for an experienced Operations leader 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.

You will join an emerging business with 20 people – one that is expected to double in size over the next 18 months. The position comes with a mandate to help grow and scale the company operations to meet the increasing demand of customers participating in a rapidly changing industry as global supply chains get reengineered and increasingly digitized.

Reporting to the President, you will be responsible to the people, processes, and infrastructure necessary to support a growing business, managing the Customer Support, IT & Administration, departments while liaising with other departments. Serving as a key member of the senior management teams, you will be at the intersection of a company working in a multi-faceted role that involves internal departmental communication, and external customer communication, in equal measure.

Candidates should have at least seven years of experience in an Operations role with a software business. You will have a strong bias for action and a history of executing on your priorities. The candidate must have the ability to work well with all stakeholders – customers, colleagues, and partners – to create a customer experience that will set the new benchmark in the freight transportation industry.

Candidate should also have strong verbal and written communication skills, combined with a coaching ethos. The ability to work directly with customers to model best practices for staff is essential to this role. Complementary to these abilities is strong technology knowledge and orientation towards scalable process development.

The company offers a competitive salary, plus an incentive on revenue, along with a benefits package that includes a gym membership to a facility 100 yards away. Located in Delta with free parking allows you to avoid the traffic and congestion of a downtown commute.

Opportunities to participate in employee equity program available after one year of employment.

Tailwind promotes a balanced work-life environment, supporting employee wellness, strong communities, and environmental sensitivity.

Please submit your resume with Introductory letter to

Business Development Representative

Location: Delta, BC

Tailwind Transportation Software, a leading software as a service company serving logistics and trucking companies across North America, is looking for passionate, professional and ambitious sales representatives who want to join a fast-growing software business at our Delta, BC location.

Candidates should be comfortable connecting with customers in a multi-channel universe: phone, email, chat, video. Work involves following up to inbound phone inquiries, internet leads, and outbound phone calls, capturing information and details in a CRM system.

Must be computer literate and a good communicator, with the ability to write and speak English fluently. Additional language ability is also desirable.

Successful candidates will be selling software subscriptions, start-up implementation packages, along with ‘Pre-pay Discount’ contracts to trucking companies and freight brokerages across North America, and around the world.

Skills and qualifications required:

  • Good phone presence
  • Customer focussed with high attentiveness to customer service and follow-up
  • Computer literate – strong keyboarding skills
  • Familiarity with CRM software applications (Salesforce)
  • Strong communication skills – listening, speaking, writing
  • Some post-secondary education
  • Ideal if you are familiar with the trucking or logistics industry


  • Salary
  • Generous commission program
  • Benefits
  • Gym-workout benefit (gym facility 75-yards away)

Work for a company that promotes life balance, and is focused on servicing one of the fastest growing technology sectors in the world – global supply chain systems.

Tailwind is an equal opportunity employer and complies with all employment guidelines and regulations in the province of BC.

Job Type: Full-time

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

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.