Who Uses This Software?

Small to medium-sized trucking companies with three to a hundred trucks. Companies moving from pen & paper and Excel, to those who are experiencing and need to effectively manage rapid growth.


Average Ratings

38 Reviews
  • 4.5 / 5
    Overall
  • 4.5 / 5
    Ease of Use
  • 5 / 5
    Customer Service

Product Details

  • Starting Price
    $69.00/month/user
    See pricing details
  • Pricing Details
    Three packages to choose from starting at $69.
  • Free Trial
  • Deployment
    Cloud, SaaS, Web
    Mobile - Android Native
  • Training
    Documentation
    Webinars
    Live Online
    In Person
  • Support
    Online
    Business Hours
    24/7 (Live Rep)

Vendor Details

  • Tailwind Transportation Software
  • www.tailwindtransportationsoftware.com
  • Founded 2002
  • Canada

About Tailwind TMS Software

True web-based trucking software. No set-up fees. No contracts. Free 30-day trial. Tailwind improves cash-flow & profits for small to mid-sized trucking companies and freight brokerages - and those that do both - allowing them to compete with the big operations without the $30+K price tag to get started. This all-in-one TMS helps manage operations, customers, dispatch, admin & accounting. It also includes the free 'POD Complete' Android trucking app, and integrates with QuickBooks Online.


Tailwind TMS Software Features

  • Billing & Invoicing
  • Customer Database
  • Dispatch Management
  • Driver Management
  • Driver Settlements
  • Fuel Card Management
  • Fuel Management
  • Load Optimization
  • Maintenance Management
  • Mileage Tracking
  • Quote Management
  • Recruiting Management
  • Routing
  • Scheduling
  • Trip Logs
  • Vehicle Tracking

Tailwind TMS Software Reviews

The culture of Tailwind is quality and everyone is very knowledgeable, helpful and kind.

Aug 10, 2017
5/5
Overall
5 / 5
Ease of Use
5 / 5
Features & Functionality
5 / 5
Customer Support
5 / 5
Value for Money
Likelihood to Recommend: 10.0/10 Not
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Pros: The fact that Tailwind is an "all in one application" helps us run the business more effectively and we have access to it from any device. The features are unique and the platform is constantly improving to fulfill every need.

Cons: I have a hard time coming up with something because if I do have an issue that needs to be resolved right away, I immediately have a solution from Tailwind's support system.

Overall: All I need to make our business going : Database, Accounting & Administration, Equipment and Driver Management, Quotes and Orders, Alerts and Load Tracking & Reporting. Among many other operations. Thank you, Tailwind!

Customer Support is superb! They develop software targeting user feedback. Best service in my book!

Jun 03, 2017
5/5
Overall
5 / 5
Ease of Use
5 / 5
Features & Functionality
5 / 5
Customer Support
5 / 5
Value for Money
Likelihood to Recommend: 10.0/10 Not
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Pros: Dispatch and operation work flow. New order screen has all features on one page. This was created after listening to customer feedback. Their updates happen so fast following feedback, big thumbs up to the development team.

Overall: As a startup business I easily completed integration and worked efficiently from day one. The invoicing is very detailed collecting information from the normal workflow of dispatch to billing. Tailwind has developed a very powerful platform with customizable features for any size business. During integration their customer support via live chat that stays with you on each screen is amazing. It's as good as having an in house IT department in your office working on your system all day. Truly amazing customer support. The training videos allows you to continually go back and learn the basics. The way the system operates and the access to training videos, makes on boarding new employees a snap. They basically do it for you with all of the videos. Lynda is the dedicated trainer and she rocks!!!!

Easy to use with excellence!! Sophisticated and very well designed!

Apr 11, 2017
5/5
Overall
5 / 5
Ease of Use
5 / 5
Features & Functionality
5 / 5
Customer Support
5 / 5
Value for Money
Likelihood to Recommend: 10.0/10 Not
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Pros: User friendly, excellent technical support, friendly team

Cons: Nothing I can think of right now

Overall: IN the past, I worked on different dispatch software, however, when I was introduced to TAILWIND, I fell in love with it. It is very user friendly, outstanding technical support, very well organized training with super friendly TAILWIND team, who are always there for you, whenever you need them...........TAILWIND rocks my transport dispatching world!

Recommendations to other buyers: TAILWIND provides excellent training. Attend the training sessions, listen carefully and ask questions. Lynda will teach you to become a pro with the software.

Great Software Very User Friendly

Jan 31, 2017
5/5
Overall
5 / 5
Ease of Use
5 / 5
Features & Functionality
5 / 5
Customer Support
5 / 5
Value for Money
Likelihood to Recommend: 10.0/10 Not
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Extremely
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Pros: They have simplified the settings to the point you can customize it to fit your business whether its asset based or brokerage or owner operators

Cons: I have not found anything i dont like they have addressed all our concerns and adjusted their software to fit us

Overall: Just got off the phone with rep and I wanted let everyone at Tailwind know how impressed we are with your system. This is the most user friendly and customizable software we have looked at. You are headed in the right direction because not everyone does it the same and you have created your software with that understanding in mind. Thanks for all the hard work and listening to our ideas and being able to make those ideas work.

Excellent TMS

Jun 23, 2016
5/5
Overall
5 / 5
Ease of Use
5 / 5
Features & Functionality
5 / 5
Customer Support
5 / 5
Value for Money
Likelihood to Recommend: 10.0/10 Not
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Pros: We are continuously utilizing more and more of the components of the software every day. TW can be as small or as large a part of your TMS system as you want it to be.

Overall: Tailwinds is very user friendly and has customizable features that can be done at the user level or through their support network.
Run into an issue? Just call or email their support team, responses are always quick and solutions just as good.

Tailwind is great!

Jun 20, 2016
4/5
Overall
4 / 5
Ease of Use
4 / 5
Features & Functionality
4 / 5
Customer Support
4 / 5
Value for Money
Likelihood to Recommend: 10.0/10 Not
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Pros: Data only needs to be entered once
Fewer errors
Allows tracking of previous loads so you can look at history to help with the future loads

Cons: There are a few bugs we are ironing out.

Overall: Our initial experience with Tailwind was a little "rough". However, John and Kyle worked with us and saw us through our implementation problems. What I really like about Tailwind is the support. The support team is responsive and appropriately reactive. With respect to the program, it is organized and user friendly. We broker in our business and had tried some demos with other transportation management systems but they didn't fit as well as Tailwind has. Tailwind makes our work more efficient, there are fewer mistakes made as you only have to enter the data once and we can see the process through to billing. Tailwind has helped our business to grow and become more profitable.

Tailwinds rating review

Jun 17, 2016
4/5
Overall
4 / 5
Ease of Use
4 / 5
Features & Functionality
4 / 5
Customer Support
5 / 5
Value for Money
Likelihood to Recommend: 8.0/10 Not
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Extremely
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Pros: It efficiency handles booking and costing of loads, has good credit capabilities built in for reference of potential credit issues, reporting is good with most being able for export to Excel if further analysis is needed, and the cost is reasonable for well working software.

Cons: Sorting capabilities should be based on more than one criteria. This would probably be an easy fix with TW software people.
Clients should get a workshop how to build report generators tailored to their business needs rather than requesting TW software team to built it.

Overall: We started with Tailwinds in 2013 and found that the software developed our internal system to where we could increase both dispatchers and accounting efficiencies. Working together with Tailwinds, we've increased our business significantly without any development problems with the volume increase.

Recommendations to other buyers: Software team are good to work with and good at understand issues without having to explain them at length.

Very pleases with the classes and satified with Tailwind

Jun 09, 2016
5/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Comments: The training classes were informative and Lynda thoroughly answered all of my questions. I am very new to the transportation industry - Lynda took the time to explain the terminology to me so I have a better understanding of the industry in general and my business specifically. The program is fairly easy to understand once you go to training and if you access Lynda to have a private session. The program absolutely saves me time by helping me to get organized with my tasks. I deal with the accounting side of the business and because Tailwind has a colour coding system in place, I am able to see what invoices are due ahead of time. I will be able to get my invoices in and out ON TIME. My staff in the Dispatch side of the business tell me that Tailwind has really helped them to do their jobs well. Lynda, has a very nice demeanour and voice so she is not only knowledgeable but also very easy to listen to.

Gretchen Hayes, Reliable Source Logistics
Account Manager

Great Tool & People

Jun 02, 2016
5/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Comments: We were able to adapt the Tailwind platform with ease and the learning curve was short. System has a lot of functionality and the support by their staff is excellent! Greatly enhanced our capability to manage our transportation services.

I would definitely recommend Tailwind!

I have used the software since its inception and experience all the updates

May 26, 2016
3/5
Overall
4 / 5
Ease of Use
3 / 5
Customer Support

Comments: The software is easy to understand and provides all TMS functions from dispatch, AP, AR, to account management reporting. It has some nice features due to its integration with mileage programs, posting sites, and reporting. CMS supports multiple users and most importantly works using multiple currencies for CDN and USD.

Some sections need improvement because of extra page clicks, but I am told this will be addressed soon.

Useful, easy-to-use software and excellent customer support

May 25, 2016
4/5
Overall
4 / 5
Ease of Use
5 / 5
Customer Support

Comments: The software is good for tracking shipments and for the visibility it provides for all of our employees. Anyone in the office can pull up the orders and dispatches and know exactly what is happening. We phone in to the support department to ask for help with invoicing and generating reports. I appreciate that they get back to us promptly, within the same business day, and that they have a great way to connect with us on an interpersonal level. The software is easy to learn and we know who to call to get our questions answered. The support department is great at explaining the system to us in plain language that we can understand. As our business grows we continue to learn about how the system can help us further.

Great Product, easy to learn

May 16, 2016
5/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Comments: Tailwind is easy to use, and very compatible with our needs. The support staff is helpful. We have had great business success with Tailwind

Excellent

May 16, 2016
5/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Comments: We needed a system to make confirmation sheets and were using pen and paper to run our business. I contacted Tailwind and had a demo with Lynda. We got our logins and watched two training videos on our own time. The program was super easy to learn on our own. It was extremely self-explanatory. It took me one month to learn how to use the system. I could have learned it in one week, but I was really busy at work. If I had a question, I got an answer from your support department and your trainer within 1-2 hours. Tailwind stayed in touch with me regularly. I never felt alone in learning how to use the system. Now our business is more organized and I can work from home when I need to.
Kourtney Haese
Seven Oaks Dairy

Great!

May 13, 2016
5/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Comments: I have had a great experience with the software there are a lot of functions included that I do not utilize however should I choose to the staff is very responsive and would gladly be able to train me on anything I needed to know.

Easy and efficient

May 13, 2016
5/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Comments: Tailwind has made our daily routine much easier and efficient. Tracking equipment, payables and receivables, as well as, sending orders and quotes is quite simple. Tailwind's support department is good, anytime we have a problem we are able to get answers promptly. I did a little bit of training with Tailwind's trainer, but I mostly learned how to use the system by navigating through it on my own. I found it easy to use, it made sense to me.

This software IS awesome!!

May 13, 2016
5/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Comments: We are a small company, it's just me, my emlpoyer and 5 drivers. We just received our authority two years ago. The old software we were using was very tedious and I never heard back from their support department when I needed help. With Tailwind I can punch in 5 dispatches in less than 15 minutes, it used to take me about an hour. I save a significant amount of time using Tailwind. The training is wonderful, I appreciate the Q&A classes and the structure that is available to learn how to use the system. Your trainer is quick to accommodate and can answer all of my questions. Tailwind's support department is incredible, I have a solution to a technical problem within 20minutes they have called me directly instead of sending me emails, making it easier for this old dog to learn new tricks

Tailwind

Mar 09, 2016
5/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Comments: "There is no other way to go than being on a maintenance and support plan with Tailwind. I have noticed a huge improvement with the new Customer Success Platform that is being offered. Previously, we were not using the system to its full potential. Angelena reached out to us this year and ensured that we are receiving the attention we require. Specifically, as a Platinum customer I will receive a one on one session with the "awesome" Lynda Clare. I am confident that as a result of this intervention we will receive all the help we need to learn how to use the system comprehensively and to run reports that will further align my business needs with the Tailwind Software. If we have a technical problem your support team helps us immediately and our issues are resolved. I have enjoyed the stability of your support team; Mark, Sandy, Eg and Richard are all great at their jobs and walk us through to the answers we require. Working with Tailwind in 2016 will enable me to get my business to the next level of success."

We made the transition from a custom DOS program to Tailwind last year 2015

Feb 03, 2016
5/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Comments: Our old system was DOS based and when we upgraded our computers we needed to get a new Transportation Management System. After a year of using Tailwind, I feel like I understand how to use the system, I can get help when I have a problem and I have the ability to cross-train with my staff so the system is continually adapting to our evolving business needs.
In just 1 year Tailwind Support has grown and it shows. As a Platinum customer, when I call in with a technical issue, your support team answers the phone promptly and logs into my system to help me. They can see my screen, I love learning and your support team helps teach me how to tackle my software issues. Customer service is better than ever. I would recommend to all of your customers to choose a Platinum level Maintenance and Support Plan.

Adaptive Software with a Terriffic Staff

Jan 20, 2016
5/5
Overall
4 / 5
Ease of Use
5 / 5
Customer Support

Comments: Tailwind has been a wonderful company to work with! As a specialized transportation company, it was very difficult to find a software program on the market to fit our dispatch, accounting, and maintenance needs without breaking the bank. Tailwind has been able to meet all of our needs and is continuously adapting to make sure the software works for our business. The support team is very responsive and always finds an answer to our problem. We are still adjusting to a new software program, but we are thankful that we chose Tailwind!

excellent. always there when we need them.

Nov 20, 2015
5/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Comments:
Jag Nahal Owner of Manney Transport:
Tailwind is a huge part of running our business and a necessary tool for all companies who handle varying types of loads. We specialize in local, flat bed, intermodal, and long haul loads, they are all different. Tailwind is easy to customize making it efficient for us to track our loads including the multiple picks and drops we need to follow. I know that dry van and reefer load tracking is just as strong within Tailwind. We also are able to track and complete all our accounting functions, which is invaluable and necessary for any company. I've never had a complaint with the ability, and availability to receive support when learning a new feature or adding to the vast capabilities of Tailwind.

Excellent

Oct 09, 2015
5/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Comments: Tailwind has given us greater visibility into our dispatch and invoicing, as well as our daily operational challenges. It is extremely rewarding to work with a company that has such exceptional customer service!

A Complete Trucking Software Package

Oct 05, 2015
4/5
Overall
4 / 5
Ease of Use
5 / 5
Customer Support

Comments: Pros: Ease of use, simplistic tracking, comprehensive billing.
Tech support is very responsive

Cons: Some quirks when synching to Quickbooks

the software is excellent and very detailed; it takes some getting used to, but it is thorough!

Sep 23, 2015
5/5
Overall
3 / 5
Ease of Use
5 / 5
Customer Support

Comments: About two months ago I temporarily suspended my subscription with Tailwind because I was not fully ready to start my new brokering business. This week I decided to return to tailwind because I remembered how professional and caring the Tailwind team was (specifically, Lynda Clare, Implementation/ Training Manager and Angelena Helten, Client Success Manager). Tailwind left a long-lasting impression that will resonate with me as nothing more than "A1, first-class service!"

Great support

Dec 18, 2014
5/5
Overall
4 / 5
Ease of Use
5 / 5
Customer Support

Comments: Pros:
- Support team is quick to respond to requests and provide solutions.
- Software is easy to use and understand.
- Customizable to match our specific business needs.

Cons:
- User interface could use a refresh.

We have been using Tailwind for over 10 years and it has been a big part of our growth. We have recently reviewed the marketplace to ensure we were still being well looked after. After this review it was clear that Tailwind was the best at managing our specific business needs. Including the ability to manage bulk commodity billing, fuel invoice importing, satellite dispatch integration, and freight brokerage.

12345

Mar 06, 2012
3/5
Overall
5 / 5
Ease of Use
2 / 5
Customer Support

Pros: Been with Tailwinds since the start. Gave them alot of ideas to update and make changes. always good to work with.

Cons: Trying to get a straight anwser on features that have to be fixed.

Overall: Program works great when it works.

Teaching Tailwind

Oct 01, 2010
5/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Pros: Love the program. As a teacher at McBride instructing Dispatch training, I find the Tailwind program perfect. Even students with minimal computer skills find the program easy to use. As I don't have 20 years worth of computer skill, I was unsure as to how quickly and how well I could learn the program. Rest assured, if you can turn on a computer, then you can do tailwind. I would recomend(and I have) the Tailwind program for anyone looking for a good dispatch software program.

Cons: no complaints

Overall: Use it, you won't be disapointed

opp Manager

Sep 30, 2010
5/5
Overall
4 / 5
Ease of Use
5 / 5
Customer Support

Pros: I WOULD SAY IT IS A REALLY GOOD SOFTWARE WHICH MEETS YOUR NEEDS , BUT IT WILL TAKE SOME TIME FOR YOU TO GET USE TO IT. AND ONCE YOU DO YOU WILL BE ABLE TO MAKE YOUR DISPATCH ALOT EASIER.I HAVE USED SOME OTHER ONES THEY ARE PRICEE , SO THE BEST THING ABOUT THIS ONE IS YOU CAN PAY IT ONCE AND MONTHLY COST IS VERY LOW. MOST OF THE SOFTWARES YOU ARE PAYING ANYWHERE FROM 150 TO 200 $ WITH THIS ONE YOU CAN GET AWAY WITH ABOUT $50

Cons: THERE IS NOT MUCH I CAN SAY

Overall: I WOULD FULLY RECOMMEND TRUCKING COMPANYS TO USE THIS

Square peg in round hole

Jul 13, 2010
2/5
Overall
1 / 5
Ease of Use
3 / 5
Customer Support

Pros: SQL back-end, integration to Crystal Reports.

Cons: Well considering we have had the software for a YEAR and still haven't got it implemented because of a long series of workarounds and changes in direction, i would say this software's grasp exceeds it's reach.

It has been a very frustrating experience and it does not suit the bulk trucking market well at all. The software is not well designed from a user interface point of view, or a database design point of view - it is incredibly slow even running on new hardware, and is very inflexible in terms of managing billing and payouts. Poor implementation across the board - looks nice on the surface but underneath it's ugly.

They have packed it full of too many under-developed features that are very unfinished and rough-edged - they do not have enough development staff to support this product despite their best intentions, and it forces you to follow a very linear path to get anything done. VERY high maintenance and does not inspire confidence at any level.

Overall: Not recommended for anyone in the bulk transport business or with a high volume of shipments, or for anyone who wants something easy and intuitive.

Excellent program for Transportation.

May 09, 2009
4/5
Overall
3 / 5
Ease of Use
5 / 5
Customer Support

Pros: Very user friendly, very simple and easy to find information. I can get information from 3-4 years from using the system about driver, power units, trailers, customers, vendors etc.

Cons: Load Planning could be a little better.

Overall: Excellent program for Transportation.

9.5 on a 10.0 scale

May 07, 2009
4/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Pros:
has centralized all of our info into one database, with up-to-date tracking information at all times. We

With three locations stretching from coast to coast, our database is centralized. All tracking information is now "real time" and accessible at all times.
We would recommend Tailwind software without hesitation!"

Cons: Cost of additional users is high

Overall: 9.5 on a 10.0 scale

The system is a very good value , customer service is excellent.

May 06, 2009
4/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Pros: Very user friendly, the ability to use templates makes order entry fast & easy.
Integrates very well with Quick-Books

Cons: Would like to see a driver/ tractor planning feature to pre-plan trips.

Overall: The system is a very good value , customer service is excellent.

It's good value for the money spent and I would recommend it to others.

May 06, 2009
4/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Pros: Order entry and dispatching are easily handled with CMS

Cons: Having to use a separate accounting software for financials

Overall: It's good value for the money spent and I would recommend it to others.

Overall, I would recommend this program to any dispatch in the industry.

May 06, 2009
4/5
Overall
4 / 5
Ease of Use
5 / 5
Customer Support

Pros: Tailwinds provides a clear board that uses a variety of colours and headings to make it easy to read and offers a great deal of information. The setup of the program is straightforward, allowing for smooth work processes. The error popups provide a clear explanation of the problem so you know where and how to correct the error. They also have excellent customer support services with representatives who are able to explain things in a manner that is easy to understand. Overall, it is very user friendly.

Cons: The warnings can cause an inconvienence when they continuously popup everytime something is resaved. In addition, refreshing the screen can take a great deal of time in the receivables section.

Overall: Overall, I would recommend this program to any dispatch in the industry. It is a very user friendly system that provides all the necessary information to complete the required daily processes.

I would recomend this program to anyone who is interested in have a user freindly program.

May 06, 2009
5/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Pros: This is a very user freindly program. All features are great and can be user altered for their own preferences. Tailwinds provides excellent support and is willing to work to meet your needs.

Cons: There are no cons to report.

Overall: I would recomend this program to anyone who is interested in have a user freindly program and a support staff second to none. The cream of the crop as far as support goes. I have never experienced anything as good.

Our customers are happier since we installed the software. Their invoices are much more detailed.

May 06, 2009
4/5
Overall
4 / 5
Ease of Use
5 / 5
Customer Support

Pros: Orders will never be lost. If an order is not delivered it cannot be billed. Even if the paperwork is misplaced and the order delivered, we will still have the order in the system to bill.
The ability to sync to our accounting makes our accountants job easier.

Cons: None that I can see.

Overall: Our customers are happier since we installed the software. Their invoices are much more detailed. We can quickly and accurately track loads and never lose orders which has saved us and the customers time and money.

I would recommend this system to any company that had a large enough fleet.

May 06, 2009
5/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Pros: This system is great for trucking businesses. It is fairly easy to learn and has lots to offer. I have yet to stop learning new things from this system. The Driver Pay Wizard is very handy for my department. I am able to immediatley determine if PRO#s have or have not been paid to a driver. My old method was to look through every check they have received from us!

Cons: I sometimes receive some errors that are just randomn. Customer support is always there to help! Thank you Kenny and Kyle...

Overall: I would recommend this system to any company that had a large enough fleet.

The system is very user friendly.

May 06, 2009
5/5
Overall
5 / 5
Ease of Use
5 / 5
Customer Support

Pros: easy to use

Cons: none that comes to mind

Overall: The system is very user friendly. It's so easy to enter new orders, make corrections, research and do invoicing.

We also like how easy it is to look up the company financial sales, cost and receivables by using the report

function that is available. We highly recommend Tailwind; it's been a number one tool for us.'

We are in awe that our dispatching and invoicing can be so streamlined and easy.

May 06, 2009
4/5
Overall
4 / 5
Ease of Use
5 / 5
Customer Support

Pros: Ease of use
Eliminates paper
Security settings for personnel
Management Reports

Cons: Didn't understand just how great the program was thru the sales process until we started using it

Overall: We are in awe that our dispatching and invoicing can be so streamlined and easy and wondering why
we didn't take this step long ago.