Jason Traff of Shipwell: How To Communicate With Your Team Effectively Even If You Are Rarely In The Same Physical Space

Interview With David Liu

Breaks help. We strongly encourage screen breaks throughout the day to mitigate Zoom-fatigue and sustain team productivity.

Virtual syncs hold value. These help to ensure our teams stay on the same page and complete the tasks at hand. During our daily sync-ups, we even push for a strong “video on” culture to help keep the team feeling connected to each other.

We are living in a new world in which offices are becoming obsolete. How can effectively communicate if they are never together? Zoom and Slack are excellent tools, but they don’t replicate all the advantages of being together. What strategies, tools and techniques work to be a highly effective communicator, even if you are not in the same space?

In this interview series, we are interviewing business leaders who share the strategies, tools and techniques they use to effectively and efficiently communicate with their team who may be spread out across the world. As a part of this series, I had the pleasure of interviewing Jason Traff, President and Co-founder of Shipwell, a cloud-based TMS solution that is transforming the supply chain industry by replacing opaque and manual processes through a tech-enabled, fully connected logistics ecosystem. Prior to Shipwell, he co-founded and ran CopyCat Paintings, a global art reproduction company based in Shenzhen, China that employed more than 1,000 artists and shipped to four continents, and Leaky, an insurance technology startup backed by Y-Combinator that provided over $300 million of insurance quotes. He is a Chartered Financial Analyst and holds an MBA from the MIT Sloan School of Management.

Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

For my undergrad, I went to Texas A&M where I studied finance, mostly because I didn’t know what I wanted to do but knew finance would be beneficial to me in the future. My first job out of college took me to Hong Kong, which I loved. As a private equity analyst for an infrastructure investment firm called ‘AIF Capital’, I was able to travel across Asia and learn about new companies, industries and logistics often.

From there, I started an oil painting reproduction company called ‘CopyCat Paintings,’ which grew to employ around 1,000 people and ship paintings to four continents. I later got my MBA at MIT and started an insurance technology company funded by Y Combinator.

The idea for Shipwell actually came from when Greg and I would share stories of our experiences. It was then when we realized that gigantic companies were all having the same logistical issues that I had with my oil painting business.

Can you share the most interesting story that happened to you since you began your career?

In my first ‘real’ company, CopyCat Paintings, my cofounder was kidnapped by our company driver. Within a few hours, everything was resolved, but it became a running joke that this wasn’t even the biggest problem we had at the company. We faced a lot of issues, but the only one we never fully solved was shipping — for our business, customers and their experience, the biggest issue was still shipping and the lack of visibility and timelines around it. For my cofounder, it was a really bad day, but quickly solved whereas shipping was a pain point until CopyCat Paintings was sold.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Life is not always a matter of holding good cards, but sometimes, playing a poor hand well.” — Jack London.

I like this quote because as an entrepreneur, there is so much that is outside of my control, whether it’s the market, competitors, or something out of the blue. There are only a few things that we can absolutely control, such as how we treat customers and how hard we work at providing a product that improves their lives.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My father. He ran his own business so at an early age, I knew I wanted to start something myself. Just seeing his passion for something he created inspired me to become a self-starter as well.

Ok wonderful. Let’s now shift to the main focus of our interview. The pandemic has changed so many things about the way we behave. One of them of course, is how we work and how we communicate in our work. Many teams have started working remotely. Working remotely can be very different than working with a team that is in front of you. This provides great opportunity but it can also create unique challenges. To begin, can you articulate for our readers a few of the main benefits of having a team physically together?

Of course physically being in the office has tons of benefits, especially for a fast-paced logistics company like ours. But there’s something about in-person interactions, team meetings and brainstorms that is very hard to replicate virtually. Connections are built faster, work is done more collaboratively, improv learning opportunities are available, training is clearer and more efficient, and so on.

On the flip side, can you articulate for our readers a few of the main challenges that arise when a team is not in the same space?

There’s quite a few, but Zoom fatigue is one of them. Staring at screens all day is definitely a concern we have for our team. On top of that, being at home all the time isn’t easy. We all have to make a conscious effort in prioritizing our mental health. We’re all longing for the face-to-face interactions and deeper connections with our colleagues.

Fantastic. Here is the main question of our interview. Based on your experience, what can one do to address or redress each of those challenges? What are your “5 Things You Need To Know To Communicate With Your Team Effectively Even If You Are Rarely In The Same Physical Space ? (Please share a story or example for each.)

1. Breaks help. We strongly encourage screen breaks throughout the day to mitigate Zoom-fatigue and sustain team productivity.
2. Virtual syncs hold value. These help to ensure our teams stay on the same page and complete the tasks at hand. During our daily sync-ups, we even push for a strong “video on” culture to help keep the team feeling connected to each other.
3. A strong workplace culture can still be achieved. Just because we’re not in office, doesn’t mean we can’t continue building a close-knit team. Virtual activities like daily trivia, “Guess Who” baby pictures and even recipe exchanges keep our culture alive.
4. Stay open and candid in communication. Now more than ever, it’s critical for our teams to understand what the future looks like at Shipwell and that we give them full transparency into what leadership is doing to achieve that future.
5. Empower your team with the tools and resources they need to do their job in a new environment. This goes beyond physical tools like laptop, desk, etc. — flexible hours.

Has your company experienced communication challenges with your workforce working from home during the pandemic? For example, does your company allow employees to use their own cell phones or do they use the company’s phone lines for work? Can you share any other issues that came up?

Whether it be a dog barking during a call or poor wifi connections, I’m sure a lot of companies can agree that the transition to work from home hasn’t been completely seamless. That being said, corporate culture is now seeing the human aspect behind work and is growing towards empathizing with employees and providing accommodations. At Shipwell, we transitioned remote in a single day. This brought some challenges with:

• Phones
• Equipment
• Learning to balance meetings vs. quick calls vs. emails

Let’s zoom in a bit. Many tools have been developed to help teams coordinate and communicate with each other. In your personal experiences which tools have been most effective in helping to replicate the benefits of being together in the same space?

Zoom and other video conferencing tools have been great at replicating being together; for me, it’s been nice that I can virtually visit customers from coast-to-coast without losing time to travel.

If you could design the perfect communication feature or system to help your business, what would it be?

The most important parts of communication, whether in-person or virtual, is that it feels fluid and seamless.

My particular expertise and interest is in Unified Communications. Has the pandemic changed the need or appeal for unified communications technology requirements? Can you explain?

Now more than ever there’s a need for unified communications. We all have to be on the same page and not physically being in the same space challenges that. To ensure this, it’s important to be overly communicative during this time. That’s why our teams meet at least once daily.

The technology is rapidly evolving and new tools like VR, AR, and Mixed Reality are being developed to help bring remote teams together in a shared virtual space. Is there any technology coming down the pipeline that excites you?

I see a lot of promise with AR and Mixed Reality to virtually bring people together with a deeper connection than what you can get out of a video conference.

Is there a part of this future vision that concerns you? Can you explain?

I think there’s a lot of unspoken communication that humans are particularly adept at interpreting when we meet in person, and I think you lose some of that fidelity when meeting virtually. For me, the ability to look towards VR, AR, or Mixed Reality to replace in-person meetings depends on the richness of that experience.

So far we have discussed communication within a team. How has the pandemic changed the way you interact and engage your customers? How much of your interactions have moved to digital such as chatbots, messaging apps, phone, or video calls?

At the start of the pandemic, something we are proud of was being able to help many of our customers transition from their usual on-site management through the use of our cloud-based technology, a platform accessible from home. Now, mostly all of our communication with customers is done remotely via regular calls with our customer service team and personalized at-home events. We’ve hosted a few Industry Share events where our customers can relax with a whiskey tasting, cocktail kit or wine tasting and then network with other people in the industry. We discuss things like upcoming trends, strategy and challenges they’ve been experiencing in the past year.

In my experience, one of the trickiest parts of working with a remote team is giving honest feedback, in a way that doesn’t come across as too harsh. If someone is in front of you much of the nuance can be picked up in facial expressions and body language. But not when someone is remote. Can you give a few suggestions about how to best give constructive criticism to a remote team member?

One thing that I’ve found useful is to ask people how their day is going, and to have them give me a green, yellow, or red light example. This way I can have a better understanding if that person is struggling with something material, such as a personal stress, before shifting to a topic that they might be particularly sensitive or unreceptive to at that moment.

Can you give any specific ideas about how to create a sense of camaraderie and team cohesion when you are not physically together?

We’ve experimented with a number of virtual events to create fun shared experiences. One of them was a virtual escape room that we did as a team, where you directed a real person that streamed the escape room experience. It was so much fun!

Ok wonderful. We are nearly done. Here is our last “meaty” question. You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Ever since starting Shipwell, I’ve realized how much waste and inefficiency plays a role in people not having access to food or clean water. In the early days of Covid-19, when shelves were bare, Shipwell helped deliver over 50 million pounds of food and 10,000 pounds of medicine. I thought that was amazing, and the world would be so much better if everyone had access to clean water and food.

How can our readers further follow your work online?

My LinkedIn profile.

Thank you so much for the time you spent doing this interview. This was very inspirational, and we wish you continued success!