Leading in a post-COVID World—a Conversation about Leadership with James Stirk, Tradeshift

A couple of weeks ago we sat down to talk with James about his very personal journey with mental health issues both in the workplace and at home. Today, we’re publishing a video and transcript from that same interview where he spoke about his leadership style and how it has evolved over the last couple of years.


Can you tell us a little bit about your career path and what brought you to Tradeshift? 

James: At the beginning, I never thought I’d get into technology technology—who wants to be a techy? Truth is, most people are now. I’ve had quite a varied experience. 

I’ve been a support analyst I’ve been in direct sales. I carried a bag in the field as an AE, and I’ve been through various leadership roles. And that experience has given me a really varied lens on how to make decisions. I consider myself very approachable. I think gone are the days of those big scary managers that nobody dares approach or talk to.

Leadership is about empowering people and giving them the confidence to ask for help.  One thing I learned in my own journey was to not be scared to ask for help if you don’t know how to do something. And there are many individuals in the world who are afraid that by putting up their hand and asking for help they’re actually exposing a weakness.

And that’s such the wrong mentality to take. If you don’t know, it’s important that you feel you can ask.


You introduced us to The 4 Ps recently, why are they important to you and which one is your favorite?

James: So here’s a quick refresh for everybody who hasn’t heard of the 4 Ps before: they are People, pipeline, partnerships, and process evolution. and they’re really what I believe to be the building blocks to achieving growth, sustainability, and stabilization for any organization.

The first P, People, are the most important asset in any business—all of those other things become irrelevant if you don’t get the first one right. So really, for me as a leader, it’s how you embrace the people and nurture those people into being the best that they can be because the best they can be makes us the best we can be.

In a sales organization, the second most important thing is pipeline. Without pipeline, we can’t sell. Next, partnership enablements are critical in terms of internal partnerships between the different lines of business and also with our partner ecosystem on the outside. And then, finally,  process evolution—If some process is not working somewhere then we have to evolve it, change it, or get rid of it.

There’s a huge amount of work under each one of those 4 P’s that we—I, all of us—need to achieve, but if we identify what those work streams are and address them, it’s a win-win for everybody.


How do you coach your team to handle both success and failure—And can we learn more from one than the other?

James: We learn more at failing than we do at succeeding because in human nature, we don’t want to fail. And I think some of the most successful people I’ve worked with, you know, it’s how you embrace and learn from those failures that makes us all bigger, stronger, and better people. So somebody that comes to me and says, you know, I’ve got a hundred percent track record. I’m the best thing since sliced bread.

I know that’s not true. They know that’s not true. We have to learn. And the only way we learn is through failing.


Let’s talk a bit about culture; Rucker famously said that culture eats strategy for breakfast. Is this a statement that you believe in and if so, why?

James: I believe that culture does eat strategy for breakfast. Now, one of the reasons I joined Tradeshift was around the culture. I mean, let’s just look at where we’re at. We have an amazing product portfolio. 85% of what we do—Digitizing transactions, invoicing—It’s done, manually. The ability for us to grow prolifically and succeed is enormous. It’s, it’s ours to lose if we don’t get it.

That’s why there’s so much work that I and the senior leadership team are doing. To evolve and connect and make the right things happen. And in my short tenure with Tradeshift I haven’t found anything yet that is broken. There are inefficiencies and things we need to do differently but all the building blocks are here.

AP automation can be a dry subject matter—building the world’s largest network or community, not so much.


Any final thoughts?

James: The total addressable market for Tradeshift is enormous. Nobody else out there can do what we can do. There are many players, many, many competitors but the network and the surrounding applications we have for this are colossal. So really, we’re looking at how we can evolve our business and become something special.

It’s time for every single one of us to believe in what this opportunity represents. If we get this right.

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