The 5 Phases of Growth with Jesse Kaufman at Shipping Tree

Growth is the goal of many driven, hungry entrepreneurial leaders. I have been researching fast-growing companies to see the patterns. In this episode, we look at my work and ability to codify the phases of growth. Today’s guest is Jesse Kaufman, CEO at ShippingTree. Inc Magazine ranked his company #212 on the 2020 Inc 5000 list. ShippingTree is the complete e-commerce fulfillment solution for consumer product companies of all sizes. ShippingTree is a provider of cloud-based logistics and e-commerce fulfillment services for consumer product companies around the world. Jeese and I look through the lens of my research with the five phases of growth. He shares his journey through the leadership of his company. See where you are in the five phases of growth.

Don't miss an episode. Subscribe to Growth Think Tank.

Jesse Kaufman: The Transcript

About: Jesse Kaufman is CEO and founder of ShippingTree, a provider of cloud-based logistics and e-commerce fulfillment services for consumer product companies around the world. With Jesse’s experience establishing scalable customer service techniques, he has continued to drive customer retention and increase conversion rates for retailers. As a result, ShippingTree can improve a brand’s visibility, efficiency, and quality of service while simultaneously reducing operating costs, increasing margins and promoting brand loyalty. By streamlining vital operations of global supply chain service providers and seamlessly integrating with online shopping carts, ShippingTree is a one-stop-shop for e-commerce logistics and fulfillment.


Share the LOVE and TWEET about this episode.

Disclaimer: This transcript was created using YouTube’s translator tool and that may mean that some of the words, grammar, and typos come from a misinterpretation of the video.

Jesse Kaufman: [00:00:00] You have to come to terms with that. There’s a lot of people out there that are way better at doing most things than you are. So you’re like, I was okay at doing customer service for a bit, but I could hire people that are way better and like, don’t get as frustrated as I do sometimes. So I think coming to grips with the offload. Some work to people that you’ve essentially just met. I think that’s a super important skill as a founder too, or a super important blade to keep sharp,

[00:00:32] Intro: [00:00:32] Welcome to Growth Think Tank this is the one and only place where you will get insights from the founders and the CEOs, the fastest-growing privately held companies. I am the host. My name is Gene Hammett. I hope leaders and their teams navigate the defining moment of their growth. Are you ready to grow?

[00:00:49] Gene Hammett: [00:00:49] Every leader goes through five phases of growth, five phases of growth. One thing that I have been organizing with the work I do with fast growth founders, CEOs, to help you understand where you [00:01:00] are, what’s next and how to keep you moving toward what’s really important for you to grow as an individual leader inside of a fast-growing organization. When you think about the chaos of fast. It requires a lot of you to manage that chaos, but it also requires a lot of you to be intentional about what’s next for you so that you can step into that as soon as you’re ready. And as soon as the company is ready for you to move up the level, there’s a lot of content that I’ve created around founder to CEO.

[00:01:29] Today, we talk about that briefly, but we do it in the context of the five phases of growth. Our guest today is the founder of shipping Tree Jesse Kaufman. Jesse is number two 12 on the 2020 Inc list a really impressive growth with their team and really is exciting to see how fast they’ve grown and how he’s made the transition over the five phases of growth. We look at some of the specific details today. I think what you’ll learn most about this is you’re not alone and that you actually can move. To the [00:02:00] next level, some of the mistakes that he has and the regrets he shares openly to help you as a founder, CEO of a fast-growth company. And one of the things I want to remind you before we jump into this interview is if you haven’t already checked out the see if that’s a fit for you because there are people out there gathering together, helping you overcome the challenges that are inside your business. Helping you become a stronger leader, helping you create a culture that drives beyond just your number of hours of work, and creating that is done with intention. If you want to hang out with others and build a community and join us, then make sure you check out you can apply if it’s right for you.

[00:02:38] But the real key here is I will be your coach and your guide through all of these things. So, if you think about what you’re about to hear, I can help you through any of the challenges you are going to face because this is what I’ve done for the last decade. I’d love to help you grow as a leader, just check out and see if it’s a fit for you.

[00:02:57] Now here’s the interview with Jesse, Jesse. See, [00:03:00] how are you?

[00:03:00] Jesse Kaufman: [00:03:00] I’m good, Gene thanks for having me on,

[00:03:02] Gene Hammett: [00:03:02] Excited to have you on the podcast to talk about leadership and the growth of fast-growing companies. , before we get started into this topic today. Tell us a little bit about shipping tree.

[00:03:11] Jesse Kaufman: [00:03:11] So shipping tree is a full-service e-commerce fulfillment company and where we’re platform-driven. So we’ve developed our own merchant-facing order management system and internal facing warehouse management system.

[00:03:25] Gene Hammett: [00:03:25] Love that.  Everyone knows that even though the pandemic and even before that, a lot of shipping. It’s been going crazy and products and online ordering. Have you guys seen a lift in the last year?

[00:03:37] Jesse Kaufman: [00:03:37] Yeah, for sure. It’s, I guess it’s, it’s kind of leveled off now,  in terms of, new entrance to the market, but volume is still very high.

[00:03:46] Gene Hammett: [00:03:46] How long have you been running shipping tree?

[00:03:48] Jesse Kaufman: [00:03:48] So I’ve been at it five years, but we only launched our platform in early 2018. So I really consider the moment we launched our platform when shipping tree really started.

[00:03:59] Gene Hammett: [00:03:59] How many [00:04:00] employees do you have? ,

[00:04:00] Jesse Kaufman: [00:04:00] So full-time, we have 19 right now.

[00:04:03] Gene Hammett: [00:04:03] Okay.

[00:04:04] Jesse Kaufman: [00:04:04] And overall, probably close to 60.

[00:04:06] Gene Hammett: [00:04:06] What I’ve found is that a small company. Have to continuously get done more with less people. There’s a lot counting on each individual person. No one person is, is considered, kind of a commodity and whatnot. You wouldn’t be where you are today without having a strong team by your side. Is that fair to say?

[00:04:24] Jesse Kaufman: [00:04:24] Yes, for sure. And probably, my biggest regret as a founder. Not hiring people quicker than we did.

[00:04:32] Gene Hammett: [00:04:32] Well, let’s dive into that a little bit because today’s topic is about, you know, really making that switch. That transition from founder to CEO. You talked about the biggest regret. Why, why would you say that’s your biggest regret?

[00:04:45] Jesse Kaufman: [00:04:45] Because just looking back at the velocity that we were like post key hire that we achieved, you know, I think this whole journey could have been accelerated a year or two, honestly.

[00:04:57] Gene Hammett: [00:04:57] You know, when you think about you [00:05:00] in the early days of being a founder, you really are the doer of all of this. And, and I know that you quickly moved into a place. Building out a team to build a platform, but let’s go back to the early days. What was it like when it was just you and a handful of people?

[00:05:15] Jesse Kaufman: [00:05:15] It’s tough, you know,  your focus is all over the place. You’re not doing anyone thing, particularly well as a company, to be honest, you know, I think it’s good for founders to be Jack of all trades or polymath, but I don’t think it’s a good attribute of a company to be a Jack of all trade. You know, companies. A good focus.

[00:05:37] Gene Hammett: [00:05:37] And in the early days, were you bringing on people with a specific skill set that allowed you to build the platform and be able to get where you are today?

[00:05:45] Jesse Kaufman: [00:05:45] Yeah, so we, the platform was built half in-house, half with contractors. Due to the speed, we wanted to do it at and everything. But our first, the first hire that really made a difference for me was [00:06:00] an operations analyst slash director. So someone who was much better at running warehouses than I was. That that higher just really allowed us to accelerate quickly.

[00:06:12] Gene Hammett: [00:06:12] I’m glad you went to this first key hire.  What did it, what an impact that really have on you as you were running the day-to-day is having someone that you could offload this one big key.

[00:06:23] Jesse Kaufman: [00:06:23] Oh, it was massive. Like all of a sudden I had, you know, probably 30 to 40% more time to focus on the actual product we were developing and building relationships with existing clients of ours, forging new relationships with prospective clients. It’s like, that’s why, that’s why I said, I wish I hired someone like that 12 months, 12 or 18 months earlier.

[00:06:45] Gene Hammett: [00:06:45] Well, I always feel like it happens when it needs to, because usually there are cashflow concerns and, you know, the timing is really imperfect finding that right person, just, you know, you have to be in the right position to be able to hear that offer and go, yeah, that’s the right fit [00:07:00] for us. Because earlier in, the process you might not have been ready for it. Is that fair to say?

[00:07:04] Jesse Kaufman: [00:07:04] Yeah. Yeah. Like the impetus for hiring that person was we, we signed this merchant. That was massive. And we, I was like, okay, I can’t do this and this at the same time,

[00:07:15] Gene Hammett: [00:07:15] So we look back at it and things had to line up, for that key hire to take place. I want to kind of fast forward, right after the key hire, opening yourself up to some of these more valuable projects that only you could do as the founder, the key relationships, and maybe even, you know, growing the company in new areas. What opportunities did that open for you?

[00:07:36] Jesse Kaufman: [00:07:36] You know, in this business it’s so important and like in most service-based businesses, it’s so important to have a close relationship with your, your customers, especially the key ones. So it really allowed me to build that relationship outside of the direct operational relationship between our two companies. So that was big. And then, like I said, focusing. [00:08:00] On the product we were developing, which is really like the secret sauce to shipping tree.  Before this key hire easily, half of my time at least was spent in the warehouse, making sure you know, the right things aren’t happening there and that there’s enough labor, or anyone who’s running a warehouse knows what goes on.

[00:08:19] Commentary: [00:08:19] Hold on for a second. Jesse just talked about what happens after the keys. Well, when you think about your job as a CEO, you want to make sure that you are continuously leveling, what you’re focused on, and you have to focus on the most valuable projects. Jesse talked about the strategic partnerships and the product itself. Maybe that’s what you have to focus on next. Or maybe it’s the equity raise that you have to go after. Maybe it’s the culture and the people and hiring the right. Maybe it’s removing challenges that we can’t even see because you’re so deeply entrenched in the vision of what’s going on in this company.

[00:08:55] Your job as a CEO is to hire the right people so that you can focus [00:09:00] on the most valuable. But the problem is a lot of people get stuck. They get, they hold on for way too long. The regret that Jesse said earlier in this episode, he really wished that he would’ve done this sooner. Well, everything happens for a reason, but you’ve probably had similar regret in your own journey as a CEO of a fast-growing company. So just keep that in mind, as you continue to evolve. And back to Jesse,

[00:09:22] Gene Hammett: [00:09:22] Jesse, when you think about the continuous work that you have to do to go from founder to CEO, walk us through some of the milestones that you had to. Many of them can look back at that first hire, but there’s a lot of steps after that. What comes to mind for you?

[00:09:37] Jesse Kaufman: [00:09:37] Yeah. So after that first hire, there was kind of like an epiphany I went through where you have to come to terms with that. There’s a lot of people out there that are way better at doing most things than you are. So you’re like, I was okay at doing customer service for a bit, but I can hire people that are way better and like, don’t get as frustrated as I do sometimes. So I think coming [00:10:00] in. To grips with, offloading some work to people that you’ve essentially just met. I think that’s a super important skill as a founder too, or a super important blade to, to keep sharp.

[00:10:14] Gene Hammett: [00:10:14] Now, I don’t know if you think about this intentionally the way I do, because I get a chance to talk to a lot of founders, just like you, that are in the overwhelm of day-to-day. Even with 19 employees, I know you’re still in. You know, heavily into customers and product development and whatnot, but are you consciously thinking about how to fire yourself from the next role so that you can bring on someone else or raise someone else that’s already on the team to take over that responsibility for you?

[00:10:41] Jesse Kaufman: [00:10:41] So I think at the stage that we’re at now, it’s less about firing myself overrule. And more about giving those people I’ve put in position support and making sure they have the support because as the company grows like that key operations hire is essentially in the same [00:11:00] position I was when he hired him like there’s so much stuff going on in his department than his time. I know his time would be better spent, on certain things. And there are other things that are eating up too much of his time that I could put someone in there under him to support. So I think as a company grows, the founder’s job really becomes,  like the general manager of a sports team is like making sure the pieces are in place so that the company is healthy, ready to go. At all times,

[00:11:27] Gene Hammett: [00:11:27] I use a lot of sports analogies because most of my clients are men. Women get some of the basics work analogies as well, but managing the sports team has a really good fit there because no longer can you always be the person doing the work, but you gotta be the person that sits in the office. And make sure that people have all the tools, all the resources and you are aligning things together and keeping everyone aware of what’s going on through proper communication. , is that, that fit kind of the way you roll now?

[00:11:57] Jesse Kaufman: [00:11:57] Yeah, my job is,  [00:12:00] making the company’s vision extremely clear for the employees, and for my team and making sure my team has what they need to. So division,

[00:12:09]Gene Hammett: [00:12:09] I’ve recently mapped out five different stages of this. I want to ask you a question in each of the stages, just to get your feeling and your input on that. I’ll give you an idea of the top stages is our vision, , leading, directing, managing, and doing it. So we’re going to go down to the bottom, to the doing stages. And I know we talked about this earlier, Jesse, but when you were doing the work, what was the main thing that you were feeling and what was really going on inside of, of what was going on inside the company?

[00:12:39] Jesse Kaufman: [00:12:39] You feel like, at a certain point, you start getting at the beginning, it’s crucial so that you understand. What needs to be done, but at a certain point you start getting overwhelmed and you really feel your focus begin to splinter and the quality of stuff you’re putting out there diminishes for sure.

[00:12:57] Gene Hammett: [00:12:57] Perfect. Now the next one’s around [00:13:00] managing and I kind of jokingly call this managing the chaos, because if you are in fast growth, nothing is controllable managing chaos. See the smile on your face.  What’s it like when you’re managing chaos? ,

[00:13:11] Jesse Kaufman: [00:13:11] Like the once you’re in, you start building a team and you go from like that solo operator to, in the trenches with a team that you’ve built. That’s like a, I look back on those times, it’s fun and, you know, figuring out things and setting up systems that we’re still using today.

[00:13:28] Commentary: [00:13:28] Hold on for a second, I know I quickly went over what the five phases are, but I want to take a little bit of a moment here to share them with you in detail. , this is very quick, but, , you want to make sure you understand what these different phases are in the five phases of growth. The first one at the top layer is visioning. Are the vision for the company you create what it will look like when you get to where you’re going? Well, your job is to communicate that as much as you can, but the problem is you can’t do it all the time in the early stages. So you’ve got to also lead the people. So if you’re spending more [00:14:00] time leading, then you’re in the leading right.

[00:14:02] That is where you’re developing people. You’re making sure the right people in the right seats and you are mixing, removing any energy blocks or toxic people to the culture. And to really got your finger on the pulse of leading the people across the organization. Now below that is directing, directing really is that whole concept. You’ve let go of a lot of things, but you’re still hands-on, you’re still kind of, you know, going to a lot of meetings, but you’re directing the work more than you’re leading the people. And that’s what happens with a lot of companies. You get stuck right there and you’re not spending as much time leading and visioning as you can.

[00:14:38] Now below that is the managing phase, which is really that first phase after doing. So we’ll go to doing first doing is so important for the business to get off the ground, finding product market fit doing is that those initial things that where you and maybe a handful of people are creating something meaningful, but managing the cases. Is the painful [00:15:00] part. It can be fun, but it also can be a place where you get stuck and overwhelmed and managing chaos and managing people, managing work, managing numbers, managing all of this stuff becomes your primary focus. You’ve got to learn to let go of that. So you can ascend up the five phases of growth. I want to go through this with you today because it’ll make a put in context. A lot of the things that we’re about to talk about inside of today’s interview with Jesse. Back to that interview.

[00:15:27] Gene Hammett: [00:15:27] I’m going to add a second question there. It’s fun until it gets, we do much, right. That’s when you’ve got to hire those key players, that’s when this really starts to take off is you’ve got, you’ve got a little bit of money to focus. You talked about, you know, bringing in this operations analyst and director, At the end of that was you move into this, directing phase, which I think is kind of where you are now. You’re directing the systems and the people around the organization. Is that fair to say?

[00:15:55] Jesse Kaufman: [00:15:55] Totally. Yeah.

[00:15:56]Gene Hammett: [00:15:56] What’s it like to be in this directing phase? What does it feel like?

[00:15:59] Jesse Kaufman: [00:15:59] When you [00:16:00] first get there? I just want to make it clear for people listening. It’s not like. You walk through a doorway and he was like, oh, I’m in the director’s face.  It’s just like, it gradually happens. And you have to be self-aware that you’re as a company, you’ve brought it to this phase and super important because you don’t want to get in the way of the people you put in place. It’s strange. Cause like I want to be hands-on and I feel like I still could be hands-on with it with every department, but it’s important to trust. The people you put in place and let them do their thing.

[00:16:35] Gene Hammett: [00:16:35] Absolutely directing is, is one of the hardest places to be, because you are kind of doing a little bit of visioning doing a little bit of leading and still inside the day of this business.

[00:16:48] Jesse Kaufman: [00:16:48] Yeah.

[00:16:49] Gene Hammett: [00:16:49] I put there are two levels above this, as you really think about going from founder to CEO because you want to be really intentional about leadership. I know you’re spending a lot of time [00:17:00] right there, but you’re probably not able to spend a hundred percent of your time in leading the people, but what is leading the people to you?

[00:17:07] Jesse Kaufman: [00:17:07] Like it’s, you know, galvanizing the team, you know, culture is such an important thing. Of the company as it grows. And that’s like a, almost a full-time job as a CEO is like making sure people buy into the vision. They love what they’re doing. They love the clients we’re working with. I think that’s definitely a part of it.

[00:17:30] Gene Hammett: [00:17:30] I, I appreciate you mixing those two together, the vision and leading because it really is kind of a, they do go together, but at some point in time, when you’re the chairman of the business, You will be mostly on visioning and not doing the day-to-day leading D D can you see that in the future? Maybe it’s two years or five years down the road.

[00:17:50] Jesse Kaufman: [00:17:50] Yeah, I think it’s a natural progression and, I could definitely see that. I don’t know how comfortable I will be in that position right now.

[00:17:58] Gene Hammett: [00:17:58] Well, just like [00:18:00] everything. It takes a little bit of time. You’ll get used to it more and more. It’s a gradual transition. It doesn’t happen overnight but the idea behind a lot of companies, when you, when you’re at your stage is you want to be looking toward how do I spend more time on visioning and less time on doing less time on managing less time on directing less time on leading because.

[00:18:21] The vision becomes such a central part of it. And then you’ve got the right people in place for leadership and all of those other phases below you. Jesse, I want to kind of just ask you this. Like a lot of people struggle in moving from founder to CEO. One of the biggest struggles is they’re just so comfortable doing that. It’s tough to let go. I know you’ve had an easier transition than most people. You’re more of a Jack of all trades. And so it’s been easier for you because you’re hiring people that have certain skill sets and a better fit. Walk, walk me through a little bit of that.

[00:18:59] Commentary: [00:18:59] Now this is a [00:19:00] very special episode. If you are listening on your phone, I get it. This is the most convenient way for you to probably take in this content, but there are some visuals that we’re going to put inside of this that will help you as you are going and understanding the five phases of growth. So if you want to check that out on YouTube, where you get the full video, just go to forward slash YouTube. There’s special content that we only put on YouTube to make you a better leader to make you prepared for. What’s about to come down the road of your journey of fast-growth just go to forward slash YouTube subscribe. So you don’t miss an episode.

[00:19:33] Jesse Kaufman: [00:19:33] So I think what really, I had a conversation with a mentor a few years ago and he said to me, he was like, it was a very well-known everyone listening to this podcast knows who this guy is probably. And he said to me, You know, do you want to build a lifestyle business or do you want to build like a generational business? Because if you keep on doing everything you’re, you’re on your own. You’ll probably [00:20:00] build a great little lifestyle business. If you’re really lucky, putting away, you know, a very comfortable living for you and your family. But if you wanna build a generational business, you’re going to have to step away. From the minutia of running it and get further and further removed from that process. So that’s what really got me going and got me thinking. And I think that’s a question I would pose to anyone struggling at that phase of their company’s journey is like, what type of business do you want to build

[00:20:33] Gene Hammett: [00:20:33] And either okay. But the problem is when you’re trying to run a generational business, but you hold on and treat it like a lifestyle, trying to be

[00:20:42] Jesse Kaufman: [00:20:42] exactly. Yeah. So like figure out that either one is fine, you know, some people, yeah. Either one is fine. So figure out what you want. And then,

[00:20:52] Gene Hammett: [00:20:52] Well Jesse, I really appreciate you sharing some of your background in this. Having a fast-growth company is not something that people should take [00:21:00] lightly. It’s not something that, , should you just be cast off and that’s one reason why I’m obsessed with understanding. How founders, like you, make that transition to CEOs and I appreciate you sharing your wisdom.

[00:21:11] Jesse Kaufman: [00:21:11] Yeah. One more thing to add. So I know I said it’s really important to hire, like hire quickly, figure out what type of company you want to build and hire quickly, equally important is, and this sounds a little bit mean-spirited, but fire quickly as well. So, you know, use that the first 90 days with key hires really put them through their paces. And if you get a gut feeling or your instincts are kicking in that it’s not a right fit, like cut ties as, as quick as possible.

[00:21:39]Gene Hammett: [00:21:39] I appreciate you taking you, you know, given that little detail there, because I do think that we hold onto people way too long as leaders and founders, we see hope in people. We also don’t want to be wrong in a higher, but we have to understand that some people just aren’t in the right fit for what we’re doing. So that’s a very good point, Jesse. Thanks for [00:22:00] being here and sharing your wisdom and talking about shipping tree.

[00:22:02] Jesse Kaufman: [00:22:02] Yeah. Thanks for having me on.

[00:22:04] Gene Hammett: [00:22:04] So as I bring us back here for a second, I’m just going to wrap this up. And when you think about your journey of going from founder to CEO, there’s a lot of milestones that you have to fit. We went through the framework around this, you’re going to be doing, you’re going to manage the chaos. You’re going to be directing leading envisioning. And each of those distinct phases have. Certain challenges. You’re going to play a little bit at all levels at certain times, but when you play mostly at leadership or visionary level is when you truly are empowering people, to really drive around you. And you’ve got to have the right mindset for. We didn’t dive into the details of that. But if you’re curious about what does it take to make that transition from founder to CEO? Make sure you reach out. We’ve got plenty of content on here, and if you want to be connected, what about with other peers and other people that are growing fast? Check out inside that [00:23:00] is a group of people that we get together. We talk about the challenges we talk about how we move from those different phases, how we support each other. I guide them through coaching exercises and frameworks. If you think you’re a good fit for Fast Growth Boardroom just go to apply at as always lead with courage. We’ll see you next time.

Disclaimer: This transcript was created using YouTube’s translator tool and that may mean that some of the words, grammar, and typos come from a misinterpretation of the video.




And lastly, please leave a rating and review for the Growth Think Tank on iTunes (or Stitcher) – it will help us in many ways, but it also inspires us to keep doing what we are doing here. Thank you in advance!

If you want more from us check out more interviews:

Transformational Leadership
Productivity Tips
Best Selling Author Interviews