We were thrilled to host Zack Levine, the VP of Revenue at Checkout.com, for an engaging fireside chat at our offices in Tel Aviv. Zack provided valuable insights into the process of building a sales team during Checkout.com's North American launch and shared his tried-and-true strategies for effectively scaling sales in the early stages.

Watch the full video or read through the highlights below.

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Focused Approach - “Shake the Tree”

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“One of the advantages that I realized we had when we were launching in the US is that we had some legacy pipeline. We'd had conversations in the past with a very select group of customers, so we went through this exercise called 'shake the tree' where we really tried to focus on whatever fruit was on the tree that could actually be profitable for Checkout and generate revenue. We honed in on that and cut everything else.”

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Building Momentum with Intermediate KPIs

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"We set KPIs that were not necessarily the KPIs that we were going to care about in six months or 12 months, but KPIs that would allow us to start showing momentum - intermediate KPIs that we had control over.

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These included things like the number of calls and the number of opportunities created for every opportunity that we put into the CRM. We also considered how detailed each opportunity was, how much we knew about the customer, and how many different people within the account we were targeting had we been in touch with. So, there were several intermediate KPIs that would allow us to start building the right behaviors of the team and also show momentum."

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Leadership and Tough Decisions

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“Sometimes it stinks to be a leader, and you have to fire people if it doesn't work out. You can't be afraid to do that because ultimately, if you hang on to people where there's no light at the end of the tunnel, it's going to be an anvil for a high-velocity team, and you need to not have the fear to be able to make those decisions.”

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Selecting the Right Opportunities for Long-Term Success

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"Selection is super important to be very efficient.

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So, if you go after the wrong accounts and spend a lot of time on an opportunity that has very little revenue or is in a very complicated case in the business space, that's not going to be a long-term customer with strong sustainable revenue. Even though it might be the opportunity that's right in front of you.

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It’s sort of like looking for a job. Sometimes the opportunity finds you, but most of the time you have to go out and be very, very clear about what you're looking for in a new job. And then if an opportunity comes in, that's great, but going out and looking for the opportunities that meet what you're trying to achieve is usually the best way to get a job that you end up in."

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Remote or In-Person Teams

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“When we started hiring the teams in early 2022, my hypothesis was that coming out of COVID, there would be a very upmarket sale. I needed salespeople who were able to meet buyers in person, go out for dinner and drinks. We had people in every major location in the US. We had a hub in New York, with about half the team split between New York and San Francisco, and the other half of the team working remotely in key markets. And I actually think that was a mistake.

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People can always get on a plane. It's important, when you're building from zero to one, to have everyone together in the office. I think the benefit of convenience is outweighed by the collaborative ability that comes with being in the same physical space.

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It allows for a different kind of collaboration than what you get when you're on Zoom calls all day and you don't see the person in their environment side by side. It's a hot-button topic with the return to the office. So, I'm not saying it's the right way, but if I were to do it again, that's what I would do.”

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Relocating to the Target Market

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“To help us grow in 2023, at the end of Q3, I brought our CEO to the US. We spent the whole year building this pipeline, and having the CEO parachute in is very beneficial to advance the pipeline and close deals. Of course, everyone wants to meet with the CEO, the person who ultimately makes the decisions. Additionally, it had the added benefit of allowing him to see the team, how we're building the business, the talk tracks we're using, and how they differ. I believe I also learned a lot from him, and he learned a lot from what we were doing. So, I think it depends on what stage you're at. If you have the right leaders and infrastructure in place, then maybe you don't need to relocate. However, if you're an earlier stage company, it's probably important to be close to the customer.”

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Qualities of Effective Leaders in Sales Teams

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"The things that we look for are, first of all, their ability to think and solve problems clearly with the right thoughtfulness behind solving those problems. So maybe it's the ex-McKinsey consultant brain in me, but I need to be able to trust that when a problem arises, they can solve them.

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The job of a leader is to solve problems. When a problem arises, I need to have confidence that our leaders are taking the right inputs in, being thoughtful about their response, considering all the factors, and then conveying it to the team. If they don't have the ability to solve problems in a thoughtful way, it becomes really hard for me to trust them to do the core part of their job. So that's the first one.

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They also need to be really good examples for the team. One mistake I made is that I hired someone who did not have the qualities of a leader and was disliked by the rest of the team. We removed them after 45 days, but that was a cultural cancer within the team. And it took me two quarters to fully resolve that. It was things like nitpicking on accounts and not being a mensch and a leader that operates with the right ethos that I saw were key. So that's the other thing, they need to be a really good example and representative of the type of employee we want at the company.”

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Tailoring Onboarding and Sales for the US Market

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“It's a similar challenge in early-stage companies. You pick template decks from other companies and template programs. That just didn't work for us. We had a big, robust curriculum that was mostly European-centric. With Europeans and Americans, it’s not the same culture, not the same product, not the same skills that you want to train. So we rebuilt the entire onboarding curriculum. That was not foolproof, but it got us closer.

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American culture is unique. So there are certain ways of selling, certain ways of engaging with clients - soft skills. I'll give you one example, a tactical example. Our team does not use a pitch deck. We don't use sales presentations.

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I'm a former consultant, I'm supposed to like presentations and slide decks. People see a presentation, hopefully this doesn't happen to you, but you see a presentation and your eyes gloss over. So most of what we wanted to instill was really question-based discovery and have a conversation and get to know the client because for most of the accounts in the US, as opposed to Europe where we have been for many years, it was the first time we were talking to them.

So in that first conversation, it can't be a sales pitch, it has to be a relationship that you're building. And then over time, it'll become more and more commercial.”

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Leveraging Key Accounts

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"The thing that allowed us to unlock the exponential growth we saw later on was getting a couple of key accounts to go live because then we were able to show those logos around. And just a tactical suggestion, we gave up economics with those top accounts in order to get them to talk to prospects that I wanted to introduce them to. So rather than knife fighting for revenue on that particular account, we signed the contract where if I called and asked our client to talk to a prospect, they would talk to them in the next 48 hours and tell them about their experience with us.”

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What to Look For in Your First Sales Hire

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"I don't think the traditional sales persona is the best first sales hire because you are still trying to learn about the market and synthesize customer feedback. You need someone who is a little bit more strategic, thoughtful, and creative than a traditional sales manager.

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You need someone who has an interest in the product, someone who has an interest in marketing, and who can iterate. You need someone who will introduce the product team to customers so that the product team can hear the feedback directly from customers. It's hard if you have a sales manager who is just trying to go out and win deals and meet quotas. You can choose that route, but I'm not a big fan. I advise smaller, venture-backed companies that are growing, and the theme that I see, especially in the early stages, is that founder-led sales are still going to be a big part of the process. The more you can have a deputy who can contribute to that strategic thinking and help lighten the load, the better.”

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How to Screen for Curiosity and Learning Ability

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"You want to be very clear on what the things are that you care about versus what you don't care about. So we had a scorecard of different traits that we cared about with different weights attributed to each one of those traits. And every candidate would go through the same scorecard to figure out where they stood. I do have questions that I like to ask. So I'll give you a practical example. Payments is super complicated. I didn't come from payments. I actually don't feel like you always need to hire people that have payments experience to do well selling payments or being an account manager within the payments industry. But the thing that you do need is curiosity and the ability to learn.

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So one of the screening questions that I would ask, particularly for non-payments candidates, and even for payments candidates, is to tell me about something that they had learned about. A lot of people would say, "Oh, crypto, I learned a lot about crypto." And then you ask them three or four follow-up questions that are pretty basic, and you can see if they actually learned about the thing. And a lot of times, people bullshit. And that was the opposite of the team that we were trying to build."

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Why Leaders Should be Involved in the Details

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"Your leaders and team members should be highly involved in the details. They should be able to sit with you and answer almost any question without needing to check their notes. Last night, at 11 PM Israel time, I received a WhatsApp message from our CEO inquiring about the latest updates with a client. It's his way of testing me, and I understand that. I believe this is a beneficial habit to cultivate in order to maintain the speed, intensity, and seriousness required for continuous growth.

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One important action I would take is to screen and ensure that your leaders have a solid understanding of the actual details. Often, I have observed that individuals with impressive titles at the top of the organizational chart lack substantial knowledge and delegate all the expertise to others in the team, instead of actively engaging in managing the details themselves. The more you involve yourself in the details, the more problems you can solve."

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Three Main Lessons for Building and Scaling Sales

"The three main lessons that I learned along this journey are:

1. People are super important. It might not seem like it, but when you have the wrong people on your team, it will be like a cancer from the inside.
2. Focus is really important. You have product-market fit with every Ideal Customer Profile (ICP) in the world. Even if you think there are other ICPs that will work, focus and prioritization are super important. Do one thing really well, and then do the other things.
3. Momentum is important - both for the team and internal messaging. It's important to create positive vibes and high energy, where everyone feels they can win. It's about leadership, making your team feel that you are going to get up this hill together. You always want to show any metric that goes up and to the right because people like seeing progress. It's engineered in our brains. So even if it's a metric that may not impact the real upward trend that you care about, show something that is moving up and to the right."

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