That One Weird Trick

Kent Holland, Copper

What do you do, in your own words?

I’m the VP of Sales at Copper, leading a global team of account executives & account managers. We work with prospective customers that are seeking a Customer Relationship Management (CRM) tool, and with our existing customers as they think about their growth objectives and getting more value from Copper to support their goals.

What might be different about selling Copper vs. other types of products/services?

Copper is a software solution, so one big difference is that when you’re selling software versus hardware there’s usually an in-depth process to help a customer understand how the software applies to their business, how it can be set up and structured, and how it can be used specific to their business.

Some software solutions are easier to sell, where people understand its purpose more naturally–CRM is different. It’s your digital rolodex. It provides workflow support for your sales and go-to-market teams. It’s your one-stop shop for capturing information about your customer pre- and post-sale.

That means a lot of different people in different roles will use the tool. And everyone wants to have visibility into what’s going on, from the lens of their role or business needs. Selling CRM is a lot more about education, capturing business requirements, and facilitating an in-depth customer evaluation process.

On your team, are you currently more focused on acquiring new customers or growing engagement of existing customers? What are you specifically focused on?

For the last year, it’s been a bit of a transition–when I first started with Copper and took over the sales team, I was primarily focused on new business. We had a product that was earlier on in its maturity. Customers expanding post-sale was primarily driven by their successful adoption and use of the core product. At the time, growing the business was about getting as much in the front door as we could and ensuring customers were served successfully. To the extent that our customers were successfully using the product, our business grew as their teams grew.

More recently, two things have happened that have converged–one is the obvious: Covid-19. That put a lot of pressure on new business acquisition as companies, particularly in the SMB space, tightened their purchasing decisions. We had to make a mental shift to think more proactively about supporting and growing an existing base of ~10,000 customers. That was an interesting transition, and it became very important that we protect and grow the customers that we had by generating as much value for them as we possibly could.

The second thing that happened in the back half of last year, is that we really started to beef up our product stack. We’re getting to the point now where we have multiple packages that present attractive upgrade opportunities for customers and unlock new use cases. For example, Copper was more focused on sales and partnerships use cases in the past that limit the target user base to primarily pre-sale or acquisition roles.

Now, we’ve worked a lot on project management as a capability, on improving our reporting functionality, and on creating a place where this information can actually come together across the entire customer lifecycle. It’s helped us open up beyond users in pre-sale roles and become more attractive to onboarding and customer success teams. We’re building out an account management team that sits within sales, focused on commercial expansion of accounts, and that pairs with our new business account executive team. The two are distinct, and we specialize the two types of rep teams to go after each separately, but we’re increasingly focused on driving value through our existing base.

How does your work contribute to building trust with users, in order to persuade them to use Copper?

When customers are looking for CRM they’re looking for a tool on which to manage the core of their business. It’s the place where all of your customer data will live. It’s a big decision, and one that folks don’t take lightly, so it’s incumbent upon us as a sales team to build trust as prospects go through their evaluation process.

They’re not only evaluating the tool, but they’re also going through the process of figuring out what their own sales motion should look like. In effect, they’re looking to talk to us not just about how the tool works, but how it works in conjunction with a successful selling process, partnership process, or other motion they want to run on top of the CRM. We work with customers on that every day and leverage that expertise to build trust and add value to our customers.

For us to be effective at building trust with our customers, we have to really understand the way in which these businesses operate. Our sales reps have to become experts in the businesses that we spend time with.

Take real estate as an example – we’re constantly bolstering our understanding of the way that real estate agents think about their client base, the information they want to have about those clients, and the the way in which they want to leverage that information to send newsletters, communicate with their clients, segment their client base, or work through core tasks on a daily basis.

Beyond becoming experts in the sectors that we work with, we put a lot of energy into providing a top-notch customer experience throughout the buying journey and beyond. The attention and time that we commit to our prospects, especially within the SMB and Mid Market segments that we operate, differentiates Copper from the pack. We lean in with our customers to help them understand how Copper works, how it fits within the context of their business, and how it can support them in achieving their objectives. At the end of the day, it’s very difficult to shortcut that trust that a human interaction can build.

From your perspective, how does personalization give a sales edge?

This concept of personalization is the center of a lot of what’s been changing about selling. The amount of choice in the market is unparalleled, and highly effective personalization is the only way that you’re going to stand out.

As a buyer, you have a set of challenges you’re trying to overcome and goals you’re trying to achieve. The sellers that are able to speak to those challenges and goals most effectively are the ones that are going to ultimately succeed in engaging with their target buyers.

In the past, sales was able to be a lot lazier in their approach. You could target a big list of buyers with a series of emails and calls, and expect certain conversion rates that typically held pretty consistently. You could work backwards from your targets and get a pretty good sense of what you needed to do.

In today’s world, you have to have a personal touch and compelling message within the right context for the person you’re speaking to. If you do, you’ll be successful in unlocking conversations that lead to value exchange. If you don’t, someone else will engage that buyer with a better message and solution to their challenges, and you’ll be left in the dust.

What’s your favorite channel or platform for communicating with customers, and why?

I have two:

  1. I love engaging with customers through chat within our application. When you can catch customers while they’re using your solution, you have the opportunity to help them move through any of the challenges that they’re going through and learn about their experience in real time. You also are catching them at a moment when they’re likely to be ready to engage with you on the topic at hand. Of course, you have to be careful not to annoy either, but it provides a great opportunity for ad-hoc conversation and often leads to powerful insights or provides an opportunity to progress with a prospect in a way you might not otherwise have been able to. You can learn a ton in that way.
  2. From a sales perspective, I love video calls–you can accomplish so much more with a face-to-face chat, and to the extent that you can look your customers in the eye I think you’re able to build a whole different level of trust. One of the things technology has afforded us is the chance to have the same type of engagement you could have sitting across a boardroom. In the past, you would have had a team flying all around the world to go make that happen. It dramatically changes the game.

It’s hard to replicate being able to look someone in the eye, when you can see facial expressions and read body language. Even via phone, which I also like, you can get caught talking about something for 30 seconds or a minute without knowing what’s happening on the other end of the line. With Covid, we’re all Zoom’d out these days, but I still think it’s the best channel to engage through.

What’s the largest single sales initiative (deal-size, etc.) you’ve participated in and what lessons did you learn from it? If discussing your current employer is off-limits, what about in a previous role?

It’s ranged a lot across the roles that I’ve had. If I look back before Copper, I spent a lot more time working with Fortune-1000 customers during my time at Box and LinkedIn. Our largest deals went well into the millions. At Copper, our larger deal sizes are in the $20-$25k range, although there are always those larger outliers.

There’s a lot to enjoy about larger deals – it’s incredibly rewarding to close one and have such a large revenue win for the business. With that said, there are also a lot of headaches that come with it. Deals take far longer and are far more complex.

You have to make sure that the entire organization is on board, you’re thinking about all of the other tools that they have in their technology stack, you’re building relationships and champions along the way, you’re supporting pilot efforts to test and probe, you’re working with IT and security teams to ensure the tool lines up from a compliance perspective, and you’re working tirelessly to build value for the solution within the context of the organization’s goals and challenges.

A lot of the same things go into my selling today, but the scale and speed is different. With smaller deals that move more quickly, I’m able to operate at a quicker pace and the feedback cycle is shortened. Both large and small deals can be extremely engaging, but they function incredibly differently.

What accomplishment are you most proud of in your career so far?

This one’s tough, there’s a lot I still want to accomplish. But I think the accomplishment I’m most proud of is from this last year, leading Copper’s Sales organization through the pandemic period. As a company that’s focused on helping small and medium businesses grow, we saw a lot of our customers go through a really really difficult time. Think services businesses like coffee shop Distributors, media agencies, and others. Those businesses had a really tough time operating through this period, and so as a result we had to make some really tough decisions about our team structure and how we approached our work. We had to let some of our team go, which was one of the most difficult things I’ve ever had to do. We had to keep our resourcing tight, but also aligned with what we needed to be able to deliver so that we could achieve our plans, uphold our promise to our customers, and keep the business moving in the right direction.

Through 2020, we ended up doing substantially better than we thought we would. On the Sales side, we kept focus and kept our energy high. We didn’t have additional attrition, and continued to help our prospects and customers operate their own businesses through that most difficult stretch.

Through it all, we’ve built a stronger and more successful business. I think it shows the resiliency of the team, and I’m just really proud of being able to say that I helped lead this group through that period. It was a really tough one, to be sure.

What are you most looking forward to working on?

The last year and a half has been all about owning and building out the Account Executive team–focused on new business. I’m now hiring a leader for that team, and will be shifting focus to building out our post-sale Account Management group. It’s an exciting step to build our commercial muscle out even further. We’re also adding a Solutions Engineering team to support us as we serve larger and larger organizations. That team growth, and supporting Copper’s overall growth, is something I’m really looking forward to.

We’ll be answering questions like “At what point do we lean into outbound?” “At what point do we start to focus more on international geographies?” The focus will shift from building out our sales process and ensuring repeatability, to scaling on the foundation that we’ve built. I’m excited about the journey ahead, wherever that takes me.

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