How to Lead Sales Transformation in a Remote Selling World with Chris O’Brien


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Large and small companies alike must adapt to the reality of remote selling. The sales landscape won’t fully be what it used to be, so to thrive, sales leaders must push for sales transformation in their organizations.

My guest in this episode of the Modern Selling podcast is an experienced leader from a 16-billion dollar company, who has a lot to say about digital sales transformation.

Don’t miss this conversation with Chris O'Brien, Chief Commercial Officer at C.H. Robinson, a global company in the services and transportation industry.

Chris has global enterprise wide responsibility for all customer related strategy and functions including overseeing sales, account management, and marketing. In addition to corporate support for these functions, his teams oversee the Global Account Centers and lead the company’s integrated relationships through the Collaborative Outsource® solutions portfolio.

At work Chris is passionate about developing the careers of others and driving change for improvements. His areas of expertise are in the fields of sales, customer management, European supply chain management, leadership, mergers and acquisitions, retail supply chains, inbound transportation, transportation outsourcing and Transportation Management Systems (TMS).

The Tenure of a Sales Leader

Chris has been at CH Robinson for 28 years, an incredibly rare tenure. The typical tenure of a sales leader today is 18 to 24 months, as people move around companies all the time.

So, I asked Chris if he thinks his experience can be seen as an advantage or a disadvantage.

“I've always tried to make it an advantage,” Chris says. “I've been in a lot of different roles. I've been in three different countries and I think for all of us in the sales and customer-facing world, that it becomes an advantage because you're in front of customers, you're talking to customers, you’re learning their language, you get a bit of exposure to everyone.”

Another advantage of growing in a company, according to Chris, is that you would be leading a job you had done before, so you would understand better those who report to you and you can lead by example.

Personally, one of the best pieces of advice I can give to the selling community is that before you take a jump from one position to another or from one company to another, make sure you've proven that you've been successful in that particular role. You must build a track record to prove that you can actually succeed in another company or position.

The Impact of COVID-19 in the Salesforce

The pandemic not only affected C.H. Robinson’s industry but also their salesforce. They had to make decisions and adapt quickly.

One thing that they did was to treat this change as permanent in order to really maximize what was going on in the world. “We would act as if part of this was going to continue,” Chris says.

First, they adjusted their sales messaging to resonate with what was going on in the Covid environment. For example, during the pandemic companies were trying to cut costs, so C.H. Robinson began to promote their outsourcing services even more.

Chris says that their sellers had to adapt and embrace video for sales. “So we jumped right away on training do's and don'ts, the good, bad and the ugly of showing up on video. We tested new technology. We really made sure that we were doing anything that we could to make this fun to keep the world connected.”

How Sales Leaders can Drive Sales Transformation

A lot of leaders are still not getting the support that they need from senior leadership to leverage the tech tools required for remote sales. For example, we know that video is the hottest thing out there right now, both face-to-face synchronous and asynchronous communications. But it is an area that many sellers have not leveraged fully.

So, how do you get the senior leadership team to drive the change and invest in the sales organization?

Chris says it starts with company culture. More than just having leaders willing to implement changes, you need a culture that is “just ready to go.”

“I think the first component is owning it and living it,” he says. “It is your own personal commitment to say, ‘I see this as a challenge, I will personally commit to coming up with the solution’ versus ‘This is a problem, what am I going to do about this?’ And I think that's too common of an approach. To me, the most important component is leadership commitment.”

I totally agree with Chris on this. As leaders, we cannot be in an Ivory Tower. We've got to be in the field, whether it's emotionally or tactically. This is especially true in a remote selling environment, where many sellers feel isolated and even depressed. Sales leaders must offer coaching and support to them.

“I believe that sales leadership and sales leaders will need to become much more of individuals who can talk on an emotional level,” Chris says, “not just work through specific items to get the deal closed. We've got to be able to relate to our people. If you needed to do it in person, how much more do we need to be doing it now in a virtual environment?”

Career Advice for People Starting in Sales

Chris has some great advice for new sellers. Given his position and authority in the marketplace, as well as his years of experience, you should listen carefully to what he says.

  • Think like your customer: “I think that the first step for me is walking in their footsteps and understanding what they really want out of the engagement.”
  • Be curious, always learning: “Your education doesn’t stop when you get a job. Keep reading books, listen to podcasts, be curious.”
  • Do not worry about your career: “Don’t worry about that next promotion. Take care of your customers and your teammates and your career will take care of itself. As I reflect on my career path, I don't recall ever putting together a plan for a promotion. I had plans for customers and developing others and I think people just notice if you're in it for them or if you're in it for yourself.”

Listen to this episode to learn more about Chris’s exciting career and how you can drive sales transformation in your own organization.

Outline of this sales transformation episode

[11:25] Advantages and Disadvantages of settling in a company for a long period of time

[23:00] How Sales Leaders can Drive Sales Transformation

[36:50] The importance of video in remote selling

[43:20] Career Advice for People Starting in Sales

214 episodes