How LinkedIn's COO Sells: The Future is All About Going Deep

Paul Petrone

Marketing @ LinkedIn

September 11, 2023

Dan Shapero is the Chief Operating Officer for LinkedIn, a $15-billion-a-year business with thousands of salespeople across the globe.

Previously, from 2008 to 2014, before stepping into a product role, Dan led sales for LinkedIn Talent Solutions. In his time there, Dan oversaw LTS’ growth from a $50-million-a-year business to a $1.5-billion-a-year business, helping put it on its path to becoming the $7-billion-a-year business it is today.

An MBA graduate from Harvard Business School, Dan has also worked at Bain & Company, created and sold his own business, and serves as an advisor and investor in multiple emerging startups. His name is also on two patents and he’s the instructor of two of this author’s favorite LinkedIn Learning courses on strategic thinking and communicating with executives.

What has Dan learned leading global sales teams? Why does he recommend his sellers lean into friction, instead of shying away from it? And where does he see the industry headed?

We asked him all of that and more in our latest edition of How I Sell.

1. What energizes you most about working in B2B?

Some of the most important companies in the world are B2B companies. They provide the capabilities that power all of the brands in the world and all of the products we use everyday.

Ultimately, what I hope to do in my career is have a positive impact on people and on the world at large, and although they may not all be household names, B2B companies around the world power the world and improve lives.

Very specifically, we at LinkedIn help companies address two of their most important needs: building winning teams and growing their relationships with customers. So I appreciate the opportunity to work at the heart of what makes B2B companies successful.

2. What's your sales philosophy, in 3 sentences or less?

Great selling is about helping a customer see massive opportunities more clearly, and galvanize the customer organization to take action in pursuing them. That starts with building trust and credibility so that you can uncover the challenges your customer is facing, and then sharing opinions that can solve those challenges.

Ultimately, the best sellers are relentlessly invested in their customer’s success, and are comfortable bringing strong points of view that help the customer solve problems.

3. How are you seeing buyers changing today, and how are you coaching your sellers to adapt to that change?

Buyers want sellers to have an opinion.

They've read the information that's on the internet. They know what your product can do. What they want to know is how you can help them unlock value for their organization (and them personally). So I think a more opinionated perspective from sellers is one thing that buyers want right now.

Another thing is that buying groups within organizations are becoming larger and more spread out across the organization. It's not enough to talk to the IT buyer or the business decision-maker. You have to talk to security. You have to talk to sales. You have to talk to marketing. And the most influential people in the room are not always the most senior folks in the room, so you have to build a groundswell of support to make things happen.

So, the challenge becomes, how do you map out all of the people that have influence over the decision? And that’s only getting more and more sophisticated.

Building off that, what comes into my mind is this scene from “Moneyball” where Brad Pitt - who is the general manager of the Oakland Athletics baseball team - tries to negotiate with another general manager to make a player trade. Only to realize that an entry-level analyst, played by Jonah Hill, is the voice that ultimately influences the final decision — even though he is far from the most senior person in the room. We need to know who the Jonah Hills are at our customers.

The reason that sticks with me is there’s this sense that, to sell, you need to build a relationship with the most senior person. And I think what we're learning is there’s these hidden influencers within an organization who have a voice people listen to – and great sellers find out who those people are.

Even myself, when I’m buying, I might technically be the decision-maker. But I’ll often rely on someone I trust who is closer to the material, and their recommendation I’ll largely support.

So, I think mapping out an organization and finding that right person that's deep in the topic, yet senior enough to have a voice, is where the real magic is.

It’s finding those Jonahs.

Another thing we've learned recently is that companies don't recognize they have the opportunity to identify “hidden allies” within their potential customers who can open doors and share insights on internal dynamics. Hidden allies can be people with shared alumni, people who previously worked at your company, or previous customers who now work at the organization you’re looking to build a relationship with.

These are all potential allies because they know who you are, they know what you care about, and they see you as someone that's trusted and effective. And so I see sellers that are finding those allies and engaging with them being quite successful.

And the last thing is that buyers are increasingly curious about working with sellers who are sharing thought leadership on places like LinkedIn. I see more and more examples where sellers are building connections with buyers based on the content and perspectives they share. And I think it's making a big difference.

4. What excites you most about the future of sales?

I think the last decade of sales technology innovation has been about sending more messages to more customers, hoping they'll respond. And I think the change that we're trying to create and the change that is going to be amplified by AI is sales re-embracing its roots and being about building deep relationships with people.

The best sellers are the ones that can understand how to build connections with their customers, map out an organization, and help that organization solve a problem.

And that's all about going deep; it's not about going shallow.

And so, moving forward, the best sellers are going to be the ones that leverage technology to build deep relationships within organizations. And I think that's exciting.

5. We understand you are a believer in deep sales. Why?

Deep sales spoke to me as a pivot away from what every other company was talking about. When everyone else was zigging, we were zagging. They were all going shallow, and we were going deep.

My experience with great sellers is that they make the most of every opportunity. Deep sales unlocks that because deep sales is incredibly powerful in taking small, successful relationships that you have with a customer and turning them into huge, powerful relationships across that organization.

Many of the leaders I speak with recognize that some of the most profitable growth they can unlock is within their existing accounts. In fact, one of the things we learned is that some of the biggest upside that exists in the LinkedIn business is deepening the relationships that are already successful.

And I think deep sales really empower sellers to do that effectively, especially at this phase of the macroeconomic cycle.

6. What do you look for when hiring a salesperson?

There is no blueprint for what it takes to be a great salesperson. I've seen many different personality types be successful at sales, but there are certain characteristics that I think are helpful.

First, we often envision being an effective salesperson as what you do in the room. But so much is what you do out of the room. Are you prepared? Are you responsive? Are you able to manage many relationships and conversations at the same time?

Some of the most successful sales people I've seen are incredibly operationally sound.

Second, the best salespeople are insatiably curious and great listeners. Oftentimes, when we interview salespeople, we'll put them through a mock sales call. But the most important moments in that call are less about what they say and more about how curious they get when we share information — or do they miss the nugget we drop and miss the moment to ask follow-up questions?

The best sellers know how to spot a piece of information that unlocks a new idea or an insight in a way that gets to the deeper level of what the customer needs.

Finally, when you get pushback from the customer, do you back off or lean in? The best salespeople embrace tension in conversations with customers because behind that tension is an opportunity for a breakthrough in thinking; either in your own thinking or in the customer’s thinking.

There's a great sales leader at LinkedIn — Deina King — and I would see her lean in whenever the customer pushed back. And she wouldn't leave the topic until it was fully explored.

I think salespeople early in their career get nervous about that kind of pushback. But pushback is where you get energy, it’s where you get insight. The best sellers lean into it.

7. How can a salesperson build the credibility needed to effectively challenge their buyer?

There are a handful of tactics for building credibility.

It typically starts by sharing facts before you share opinions. So, what are the set of facts you can share to build credibility?

Maybe it’s, “I've read your usage data and see the following trends emerging…”. So, I'm not going to tell you what to do, but I'm going to show I really know how your team operates and what your business challenges are.

Or, “I've talked to your team members and this is what they say.” That's interesting. Now you're bringing me facts that I don't know. Or, another one is, “I've analyzed your peers and this is what they do that's different from what you do.”

Those are all reasons to listen, right? But then, at the end of that, you have to say something that I haven't heard before.

And so, the question is, can you make sure you have something to say that’s interesting? And what are the variety of things you've done that laid the groundwork to build credibility that make you worth listening to?

8. Is there any habit you have outside of work that you believe helps you perform better?

This is probably more from my past than my present, but I was a goalie in soccer from the time I was eight until the time I was 18. And that meant I got scored on thousands of times between practices and games.

I was pretty good, and I got the opportunity to play with next-level goalies like Tim Howard. And what I’ve seen is all the great goalies are good at getting scored on, analyzing what just happened so they can make adjustments, and then moving on very quickly to the next situation with a clear mind.

Moving between situations with a clear mind lends itself to sales where there's a lot of noise and often rejection. The key is learning from each moment, not dwelling on it, and moving forward.

I think sales can have lots of highs and lows, and those highs and lows can both get in the way of the next thing you need to do. So I think that being a goalie taught me how to figure out how to process failure and then get back on my feet and get ready for the next play.

9. What has been your biggest failure in sales and how did that experience transform you?

As a sales leader, I am frequently reminded of the fact that there is no replacement for time in front of the customer. Whenever I scale back customer time, I lose my ability to be as effective as possible.

The larger the team you run, the easier it can be to analyze the business through the lens of the numbers or market research or the different things you track.

At the end of the day, there is nothing like sitting in front of a customer and hearing them tell you what they think about your product. And trying out different storylines and value propositions with them and feeling what works and what doesn't firsthand.

This year is a year where I am massively increasing the amount of time I'm devoting to meeting with customers, because of how important it is. As the world goes through change and customers are adapting to that change, I want to know how they are evolving, what they are learning, and what we can share with them to be a great partner. It also helps me give useful feedback to our product and marketing partners on what customers are saying.

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