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The Boardroom

A talk about authenticity, artificial intelligence and the sales team of the future

On a balmy summer day in July, a group of seven New York City-based sales leaders—all at the top of their game and each now navigating day-to-day challenges and rapid growth in separate ways—rearranged their whirlwind schedules to discuss with The Modern Sale the rapidly shifting sales landscape, bleeding-edge technology, how millennials are reshaping office culture and the one trait they all share. This interview, which took place in the boardroom of SAP’s New York headquarters in the newly developed Hudson Yards section of Manhattan on July 17, has been lightly edited for space and clarity.

The Players

Stephanie Agresta
, global director, Enterprise Growth, Qnary. Qnary is an executive reputation technology platform and solutions company that empowers the voice of the professional, worldwide.


Russ Bley, senior vice president, Global Sales, NewsCred. Founded in 2008, NewsCred is a global leader in enterprise content marketing, empowering the world’s most ambitious brands with powerful technology, the largest and most diverse content offerings and proven expertise in more than 70 countries.


Steve Denton, president and chief revenue officer, Collective[i]. Collective[i] hosts a suite of applications that deliver insights to B2B sales teams and, a global network for sales professionals. The company is a pioneer in the future of work movement that combines machine learning, artificial intelligence and massive data sets in order to improve productivity and grow revenue.


Marc Jacobs, senior vice president, Sales & Customer Success, CB Insights. CB Insights is a market intelligence platform that uses machine intelligence to synthesize, analyze and visualize millions of documents and give customers fast, fact-based insights so they can make better strategic decisions.


Chris Larson, vice president of Sales, Hive. Hive is an AI-powered project management platform that helps teams across all industries collaborate more effectively with multiple project layouts and analytics.



Robert Lopez, vice president of Sales and Business Development, JustWorks. Justworks is an automated HR, payroll and benefits company based in New York City.



Morgan Mackles, vice president of Sales, is a technology company with a mission to democratize the personal assistant and an unshakeable belief that meetings should schedule themselves. makes Amy + Andrew, autonomous AI assistants who schedule meetings for clients.



The Modern Sale: You’re all captaining rocket ships that threaten outdated companies. What should legacy companies be afraid of in 2019?

Jacobs: Legacy companies focus on doing the playbook well, but they need to think about how to make sure that everyone who touches a sale feels like it’s been personalized. My salespeople can quickly adjust to the way prospects are buying by focusing on the client, not the product. This should make our competitors nervous.

Agresta: We are creating content for executives and brands, and typically companies don’t use technology to create that, so their cost is greater at scale. Another reason why we’ll win is because, as the market changes faster, our competitors are training repetition, but we are training intelligence.

Bley: NewsCred has a lot of competitors that are big and have huge budgets. We’re competing against them and winning because we’re selling a story to decision makers and buyers. Our best sellers are excellent storytellers, and we enable them to spend their time selling versus focusing on other banal tasks.

Mackles: For me, having been at both Fortune 500s and start-ups, I think we just move so much faster than incumbents. We are hiring smart people, not drones, and using AI to streamline every new feature and functionality and sale. The big companies are so behind, they will have to start acquiring AI if they are going to catch up.

Denton: Most sales professionals spend 60 to 70 percent of their working hours on non-revenue-producing tasks and only spend 12 to 14 hours per week actually selling. We have automated nearly all of the manual tasks and are collecting better intelligence through machine learning, which means we can focus on coaching, negotiating, managing resources and formulating strategy. Can our competitors do that yet? I don’t think so.

The Modern Sale: How are you approaching the paradigm shift of enterprise technology as it relates to sales?

Lopez: We are automating the lower-hanging fruit, like the acquisition of deals, so that we can move the sales folks to the higher buyer. Ten years ago, I would have handed my team a playbook and made sure they hit their metrics. Now I’m looking for ways to cut out the grunt work and cut down the time it takes to find good deals, and I’m using any new technology that fits as an advantage against our competitors. Artificial intelligence, and more specifically machine and deep learning, has vastly improved the process of selling for those willing to adopt them.

Bley: It goes back to good intelligence. We are making sure that from the first discovery call, we are expressing how we can alleviate the pain and what doing nothing feels like. We use machine learning to pinpoint the problem so we can be present at critical moments during the six-month sales process and create a sense that the buyer can’t live without the seller.

Agresta: All our competitors’ systems are basically “repeat after me,” and all our systems are personalized, smarter, better and faster. Millennials know that authenticity matters more now than ever, and reading scripts and following plays are the most inauthentic thing we could do. Ask any 20-year-old, and they can tell you the difference between a real Instagram feed and a fake one. So personalizing through technology helps us to sell authentically. Most companies train to essentially have sellers read the script whether they realize it or not, which is our advantage and, for them, the height of stupidity.

The Modern Sale: How much of an advantage does AI give? Is it all hype, or are most companies underestimating its impact and ability to improve outcomes?

Mackles: For us, we are taking a very vertical-solutions approach for now. Hopefully, we do meeting space, and Gong does the speech portion, and Collective[i] does our intelligence. But it will take time for there to be one solution. Some companies claim to be all things to all people, but when you know how the technology works, you realize that this won’t work.

Bley: If the technology and skill sets we’re looking for in our sellers are the same ones we would have looked for 10 years ago, something is wrong. I am on the hunt for AI that increases our knowledge during that 63 percent or 80 percent of the sales journey that our buyer is doing without us. AI that can help us to learn about that journey, to be present at critical points and maybe to shrink the sales cycle from nine months to six months…that would give us a huge advantage against new competition and the incumbents.

Larson: AI can bring to the surface any potential risks in particular projects so our sales team can deploy the right resources at the right time. AI allows our salespeople to take out a lot of the upfront work so we can put our best athletes in and enable them to personalize every sale. I don’t think its advantages can be underestimated.

Denton: Sales has suffered from an underinvestment in technology, but that is changing among the disrupters today. CROs that win are looking at sales from a perspective of optimization versus the historical view of incremental improvement. Soon, they will become one the largest purchasers of technology—and applications like Collective[i] means that selling is about to get very exciting.

The Modern Sale: What modern sales skills are you screening for in the interview process?

Larson: I care about what skills they have developed on their own, how they maximize their time and what their adoption curve is. Figuring this out in an interview is challenging.

Bley: Great salespeople build great networks and relationships, but this is really ground-floor stuff. I want to know how they are leveraging those relationships and using technology to gain an advantage and magnify their influence. In the end, I need my team to be great sellers and to be curious enough to seek out every possible useful tool.

Jacobs: A while back, being the guy who could build relationships was enough to be successful. But if that is all you rely on, you won’t be able to deal with as many people and issues as we have to. We aren’t hiring for 1980, we’re hiring for 2020, so we need people who use the latest and the greatest in their everyday lives and can bring that enthusiasm and knowledge to the workplace.

Denton: I’ve found that managers and sales professionals stay on a potential deal for too long at the expense of other more lucrative deals. I’m looking for many skills, but one of them is to know when to push for a close and when to write off that investment and move on. I want people who are client-centric, not old-guard salespeople who are product-centric.

Mackles: We are looking for ways to take some of the mystery out of sales, so we are facilitating the science of the deal with technology: automation, artificial intelligence, machine learning, predictive analytics. This especially appeals to millennials and those just out of school.

The Modern Sale: What is your strategy for recruiting millennials?

Bley: A lot of people think millennials are needy, but the reality is they are smart enough to know they are on the hunt for better, faster ways to get stuff done so they can move on to their interesting personal lives. They are unwilling to accept the systems we used in the past—just following a playbook and logging progress—and we let them know that we are disrupting and always looking toward the future.

Agresta: At Qnary, we are all about letting people share strategically what is important to them, so we have to live that in the office. So everyone has to understand their social media presence and their personal brand and create their own platform. We know that millennials want to be able to bring their whole selves to work, and that includes who they are online.

Lopez: People don’t want a job, they want an experience, so we try to make JustWorks part of that experience.

Mackles: The best people won’t go work for old-school companies, where sales is the only piece of the enterprise still doing things the same way as 30 years ago. The millennial workforce doesn’t want to sell the old-school way. They want authenticity, efficiency, personalization and a human touch. So we emphasize that we are automating the boring data input and letting them be their authentic selves.

Denton: Millennials have never had a technology where they have to manually do the basics. For us growing up in the CRM era, we sometimes think that the logging is the work, so we think they are lazy. The reality is they are right, so we focus on technology that does the basic work for them and then focuses on insights that let them be faster or smarter. All the technology we use is socially or network driven. There is no part of anyone’s life where that is not the key, so we just accept the change and work toward getting the most out of it as opposed to fighting this change and clinging on to what the world used to be. Millennials appreciate that, and the smart ones worth recruiting want to get in on this early phase of machine learning and intelligence as it applies to sales, which, as everyone seems to agree, is the last place to modernize in the enterprise.

The Modern Sale: How important is real-time collaboration to being client-focused? Is there another advantage smaller sales teams can exploit?

Larson: That goes back to investing in the right tools. We use Hive, ZoomInfo, ConnectandSell and Collective[i] to help identify which deals are real and which are not. A few years ago, the CRM vendors would bring innovation. Today if you wait for them to innovate, you will fall behind. Modern sellers look for tools that build relationships, leverage their organizations and find ways to better understand their buyers from networks. With CRM, you only know what you know, and that is so old-school. Marketing learned this lesson 20 years ago and has never looked back. Sales has been the laggard, but for those who see that, they get huge advantages.

Agresta: We use Slack to connect the product team, and Zoom and Zoho. Google chat allows everyone to always be available to one another, which is incredibly useful, especially for a flexible workplace. When you’re in the office, you can focus on personal intersections, but I don’t like to talk too much about a sale. Too much internal chatter can be bad. I think you need to let people do what they do in their own space.

Denton: I really loved listening to all of us, and what we all have in common is that we are talking about leveraging new technologies and people who understand how to use them. We are talking about everyone in the organization being leveraged to work together to get a deal done collaboratively—which means we are not talking about tech for our salespeople alone! We are NOT talking about manual tasks, like logging data into a CRM. I think all of us are constantly looking for ways to ensure we personalize every client interaction to be the most authentic. From the outside, this may seem just like words, but when you look deeper, it’s the most disruptive change to sales in my lifetime. And it’s only moving faster.

(Ebbe Sweet images)

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