SalesTechStar Interview with Mary Shea, VP, Global Innovation Evangelist at Outreach

Mary Shea recently joined Outreach as their VP, Global Innovation Evangelist; she joined us for a quick chat to share more about her role and upcoming plans at Outreach while sharing a few trends she’s been observing in sales intelligence and sales engagement today.

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Hi Mary, we’d love to hear about your new role at Outreach, how’s that been going; take us through some of the biggest plans you have here at Outreach?

My role as Global Innovation Evangelist at Outreach includes several different things. First and foremost, I’ll continue to do what I love most – conducting and writing provocative research about buying and selling in the business world. I will, of course, continue to follow the sales technology landscape very closely and help the market understand and prepare for consolidation that I expect will accelerate very soon. Based on the research I do and all the conversations I have with revenue leaders, I will help the market, and specifically, Outreach’s customers and prospects, prepare for those changes and understand what building blocks to put in place to have a thoroughly modern and predictable revenue organization.

I’m also working closely with our commercial and product teams. On the commercial side – to help those teams deliver more and differentiated value to our customers and prospects – such as trend presentations, workshops, and tech maturity assessments. I expect to identify and bring in more partners to our ecosystem to extend the value on the product side. I will be a “voice” for the market and our customers to ensure our product road map is in lockstep with our customers’ needs and what they don’t know they need yet.

As a futurist, what are some of the biggest trends you’ve been following and the biggest predictions you have for the near-future?

There are a couple of different trends that I’m seeing. On the buy-side, buying committees are expanding, so you see more folks involved in the decision-making process. We also see very distributed buying committees, which we already saw before the pandemic, but now we see teams distributed even more. We have more millennials in the global workforce – they’re over half the global workforce now – and in decision-making roles, such as economic buyers, influencers, and coaches, many tend to lean into a consensus-building, decision-making style. So modern business buyers are looking for efficiencies and collaborative interactions with their selling teams.

There’s been the proliferation of SaaS outside of just pure technology. All types of industries embrace as-a-service (XaaS) delivery models, dramatically changing the expectations for the type and frequency of sales interactions. With XaaS models, this big one-time spike before the deal gets closed or 90 days before the renewal is up, has kind of gone by the wayside. These buyers now want continuously connected value with all interactions on all channels across the entire customer lifecycle.

On the sales tech side, we see the last of the point solutions out there with a big movement to the platform. A great example is with Conversation Intelligence – in the early days – it was an innovative new category.  As the technology matures and technology buyers gravitate to a single integrated platform, Conversation Intelligence is now a new capability on the sales engagement platform. We recently launched Kaia, a voice-and video-enabled virtual sales assistant that surfaces relevant enablement content based on real-time buyer prompts. Kaia’s in-the-moment coaching allows sellers to answer complicated product or solution questions on the spot, leading to faster deal cycles and better buyer experiences. The boundaries between sales technology categories soften and begin to converge. I expect revenue operations, revenue intelligence, and sales engagement will come together with engagement data at the center of everything. There are many exciting things that are happening as we look at the broader sales and sales technology landscape.

Over the years in tech, how have you seen technology redefine the way sales people and marketers work, hire and form/shape teams to align to business growth?

Sales technology is having a moment right now. If you were to transport yourself back to 2009 when all the marketing automation point solutions were consolidating and marketing automation transformed outbound marketing — that’s where we are today with sales tech. Market digital transformation came first, and now all types of organizations — not just the tech that companies need to digitally enable and transform their selling systems.

Automation and AI have matured such that when embedded into sales engagement and other platforms, they can transform the selling and buying process – delivering better seller and buyer efficiencies and greater seller effectiveness. That’s the world we are in now! But companies and business leaders are in different places in the maturity continuum. That’s why it’s essential to have analysts, evangelists, and other individuals out there that demystify these tech decisions and business leaders think through some of these complex decisions.

I have a vision that I don’t think is too far in the future. It’s a world where, instead of 20% of employees making up 80% of the quota, 80%- 90% of the sales team hits their quota. Sales teams will be smaller, more agile, and fully-abled with technology. Sales leaders will rely on data versus gut-level decision-making and gain leverage through training and smart tooling. Sellers, relieved of administrivia and armed with the very best engagement and intelligence platform, will be consultative; they will consume data inputs and decide what to do next. Maybe these sellers will be so effective that they will only need to work three or four days a week. I can’t wait to see how it all plays out. But one thing I am certain of is that B2B sellers will continue to play an important — albeit different role — in the buying and selling process.

Can you talk about some solutions that sales teams should adopt that help drive better business outcomes?

I read this book recently, AI Superpowers, written by the former head of Google China, and it’s an interesting read. He wrote about how automation and AI are going to replace jobs. That may be true for some industries, but sales are probably always going to be in-person, even though we can use all of these algorithms in the backend that are telling teams what to say to generate the best leads. There are certain professions where empathy, authenticity, and human connection are critical, and I firmly believe that B2B sales is one of them.

But you’ll see salespeople of the future hyper-charged with technology and that’s what I’m interested in…

A few thoughts on what you feel today’s sales leaders need to do to motivate, train and uplift their teams to optimize business and sales performance, and the sales technologies you feel sales teams should have more of (implementation / better training) to drive goals?

I think empathy and intentionality are paramount. I was just talking with an Outreach sales leader, and I asked him: “What did you do that was innovative with your team during COVID that you will keep doing after the pandemic?” He has about 50 folks, all relatively early in their sales careers, that report into his group. Once COVID hit, the first thing he did was start to focus a lot of extra time and attention on their mental well-being. He also said he narrowed the span of control for his managers. Instead of having eight reps, they went to six, so that each manager could be there during this time when everybody was remote and potentially could feel disenfranchised. He also created a massive spreadsheet to monitor his intentional touches with every member of his organization, and he would interact 1:1 via text, social, or social email or phone once a week. He has intentionality about the process, and he plans to keep that.

Before COVID, you could get by with minimal engagement in the office. If somebody missed a meeting or you forgot to say something, you’d see somebody at the watercooler. Now, sales leaders need to be very intentional with their communications.

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