Advances in sales technology transform how we reach customers and prospects, but the human element is still essential. To build personal relationships, we must understand who we’re talking to and how to capture their attention. Join Jill Rowley, Founder and Chief Evangelist at #Social Selling, as she shares how to be more relevant, personalized, and human in your sales.

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Tim Clarke: Thank you for joining the Quotable Podcast. Today we’re speaking with Jill Rowley, Founder and Chief Evangelist at #SocialSelling. Welcome, Jill.


Jill Rowley: Thanks, Tim and Kevin. I’m excited to be here.


Clarke: I know this is the second Quotable Podcast that you’ve been on with us, so tell me what’s new. And, perhaps, also, for any listeners that aren’t familiar with you and some of your work, perhaps you can give a bit of background.


Rowley: Sure. A little bit of background about myself, I am a sales professional trapped in a marketer’s body. My [bio] was marketing for over a decade. And part of being a great successful sales professional is really knowing your customer and understanding the world in which your customer lives. So I know a ton about modern marketing, but true and true, I am a sales professional.

Today I spend most of my time evangelizing digital sales transformation, of which social selling is a component of that. I work with really large enterprise companies, but also half of my time is spent with my portfolio of startups. And they range in marketing technology, sales technology, and probably my nerdiest one is predictive maintenance in the industrial IoT space.


Clarke: Sounds thrilling.


Rowley: Yes, it is.


Clarke: Well, I’m Tim Clarke, Marketing Director at Salesforce. And I’m joined today by our guest host, Kevin Micalizzi, Product Marketing and Senior Manager at Salesforce, and also the Executive Producer of the Quotable Podcast. Welcome, Kevin.


Kevin Micalizzi: Thanks, Tim.


Clarke: So today we’re going to be speaking about how to sell like a human. And I know this is a topic you were speaking about at Dreamforce 2016, Jill. From my personal sales experience we have touched on using different social tools. And this is something I know you have talked about quite a bit.

But I’m sure we’re all very familiar with the fact that we’re all receiving these different automated emails that are meant to sound like a human, but we know that they’re not. So just at a high level, what do you mean by this whole concept of selling like a human?


Rowley: I’m a huge fan of tools and technology that make us more efficient, and that automate manual processes, but you cannot automate building human relationships. And the challenge that I see now is that almost every company is running the same sales play. Meaning they’re hiring more salespeople to send more emails and make more calls. And that is causing the buyer to receive more automated, not targeted, not personalized, not specific, interruptive messages into their inboxes.

And on top of that, now that contact data has really gone to zero in terms of, I can get an email address for just about anybody, I can get just about anybody’s phone number, and now everyone has access to do more emails and calls, our initial reaction is to, if we don’t recognize the sender or the subject line, we ignore. And so more isn’t more better, more relevant, more personal, more human. It is how you’re going to get through to someone. That’s what I mean.


Micalizzi: So, Jill, there’s a lot of talk now about artificial intelligence, and how it’s going to make all of this so much simpler and so much easier to make that connection. And I know some folks talk about it in terms of augmented intelligence, where it’s supporting the sales rep in what they’re doing. What do you see as the balance we’re going to need to find here?


Rowley: I think the augmented intelligence — and I like that — is what is going to help do the manual work that the best salespeople do today. Let me give you a very specific example. So I’m on the board of a company called Affinio. And one of the sales reps reached out to me today and he said, “I see you have connections at Bain & Company. And we’d like to have conversations with Bain.” And so I went and I looked on LinkedIn to see to whom I’m connected at Bain.

I did a search for Bain, and then digital and found a whole series of people. I’m not actually connected to the woman who leads the digital practice, but I then found videos of her talking about digital transformation. I found that she had been on a list for top women in consulting. I found the blog post that she had written. I found her on Twitter and what she tweets about. And all of that was pretty much done very manually.

What would be ideal is almost [bot]-like if I could type in Bain digital and that work was done on my behalf. So then, as I was synthesizing and pulling out the relevant insights and crafting my message via LinkedIn or Twitter, whatever it shows is her most active network or where she would be receptive to a message, that work was automated.

Today that was a very manual process on my end.


Clarke: But at least you’re doing that research. I think even just going back to basics, there are still so many organizations where perhaps on an individual level they get it. There are some great reps that understand what they need to do, all the things that you’ve talked about. But on an organizational level they’re still not there yet, saying that this is the standard way and the standard practice, etcetera.

And I think, again, we’ve just received all these generic emails. So I target a sales audience, everything that myself and Kevin do. We’re all about giving back to the sales community. We’re working on [this incredible] content, the podcast, the videos. So when I receive an email that says, “Hey, Tim, I know that you target the chief marketing officer, and we can help you put on events and get you access to CMOs …” 


Rowley: Wrong.


Clarke: Right. So the question, I guess, here is — is that an example of someone that’s not doing their research? Or could it be, perhaps, an example of someone that isn’t being human, i.e., it’s technology and they’re not using the data correctly?


Rowley: Yeah. I think that’s an example of a mess. So either they aren’t doing the research, it is being automated, so there was no human aspect to that. And it stood out to you because it was wrong, so it left a bad, negative impression on you.


Clarke: Right.


Rowley: I think that what you said hit me, that there are great reps who are doing what I just described. At an organizational level we have not seen sales leadership move to requiring this more relevant, more human, more personalized. They’re still running the volume play of more emails, more calls, more contacts.


Clarke: Spray and pray and hope something hits.


Rowley: Exactly. And it’s not getting the job done. And so I’ve been speaking a lot to the sales individuals. I’ve built a community of salespeople, or I’m part of the community of individual salespeople and helping them learn best practices. Then I’ve really tried to take it up to the enablement level. So sales enablement and thinking about this at a programmatic level — what kind of transformation do they need to drive at a programmatic and an organizational level?

But what I realized, Tim and Kevin, is that at that sales leadership level, if that strategy, if the plan doesn’t change at that leadership level, then everything else is for naught. And that’s where the education has to occur, that sales leadership level.


Micalizzi: Which makes absolute sense. I think that’s the biggest question in my mind. Sales reps and even sales leaders are being asked to do so much more. And we have artificial intelligence, augmented intelligence coming, but not really at the level like you were talking about. So doing that kind of social research does take a lot of time. How do you scale what you’re doing to really meet the level that the sales reps and the sales leaders need?


Rowley: You have to look at it through the eyes of the salespeople on your team. And I think you need to actually spend some time with those salespeople and understand how they work today. And then spend time understanding what the future of sales looks like. So you need to understand the current state of your organization. You also need to understand what the future state of sales looks like.

Hence, why I attend events like Dreamforce, why I go to Forrester’s B2B Marketing and Sales Enablement Conference, why I spend time with the analyst at SiriusDecisions and CSO Insights. I need to know what the future of sales looks like. I need to have a really firm understanding of how we’re operating today to be able to map from where we are to the desired future state. Digital transformation as a broad topic is on every CEO’s agenda.

It is now something that every CEO is forced to think about, every CIO, every CMO, every head of support and customer experience. But who is missing from that conversation is the chief sales officer. And it’s time that the chief sales officer understands that everything else is changing around them, and that at an organizational level they’ve got to change the way they sell.


Clarke: Where do they even start? [Unintelligible] sales leaders, sales managers on here. And we’ve been talking about this conversation for 10 years now. Social selling, you should do it, or there’s another layer of [broader] selling. Hopefully, now we’re in broad agreement of the fact that there is another channel to market. But what are some of the steps?

You mentioned at the beginning you’ve worked with a whole variety of organizations, small and large. What are some of the steps that you would recommend, or tactics for people listening to this podcast?


Rowley: Yeah. I’ll just borrow from Jeff Immelt, the CEO of GE. And when he talks very broadly about digital transformation, he looks at it from culture. What is the culture of the organization? Do they move fast, or did they move slow? Do they have a lot of internal processes, old technology, or do they have more modern infrastructure? So he looks at it from a culture, from a talent. Who are the people in his organization with the right skills?

Is there upskilling that needs to happen? Do they need to hire to a different profile? Technology, what kind of technology do they need to invest in to support moving fast, not slow, to support engaging with their customers digitally, not analog?


Clarke: And on the technology side, I guess it’s also making sure that you don’t go too far that you sound like a machine, going back to the point of this. Actually implementing and thinking of the strategy behind using that technology, right?


Rowley:That’s exactly right. And tying it to the relationship aspect, not just automating low end touches, not a more approach. And then, finally, ecosystem. He knows that this transformation requires getting outside expert help, right? So in all areas, in their engineering, in their supply chain, in their manufacturing, in their marketing, and in their sales. And so they’re looking at an ecosystem of experts.

Maybe they’re the big consultants, entrepreneurs in resident that they can bring on, who actually study the future of sales and how to leverage technology to drive transformation, and then also from technologies and vendors that they work with. So if I look at digital transformation at that highest level, culture, talent, technology, ecosystem, I would say to a sales leader, “Do the same.” What is the culture of your sales organization? What is the makeup of your sales team and what kind of skills do they have?

What are their digital competencies? What are their social competencies? I was talking with someone yesterday who is in the construction industry. And I said, “I don’t know the construction industry the way that you do. You have to tell me, are your customers digitally savvy? Are they socially savvy? Are they spending time in digital and social? I don’t know the construction industry the way that you do. But you need to answer that. And if your customers are learning in digital and they are engaging in networking and social, your salespeople need to be, too.”


Clarke: And it’s almost a level down from that, as well. Because, for example, now there are so many channels. If you look at someone like Gary Vaynerchuk, he and his team are clearly covering every single channel. I know this is an interesting topic on whether you choose one or choose them all.

And something you said, obviously, you go where the buyer is; is it Snapchat, Instagram, Twitter, Facebook, LinkedIn? There is too much out there. And I, personally, believe you can’t be everything to everyone.


Rowley: Getting dressed in my closet this morning I had my Mac with me and I was watching a video on CNBC with Clara Shih the CEO and Founder of Hearsay Social. She’s absolutely brilliant. She’s a former Salesforce employee like myself. And the CEO of Reddit and one other person who was being interviewed on CNBC. And it was all about millennials and connecting with the millennial generation. And they are on Instagram, they are on Snapchat and I’m frightened.

I’m 44-years-old and I am not on Instagram and I am not on Snapchat. I am just to monitor my children’s activity, but I’m not there. And when I do spend time just trying to understand those channels, I don’t fit in there. I can relate to the baby boomer generation. My husband, he is the 50-plus-year-old white guy, who reads the Wall Street Journal in print.

And so I look at even my own uncomfortableness in the more modern networks and I know I’m not there, and I do worry, Tim and Kevin, whether I should be there. Because if I am trying to build relationships with the generation that are using those networks, I need to be there.


Clarke: Right.


Micalizzi: Jill, I want to back up a little bit about the digital transformation you were talking about. It sounds like you’re talking about it needing to be a top-down. And I’m thinking about our listeners who are probably in organizations that have not embraced change. And I’m curious what your advice is for them to make changes in how they’re selling.


Rowley: Absolutely. You can’t wait for that mandate to come top-down to change because you have to make your number. So you have to take on personal development. You have to take responsibility for your own personal development. And there are plenty of resources out there. I actually have a copy in my bag right now, Jamie Shanks’ book, Social Selling Mastery.

And within this book it’s written for two different audiences: one, the individual social seller, and how do you optimize your digital presence for the buyer. How do you grow your professional network? How do you learn how to expand your network with not only people who can buy from you, but people who influence the buyers that you’re selling into? How do you curate content and share content across social networks, so you can be more visible and valuable to your buyers? So this book, that’s one resource.

There are lots of other, not only books out there, but podcasts that salespeople can listen to. The Quotable —


Clarke: Well, what’s your number one podcast?


Rowley: My number one podcast is Quotable.


Clarke: Very good.


Rowley: So there are tons of podcasts, and there are communities, too. There is the sales hacker community. There are a number of resources out there. And if any of the listeners want to send me a tweet or connect with me on LinkedIn, I’d be happy to look at their background, what industry they sell into, what company they work for, what demographic their buyer is in, and make some very specific suggestions to them on an individual, human level. 


Clarke: Let’s talk about some of the negatives if you don’t get this right. I think we’ve seen a few examples — and we don’t want to necessarily be too specific right now — of people prospecting into senior [execs]. Like one recently prospecting into a cloud company saying, “Hey, are you ready to move to the cloud?” Then some people, perhaps on the receiving end of that, I know for myself, I get one email prospecting towards me, and then they respond, “I still didn’t hear from you.”


Micalizzi: You get the bumps. They’re trying to bump it up in your inbox.


Clarke: Exactly. And then the frustration builds and builds. I sometimes have to hold back from posting that on to a social network and say, “This is an example of not selling like a human.” A sales professional that is, perhaps, being empowered by their marketing team with some great technology for prospecting, what is the risk to the salesperson if they don’t get a right balance of ensuring they sound like a human?


Rowley: Their own personal brand is the risk. So it is their own brand. Of course, when you’re in sales you are measured on a monthly or quarterly number. And you are held accountable to that number. And a lot of times you’re managed by fear. If you don’t make the number, you’re out. So we have this looming, monthly, quarterly pressure to make our number. But I challenge every sales professional to think about their longer-term career and their personal brand. Because we’re working for companies on average under two years now, is the tenure.

So there is this need to push back and to say, “This is not an approach I support.” You might actually have to leave that company. It’s that serious. But this is your personal reputation. And as it relates to sharing examples of things that aren’t as practiced, I’ve written a post, “I’m angry and here’s why.” And I actually do tweet. I take screen chats and I will share on Twitter bad examples. Hank Barnes at Gartner, he has a “Friday Fails.” He does the same thing.

Most times I will black out the person’s name or their company name, but I have on occasion included that and, in particular, the ones that threaten me. I will get emails, “This is your last chance.” Are you serious? You’re going to threaten me because I haven’t responded to your last 12 ridiculous emails that don’t know who I am? Your offering isn’t relevant to my world, my business — nd now you’re threatening me?


Clarke: And some people just don’t get it. I know Kevin and I have had this on the podcast, as well. For example, people are inquiring: Perhaps we want to look at promoting it on other people’s podcasts? And they seem to think by taking an angry approach that that’s going to get some sort of reaction and that, perhaps, it may turn into a business opportunity.


Micalizzi: Jill, how should people be balancing their time between the two different activities? The content creation and curation to build your brand identity versus really researching and developing greater depth for prospecting or for finding new opportunities?


Rowley: It depends on your role. If you’re in sales and you’re measured on getting meetings, you need to work and balance the amount of time you spend researching those buyers to get the meeting. If you are a named account rep or a national account and you only have one customer that you manage, the amount of research that you do on that specific customer will be much more in-depth.

You will spend a lot more time researching that one account and the people within that account, the company and what’s going on at a company level, the industry in which that company actually operates, and understanding the top things that are affecting that industry. So you have to look at it as it isn’t a one-size-fits-all. But the other thing I want to say is, you have to embed social and digital and this new way to work into the existing sales cadence and methodology and systems and processes.

And this is why it’s so important that at an organizational level sales leadership and marketing leadership come together on this, and that they bring sales enablement and training into this new way to sell conversation. And they look more holistically at what needs to change internally to respond to what has transformed externally. At an organizational level you also need to think through compensation.

How are you compensating your sales team? You have to think through territories. And traditional territory models really don’t make a whole lot of sense oftentimes in the new way that people buy. So I think that there is a balance in terms of how much time is spent based on your role, but more holistically, this really does require an organizational lens.


Clarke: So, Jill, we’re nearly up on time here. I’m going to ask you one more question and I’m going to focus on one of the words you used there: balance. I’m always personally interested in the balance between, if you can access all this data, how much of it you actually use. So, for example, if people look at my social networks, they will see that I have a beautiful puppy recently.

But at the same time, do I want to receive a prospecting email that says, “Hey, Tim. I see you. . .” and it has a little sideline about it? Maybe that’s OK and maybe it’s not. I want to throw it to you. Any advice you have here on if you have access to information, what should you use and what shouldn’t you use to avoid being creepy?


Rowley: I love that question. If you are sharing puppy pictures in Instagram, and I want to connect with you about your puppy and I’ve never met you, sending it in an email would be inappropriate. But commenting on your puppy picture in Instagram is appropriate, because you’ve put it out there in that network. I’ll give you a very specific example because I really want to be practical.

Brocade is a company I’ve been having conversations with for a very long time. There’s a woman who is very instrumental to the program that we’re trying to drive. I am connected with her on LinkedIn and I follow her on Twitter. I do admit, as we got farther in our relationship and I really like her and I’m connecting with her on another level, I went to Facebook and I checked out her Facebook page. I see that she’s now recently pregnant and I saw photos from her wedding, and that her and her husband are very big sports fans.

They’re Giants fans. Have I mentioned any of that to her in conversation on the phone or in email? Absolutely not.


Clarke: Well, she’ll know now.


Rowley: She’ll know now. Right, exactly. I’ll send her a Giants onesie.


Clarke: Right.


Rowley: But I think you have to have sensitivity. If you’re learning information in a network where you’re connected to that individual, stay in that network. But don’t take what you learn in Instagram to try to craft a cold email.

I do think that becomes a bit creepy.


Clarke: Jill, I really appreciate your time. I think you do have some great insights here for the audience on how to sell like a human. We all know that buying is changing and selling is changing. But most important, the thing that, perhaps, isn’t always talked about is technology is evolving so rapidly, as well.

And just because the technology is available it doesn’t mean that we need to start automating everything. We need to automate the right things. But there is still, I believe, a massively important role for salespeople to play in being those consultants and offering true value. So, Jill, you’ve got 30 seconds. Any final points? Any areas you want to wrap up on?


Rowley: I’m super excited about the transformation that’s occurring. And I feel like I have seen this movie before, because I spent a decade working with the marketing professionals to transform the way that they marketed to the modern buyer. And I see the same thing. If you look at Scott Brinker’s Chief Marketing Landscape diagram going from 100 tools to 4,000 tools, we’re going to see a very similar thing happen in the sales industry.

And I think your point about not leading with the technology, but not being afraid of it and not ignoring it and striking the balance between that, is really important. So I’m a resource. I want to help. I genuinely want to help people and organizations sell the way that people want to buy. And I don’t want to try to erase the word “sales” from Wikipedia because it has such a negative connotation. I actually want to transform the perception of sales to be something that is very positive.


Clarke: OK. And, clearly, it’s something we’re really passionate about here at Salesforce and with the [unintelligible] team, as well. Thanks, Kevin, for joining us today as our guest host.


Micalizzi: Thanks, Tim.


Clarke: And thanks, also, to Jill for joining us and sharing her insights today.


Rowley: Thanks, Kevin. Thanks, Tim. Appreciate it.


Clarke: And thanks to everyone for listening in. And if you like what you hear, please take a minute to give us a five-star rating and feedback on the Quotable Podcast. And don’t forget to share it with your peers, your customers and prospects, and also subscribe to Quotable to get even more great sales insights at Thank you.

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