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The 3 Essential Steps to Mastering Social Selling [Interview with Jack Kosakowski]

Forster Perelsztejn author on Overloop the sales engagement, cold email, and LinkedIn automation software blog
Forster Perelsztejn Jan 23, 201810 min read

If you ever wondered how to approach social selling, this is it: Jack Kosakowski is nothing short of one of the leaders in the field.

In this interview, we talk about: social selling, sales and marketing alignment and why loving your customers is essential.

Check out his website (Social Selling For Leaders) and get social with him on LinkedIn!

Hey Jack, thank you for doing this! Why don't you start by introducing yourself to our readers?

I'm a 14 year sales professional, and I always make a joke that I'm kind of the Bruce Jenner of sales and marketing. I was sales. I thought I was all sales for a long time, and then worked at Act-On software as a regional sales manager for three years, and as I was selling a marketing technology, I was told by a CMO that I was a really good sales person, but I knew nothing about marketing when I started.

I decided I'm going to figure out marketing, so I started to try to understand and use social media from a marketing perspective. Essentially, I've learned that I could get a lot of sales conversations from from LinkedIn, from Twitter, that I couldn't get anywhere else. So I said: "You know what? I'm going to prove that this Social Selling thing actually works." Because everybody else in the Social Selling space was a marketer, and I'd never carried a bag or had to hit quota, so I said I'm going to figure this out.

As I started to have success, I started to write about it, and then little by little, I started to build a personal brand and really understand social at a deeper level. Then, I started to become a content marketer, which I had no clue what that was at the time by writing on LinkedIn. Then, the next thing I know, I was one of the top – I was always the top sales rep, but I was crushing my number because of that, and then I met my business partner on Twitter. At the time, he became an Act-On customer, and then he asked me to open up the US division of his agency. That agency is in the UK, and they were very, very successful. At the time, they had five or six of the Fortune 500 as clients, and I opened up a marketing agency; didn't know what I was doing. Now I'm the CEO of a really thriving US division marketing agency.

Alright, so just to get everyone on the same page, how do you define social selling?

I look at social selling as an outbound approach. It's a one to one strategic approach that sales is using to create, strengthen, and influence one to one sales conversations from online revenue to offline close.

When you educate or train sales teams, in general, what is generally the biggest mistake or misconception you see about social media and social selling because when I'm on LinkedIn, I see a lot of people writing about how they get pitched on social media, and it was terrible. So it gets me thinking that a lot of people don't have a good approach, so what are the biggest mistakes or misconceptions you see around?

That it's easy. It's absolutely not easy. Social selling goes against the traditional sales approach, which is ask first value. You're asking for something that you don't deserve, essentially, is what the traditional model of sales is, right? Social selling is a whole different approach because what it essentially does is it forces you to give a certain amount of times and to give a lot more value before you ever go for an ask. It's a really tough thing for sales leaders and sales people to wrap their minds around because it actually goes against all the traditional ways that they've been taught to sell.

Let's say I want to get into social selling? What should I do? How much time should I invest every day? 

I think the average sales rep should spend no more than 45 minutes a day using social media, doing social selling. Really the problem with most sales people is they don't understand the tools that you need to be efficient with social media, and they don't have any formal education of how the technology and the tools work, so a lot of times, they're just winging it, and they don't understand how the strategy works. Just like anything else, right? You don't become Hussein Bolt overnight. Sales people need to at least understand the tools before they just start diving into this or they'll just waste their time on social all day.

Interesting! So what tools are we talking about?

One of my favorite tools is Sprout Social for salespeople because essentially what it does is it aggregates all your social media channels into one inbox email. Just alone, if you watch salespeople that don't know how to use Twitter, if you watch them try to find a notification or find how to reply to something, it's pretty hysterical, right? Just being able to take LinkedIn, Facebook, Twitter, using a multi-channel approach, and aggregating them into one inbox will make you a ton more efficient. Then also, being able to schedule out and find content more effectively. It can all be done in one single platform.

We use Sales Navigator. It’s huge for us. Yeah, Sales Navigator and really defining who your target accounts are, with multiple decision makers, understanding how many people are influencers to an actual decision maker because everybody wants to go after a decision maker, but using these tools like Sales Navigator, you can understand who's the tree of influences around the decision maker and really open up the engagement model to be able to use social to be able to get to people who aren't on social, but they are the ones that are influencing the decision makers to actually take a look at something.

Great answer, thanks! As you said, social media was first used by marketers. Actually, you run a marketing agency and you're a sales guy working with marketing teams. What common problems do you notice between sales and marketing? How do you envision the future?

I think the future of any scalable business is the integration and the alignment of sales and marketing. At the point that we're at right now, there's so many digital things going on, and now sales is forced to become part of this digital process that only marketing was siloed to do. In the future, the two are going to have to align because even sales people are writing content now. It's crazy to see that marketing is not on the same page, and they're not all using that content together in their marketing and sales process to get a buyer into a sales conversation. The companies that are siloed right now, they're not going to last long.

That makes sense. Talking about content, how do you use it to create a sales conversation?

Everything that you do in life is based around content, right? Every sport show we watch, every TV show, everything you watch on YouTube. Everything that we do in our life is all around content, so understanding how do we get the right content in front of the right people that can make a buying decision is crucial right now because of all the noise, and it takes sales and marketing to be able to make content work over time to get a sales conversation. That's strategic. Most companies go wrong because they think content has to be about their company, which is completely false.

You're trying to capture somebody's attention because if you can give value to them personally and professionally, whether that's through humor, education… that's when you're going to start to win, and you have to do that over time. The tough part was you used to be able to get one piece of content and get somebody to download something, and then make a phone call when it wasn't so noisy. Now, you've got to get them to watch and come back to your blog*. You've got to get them to come back multiple times to get them to actually take an action that would show a behavior that's "Hey, I'm ready to have a sales conversation!" You need sales and marketing to work together to do that. Otherwise, it's almost impossible.

*We know how hard it is, so here's our favourite guide about how to start a blog.

Okay so… 45 minutes a day on social media: how do you go about content? How much time should you be spending on it?

There are three steps to this.

The first step is to find really, really good content, and post it. You should be posting a minimum of three times a day on LinkedIn. You should be posting eight to ten times on Twitter per day, and you should really focus on finding quality content that fits the structure of your buyer and what really drives major value to them on a professional and personal level. You've got to make a commitment to 15 minutes a day of scheduling out that content inside of a social platform.

The next thing is, you've got to spend time to do some outbound engagement to your strategic accounts. You've really got to understand how to use Sales Navigator, so you can aggregate all of the accounts and all of the people inside of those accounts, and really 10-20 minutes a day, you should be spending just one-to-one outbound engagement. Looking for good articles to read, to share, to really get you to connect to that buyer in a value versus ask way.

The third piece to this is just reading and learning. I think a lot of sales people don't understand that you're connecting through engagement with your buyers. You want to do that proactive. You want to do that six months before they even know they're ready to buy, right? You want to build up your capital, your value capital.

You've really got to be understanding your buyers, and the only way you can do that is through reading. I think the third part of the 45 minutes should be spent reading. What are your buyers writing? What's going on in your industry? Using that as time to consume wisdom, so that you know what to share, what's going on in the industry, and not only that, but when you get offline, and you have these sales conversations with the people that you're connecting with, you have a level of wisdom that captivates them and will have them want to listen more because they know that you have the keys to the castle.

Besides the tools you already mentioned; in terms of automation, how important are tools in your organization?

We use Act-On. We use Marketo, as far as marketing animation technologies go. Those are big because where a lot of companies go wrong with their sales team is there’s all these things going on in marketing, right? There's emails going out. There's ads being run. There's tweets going out. All kinds of different social posts on different channels, and sales has no insights into real time behaviors of what people are doing with that content, so the marketing animation platforms integrate into your CRMs, and your salespeople can see real time who's been on the website.

What did they engage with? So that they know what channels they should engage back with these people, where they live, but on top of that, they understand what conversation they should have based around the behaviors. Marketing automation and the insights you get behind that are huge to really align sales and marketing and allow sales to get the information they need to make a sales conversation effective.

In one of your recent posts it said that you love your customers. Most companies only consider their customers as a source of income. How important is it to love your customers?

If you don't love your customers, you've got to get out. You've just got to quit. I mean, you're not going to always love your customers, but in the agency world, I'll tell you this, and even in the SaaS world, if you have customers that you don't love, you are going to be miserable. I can tell you that we, in the beginning, took on a few customers that weren't very smart, and we learned a hard lesson. From this day forward, I only take on customers that I love because I believe in what they're doing. I believe that they have a technology that works. I believe that they have the right mission statement. They're good people. There's a lot involved in this because otherwise, it's really hard to make people successful that you can't stand.

You've already delivered tons of value today. I just have one last question: what’s the best piece of sales advice you've ever received?

The best advice I ever got was from a CFO, and it was the one that said: "You're a really good sales guy, Jack. You're one hell of a sales guy, but you don't know what it's like to be a day in my shoes, and I think more sales people need to get out of the office, and they need to go spend a day or two with their customers. They need to do it on a regular basis. They need to see everything that their customers do from what time they get into the office to what's their daily life look like because I think most salespeople sell to trained pain, which is what they're taught in training, but the problem is that that's not how the real world works."

A CMO has a lot more problems than what you're trying to sell them, and a lot of times, you don't understand what type of priority you are until you live a day in the shoes of your buyer, so get out of the office. Ask your customers can I come just shadow you for the the day, and really understand what they go through.