Breaking the Grade

LinkedIn Connection to Contract: Josh's Proven Six-Step EdSales Method (No Paid Ads/Funnels/Cold Calls)

Josh Chernikoff

You’ve added decision-makers on LinkedIn.
You’ve liked a few posts, maybe even commented.
You’re showing up… but nothing’s turning into a call, let alone a contract.

Sound familiar?

That’s what I call the LinkedIn illusion—where activity feels like progress, but the results just aren’t showing up in your pipeline.

Here’s the truth: If you're an education company trying to sell into institutions, LinkedIn isn’t about going viral. It’s about using consistency, clarity, and credibility to turn conversations into clients.

🎯 This episode of Breaking the Grade reveals the Connection to Contract Framework—the same system I use with our clients who own successful education businesses that book 12–20 qualified sales calls a month organically.


Absolutely – No paid ads. No funnels. No cold calls. No gimmicks. Just a proven process that builds trust and moves the right people to take action.

And no—it’s not about only posting more. It’s about positioning yourself so the right people stop scrolling, start paying attention, and ultimately raise their hands to talk.

🎙️ Tune in to hear:

  • The #1 reason your messaging isn’t converting—and how to fix it.
  • Why “value” isn’t enough—education buyers want clarity and consistency.
  • How to build trust with your ideal client before they ever hop on a call.
  • The power of listening on LinkedIn (and how it leads to real contracts).
  • What working closely with dozens of education companies taught me about the long game.
  • Why most education companies stall after connecting—and the simple process to convert those connections into real contracts.

You don’t need a new tool. You need a tighter message and a smarter process. And - our six Cs. 

If you’re still wondering whether LinkedIn works for education sales—this is your answer.
This is the method.

#EdSales #EducationMarketing #LeadGeneration #LinkedInStrategy #BreakingTheGrade



Josh Chernikoff (00:01)

Our students are the future. How we advance innovation and impact and approach equity in their classrooms will determine how we thrive as a world community. The status quo just won't cut it. That's why we're here to break the grade. Hello, breakers and difference makers. I'm Josh Chernyakov, host of How I Broke That. I'm a two-time entrepreneur in the education space, and I've successfully exited

both of those companies. I've experienced my fair share of breaks in my life and I'm here to bring my signature approach to my new show, Breaking the Grade.

I'm embarking on this special journey alongside my good friend and mentor, John Gamba, Director of Innovative Programs and Entrepreneurial Residence at Penn GSE. In our podcast, you'll hear from emerging business owners in the education space who are working to transform education as we know it. Tune in as we hear about industry trends, unique principles and practices, and the attempts that have and haven't worked.

for our grade breaking guest. So fellow entrepreneurs and educators, what do you think? Are you ready to take a hammer to the education space and break the grade? Welcome to Breaking the Grade.

Welcome to another edition of Breaking the Grade. This one is important. This one has been requested by the audience of Breaking the Grade. From connection to contract, how education companies win on LinkedIn and in some cases very much lose on LinkedIn. Let's cut to the chase. You're building something very impactful, something that changes lives.

And you need people to notice you. You need people to believe that you have credibility. And there are lots of places to do that. Conferences, quality emails, other areas that you can message correctly. To me, one of the best places to do it is on LinkedIn. And when you do build your credibility on LinkedIn,

People will begin to notice you. People will begin to listen to you. And you will be able to go from connection to contract and everything in between. And I've got six C's that I want to talk to you about today when it comes to LinkedIn. Here's the truth. LinkedIn is not, I repeat, is not a magic wand. No, no, no.

It's not about blasting generic pitches or just being loud on LinkedIn. In fact, it's about building credibility. want you to think about LinkedIn as a conference. Okay. Would you go to a conference and just be loud and just pitch? Hopefully not. We know that doesn't work from one of our shows that we just did. LinkedIn.

Think of it like a conference in the sense that the conversations are going on in big rooms and you should be joining those conversations or leading them. Those conversations are going on in the comments and you can think of those as breakout rooms and you should be leading or joining those conversations.

I want you to also think of your LinkedIn profile as a digital handshake. It's where district leaders, decision makers, potential partners, where they are getting their first impressions of you. That's your digital handshake. That's your first impression to these people. And those impressions are going to lead to conversations. And that's fantastic. Now, do you want to have long

good, deep conversations, or do you want to quick conversations that, sorry to say, are potentially meaningless? Here's the thing about LinkedIn. It is a step-by-step process, and it's not two steps from connection to contract. As I said, there are six steps. And today we're going to break down those steps, and I want you

to understand how LinkedIn can help you grow your education business. And it can also lead to more credibility, more clarity in your own business and your own confidence will grow. So we're talking about six C's. Connect, comment, credibility, conversations, contracts, consistency. So if you're ready to stop wondering how LinkedIn can work for you,

This show is right for you. Now, I want to preface this though. Please remember, we have another show and I'll put that in the show notes here with my team about optimizing your LinkedIn profile. And you need to also optimize your LinkedIn profile for these six Cs to work. So you can't just have a LinkedIn profile that has no banner.

No picture, no headline, no about section, no featured section, no experience section, no recommendations, down the line there. No, you have to optimize your profile as well. But when you do optimize your profile, the six Cs, connect, comment, credibility, conversations, contracts, and consistency will work for you. Now, let's start with connect.

Your core message has to be connecting with the right people. And that should be the core message to yourself. That's even before you start messaging anybody else, you have to understand that you want to connect with the right people and not everybody. So you should use LinkedIn search filters. They're pretty easy to use. So find the right people.

One pro tip, look for people who are active on LinkedIn. That's a search filter. You can use personalized notes. Again, this is not about 5,000 contacts. It's about 500 in the beginning. This might just be about 50. Try and get 50 a week. You can personalize 50 notes. And LinkedIn algorithm,

Okay, that algorithm, it favors relevant connections. So that will increase your visibility to your connections. What does that mean? That means that if you connect with relevant people to what you do, LinkedIn is going to put you and your message and your credibility and your offer and your value right in front of those people.

It's like going to the front of the line when you're at a conference if you're asking questions because you have a relevant question or comment for other people to hear. I want you to think about commenting. It's not all about posting. Okay? It's not all about posting. Visibility starts with engagement in your ideal client's world. Now, this is weird and I've said it before. If LinkedIn, if you think of it like a gym, okay?

And if you went to an actual gym and people were just working out on the treadmill or lifting weights, and you went up to the person who was running as fast as they could, and you said, you got this, you got this, you got this, that would be weird, but that would be nice of you. If somebody was trying to lift 400 pounds and you went up there and you gave them a spot, you said, you got this. Again, that would be weird. That would also be very nice of you. So.

Think of commenting on LinkedIn as going in there to support others. Okay? So you don't have to create the world's greatest post. You can go in there and leave insightful comments. You can ask follow-up questions. You can start a conversation publicly in somebody else's post. They'll appreciate that. And now your visibility is on the rise. How do you do this? Like the gym, you schedule it in.

your calendar, right? So I have 30 minutes a day in my calendar, seven days a week. I don't go to the gym seven days a week, but seven days a week for LinkedIn. I call it LinkedIn and learning. And think of it this way, okay? When it comes to commenting, it cannot hurt. You can do it as much as you want. Can you over post maybe? And we'll get there, but we're just talking about

the second C, which is commenting. And I do not believe that you can over comment. Third C, credibility. Maybe the biggest C. Your profile is your digital storefront. I've said it before, I said it again. Showcase expertise through your optimized profile, of course, and value driven content. Now I'm not going to get into that optimized profile again.

Okay, you know you can get me started on that. Talking about really in this point, value driven content. But if you did want me to mention the profile, I will, I will, I will. We've got the banner. We've got your professional picture. We've got the headline. Okay, that headline is maybe the most critical part of you building credibility.

the headline, the formula, I help who using what method get which results. We've got your about section. Your about section should sell to people. Check out my LinkedIn profile if you'd like. It works pretty well as a sales funnel. It's not a resume. My featured section. I love my featured section. I'm always, hopefully adding value to people who go to my profile by putting

my featured posts up there. Then you've got the experience section, your recommendations, your skills. So you've got to optimize that profile. And then we've got that value driven content that will help build trust. Your value driven content will help you build trust. How do you do that? You have to think of good posts. You have to think not of good posts in the sense of this is 500 words.

or I tagged a bunch of people in, which is not cool in my opinion, just tagging people in. Value-driven content, in my opinion, is telling a great story and then also giving people value, something they can walk away with. I did this a couple weeks ago when I took a virtual trip to Lithuania on a Thursday and I was part of a sales roast.

for 13 Lithuanian companies and in my post I had a picture of me and my wife in Europe. Now you would say why, why do that? That's because our family eventually wants to move to Europe. And I think I'm taking one step closer to being able to do that by getting to work with some Lithuanian companies in Europe in the ed tech space. So I put a picture of my wife and I, and I could put that into the show notes.

It's post I'm really proud of. A lot of people were interested in it. And then I provided value after. I talked about how we want to move, and the picture's really special to me. And then the next day, I put this really cool post because I traveled from virtually Lithuania to Argentina, which is where my wife and her family are from. I had this really cool picture of my father-in-law, probably from the 1960s.

cool beard, cool dude, black and white, smoking a cigarette, sitting in a car. He's from Buenos Aires, BA. And so I used that picture in the post. And then I talked about the value I was going to drive towards these ed tech companies that I was coaching up that day. So I think of that as being value driven for two reasons because A, it's an interesting story. B, cool picture.

Being a little vulnerable there, by the way, I only got to meet my father-in-law once. So I know he would be proud of me having coached these companies in Argentina and he had tech space. And then C, I did bring value information that people could use. Now let's talk about C number four, conversations. DMs that build relationships. So DMs are.

for building relationships, not immediate pitching. Start with context and curiosity. That could be two more Cs, but I'm not gonna put those in there. What's really smart is to reference posts or mutual connections when you DM people. Lead with questions and definitely do not lead with pitches. An example of that, I wrote this out. I saw your post on dot dot dot.

How are you addressing dot dot dot right now? Or, hey, we have a mutual connection and they mentioned that we should potentially work together. Those things are really helpful to get conversation started. Again, think of LinkedIn as a conference. And if you walked up to somebody at conference like that, hey, I saw your post on this or we have a mutual connection, you think they would start talking to you. Now, you might say I'm not comfortable reaching out.

in a DM type situation, you should be more comfortable with the way I described it because this is not salesy and this is not pushing. So hopefully that works for you. Number five is the one you've been waiting for. That's contracts. How do you convert conversations to calls and then to eventually contracts? Now, how do you do that? You focus on discovery at that point.

and value again and not pitching. You can frame the calls as a chance to listen to each other and especially a chance for you to listen. That you really just want to understand their needs and let them know that there will be no pitch. That you are truly there to listen. We call this the Raise Your Hand Campaign in the Ed Sales Elevation Experience. If you want to hear more about it, let me know. It's

Very effective. So an example, let's hop on a quick call to learn more about your initiatives and explore potential synergies. No pitch there. Or, hey, if you've got a good headline, I help companies do this. I help schools do this. I help universities do this. I'd like to learn more about your challenges and see if I can help you at all. No pitch.

no sale coming, just wanted to listen. So focus on understanding their needs. And that gets you one step closer to that contract. Finally, the last C is consistency. And I'm gonna bring it back to the gym because if you don't consistently go to the gym, you will not see the results.

You need to consistently go to the LinkedIn gym to see the results. So you guys know I have LinkedIn and learning in my calendar every single day. You could do that maybe every other day. If you want to consistency builds recognition and will drive opportunities your way. LinkedIn's algorithm rewards this serious. LinkedIn's algorithm.

rewards consistency. So again, fine. Don't block 30 minutes like I do, just block 15 minutes. Schedule content. Engage. Think about when you go to the gym and you don't have a plan for that day, you walk around the gym and you just basically don't know what you're doing there and you're just trying to get done. But when you go,

to the gym with a plan, you execute on that plan and you feel very good about what you've done and you see the results. That's LinkedIn. If you schedule your content, so get ahead. If you engage, you're going to leave the gym each day feeling very good about what you did and then you're going to see the results. So let's recap here. Remember the six C's. Connect, Comment,

credibility, conversations, contracts, and consistency. You cannot go from connection to contract. You cannot go from connection to contract, especially if you don't have an optimized LinkedIn profile, but that's for another show, even though I couldn't resist myself. So what's your biggest LinkedIn challenge right now when it comes to growing your credibility?

the most important thing you can do on LinkedIn for your education business. Please message me on LinkedIn. Comment in our show notes. I'd love to hear your thoughts and you probably know by now if you listen to this show, I'd love to help you too. The last thing I'm going to do is that if you reach out to me, I've got

really good pre-made checklists that can help you with this. So all I need you to do is reach out and I will send you those checklists. And you can kind of see how you can improve your LinkedIn profile, how you can improve your LinkedIn credibility, the big C. And hopefully the show, our show, Breaking the Grade has been critical, another C, in helping you with that. And if it has,

What I would really appreciate is if you would review our show. Five stars are always welcome. Reviews are always helpful. If people in the education space, our colleagues, another C, see us making progress here, they'll listen more and more to the show. I believe in a rising tide. So LinkedIn is where deals are made. If

You do things strategically and you can now. And if you need any help, I am here for you. Coach Chernikoff is here for you. That's my last two C's of the show. Thanks for listening. Hey, breakers. Thanks for joining us on Breaking the Grade. If you want to get to know your fellow breakers in education better, please join us in our community in Mighty Networks. You can also follow us on social media for lead generation tips.

information about the community and the social media in the show description. And if you want to help us out, please like and subscribe to the show. Keep on breaking you lead gen legends.



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