Closing Time

Why “Connect-to-Market” is the New “Go-to-Market”

Are you truly connected to your customers?

Too many marketers think they know their buyers—but can you name seven of your customers by first and last name? If not, you might be suffering from disconnected marketing.

In this episode of Closing Time, Casey Cheshire discusses why go-to-market needs to become connect-to-market. Casey points to three areas where you should be making better connections with your audiences: Partnerships, Community, and Podcasting.

Stop assuming what your customers want. Instead, connect with them and ask. Learn how in this episode.

Watch the video:
Key Moments:
The Problem: Disconnected Marketing

Most marketers can rattle off the logos of companies they’ve worked with. But how many can name the actual people behind those logos? That gap signals a deeper issue: a lack of direct connection with buyers. Without those conversations, marketing becomes a guessing game. Marketers end up “hallucinating”—filling in the blanks with assumptions rather than real insights.

Disconnected marketing looks like this: Low engagement on emails and webinars, declining ad performance without a clear reason, marketing messages missing the mark with customers, events and campaigns that don’t attract the right audience. 

Casey argues that these issues aren’t just about poor execution. They’re a symptom of marketers losing touch with the very people they’re trying to reach.

Connecting With Customers via Podcasting

To fix this, marketers need to replace broad, impersonal go-to-market motions with a connect-to-market approach. That means prioritizing direct interactions with customers and prospects. Casey highlights three key ways to do this: Podcasting, Community, and Partnerships. Let’s start with podcasting. 

Connect-to-market - Closing Time Full Screen Assets

A podcast is more than a content engine—it’s a relationship-building tool. When marketers invite customers and industry leaders to speak on a podcast, they’re sending a clear message: “You matter. We want to learn from you.”

The best part? These conversations become valuable content that can fuel everything from blog posts to sales enablement materials. And because podcasts focus on asking and listening, they help marketers move away from assumptions and toward real insights.

Connecting With Customers via Community

One-on-one conversations are great, but communities take it to the next level. A well-run community fosters ongoing engagement, where customers share experiences, swap advice, and deepen their relationships with a brand.

Casey stresses that communities shouldn’t just be about the platform they’re hosted on. What matters is the interaction—the real, human exchanges happening within them. Whether it’s a LinkedIn group, a Slack channel, or in-person meetups, the goal is to create spaces where customers feel heard and connected.

Connecting With Customers via Partnerships

Partnerships are often thought of as logo swaps and co-branded campaigns. But the real power of partnerships lies in personal connections between people inside those companies. When two brands collaborate in a way that genuinely benefits their shared audience, they create new opportunities for connection.

Casey shares a simple but powerful framework for making partnerships actionable: the “Three-for-Three” approach. Each partner identifies three potential customers that could benefit from a joint effort, then they strategize together on how to help those customers. This approach makes partnerships more than just talk—it turns them into meaningful action.

The Call to Action: One Simple Step

If marketers want to reconnect with their audience, Casey suggests starting small. Pick up the phone. Schedule one call with a customer this week. No sales pitch, no agenda—just a conversation.

Ask simple questions: What challenges were you facing before using our product? How has our solution helped? What’s your next big challenge?

These conversations don’t just help marketers refine their messaging. They build relationships that drive long-term success.

The future of marketing isn’t about bigger ad budgets or more automation. It’s about deeper connections. Moving from go-to-market to connect-to-market means listening more, assuming less, and building real relationships with the people behind the brands.

So, who’s the last customer you had a real conversation with? If you can’t remember, it’s time to make that call.

Transcript

Building your audience is more important than ever.
Learn why you should switch go-to-market to connect-to-market
in this episode of Closing Time.
Thanks for tuning in to Closing Time, the show for go to market Leaders.
I’m Val Riley, head of marketing for Insightly and Unbounce.
Today I am joined by Casey Cheshire.
He is the chief evangelist at Ringmaster Conversational Marketing.
Casey, welcome to the show. Thanks. I’m so happy to be here.
This is a very cool show. Awesome.
Well, one topic. I hear from go to market professionals
is that they feel disconnected from their buyer
and you posed a really interesting question in our pre call
that made me think it was about something about naming seven buyers
for your company?
Yeah, yeah.
You know, it’s
this challenge I like to stir the pot with, with my fellow marketers.
And listen, and I am guilty of not necessarily answering this the best way.
If I were to ask you, Val, to name seven, and I’m not, I’m
sort of rhetorically asking you.
But for those listening too, if I were to ask you to name
seven of your customers by company name, can you do it?
Can you name seven of your customers by the name of their company?
And so and then you pause a little bit and then, okay,
give people a chance to think about it.
Can you do it? Probably.
Those logos on the website tend to remind you of that.
It’s a little easier to remember a brand, but then if I were to say, can you name
seven of your customers by first and last name,
like the actual customer, can you do it?
And when I when I ask groups of marketers these questions,
the looks, the left looking,
you know, the head down, the walk away,. I’m going to go get an app from the
you know, like everyone sort of disperses and it’s and I’ve been there
to where I was aware of the brand, but. I didn’t actually know who the person was.
And for me, this is what I would call disconnected marketing.
Yeah.
It’s funny because we can
we all have that NASCAR logo slide in our, in our decks or on our website.
So you can probably do that.
But taking it a level deeper. I agree is probably a little bit harder.
So so you identified a disconnect there.
Talk about how you see that disconnect manifest within companies.
You know, people talk a lot about AI hallucinating
when it doesn’t have all the information.
But guess what?
We’re the original hallucinaters here, as as marketers.
Because if we haven’t connected with our buyers to actually know
what their problems are, and I know we talk about it,
of course, we talk about know what your problems, your buyer’s problems are.
But if we don’t know their name
and we haven’t really talked to them, maybe we’ve done surveys.
Like if we don’t really know if we’re disconnected,
then we probably don’t have the data that we need.
And and I felt this too.
And a lot of people that I chat with that you feel this, you feel you know,
I think I know, and I think we’ll go out on a limb
and make this webinar about a particular topic.
But is this really what keeps your prospect up at night?
Right.
We talk about these things,
but we don’t actually go the extra step to find them out directly from people.
And so when you don’t have that information,
we hallucinate, which means we’re going to start putting information in there
that may or may not be true.
And then we all of our marketing campaigns start taking shape
to to go after some unknown prospect and
a good
sign that this might be happening to you, as if you send an email out
and it looks great, it looks good content’s great.
Everyone loves it in the team, and it gets really subpar engagement
or a webinar or a subpar engagement, or I even joke you one time,
when I was really, in this mode,
a whole lunch and learn like a breakfast.
Breakfast and learn and a whole thing of bacon when, like,
I had to eat a whole thing.
I didn’t eat the whole thing, but, like, no one really came.
Like two people came, and not 50, because we were hallucinating about
what would actually be helpful for them to come that morning.
Right.
So you see, when you’re when your campaign start
getting sluggish and when you see your PPC not being as effective anymore,
and when you see your emails and all these different campaigns
and the stats are going down and you haven’t necessarily done
anything worse, you might be disconnected, you might be hallucinating.
Yeah.
It’s it’s that assuming rather than asking. Right.
So, you point to three areas that where we can get better at customer connections.
And they are community, partnerships, and podcasting.
Let’s talk through each of those.
Let’s start with podcasting.
Yeah.
You know, these are just different ways that you can reconnect.
and it could be as simple as just have a phone call.
But the idea is if you’re going to have the phone call, maybe you record it.
Maybe you let other people learn from that conversation too.
So a podcast is a great way to reconnect.
And the most important thing about it is with a podcast like this one,
you’re saying to the guest, you’re important.
I want to know the answers you have to these things.
It’s not about me, it’s about you.
Let me ask.
Let me learn from you.. And that’s such a gift.
So when you give people gifts, they’re happy to jump on the line with you.
And this is a great way to get a future customer, current customer to hop on,
answer some questions,
share their insights, and to give them a gift at the same time.
So it’s it’s just a great mechanism for doing that.
And I found it works great for actually connecting
with future customers that you don’t even know.
And again, it’s not hey, you get on a sales call.
Let me trick you on to a sales call.
It’s let me give you a gift and and learn more about you.
That’s really the goal here,
because I want all the rest of my marketing to really reflect that.
Community is just taking this 1 to 1 conversation and expanding it a little bit
and and adding in other people who also feel the same way.
I’ve seen this work so well and with community,
it’s not always necessarily about, hey, what what platform are you on?
Always comes up.
It’s not even about that.
It’s who’s in the community, who’s chatting?
There’s been some communities I’ve joined.
I know there’s some
some coffee that gets drank at certain days of the week with certain
occupations, but there’s a community
I’m a part of where I will almost always join that meeting.
And, what am I going to expect when I get there?
But when I get there,. I always have a great experience afterward
because not only did. I learn from someone in that event,
but I also get a chance to do these breakouts
with just a couple other people just like me who are having challenges
just like I am, and we were able to chat with each other
and have even at a minimum, we were able to share.
Yeah, yeah, we’re having this problem too.
You’re not alone in this.
And in that kind of community expands on that individual 1 to 1.
It becomes a one to many.
But it’s it but it’s still targeted.
It’s still efficient and effective.
And then partnerships takes that and scales it a little bit further.
How many other organizations are having conversations like these?
Have communities like these have podcasts like these?
How can we collaborate with these other people individually in a partnership?
Yes, it’s logo to logo, but it’s also a person to person inside
each of those companies who are
relating to each other, having phone calls, maybe having podcasts together.
And again, it’s trying to get away from hiding behind the tech.
The tech can be amazing, but we have to make sure we get out in front of it.
Have the the human conversation first.
I can share.
I’ll validate every time I’m in
any sort of community, whether it’s virtual or in person.
It’s the kind of thing that you see on your calendar
and you think, oh,. I don’t know that I have time for this, or
I don’t know that. I should prioritize this.
And then every time you attend, you always walk away.
You feel energized, you feel connected.
You feel like you’ve learned something, like it’s always worth your time.
You just sometimes have to talk yourself into it a little.
Right. 100%.
And let’s talk a little bit more about partnerships, because
and partnerships as a mechanism to facilitate connection.
How do you see that?
Do you see that that as a company, expands its types of partners,
that it’s just invariably going to be connecting better to different audiences?
Partnerships is, It’s not easy.
It’s not easy.
But when done right and done with the right intention.
Just like knowing the customer on
1 to 1 basis, knowing your partner and being a very mutual relationship.
I’ve had an opportunity over the last several decades to have great partnerships
and not great partnerships, and I don’t remember
they’re not great ones because they never went anywhere.
And I think a lot of times what people experience is a initial conversation
where we all say, yeah, this is good, this is good.
Let’s we should do this.. And then nothing ever happens.
And sometimes it’s this is good, this is good.
Let’s spend days working on a partner agreement and then nothing ever happens.
So I think there’s a lot of again these are, these are
this is resistance and friction in the process.
And great guy Zak Pines. I had a chance to interview him on my pod,
and he shared one of his
his favorite tips on forming a mutual partnership is called a three for three
where, to start this process, to get some momentum
because it’s it’s like a train trying to get out of the station.
You go ahead and look up, hey, who are three
potential customers that would benefit from like a co-sell here?
And then I’ll go find them.
I’ll go find three
that might benefit from a co-sell, and we’ll get on a call
and we’ll talk through each one and we’ll plan out
how can we help these customers out that we both share and talk through
how we get involved and really put something specific on it
so that we’re not just talking in, in, like, niceties and we’re never going
to actually be a partner, but let’s actually try to help each other out.
I love it. It’s mutually beneficial.
So I’m going to ask a question here.
Because I feel like we try to blame the pandemic for a lot of things.
And so, but do you feel like the disconnect that
we’re sensing in marketing, do you feel like it was fueled
by the pandemic or was it inevitable just because of technology?
Or perhaps a combination of both?
You know what?
My son would probably be proud of me wearing his Spiderman outfit.
He would invoke that with great power comes great responsibility.
And I think it’s just we’ve continued
to grow in our power with all the technology around us now.
And not not even with AI.. But now we add AI in there.
There’s so much power and, you know, and I’ve been guilty of this too.
We haven’t always been as responsible as we need to be with that.
And and sometimes it’s a little safer to just
to be behind a tool and looking at numbers.
And hey, we needed to look at numbers,
but we also need to not forget the other part of marketing, and not just
let sales be the one that talks to people outside the organization.
Marketing used to be the voice of the customer.
We used to be
the ones that talked to the customers, most of the time even more than sales.
And they would even ask us, hey, what’s up with these people?
Like, how do I go about this?
And we’d say, well, here’s what they they’re really thinking and feeling.
Here’s what they’re scared of, here’s what they think about at night when they’re,
you know, thinking about feeding their family here.
Here’s who your customer is. Now go sell. Right.
We used to be that and that I talking about I see the table
that is the seat at the table when you own the customer voice.
So I’m just trying to get back to that.
I’m just trying to get us back to the part where, you know, yes, the technology
can help us, but we have to be, you know, connecting in a direct way.
So we’d like this podcast to be super actionable.
Casey.
So, someone who’s listening to you right now, what is one thing
that they could take away to reconnect with customers starting this week?
Make make one call
or schedule one zoom call with a customer and it.
And in the challenge sometimes is what do we talk about?
Or how do I get them to join.
And it’s kind of one of those, like, limiting beliefs.
They’re actually happy to chat with you though.
You’re happy customers are happy to chat with you,
because they love your product.
So ask suggest.
Hey, love to get on a zoom if you can offer them something afterward,
that’s great, but that’s not why they’re joining the call.
So I do like sweatshirts, but that’s not why they’re joining the call.
And swag and all those kind of things.
They love it.
You’re solving a problem for them.
I think sometimes as marketers we forget we are solving problems for people.
These tools are helping people.
So schedule one, call and
and sit down and ask and and there are questions you can look up.
You really want to go over a lot of things.
But one is, hey, when you first were looking at these kind of tools,
what was going on?
What was the situation, what was going on before you had this?
What was the challenge and has it, how is that help with the challenge?
I just get it is conversation.
And then finding another question is, you know,
now that we solved those challenges, what else?
What is you know, what’s the new challenge for you?
And remember, these don’t have to be challenges that you can solve.
You just trying to get to know these people.
So have a conversation.
Enjoy that.
If you can do it in person, even better.
Coffee can help.
You know a warm cup in your hand can help you, ask those questions.
But yeah, just do that.
And if you’re if you’re still even shy, don’t even do the video.
But like I recommend do the video.
These customers are so happy.. They’re so thankful.
Just have one call.
All right.
Great advice.
Everybody out there listening.
Go make that call right now. You.
We’re challenging you.
And we would love to hear in the comments how that call goes for you.
Casey, thank you so much for visiting us today
and telling us all about how we should connect to market.
Thank you so much for having me on here.
I loved this conversation. Awesome.
And remember out there,
if you want to get closing time delivered right to your inbox,
just click the link in the show notes and we’ll hit you up every week.
Thanks so much for joining us. We’ll see you next time.

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