Closing Time

Show Me You Know Me: Mastering Personalization in Sales Outreach

Still sending the same boring emails? You may get lucky here and there, but your open and response rates are likely abysmal.

Sam McKenna, CEO of #samsales Consulting, says that personalization in sales outreach is the key, but you need to take it even further. Genuine, research-based engagement will always win over generic, high-volume tactics.

In this episode of Closing Time, Sam shares practical examples of using her trademarked “Show Me You Know Me®” model in cold email, nurture email, social media, and more. 

Tune in to learn how to cut through the noise and make your outreach truly stand out in a sea of same.

Watch the video:
Key Moments:
Current State of Sales Tactics – What's Working & What's Not

Nearly two years ago, Sam joined Closing Time to discuss her approach to personalization, called “Show Me You Know Me.” Since then, the landscape of B2B sales has seen both changes and stagnation.

One thing that remains unchanged is the persistence of outdated tactics. Many sales professionals still use the same methods they’ve relied on for years. Sam says there’s a significant opportunity to rethink how to engage with today’s market, focusing on understanding and addressing buyers’ needs.

Buyers are increasingly numb to generic, scaled efforts that lack genuine engagement. They desire interactions with someone who has done their homework, presents a unique perspective, and offers real solutions to their challenges, rather than just pitching products.

Despite this, the prevalent strategies in B2B sales haven’t evolved much. Techniques like smiling and dialing, personalization at scale, spray and pray, and spam emails are still common. These methods lack authenticity and fail to resonate with modern buyers.

However, those who succeed are the ones who embrace the “Show Me You Know Me” approach. They invest time in research, genuinely listen to their buyers, and provide thoughtful, tailored solutions.

Show Me You Know Me - samsales consulting

In the age of AI, there are more tools than ever to assist with this. AI technologies, from ChatGPT to various other applications, can help speed up learning and improve efficiency. Yet, it’s crucial to blend this technological advantage with personal touches like heart, soul, and humor.

Sam believes that the winners in B2B sales will be those who leverage AI to enhance their “Show Me You Know Me” efforts while maintaining a human touch in their interactions.

Show Me You Know Me – Explained

The “Show Me You Know Me” strategy is about understanding and empathizing with buyers. Rather than bombarding potential clients with generic messages, salespeople need to step into the buyer’s shoes and consider what would make them stand out amid the flood of communications. Simply sending a high volume of impersonal emails isn’t effective.

For example, Insightly CMO Chip House’s inbox (see image below) is filled with spammy, irrelevant subject lines and messages. Sam explains that this is the norm for executive prospects, and it’s the seller’s job to find ways to cut through the noise and stand out.

CMO Email Inbox Example Flooded with Spammy Emails

In practice, “Show Me You Know Me” involves identifying commonalities, understanding the challenges buyers face, and acknowledging their activities. It’s about knowing who your buyers are, the companies they work for, and the industries they operate in.

It’s not just about introducing your product or service but demonstrating an understanding of the buyer’s situation and showing how you can help.

Sam emphasizes that this approach isn’t difficult—it’s about taking the time to do the research, listen to the buyer, and offer tailored solutions.

Using SMYKM in Email Subject Lines

To cut through the clutter of generic emails, Sam suggests creating subject lines that make sense only to the intended recipient. This demonstrates that the sender has done their research and understands something personal or relevant about the recipient.

For instance, she mentions Chip, who loves playing drums, and the band Rush. An effective subject line for Chip could be a drum emoji plus a Rush lyric and #samsales. This unique combination signals to Chip that the email is personalized specifically for him, making it more likely that he will open it.

Email Subject Line example 1

Sam also shares a few examples of how this practice worked in her business outreach. She once reached out to the Chief Revenue Officer of a recently acquired company with a subject line referencing his Australian heritage, the term ‘deep dives’ he used in a recent discussion, and her company name, #samsales. The result? 19-minute response time and meeting booked!

Email Subject Line example 2

In an email to a Nike division’s head of social media, Sam mentioned the prospect’s leopard shorts and SoulCycle, something personal she had talked about recently.

Email Subject Line example 3

The key takeaway is to make an effort to know your recipient and craft subject lines that reflect their interests, business, or challenges. The goal is to not only grab attention but also demonstrate genuine interest and effort, making it more likely to receive a positive response.

Using SMYKM in Nurture Cadences

If you’ve sent several emails with no response or opens, that signals a need to reevaluate your approach. You might move the prospect into a broader nurture sequence, possibly handled by marketing if they’re already a Marketing Qualified Lead (MQL). However, if a buyer responds positively but indicates it’s not the right time, you should shift your strategy.

For engaged buyers who express interest but suggest a future follow-up, the typical sales rep might set a reminder in Insightly CRM to contact them later. Sam advises going beyond this by continuing to nurture the relationship. This means regularly providing value and educational content that’s relevant to their needs. By doing so, you might accelerate their decision to meet sooner.

Email Nurture Framework - Samsales consulting

In cases where a prospect is actively evaluating your product against competitors or working through a Request for Proposal (RFP), “Show Me You Know Me” can be a game-changer. If a new decision-maker like a CRO or CMO comes in and needs time to get up to speed, use this period to nurture them with tailored information that demonstrates your understanding of their role and current industry challenges.

Maintaining a personal connection is also important. Just as you’d occasionally check in with old friends, you can keep the relationship warm by sharing relevant content or simply checking in on personal interests you’ve learned about them. This continuous engagement shows that you’re attentive and invested in their success.

Using SMYKM in Social Selling on LinkedIn

If you sell SaaS, there’s a more than likely chance your buyers are on LinkedIn–which means you also need to be on LinkedIn.

Sam highlights how “Show Me You Know Me” can be effectively applied to social selling and used in direct messages (DMs) or through commenting on posts…but timing is everything.

For instance, if a prospect like Val responds with interest but asks to reconnect in three months, connecting on LinkedIn and using DMs strategically can help maintain the relationship.

One smart tactic Sam shares is “bubble hunting.” On LinkedIn, a filled green bubble next to a contact’s name indicates they are online. This is a prime opportunity to engage with them, as they are likely active and receptive.

LinkedIn Bubble Hunting

By spending a little time on weekends or other off-peak hours, sales reps can spot these green bubbles and use the opportunity to send thoughtful nurture messages.

For example, sending a quick note like, “Val, I was just thinking of you. I’ve been meaning to send you this podcast,” can keep the conversation going.

Unlike emails, DMs on LinkedIn are more conversational and can lead to quicker responses. Additionally, tagging executives in comments can keep you on their radar. If you’ve had previous interactions, you can reference those in your comments to remind them of your ongoing connection. For instance, mentioning a point from a previous email in a comment can reinforce your presence and keep the dialogue alive.

Sam suggests creating a drip campaign similar to those used in marketing but for sales engagement. This involves a mix of emails, LinkedIn DMs, and comments to maintain visibility without being intrusive. The goal is to continually remind the prospect of your presence and expertise.





If you enjoyed this conversation but want to learn more about sales outreach and personalization, follow Sam on LinkedIn and check out the #samsales website for additional training materials and resources.


You know that personalized outreach works.
Let’s roll up our sleeves and get super specific tips on putting into action
in this episode of Closing Time.
I’m Val Riley, head of content and Digital marketing at Insightly CRM.
And today I am joined by Sam McKenna.
She is CEO of hashtag. Sam Sales Consulting.
Welcome to the show, Sam. Thanks, Val.
So good to see you.
I feel like you know how Saturday Night. Live does the the jacket for like
multiple time hosts on the show?
Where is my crested jacket?
I think you are the guest we have had on most frequently.
So congratulations on that honor.
And I mean, it’s honestly just because people love hearing your perspective.
So, again, thank you for joining us.
Thanks. That gives me good ammo against Todd Caponi.
So thank you so much for.
Thanks so much for that.
So nearly two years ago, we had you on the show and we talked
about your approach to personalization, which is called Show Me You Know Me.
A lot has changed in that time, but sadly, a lot has not changed.
Now, I know you trademarked the term Show. Me You Know Me, which I love.
But let’s talk about what’s changed and maybe, unfortunately, what hasn’t.
I think what hasn’t changed
is we’re still using the same tactics we’ve used all along.
There’s such an opportunity for us to really think about where the market is
now, how to get in front of our buyers, and more importantly, to listen to
what they’re saying.
And what they’re saying is that they are numb
to these scaled and veiled efforts to get their attention.
That they just want somebody
who does the research, that shows up with a point of view,
that offers a perspective on how you could actually solve a challenge,
not just saying, quick question, here’s what we do, want some of it?
So I think that has stayed the same.
But what hasn’t changed is the way that we go about our efforts, right?
From smiling, dialing 100 times a day to personalization at scale,
trying to use brackets to pull things in and fake authenticity,
spray and pray emails, spam emails, the quick
question Val emails that show up in our inbox all the time.
All of that is still the same.
I think
when you really think about it, the ones that are going to win
are the ones that are putting in the effort doing the Show Me
You Know Me, doing their research and just listening to what buyer’s say.
I think also in this age of AI, that continues to change.
AI, I feel like AI evolves every single day from ChatGPT to everything AI can do.
But I think you can use. AI to speed up your learning
to be efficient in terms of how you find your Show Me You Know Me
while still mixing your heart and soul and humor into the equation.
Those are the people that I think are going to win.
So, you know, it’s clear, Sam, that, you know, sales
directors want to have metrics, but that number of emails,
and number of dials metrics, they are just the wrong metrics.
And to prove that, we actually took a screen capture of
the inbox of the CMO of Insightly, my boss, Chip House,
and we’re going to share it with the viewers on the screen right now.
And I mean, I think you’ll agree this is a little bit painful.
Yeah,. I mean, I think when you think about this,
like all of the spam that comes in, how are we cutting through the noise?
What are we doing to actually stand out and just sending volume, Right.
Just sending a thousand emails a day, 500 times a day isn’t going to cut it.
You have to think about putting yourself in that buyer’s perspective, putting them
and putting yourself in their shoes, and then thinking,
If all of those emails are my competition, what can I do to stand out?
I just cannot stand to get another email that tells me, Hi, my name is blank.
I see you are the director of
Digital Marketing as Insightly like I know who I am.
I know what I do and I don’t care what your name is.
It’s a little rough out there.
And you’ve had Kim on our team on Closing Time
and one of her favorite emails that she got was where It said, Rumor
has it that you are the VP of Strategy and Enablement and she is like rumor?
She’s like, It’s a fact. It’s right there in my profile.
But also we can be a little smarter about the semantics that we use.
For sure, for sure.
Okay, So let me know if I get this right.
If I’m defining, Show Me You Know Me in practice is about identifying
commonalities, challenges, and maybe even activities that resonate.
You want to show someone that you know who your buyers are
as people, the companies they are with and the space they’re in.
You got it. Is that a pretty good summary?
Pretty good summary.
And really, at the most basic level, it’s just figuring out
who is the person you’re selling to, what’s happening with their company,
what are the challenges that you’re resolving for them?
It’s that it’s not just showing up to say what you do,
but it’s saying,
I know a little bit about you,. I know a little bit
about your challenges in your company, and here’s how we can help you.
It’s not that hard.
Right? Right.
So let’s talk first about how Show Me. You Know Me shows up in cold emails
because that’s something that a lot of AE’s really struggle with.
I think you think about the very first thing as our subject line.
We have two things that we’re fighting for.
One, we’re fighting for an open, and two, we’re fighting for a reply.
So let’s think about how we even get the open. It’s
the subject line and the first sentence that are the most important thing.
You look at that screenshot, right of Chip’s inbox
and it’s a whole lot of not good stuff, right?
So instead, how do we stand out?
Show Me You Know Me is about writing a subject line
that makes absolutely no sense except to the person reading it.
So we talked about this with Chip before, right?
Chip has been playing the drums for a very long time.
Chip also loves the band Rush.
So maybe I send Chip an email that just shows the drum emoji
plus lyric from Rush plus #samsales.
He has absolutely no idea, let’s say in theory with the last thing is.
But he knows that he plays drums and he knows he loves Rush.
And so clearly I’ve at least done my research,
it’s about writing that subject line again that everybody else would read and say,
No clue what that is or say drums and Rush song.
Why does it apply?
And Chip would say drums and Rush song, that applies to me.
Thinking about this too, right?
When I try to reach out to the head of social media, the chief
revenue officer of a recently acquired for $3 billion company,
the only thing I did was just do a little research. And then I sent
him a funky subject line.
It said, Toby is Australian plus deep dives in quotes because he had
just referenced doing deep dives in pipeline, plus samsales.
I reached out to somebody that was the head of social media for a
division at Nike.
She talked about her leopard shorts at SoulCycle.
I just wrote her a subject line and said. Leopard Shorts + SoulCycle + #samsales.
Both of those emails got a response within the first day,
in fact the CRO responded in 19 minutes and took a meeting.
Make an effort.
Just have a subject line that shows, you know that person or knows something
about their business or their challenges that stands out to them specifically.
That’s brilliant.
I mean, the 19 minute reply,
I don’t think anyone’s going to argue with that success.
Right. Yeah. Do that all day long.
So let’s say you’ve been through a cadence, right?
You sent your super
creative, super personalized subject line, you didn’t get a response.
And so you’re going to downshift and move into maybe a nurture cadence
does Show Me. You Know Me show up any differently
when you’re in a nurture cadence, more of an educational mode,
or are we still doing the same types of things as we would with a cold email?
I think let’s think about a couple of things.
So one, if we didn’t get a response,. I think there’s a lot to dissect there
too, around Show Me You Know Me of why we didn’t get a response.
But I think the other thing to think about is if we’ve sent several emails,
no response, no opens, no anything that sends us a message.
Perhaps we put them back in a nurture sequence that we run.
Perhaps they’re already, you know, an MQL that’s come through
and so we’ve got marketing that’s doing that.
But if let’s say we have an engaged buyer, let’s say we’ve got somebody
who responds and says, love your email, not the right time, we’d
be happy to reach out in six months or happy to talk to you in six months.
What do we do with that?
Or let’s say we have a buyer that’s actively working through an RFP
or actively looking at us for two against two or three other vendors?
How do we use Show Me. You Know Me to nurture those individuals?
So I’d say a few things.
Let’s think about this, Val let’s say we reach out to you, want to sell you
all we have and you’re like,. That’d be great.
Let’s talk in 90 days. And I say, Sure.
What most sales reps do is they set a little reminder,
they’ll add a task to their Insightly CRM, and they’ll say,
Contact this person, contact Val in 89 days.
What we should really do
is do that but then also think about how we can nurture that person.
So how do I continue to educate and add value to the balance of the world
and show her that I’ve got something really great that I can teach her,
help her with, etc., and probably advance the speed of the meeting
just by her saying this is really interesting.
I’d be happy to meet now, great.
Even thinking about this for existing deals, right?
Somebody says we have, let’s say, a proposal out
and then let’s say a new CRO, CMO, etc.
comes in and the organization says we need to wait
for this person to evaluate your proposal first.
We get introduced, they say give me a few weeks
and to get my arms around the business, how do I nurture that person?
How do I continue to educate them and show them that I know what CROs,
CMOs, Heads of content marketing are thinking about today.
And then I think there’s the other component of this, right?
There’s the personal aspect.
So perhaps I’m just trying to keep connection alive, right?
It’s like you when you send random texts to friends
you’ve had for a long time just to check in, see how they are, etc.
You’re just keeping the threads alive.
You can do this if you know something about them personally.
Let’s shift gears just a little bit and talk about the ways that Show Me
You Know Me can show up in social media
either with a direct message or even commenting on a post.
I love this too because I think timing is everything here, too.
And there’s a couple of different things you could do.
So the tagging on LinkedIn and sending a DM is fantastic also for nurturing.
So again, let’s say you’ve established a relationship,
let’s say Val, you respond to me and say, not right now, but in three months.
I’m going to connect
with you on LinkedIn and I’m going to use the DM strategically.
I’m also going to do something really smart, which is what we call at samsales,
bubble hunting.
So if you haven’t heard this term,. I want you to take a quick look at this.
Pop over to your LinkedIn profile,
hit your messaging and look at all of the names of the people in your inbox.
Next to their names,. You might spy a little green bubble.
If that green bubble is filled in, it means they’re active and
they’re online.
So what can you do to pair this strategically?
Go on the weekends, spend an hour on Saturday morning, hour
on Sunday evening, hour in the middle of the day.
Pop in your inbox and look, you might see some of the executives
that you’ve been targeting with little green bubbles,
that means they’re online, they’re active their probably reading
and nerding out on stuff.
Use that as an amazing opportunity to send them a nurture.
Val, was just thinking of you, your popped in my brain.
I’ve been meaning to send you this podcast for a couple of weeks.
It just occurred to me to do it.
I have a task and reminding myself to do it right now.
And then you create a dialog.
It’s actually how we got one of our best deals, Don’t tell them, with LinkedIn.
My previous employer is waiting for that person, seeing them online on the weekend,
bubble hunting and basically spearfishing for leads.
Don’t tell anyone. But
this is so incredible, right?
If we think about this strategically, think about the timing and think
how we can use different mediums, it really helps us.
And the powerful thing about LinkedIn is it humanizes you.
The DM just feels a little less stodgy and formal than email, right?
And it’s just quick messaging back and forth.
And I think you’ll find a lot of success if you start to do that
or even tag executives in the comments.
Let’s say that same person. I just talked about, that brand new CRO,
maybe I sent him a great email.
He says, Great food for thought.. Thanks. That’s it. Right?
And then let’s say a week later, I say.
his name’s John, I say, John, just what
I was just talking about in the email to you the other day, that’s it.
I’m also looking for a way to basically build a drip campaign
like marketers do, of reminding you that I exist, right?
So how can I send you an email?
How can I send you a DM on LinkedIn?
How can I tag you a couple of days later?
I’m trying to say, don’t forget. Sam McKenna exists over and over again
without hopefully being annoying. Got it.
I really like the idea of commenting on a post.
I feel like even though. LinkedIn is a professional platform,
I feel like as humans we still get that same little dopamine hit
that we do, maybe on other platforms that are more social in nature,
where we want people to be interacting with what we post
and we want to see engagement on our posts and executives,
even though they might be like dry and, you know, a little crotchety,
they still are people and they still might feel that same way.
I think that you,. I want you to look at something really,
really cool about this too.
If you go to any executives like let’s talk VP plus,
take a look at those who post and what I think you’re going to find
outside of a few rogue exceptions to the rule,
you’re going to find that the majority of them have a few dozen
or even a few hundred likes on their posts.
And yet.
there are almost no comments on their posts.
People are lazy.
People don’t know what to say, they think a like is enough, right?
They get nervous.
And I always equate it to this, you have your buyer
that is standing on a trade show floor and talking about something, right?
Whatever that post is.
And then you’ve got 198 people standing around them that are like, this is great.
Thumbs up, the hearts, the whole nine yards.
And then you have three, four, five people who have gone up and said a comment.
And who are those people usually?
It’s usually people in their company that are trying
to kiss up to them and get attention.
So you have an incredible opportunity to be like, hello,
I’ve got a point of view.. I’ve got something to say.
I’m going to go ahead and comment.
I’m going to add something of value.
And for everybody who is listening, who says but my buyer’s
not on LinkedIn, maybe, but maybe not.
And even if they’re not,. I bet you the people that report to them
or their report to them, people who are key
influencers are what a great opportunity for you to get in front of them
and slowly build your way in.
Sam, another great episode.
Thank you so much for all of these insights into Show Me You Know Me.
Really appreciate your time.
Thanks, Val, so great to be here.
Our pleasure. Really.
And thanks to all of you for tuning in to closing time.
Remember, you want to like this video, hit the button for notifications
and subscribe to the channel so you don’t miss an episode.
We will see you next time.

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