Sales, Comedy, and Coping: The Rising Role of Humor in B2B Sales

There’s nothing funny about sales.
Or is everything funny about sales?
Let’s talk about using humor to cope with rejection.
On this episode of Closing Time.
Thanks for tuning in to Closing Time, the show for go to Market Leaders.
I’m Val Riley, VP of marketing for Unbounce and Insightly.
Today I’m joined by Tom Boston.
He just left Sales Loft
as a brand awareness leader and is on the cusp of his next big adventure.
So we’ve caught him at the perfect time.
Thanks for joining us today, Tom.
Thanks for having me.
Really, really excited for this conversation.
I’ve been looking forward to this one.
Great, yeah.
We have a lot of guests on Closing. Time, Tom,
but it’s pretty rare that we laugh out loud.
So, you know, you’ve got you’ve got a big task in front of you.
Well I’ll try, I’ll try my best.
I make no promises.
But I do laugh at my own jokes.
So at least there’ll be somebody, at least there’ll be somebody laughing.
Awesome.
So the role that you just left,
you know, some might liken it to more of, like, an evangelist role.
It isn’t very common.
So I’d like to understand how you went from starting your career as an SDR
and developed it into a brand awareness leader role.
Yeah.
I mean, it’s not it’s not a common path, right?
SDR into into marketing.
And there’s this term sales influencer, which gets kind of thrown around.
And I often call myself, Val, an accidental sales influencer.
Right? That was that was never the plan.
The the only reason for putting any content on LinkedIn
as an SDR was to try to book more meetings and try to hit my target up.
That was my main driver, right, was that
we roll back the clocks to 2019.
I was fresh into a role at sales Loft.
I was unknown in the space and I was selling
to salespeople, to VP’s, to CEOs,
and I was just an unknown SDR and I knew it was going to be tough.
So, I thought, let’s just get my face out there.
Right?
I’m sending all these prospecting videos anyway.
I’m making all these cold calls anyway.
I might as well put some content on LinkedIn
and help my prospects to join the dots.
Oh, I think that’s that guy who left me a voicemail.
Or I got a video from from that guy.
And I see he’s talking a lot on the platform about some of the things
he’s mentioning in my inbox and on my voicemail.
Right. Maybe he
is legit.
Maybe he isn’t just spamming people,
maybe he is active in the space and is worth my time, right?
Because at the end of the day,
all we want from people is a little bit of their time, right?
So anything you could do to help justify that, add that credibility
I thought was only a good idea.
But then it kind of spiraled and, you know, things started
to kind of pop off a little bit, had some viral hits.
And I think the team at Sales Loft understood that actually,
there’s an opportunity to put me in a role
that built awareness for the brand as a whole,
and not just as a machine to help me hit my target.
I feel for you as a marketer,
marketing to marketers is probably the hardest thing.
So selling to salespeople has to be the hardest thing too.
Well, there’s pros and cons, right?
Because the pros are
they understand the dance and you can you can reference that a little bit.
And I used to use that a lot as a seller.
I’d even say things like on a call,
I’m going to build some rapport with you now.
Right.
This is the this is the section of the call.
And I’d get out a pen and ask them a question about the weather
and I’d say, okay,. I can tick off rapport building.
We’ve done that bit, I can we move on?
I like doing things like that for salespeople,
You know, they kind of understood, oh, this person
gets me.
They they kind of understand we are a similar person.
And that that helped me massively.
So yes, it is difficult.
But if you can speak their language and, you know,
help them to understand.
Oh yeah, this person’s probably been in my shoes,
you’ll have a much richer conversation,. I believe.
For sure.
So I mean, I would say there’s a need for humor in most every profession.
Right.
We spend eight hours a day at work and and it’s got to have some levity.
But salespeople might need it just a little bit more
because of the amount of rejection that they face in their everyday work.
I would agree with that.
It’s not easy, and anyone
who tells you that it is are either lying.
Or they
don’t know what they’re talking about because it’s tough.
And in the early days of my career,
like many others, you would get to the end of the day and you would be, you know,
head in your hands thinking,
how have I got to this stage?
Like, what am I
doing to myself? Right.
So like that light relief that, you know,
that little bit of comedy in the day,. I think it’s so important.
And then not something I really expected when I started to create content.
Right.
You know, I wanted to make people people laugh and people feel good.
But the amount of messages that I get from people say, thank you,
you’ve helped me so much this week.
I was struggling, or like, when I’m having a bad day,
I watch your videos and I, I’m then spurred
on to to carry on with my role.
I’m always like, well that’s amazing.
What what an amazing thing to be able to,
to do for people,
because we all need it,
you know, it’s, it’s much needed, I think.
So I feel like you’ve answered this question a little bit.
I was going to ask, how do you hope salespeople feel
when they view your content?
But it sounds like you want them to feel like seen,
heard, understood, and and maybe a little inspired.
I hope so, because most salespeople
will look at and I will use the inverted commas,
the influencers on LinkedIn, and they will say,
I could never do that.
And actually,
I’m here to say, look, even if you are an SDR,
one of the entry level positions in your organization, maybe a bald
with a ginger beard and maybe you’ve got a silly northern accent.
Whatever.
Whatever it may be, whatever your hang up is, there is a place for you on LinkedIn
and there is a seat for you at the party.
I often say this I.
I wasn’t invited to the party.
I very much let myself in. Right?
I was like, oh, I’m going to have. I’m going to have a place here.
And I,. I’m going to create some content here.
And and hopefully salespeople
who look at my content will think, well, actually, yeah, if he
if this guy can do it, maybe I could do it right.
But I think the key thing is, in your own way, you’ve got
you’ve got to be true to yourself.
The only reason I even look at comedy is because I love it.
That’s it’s been one of my favorite things for years.
I’ve always enjoyed watching comedy,
writing sketches, writing scripts.
I love all that kind of stuff.
But yeah, you have to create content that’s true to yourself.
That feels right for you.
For me, that’s
how you you build a presence and that’s that’s
how you utilize the platform to help you in your career.
So what aspects of the sales profession
do you feel like are the most ripe for humor?
I know, I know, you mentioned, you know, telling someone,
hey, we’ve just built rapport.
Check. It’s done.
But but are there certain aspects of the profession where you feel like,
oh, this this is primed to to have a little fun with.
You know, there are so many areas.
And when I speak to a lot of people about humor and comedy,
they might give me some pushback like,
either I’m not funny.
I often get that, well,. I’m I’m not a funny person.
All they’ll say, oh, my prospects wouldn’t like that or my customers.
I even had someone say, yeah, my prospects, are quite boring,
which I was like, okay, but sure, surely everyone
can see some humor in some aspect.
And for me it comes from pain, right?
Like usually if you’re selling something, you solve a problem.
So the problem that you solve is normally a pain for your prospects.
So how can you use humor
to shine a light on that pain to highlight yourself as someone
who understands what your prospects are going through, right?
Not that you’re the solution, because a lot of people on LinkedIn talk
about how they’re the solution and they’re the best.
No, no, no.
Highlight the the problem and use humor to do that.
Because I don’t know about you, but my favorite content
on any social media is content that puts a smile on my face.
So if you can relate that
to a problem that you know
you solve, you’re undoubtedly
going to build an audience of people that you can potentially sell to
or people that might recognize you when you do sell to them.
I often say a lot of social selling
isn’t even done on social media, right?
It’s done on the phone.
It’s done on an email.
It’s when your prospect kind of joins the dots.
Yeah, absolutely.
Just anything you can do to get in that initial consideration set is so important.
And at the end of the day,
even your seller might be in a very boring business, but
it’s still a person you or your buyer is in, you know, finance or insurance
fields that we don’t associate with being terribly fun,
but that’s still a person who has a sense of humor.
So you really just want to tap into that.
Yeah.
100% find the human element.
No matter what you’re selling, you’ll always find a way to,
to bring a human aspect to the problem.
It doesn’t have to be hilarious.
When people say humor, they often think jokes.
I’m not talking about punchlines,
I’m talking about, oh, that’s that’s real.
Like most, most humor, most things that are funny are just real.
Like a lot.
If you look at my content, there’s no punchlines.
It’s just maybe heightening
a conversation that you might have had with a sales manager
or heightening a discovery call you might have had with a prospect.
Right?
It’s the stuff that makes people go, oh yeah, that’s I’ve been through that.
That’s that’s really real to me.
That hits me in the, in the feels, as they say.
So what was the topic of your most viral video
and why do you think it resonated so well?
Yes, my
my best performing video on on
LinkedIn had over a million impressions
and it was only, I think, about 20 30s.
And I was playing a sales person who’d made
maybe 20 calls
in the last hour.
They’d done a power hour, but then somebody calls them back, right?
When they get that call, they start to panic.
I’m not sure which of the many people I’ve just called
are ringing me back, but I can’t let them know that.
So they answer with, oh, hello. Thank you.
Thanks for calling me back. Right?
And they’re frantically trying to find on the CRM
who is who is this person?
The whole video was
the sales rep just kind of blagging their way through.
Oh, no, I’ve got you.
Yeah, I remember, yeah, I’ve got you here, right?
And in the background you had, some classical music.
You had Vivaldi with,
with violins, right?
So it was very dramatic.
But I think that video, again, did well because lots of sales reps
watched that video and they were like, that’s me.
I have done that.
I have made 50 calls.
That one person call me back.
Maybe it’s an unknown number
and they have to pretend
they, you know, pretend that they they know exactly who that is.
So that that was my my biggest video.
So far. Awesome.
You’ve you’ve been able to carve out a personal brand around humor.
You mentioned earlier, you know, it’s important
for salespeople to identify their personal brand.
Why is that?
What advantage does a salesperson get if they have determined
and established a personal brand?
Well, in in this kind of modern world of
AI and automation,
actually being human
is not just something that is a nice to have, right?
Oh, that’s quite a, a personable rep.
Or like I see a human element to them.
It’s actually necessary, right?
Because we see robots are now reaching out to prospects.
So you need to, as a salesperson, make it very clear
that you’re not AI, that you are a real person
and that you have an opinion and that you’re active in the space.
So those kind of things, for me, the the only way to do that is to build
a personal brand is to consistently
create content that showcases
who you are,
has some of your personality in there as well.
Because let’s again think about humanizing the process.
Am I going to take a 15 minute meeting with someone who
I don’t think they’re very interesting.
No, right?
My time is precious and I’m only going to give that to people that I think.
Okay. Yeah, that that looks interesting to me.
Or they seem to be an interesting person.
So, yeah, I think it’s so important.
And a lot of sales reps don’t put the attention into that.
Right.
They’ll just focus on selling traditional selling,
and they’re not bothered if they look like an interesting person on
on social media. Right.
I’m just going to make a lot of cold calls or I’m going to send some emails,
but actually the personal brand is a
complement to the sales process.
And it works in tandem that you need to do both.
And I think I’m certainly proof that when you do when you get it right,
not only do you see success
from your outbound process,
but you start to get inbound leads as well.
And that was a really great moment for me, Val, when I said to my wife,
I’ve cracked, I’ve cracked the system.
I’ve I’m an outbound seller.
People recognize me when I call them
and I’m getting inbound leads on social media.
You know, it was like. I felt like I created fire.
It was magic.
As a marketer, I can genuinely say
I love it when sales reps do outbound and have success.
So you’re you’re speaking to my heart.
I love that. Yeah, yeah, me too.
I’m a huge champion of, of those, you know, SDRs right now,
who are still crushing it, still finding creative ways to
to break through the noise you know?
So if I’m a sales rep and I
need a bit of humor in my day, what’s the best way to find your content?
Well, the great thing is that, not many bald
Tom Bostons on LinkedIn, so I’m quite easy to, to find.
But, you know, I’d also encourage you to,
to look at things like hashtags, right?
So look at things like sales humor,
you know, sales comedy, whatever it might be,
and find the creators that are putting content out there.
Because I’m not everybody’s cup of tea.
Right.
You know, and that’s the great thing about humor.
It’s often subjective.
So yeah, find those creators
that put a smile on your face,
make sure that you ring their bell.
You can do that on LinkedIn now. Right?
You can top right hand corner.
You can click click that bell and you’ll get notified when they,
they post content, and get that perk in your day.
But yeah, that’s me. Happy days.
Awesome. Tom, I think you’ve inspired our listeners
to either create a personal brand or take up stand up comedy.
So I guess we’ll see what the results are.
Yeah, you could do both. Right.
I think that’s that’s the that’s the future.
Let’s let’s combine those things.
I tweeted that recently. Right.
A sales conference with stand up comedy.
This is a this is a vision of mine.
I’m going to try and bring sales and comedy together in some,
some beautiful way in the future.
So watch this space.
Awesome.
Tom, thanks so much for joining us on Closing Time today.
Appreciate you, Val. Thank you so much.
And thanks to all of you for tuning in.
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