Closing Time

How to Incorporate AI into Your Sales Process (& Avoid its Dark Side)

The future of B2B sales is here, and it’s powered by AI.

As a salesperson, what features and functions of day-to-day AI do you need to be aware of?

In this episode of Closing Time, Ross Simmonds of Foundation Marketing talks about the AI-powered features that salespeople can use today.

Learn how to incorporate AI into your sales process, avoid the dark side that comes with it, and discover why embracing this tech is key to closing more deals in the future.

The question isn’t if AI will impact us, but how we’ll harness its power to become even more effective in generating revenue and building client relationships.

Watch the video:
Key Moments:
The Short-Term Impact of AI

Imagine the drum machine you used as a kid, but instead of mimicking basic beats, it could compose full-blown symphonies that sell millions. That’s AI in B2B sales right now. It’s composing personalized marketing emails, writing captivating sales pitches, and even nudging leads on LinkedIn like a friendly AI assistant.

Ross argues that AI’s ability to mimic human tasks, like composing music and singing, signifies a deeper shift within businesses. This presents a significant change for revenue-focused professionals like us. While some may fear job displacement, Ross sees AI as an augmenting force, freeing us from repetitive tasks.

AI's role in sales process

Instead of fearing automation, B2B professionals who embrace AI as their wingman stand to become the next generation of leaders. It’s not about humans vs. machines; it’s about humans powered by machines.

Remember, the more valuable your skills are, the less likely AI is to replace them. So keep learning, keep growing, and keep focusing on what makes you truly human: creativity, empathy, and that killer closing pitch.

Two Distinct Phases in the Adoption and Impact of AI

The world of outreach is about to be flipped upside down by AI, and Ross, with his keen eye on the future, lays out two distinct phases that paint a vivid picture of both its golden opportunities and potential dark side. 

Phase 1: The AI Gold Rush (Next 2-3 years): In the first phase, Ross observes a kind of “gold rush” where businesses aggressively leverage AI to enhance their outreach. This phase is marked by a significant increase in mass messaging, using AI tools to send numerous emails and direct messages (DMs).

This strategy aims to flood the market and reach as many potential customers as possible. During this period, many niches and sectors, still unfamiliar with AI technologies like Bard or ChatGPT, will likely experience an increase in AI-generated communications. This surge, Ross predicts, will bring considerable opportunities in the next 2-3 years for those who adopt AI early, especially in areas that haven’t yet embraced these technologies.

Phase 2: The Human Touch Reckoning (4+ Years Onward): However, this initial boon leads to the second phase, which Ross describes as a corrective response to the over-saturation of AI-driven messages.

As inboxes and messaging platforms become overwhelmed with AI-generated content, both the users and technology providers like Gmail and LinkedIn will start implementing stricter protocols to filter out such communications. This shift will elevate the standard for outreach messages, necessitating a more personalized, human touch to break through the skepticism that AI-generated content will likely engender.

Ross suggests that in about four years, proving the human origin of a message will become crucial. Despite the advances in visual AI that can create seemingly personalized content, the challenge will be to convincingly demonstrate the human element behind communications. This need for authenticity and personal connection in outreach efforts will be key to achieving success and avoiding the dark side of AI. 

Tips for Personalization at Scale

Ross explores the intersection of AI and personalized outreach in sales, emphasizing the evolving landscape of sales communications. He identifies a key trend: salespeople who invest time in highly personalized outreach are experiencing better engagement from prospects, such as higher open and response rates. This is in contrast to those relying solely on pre-written cadences or standard messaging.

He challenges the notion that simply scaling outreach with AI will inherently improve results. Instead, Ross encourages a blend of AI’s scalability with a strong focus on personalization to maximize impact.

The use of video is a prime example. A personalized video tends to receive better responses when the sender in the footage is genuinely the sender. However, advancements in AI are changing this dynamic.

Tools like D-ID and HeyGen allow users to create an avatar and customize messages at scale. These avatars can change names and even backgrounds, like showcasing a prospect’s website, to simulate a highly personalized message.

Yet, Ross points out that there’s still a significant advantage in genuine, human touches that AI can’t replicate yet. For instance, mentioning a unique detail from a podcast or a shared personal interest, like being a drummer, creates a connection that AI, in its current form, can’t duplicate.

He speculates about the future, where AI might be able to mine such personal details from extensive data, but emphasizes that, for now, these human elements are critical in making outreach stand out.

The Rise of Skepticism

Ross emphasizes the need for responsibility and ethical considerations when using these powerful AI tools.

If an AI-generated video lacks the nuances like emotional expression or an accent, it can quickly become evident that it’s not genuinely the person it purports to be. This realization can lead to a loss of trust and a sense of deception. The challenge, he suggests, is to use these tools tastefully and be aware of their limitations.

Another intriguing aspect of AI in sales Ross touches on is the ability to translate voices into different languages, aiding international outreach. He shares an anecdote about a presentation he gave in Brazil, where his speech was translated into Portuguese using AI, leaving the audience amazed. This technology, he believes, can help break down barriers and facilitate global connections.

Ross also shares his experiments with AI-generated video content, noting the mixed reactions from audiences. In one instance, he published a deepfake video of himself discussing marketing trends, and to his surprise, viewers didn’t realize it was AI-generated, commenting instead on his appearance. This experience illustrates the dual nature of AI in content creation: it enables rapid scaling of content, but it also increases skepticism and wariness among consumers.

Ross invokes the famous line from Spiderman, “With great power comes great responsibility,” to stress the importance of using AI in a way that aligns with best practices and ethical standards in communication.

Next Steps for Sales Leaders

Are you a sales leader looking to capitalize on AI? Ross has two pieces of advice for you: experimentation and empowerment.

Firstly, he emphasizes the importance of experimentation. He advises sales leaders to actively engage with AI tools and solutions that can enhance their team’s capabilities. This involves setting aside time to understand and explore the technologies available in the market.

Ross suggests booking demos and dedicating time to find tools that can provide significant advantages in the coming years. This proactive approach is essential for staying ahead in the rapidly evolving field of AI-enhanced sales.

Secondly, Ross highlights the need for empowering sales teams through training and education. He urges sales leaders to secure training budgets, ensuring their teams are well-versed in leveraging AI effectively.

Ross points out that it’s not enough to rely on tools used in the past; teams must be prepared for future advancements and improvements in AI technology. It’s about investing in your people, providing them with the skills and knowledge needed to adapt and excel.

In his final thoughts, Ross encourages sales leaders not to fear AI but to embrace it. Drawing a parallel to the early days of social media, he describes AI as a transformative technology that will significantly impact professional lives. You either embrace it or get left behind.


Do you think you could spot a deepfake video from a sales person in your inbox?
Well, you might be surprised.
In this episode of Closing Time, we’re going to talk all about A.I.
and its uses in sales.
Thanks for tuning in to Closing Time on the show for Go to Market Leaders.
My name is Chip House.
I am CMO of Insightly CRM, and today. I’m super excited to be joined by Ross
Simmonds, the CEO and founder
of Foundation Marketing, which is a B2B marketing agency.
Thanks for joining us, Ross.
Thanks for having me,. Chip. Excited to be here.
Yeah, for sure.
And so, you know, when we were talking earlier,
we were talking about the emergence of AI in music.
And it’s it’s funny because I’ve been a drummer
for like 40 years, you know, since I was a little kid.
And so I’m very used to drum machines,
you know, my friends used to call it chip in a box, right? But,
you know, now you have
AI and the AI is actually composing music
and that music is maybe useful in a business sense.
But I’ve seen you speak a little bit about this.
How do you think it’s going to impact marketers and salespeople in the short
Yeah, I think it’s going to continue.
Like the fact that it’s able to compose music, the fact that you can use
AI to replicate a human voice and sing and all of these things today
demonstrate the shift that’s not happening, not only happening
culturally, but also inside of businesses and organizations.
I think there’s going to be a significant shift
in a lot of our day to day work as sales professionals,
as marketing leaders, as anyone who operates within the revenue
realm at large due to the fact that AI is now
able to replicate a lot of the things that we typically do
and a lot of organizations and a lot of people might immediately
get fearful by that idea, Oh, my job is at risk.
I’m no longer going to be needed.
The doomsday is near
when in reality what I think AI provides us with
is the ability to be augmented as people
and reduce the amount of repetitive tasks that we would traditionally do.
So non repetitive work is going to be more valuable because it is
less likely to have been replicated by an AI.
While repetitive tasks which can be trained
and can be mimicked by. AI are more likely to be able
to be completely taken off of our to do list and passed off to an AI.
So I think long story a little bit longer.
The shift around AI is significant when you think of all of the different
types of things that we do manually, whether it’s creating a pitch deck,
whether it’s actually doing a follow up email to someone,
whether it’s nudging someone on LinkedIn with a quick DM,
whether it’s crafting a brief that you want to send to your marketing team
to work on a case study or something.
All of these things can now be augmented on the back of AI,
and that provides a ton of wins and opportunities
for every professional that operates within the GTM world.
Yeah, no question.
I mean, our team has already started to leverage
AI, you know, semi significantly over the past year,
and it’s making us,. I would say, more efficient as a team.
I’m going to start out with the potentially dark side here of AI
and then let’s move into some other things because even on its own in B2B,
we’ve scaled the number of SDRs and messages that they send in the past
several years.
I think I saw Jen Allen-Knuth quoted there’s a 10,000% increase of messages
hitting your inbox and when you think about, okay, now
if we make it easier to send a large volume of messages
via email, via LinkedIn messenger
or whatever the medium, you know, how is
that going to change things?
And does the din become overwhelming?
I think there’s going to be two phases.
There’s going to be two phases, and the market is going to respond
differently to each.
The first phase is going to be a gold rush around those who leverage
AI to get mass outreach, to get mass. DMs sent to really flood
the market with communication to their ideal customer.
And it’ll all be powered in much on the back of AI.
And I think there’s going to be a ton of opportunity capitalized on in
the next 2 to 3 years from that because there’s a lot of niches
that will not even touch A.I.
Have no idea that openAI is the thing that ChatGPT is a thing.
There’s a lot of different niches
where it’s still very foreign, and over the next 2 to 3 years,
I think we’re going to see an oversaturation of it.
We’re going to see tons of emails sent, we’re going to see tons of DMs.
It’s going to be overwhelming.
And this is when the second shift is going to happen.
The second shift is going to happen when everyone as well as the people
behind the technologies like Gmail, etc., start to continue
to create more stringent protocols of what shows up in your inbox.
LinkedIn is going to do the same thing.. X is going to do the same thing.
It’s going to happen across the board.
And then what’s going to shift is going to be an elevation of outreach.
So all outreach, all communication, all approaches are going to go
from being able to get wins with AI to being seen as skeptical
and as a result of the skepticism that everyone is going to have
with everything that comes into their inbox,
there’s going to be an increased desire by humans to have a more
personalized human connection with the outreach efforts.
So I will need in four years you to demonstrate to me
much more clearly in the inbox that you are not an AI.
I need to know with confidence that you are a human.
Is it going to be difficult for you to prove that?
Yes, because now on the back of visual AI,
I can send an AI that is not really Ross
into your inbox as a Loom and have a presentation
that says your name that is going to be possible.
So it’s going to be difficult,
but if you can break through that,. I think that’s where you will get wins.
Short term AI is going to provide a ton of ROI, a ton of growth
and a ton of wins for BDRs, SDRs, anyone doing any type of outreach.
But when the market gets saturated and when the market gets annoyed,
it’s going to have a huge correction that takes place
both on the back of technology providers as well as the market at large.
And we’re going to have to see some shifts in the outreach approach.
Yeah, no question.
And you mentioned personalization, there, Ross, and I think that that’s what
I want to drill into a little bit there, because I think you’re already starting
to see a difference in the response rates for salespeople
that take the time and do highly personalized outreach, right?
The whole Show Me You Know Me concept when they’re doing the outreach,
they’re receiving, you know, higher open rates, higher response rates and things
like that from their prospects versus just using the prewritten cadences.
And so, you know, there’s sort of this fallacy, I guess, potentially
that, hey, if we can just scale everything, then, you know,
everything will be better.
And AI maybe takes that scale and puts it on steroids.
And so how do you control for that?
How do you leverage the best of personalization,
whether it’s video, whether it’s written text with AI, and have the biggest impact.
I think my recommendation would be to be willing to experiment
because there’s a lot of developments that are happening today that are making
it easier to personalize your reach and to personalize your communication.
I talked a little bit about video.
Today, if you personalize and tailor a video
to someone and it’s still really you, like physical you,
there is an increase in the likelihood that you’re going to get a response.
Now, what AI has done is it has allowed people to upload
a handful of videos to an AI tool like D-ID, etc..
And it can create an avatar for you on the screen.
You can input into that
avatar, the words that you wanted to say, and you can add variables
the same way that you would in an email that change from Hey Chip to
Hey Jim to Hey Sally to Hey Sofi, to change that first name in your voice.
That technology exists today and it will come off very personalized.
You can also include screenshots.
So when you’re talking to the screen,
it can change your background to be their website, their homepage,
and make it really feel like,. Hey Chip, I was on your website
and you have that screenshot behind you, but you actually are doing this at scale
and are customizing your outreach efforts based off of those variables.
Now that is a very wild future
to live in, but it’s also happening very quickly
and I think the people who can still scale
the more personalized message that cuts through all of that
will go a little bit further when they can reach out and they can say,
Hey, Chip, I was listening to this podcast with you and Ross,
and you happened to mention that you are a drummer.
I was a drummer too.
That can’t be replicated by AI, not yet.
Maybe I can think in my mind if you were able to at scale, download
all the transcripts and listen to find a key personalized moment in the podcast,
you might be able to get AI to customize that too, which is wild to think about.
But in the short term you can’t.
So try to still find those personalized touches
in your outreach and communication if you want to win today.
Yeah, it’s just crazy how far this technology has come
and I’ve been in the email space forever, right?
So merge variables were very common for text, even dynamic content,
which at one point, you know,
if you came from like a catalog print background that seemed incredible, right?
You can like personalize the content and the visuals and images
to every single person.
Very possible.
And now you’re talking about leveraging A.I.
to do that in video with a picture of yourself, right?
So it’s gotta have some
gain benefit, I would think is long as you do it tastefully.
And I think that’s, you know, it’s been long talked about since sort
of the invention of AI sort of the uncanny valley and are we are we truly there.
Right. Right.
Such that you can create one of those videos
and it does look like Ross Exactly.
And so the individual is not skeptical, but they’re convinced
because it feels like you. Yeah.
And the risk is that it comes off as an. AI like
the worst experience that you can give someone is that they’re consuming it.
And at first they believe, yes, this is Ross,
but then they don’t hear my emotes and they don’t pick up the Canadian accent
and then they’re like,. This isn’t Ross. This doesn’t work.
Like what?
What’s going on?
Like, he’s not speaking with that voice in that tone.
So there is a thin line that you have to kind of recognize.
Like there are limitations.
It might not be perfect
and you have to be okay with some of the risk that comes along with it.
The other piece that becomes interesting with this is like with voice
AI now you can translate that voice into different languages.
So internationalization with your outreach also becomes easier.
I was in Brazil and I was speaking on stage
and I gave this keynote and I did a quick glimpse at the end of my presentation
where it translated my voice into Portuguese,
and the audience just was mind blown by this concept.
And I think like what A.I.
is giving us as well as an opportunity, is to really break down borders
and connect on a more global scale with people and businesses all over the world.
Yeah, that’s incredible.
I can see the benefits across borders to actually bring you closer to somebody
because now you’re talking in their native tongue, right where it’s,
you know, the benefits of A.I.
driven voice are actually a positive.. Right?
So, you know, one of the best use cases. I’ve seen is
that video and be able to leverage that in social, Ross, I mean,
have you done any testing with that, you or your team or your clients?
So we’ve been testing a lot
with video content, both on the internal side, at Foundation
with our partners and clients, but also using it for our own promotion.
Then we like to really experiment in public.
So one weekend I put together a video where it was essentially
a deepfake of myself talking about concepts around marketing
and growth and content, where trends around search were going.
And I pressed publish on this deepfake of myself, and I started
to see a handful of responses back, people saying, Oh, this is great, love this.
No one was saying, Hey, this was AI,. I can tell.
People were saying, Wow,. I love your shirt.
I love your like, I like that. I love your new glasses.
Like all of these things.
And I was like, this is wild.
People aren’t picking up the fact that this is not actually me.
And I think there’s a pro and a con to this.
On the pro side, you can now scale content very quickly
on the back of these types of assets and have some amazing results.
But on the flip side of that, it makes all of us
more skeptical about the things that we are consuming online.
And we all now more than ever before, do need to be skeptical
of everything that we see.
You don’t know if what you’re watching is a real person.
You don’t know if it’s someone who is essentially leveraging
someone else’s voice and making that person say a certain thing.
There’s a lot of skepticism that needs to be
had by all of us as we go to the market.
And for those of us who do use these tools,
we also need to recognize, like Uncle Ben said
in the Spiderman movies, with great power comes great responsibility.
And we need to be careful
with how we leverage these technologies to be able to kind of stay true
to best principles and ethics around communication with these new tools.
So I have one final question for you, Ross.
And so if you were a sales leader right now, because there’s, you know, lots
of different companies that are emerging in the AI space, what would you do now?
Would you start testing some of those things?
Would you lean in and educate your team?
Is this just really a time of testing and experimentation?
I think there’s two key things that I would do if I was a sales leader
and it would be a blend of experimentation and empowering.
So on the experimentation side,. I would invest heavily in booking
my calendar as well as some folks on my team
who are in a leadership or management position with tools and solutions
that leverage AI to allow us to be augmented as professionals.
Book some demos, try to find some time to actually understand the technologies
that are available in the market and get demos to see which tools
might be able to accelerate
and give you the wins that you need in 2024, 2025 and beyond.
Now, on the empowering side,. I would be going to finance
and going to leadership and pushing to ensure that my team has training budget
so they can get up to speed in understanding how to leverage A.I..
And it’s not enough to say, Oh, we have this tool that we used last year
and AI is listening to our calls and it’s telling us that when we should follow up.
No, that was last year.
You need to be thinking forward into the future and identifying budget
so your team can be trained on what is to come and ways
that they can improve in the future.
So empowering by investing in your people and then educating yourself
through experimentation and learning about new tools.
Those are great tips, Ross, any other final thoughts for us?
The final thought that I would leave folks with
is to not be afraid of the technology.
I think a lot of organizations
are still afraid that this technology is going to replace them.
Those who get replaced are simply going to be the ones who ignore it the longest.
So I encourage you to tinker, to experiment and to try this technology.
It is one of the most fundamentally, life career
changing technologies that I’ve seen since the early days of social media.
When I walked into a library and I saw everyone playing
Jetman and I was like,. This thing is going to take off.
This is that new iteration of that.
Awesome. Well, Ross, thanks so much.
I loved your insights today and would love to have you back again some time.
Thanks, Chip.
Really appreciate you having me on. Yeah, absolutely.
And thanks to all of you for tuning in to this episode of Closing Time
and we’ll forward to seeing you next time.

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