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I’m seeing a lot of bad sales advice online:
hacks, manipulation, and even suggestions to lie to book meetings.
But sometimes you see something thoughtful and creative that deserves a closer look.
And this one involved enterprise accounts, tax leaders... and creativity.
I want to share more examples like this because it’s useful to study what great reps are doing differently, then reverse-engineer the thinking behind it.
Last week, I came across a great post from Jen Allen-Knuth about Yassine Dessouki, a sales rep at Bloomberg Industry Group who works with enterprise tax leaders.
Yassine researches the company, finds a connection between its brand and the world of tax, and uses AI to turn that connection into a personalized image.
Here’s what I could create with ChatGPT’s image model, using the concepts from Jen’s post to show you what this could look like:
Maybelline: “Because your tax strategy is worth it.”
LEGO: “Building your tax strategy together.”
Maybelline: “Because your tax strategy is worth it.”
LEGO: “Building your tax strategy together.”
He sends these through LinkedIn DMs with one sentence of text. According to Jen, he’s booking meetings with VP+ prospects using the approach.
Here’s why I think this is great outbound
1. He starts with the account
You don’t need to know where someone went to university, what football team they support, or what they posted on LinkedIn last week.
The company itself gives you enough material.
With Maybelline, Yassine used their famous line, “Because you’re worth it”, and turned it into: “Because your tax strategy is worth it.”
For Lego, he used the product itself: “Building your tax strategy together.”
They can immediately see this wasn’t made for every VP of Tax on a list.
2. He makes the relevance obvious in seconds
The more work the prospect has to do to understand your message, the less likely they are to engage with it.
Good outbound should be easy to process.
There isn’t a 150-word explanation underneath the Maybelline image.
The prospect sees the makeup ad, the tax references and the adapted tagline.
They get the idea almost immediately.
A VP doesn’t need to stop what they’re doing and decode why you contacted them. The creative does most of the communication for the rep.
That matters when you’re competing with dozens of other messages for a few seconds of attention.
3. He uses creativity as a pattern interrupt
There’s a big difference between earning attention and hacking attention.
A lot of outbound tactics try to stand out through fake forwards, misleading subject lines, double dials or whatever loophole is working this month.
This stands out because the actual message is different.
Yassine simply sends a visual the prospect probably hasn’t received from another salesperson that day.
There’s no feeling of being tricked into engaging. They might like it. They might ignore it.
But the rep earns the opportunity to be noticed through effort and creativity rather than manipulation.
4. He treats finance leaders like people
Seniority changes someone’s responsibilities. It doesn’t remove their personality.
Outbound often becomes more boring as the buyer becomes more senior because reps think “executive” means “corporate”.
Yassine is selling to Heads and VPs of Tax, probably one of the easiest personas to stereotype as conservative and serious, and still uses humour and creativity.
They’re receiving something written for a human rather than a job title.
You can still be credible without sounding like every enterprise sales email ever written.
Professional doesn’t have to mean boring.
5. He uses AI for production
The best use of AI in outbound can also make better ideas cheaper and faster to execute.
Once Yassine has the concept, Maybelline, makeup, tax legislation, AI can create an image that would previously have required design skills or help from a creative team.
The buyer gets something that feels much more considered without the seller needing hours to produce it.
And this is where I’d push back on the idea that the tactic works because it “doesn’t scale”.
It does scale.
You can automate a lot of the research, concept generation and image production.
What’s harder to scale is the judgement:
Does the connection make sense? Or does it just look like AI slop?
AI can scale the production. The rep still needs to provide the taste.
Here’s what you can apply to your own outbound
1. Start with research
I’d lead with an email/LinkedIn DM with research about the company:
an initiative from the annual report
a quote from the CEO
a challenge
Then I’d connect that to the potential impact or operational pressure for the team, and how we could help AKA your Point of View.
2. Find an interesting connection for your follow-up.
Something between their world, your world, and the problem you solve like Yassine does. Package it in a way that’s easy to consume.
In this case, one image and one sentence.
That’s how I’d use this within the different messages sent to an account.
3. Work through the process before scaling it.
I would do it manually for 10 accounts first, using AI to research each company, understand its positioning, generate several concepts, and produce the final image. I’d review the concepts and the output as I went.
This is what I do when I use AI in my workflows: work through the process manually a few times until I’m satisfied, then scale it. Everything can always be improved.
Once I'm satisfied with a workflow, I’d automate the repeatable steps through Clay or another provider that lets you use an API. That would let me scale production; prospect responses would tell me whether the outreach was working.
There’s enough content teaching sellers another trick to get a reply.
I want to share more of the opposite: reps doing relevant AND creative work for outbound.
So we can learn how great outbound reps think.
Elric
This is how I approach AI workflows for my customers: work through the process a few times, get it to a standard I’m happy with, then scale it.
These are the kinds of AI workflows I’ll be sharing inside the future Outbound Kitchen membership.