Hiring a Rep vs. Building a Brand - Which One Comes First?

By Jonathan Lipson | Founder & President | The Cigar Profit Consulting

Which comes first? The brand or the brand rep?

Introduction

In the premium cigar industry, the temptation is always to go to market before you've figured out what market you're actually for.

A new brand hits the scene, finds a rep with a decent contact list, and starts handing out samples, booking events, and hoping something sticks. But there’s a quiet danger in moving fast without moving right. It’s the danger of building distribution before building meaning.

Let’s pause here. A sales rep can introduce your product. But a brand introduces your promise.

Without a clear brand - who you’re for, why you exist, and how you’re different - your product becomes a commodity. And when that happens, you're not building equity… you're just chasing attention.

This article isn’t a takedown of reps. It’s a wake-up call about sequence. First you build the foundation - then you amplify it. Reps are multipliers, not magicians. They can elevate your message, but they can’t create one for you.

So, before you hand over your product to someone else to represent it, ask yourself: What exactly are they representing?

What follows is a conversation about getting the order right - designing a brand that earns belief before it asks for sales. Because when your strategy is sound, your reps won’t just pitch your cigars. They’ll advocate for your brand.

Let’s begin with what really matters: your difference.

What Is a Brand, Really?

If you ask ten founder-level cigarmakers what a brand is, you’ll likely get ten variations of the same answer: "It's our logo," "It's the product," or "It's the story behind the name." But those are outputs, not the brand itself.

Here’s the truth: a brand isn’t what you say it is - it’s what they say it is.

Your brand is the space you occupy in someone’s mind. It’s a gut feeling, built over time, from every interaction someone has with your company - from the cigar band to the Instagram caption, from the box design to the way your rep greets a customer at an event.

It’s the perception of value.

And in an industry where everyone claims “quality” and “craftmanship,” perception is everything. Without a brand, you’re asking customers to make decisions based solely on taste - and taste is subjective. A strong brand tips the scale in your favor before the cutter ever touches the cap.

When you think of a brand as a business asset - not just a name or a design - you begin to make better decisions. You start asking bigger questions: “What do we stand for?” “Why would someone choose us again?” “What promise are we making, and are we keeping it?”

Get the brand right, and everything else gets easier. Even the sale.

Selling ≠ Branding

Let’s clear something up - selling is not branding.

Sales is transactional. Branding is transformational.

A sale is a moment. A brand is a movement.

A great sales rep can close a deal. A great brand can open doors - consistently, quietly, and at scale.

When cigar founder-level cigarmakers hire a rep before building a BRAND, they’re often hoping the rep will do the heavy lifting: introduce the product, communicate the story, and bring in the orders. But without a clearly defined brand message, you’re asking that rep to sell a question mark. And the market isn’t kind to question marks.

Branding sets the conditions for the sale before a rep ever shows up. It builds familiarity, trust, and expectation - all of which reduce the friction of the transaction. If your branding is strong, reps become amplifiers of a message that already resonates. If your branding is weak or inconsistent, even the best reps become apologetic translators.

In a world where retailers are flooded with choices and consumers are bombarded with noise, your brand should do what no rep can: stand for something, mean something, and be remembered.

You can sell without a brand - sure. But that’s a hustle. Build the brand first, and the sales become the echo.

Branding is the Pre-Work That Makes Sales Easier

Branding isn’t fluff. It’s function.

A brand is the work you do in advance to make everything downstream easier - especially sales.

Imagine walking into a tobacconist with a product no one’s heard of, no visual consistency, no story, no proof of demand. That’s not a sales call - it’s a gamble. You’re asking someone to take a risk on the unknown. Now imagine that same call, but with a brand that already lives in the retailer’s mind - known look, clear value, strong origin story, maybe even a few customers already asking about it. That’s not a gamble. That’s alignment.

This is what branding does. It tilts the playing field.

Done well, it gives your reps something to stand on. It makes your meetings feel less like pitches and more like conversations. It sets expectations - and then helps you exceed them.

Reps are accelerators. Branding is traction.

When you build your brand with intention - the name, the voice, the visuals, the promise - you’re not just “getting ready.”

You’re building momentum before the sales even start.

Because the truth is, every sale is easier when the brand already walked in the room before you did.

The Myth of the Charismatic Rep

There’s a persistent belief in the cigar industry - and frankly, in most industries - that the secret to growth is hiring “that guy.” The closer. The schmoozer. The one with the velvet voice, the endless Rolodex, and the handshake that feels like a done deal.

Let’s get one thing straight.

Charisma might open a door, but it won’t hold it open.

Not for long.

When a business relies too heavily on personality to drive performance, it builds on sand. What happens when the star rep leaves? Or burns out? Or simply can’t replicate their magic in a new market? You’re back to square one - only now you’ve got overhead.

Worse, without a brand to back them, even the most magnetic rep is reduced to selling product. A box. A blend. A price point. And when the next brand comes along - flashier, cheaper, or sold by someone even more charming - that sale vanishes.

Charisma might spark a few quick wins, but it won’t sustain momentum.

Brands aren’t built in applause. They’re built in trust.

Branding, by contrast, is a repeatable system. It builds equity beyond the rep. It creates preference before a conversation even starts. And it gives your sales team - whether seasoned pros or scrappy newcomers - a platform to stand on. A story that sells with or without a silver tongue.

The myth isn’t that charisma doesn’t matter.

It’s that it’s enough.

What Happens Without a Brand?

Take away the brand, and what are you left with?

A product. A feature set. A price tag.

In the cigar industry, where options are endless and differentiation is razor-thin, that’s a dangerous place to be. When you don’t have a brand, you’re not in a relationship with the customer - you’re in a transaction. And transactions are commodities. They’re forgettable. Replaceable. Vulnerable.

Without a brand, your rep walks into a retailer’s humidor and pitches just another cigar. The conversation becomes a game of price, margin, and shelf space - and the odds are stacked against you. Loyalty becomes conditional. You’re one backorder or bad batch away from irrelevance.

More than that, you lose narrative control. Other people - reps, retailers, even customers - start defining your brand for you. Sometimes it’s flattering. Sometimes it’s not. Either way, it’s not strategic.

With no clear identity, you become reactive. Every decision feels urgent. Every competitor feels threatening. Every trend feels like something you’re supposed to chase.

Branding gives you the steering wheel. Without it, you’re just along for the ride - hoping your product can scream loud enough in a room full of shouting voices.

And hope, as they say, is not a strategy.

Build the Foundation First

If your brand doesn’t stand for something, you’ll fall for anything.

Too many cigar brand startups skip the groundwork and start chasing sales, assuming branding can be bolted-on later. But that’s like building the second floor before you pour the concrete. Everything wobbles. Nothing scales.

Branding is your foundation. It’s what anchors your company, sharpens your focus, and informs every customer-facing decision. Before you make your first cold call or ship your first box, you should be able to answer the following:

• What do we stand for?

• Who are we for - and just as importantly, who are we not for?

• What is the emotional payoff of buying our product?

• Why does this brand deserve a seat at the table in a crowded industry?

This is not about taglines. It’s about clarity. Because clarity breeds confidence - internally and externally. Reps sell better. Retailers commit faster. Consumers remember longer.

Your brand strategy is the compass that points everything in the right direction - from packaging to partnerships to pricing. Without it, you're flying blind.

Build first, sell second. That’s not just smart branding - it’s smart business.

Because the strongest brands aren’t made of tobacco and labels. They’re built on purpose, relevance, and trust - poured into the foundation from day one.

When the Rep Does Make Sense

Hiring a rep isn’t a mistake.

Hiring a rep too early is.

A well-connected, charismatic sales rep can absolutely accelerate a cigar brand - but only when the foundation is rock-solid. The real magic happens when the heavy lifting of branding has already been done: positioning, identity, messaging. When a rep walks in with clarity, not confusion, they can make an impact.

Because at that point, they’re not just selling cigars - they’re selling confidence.

Great reps thrive when they’ve got a compelling story to tell, a visual identity that jumps off the shelf, and a clear reason for why a retailer should make room in their humidor. Give them that, and they become amplifiers of your brand. Without it? They’re just winging it.

And here’s the hard truth - even the most gifted reps can’t fix a brand that hasn’t figured itself out. They can only cover the cracks... temporarily.

So, when does hiring a rep actually make sense?

·         After your brand knows who it is.

·         After your product consistently delivers on its promise.

·         After your brand architecture - the strategic framework for organizing your products, lines, and messaging - is clearly in place.

Only then does the rep become a force multiplier - not a shot in the dark.

Remember: great reps don’t generate demand out of thin air.

They channel it.

Your job? Build a brand worth channeling.

Brand Before Boots

There’s a tempting myth in business - especially in an industry as relationship-driven as premium cigars - that success comes from hitting the pavement. That if you just hire a few salespeople, throw them some samples, and let them “work their magic,” the sales will follow.

But boots on the ground without a brand behind them? That’s not strategy - that’s wishful

thinking.

Think of it this way: branding is the blueprint. It's how you design the structure of your company’s perception - the message, the tone, the purpose. Reps are the builders. They’re essential, but they need a plan to work from. No one builds a house by showing up with tools and guessing where the walls go.

Putting boots before brand turns your business into a constant improvisation. It leads to mixed messaging, inconsistent promises, and uneven customer experiences. Even worse, it erodes credibility.

Flip the sequence, and everything changes. With a strong brand foundation, every rep becomes more powerful. Every pitch more consistent. Every encounter more memorable.

Founders often ask, “How do I get more people talking about my cigars?” The answer isn’t more feet on the street - it’s a message worth walking for.

Brand before boots isn’t just a clever phrase - it’s the filter that separates companies chasing sales from brands building movements. One is a hustle. The other is a strategy. Choose wisely.

Final Thoughts: The Smart Play

If you’ve made it this far, here’s the big takeaway: sales don’t create brands - brands create sales.

You can’t outsource meaning. You can’t hire your way to clarity. And charisma alone won’t carry your cigars into the future. If you start with a rep and no brand, you’re essentially handing someone else the pen and asking them to write your story. And when everyone’s telling a different story? The market hears noise, not a message.

This isn’t about knocking sales reps. When deployed strategically, they’re invaluable. But without a defined brand narrative, they’re flying blind. No target audience. No messaging consistency. No emotional hook. Just effort, unanchored by architecture.

The smart play is to flip the model.

Build your brand first - and by brand, I don’t mean just a slick logo or clever name. I mean the gut feeling your customer gets when they see your product, hear your story, or light up one of your cigars. When that feeling is clear and consistent, you don’t chase customers - they come to you.

Then - and only then - bring in a rep who can carry the torch, not fumble in the dark.

That’s where The Cigar Profit comes in.

We help brand owners articulate what makes them different - and turn that difference into an unfair advantage. If you’re debating whether to hire your first rep or invest in branding,

let’s talk before you choose the wrong starting line. Click here to schedule your exploratory call.

Brand first. Then boots. That’s how you build a legacy.