Don't Hire The Wrong Marketer: Startup & Big Brand Lessons

Because not all marketers are built for where your business is - or where it's headed

Don't Hire the Wrong Marketer: Lessons from Startups and Big Brands

Most startups don’t die from bad ideas. They die from bad execution. Hiring the wrong marketer early on is one of the fastest ways to stall momentum before you even hit product-market fit. To be clear, hiring mistakes hurt at any stage. But big brands and mature businesses usually have the cushion to absorb them. Startups don’t.

Over the years, I’ve led marketing orgs of all shapes and sizes, and mentored dozens of founders across different growth stages. I’ve made the classic hiring mistakes, falling for ultra-polished resumes with impressive logos, and overlooking the scrappy, adaptable marketer right in front of me.

But the most common — and costly — mistake I’ve seen (and made) is not aligning the marketer’s skill set with the company’s stage of growth.

So I am providing a playbook below so you can match marketing talent to the maturity of your business, from early-stage startups to enterprise brands

Early-Stage – Avoid the Specialist

When you're a 0-to-1 startup, you need a marketing Swiss army knife, not a scalpel.

One of the founders I advise hired a sharp product marketer from a FAANG-type company. On paper, he was perfect. In practice, he needed a brand bible, a creative team, and a roadmap, none of which existed. Startups need doers, not decorators.

Avoid: Specialists who freeze in ambiguity
Look for: Generalists who thrive on action and iteration

Your early hire should be someone who is equal parts strategist, writer, and operator. They don't wait for briefs; they write them. They don't ask, "Who owns this?" They just do it.

Not as easy though- Hiring generalist marketers isn’t as easy as it sounds. A true marketing generalist is not someone who has just worn many hats. It’s someone who knows when to switch hats, how each hat fits the customer journey, and why each hat matters to business outcomes. That expertise takes time, repetition, and scar tissue.

These are systems thinkers who know how to sequence, prioritize, and move fast without breaking the business and in my experience, it typically takes a decade or more to develop that combined muscle.

In my observations, the best generalist marketers have cycled through at least three different roles:

• Performance or growth marketing: Metrics, budgets, and efficiency

• Content or communications: Storytelling, empathy, and positioning

• Product or lifecycle: Customer experience, retention, and monetization

They have seen how demand generation breaks without the right messaging, how brand work flops without conversion infrastructure, and how strategy dies when no one executes it. That cross-functional pattern recognition is built over a career of jumping into the unknown and figuring things out.

Mid-Stage – Avoid the "Strategy-Only" Marketer

Once you’ve found product-market fit and scored a few wins, there is a strong urge to professionalize marketing.

This is where many startups make their next big hiring mistake: bringing in a strategy-only marketer too early.

I have made this mistake. You do not need a whiteboard wizard. You need someone who can write the copy, launch the campaign, and still have time to check attribution.

Earlier in my career, I hired a senior marketer who came with all the signals. He had built teams, managed agencies, and presented to the C-suite. I thought we were leveling up. In week two, he wanted to kick off a 90-day brand positioning exercise, hire a larger agency, and bring on more marketers with unclear roles. Meanwhile, we still did not have a working email nurture sequence. There is a time for frameworks. This was not it.

At this stage, you need marketers who can toggle effortlessly between the big picture and the minute details. Think of someone who can lead a brainstorm at 9 am, jump into a marketing ops issue at 11, and write a killer subject line by noon.

The problem is that strategy-only marketers have often grown up in bigger teams. They are used to owning just a slice of the funnel, not the whole thing. They assume there is always someone to hand things off to.

In a mid-stage startup, there is no handoff, you are the team.

Avoid: Leaders who only want to manage others doing the work
Look for: Player-coaches who can plan the play and run the ball

The best hires I have made at this stage were not the best managers or those with the shiniest decks. These are folks who could launch, learn, and lead, even without perfect conditions.

Mid-stage marketing is a grind. Hire people who deeply understand that execution is strategy at this stage. They will intuitively understand the art and science of balancing growth goals, patching systems, hiring slowly, and still trying to hit numbers.

Because if you bring in a big-idea marketer who cannot execute, you end up with a beautiful Miro board and no pipeline.

Late-Stage – Avoid the Non-Scaler

You’ve found product-market fit. You have budget, traction, a somewhat of a known brand. Now it's time to scale fast and smart.

But here’s where many founders make their next critical misstep: hiring someone who has seen scale but never actually built it.

Let me share an example of what that looks like - Last month, I was a part of interview panel vetting growth marketers. I interviewed someone who had a stellar resume, managed $10M/month in media spend. Big team, good agency relationships, and good title. But when I asked him how they’d grow a $500k program into $2M over the next year, he didn’t have a good answer and made me question a lot of what was in the resume. This is not an isolated example and I have many more of these stories..

You need marketers that are scalers, not maintainers. Scaling is not about spending more. It’s about spending smarter, faster, and more repeatably while building the infrastructure to support it.

And that’s the hard part.

Avoid: Corporate veterans who confuse scale with size
Look for: Builders who have created repeatable engines from scratch

Marketers who come from mature environments are used to inheriting fully-baked systems including established attribution models, optimized channels, brand momentum, and armies of support. They know how to optimize. But they often struggle when they have to build a cross-channel growth model from the ground up, operationalize campaigns across product, sales, and data teams or create scalable systems with less, not more

When things start to break under pressure—as they inevitably do, they don’t know how to fix the plumbing.

Great late-stage marketers do more than optimize. They operationalize. They understand marginal ROI, can build scalable processes, and still think like a founder, lean, iterative, and numbers obsessed. The best late-stage marketers are systems thinkers.

You want marketers who:

• Know what a working CAC-to-LTV ratio should look like and how to adjust spend accordingly

• Can wrangle cross-functional teams without creating bloated processes

• Think like product managers: customer-first, hypothesis-driven, data-informed

• And above all, they still act like owners. Even with a bigger budget, they test. They iterate. They obsess over ROI.

• My personal favorite – They still feel a little uncomfortable with “too much” budget, and know how to justify every dollar

In the interviews, just ask, "Tell me how you turned a $100k experiment into a $1M program and how you knew it was ready." If they cannot answer with clarity, data, and hard-won lessons, they are not the scaler you need.

Remember that scaling isn’t just growth. It’s growth with infrastructure.

Note: If there’s one thing to prioritize, it’s this: get your marketing leader in early. Seriously. It’ll save you from painful detours, missed milestones, and expensive clean-up jobs down the road.

Hiring Marketers for Big Brands and Mature Organizations

In mature companies, you’re not just looking for builders—you’re looking for navigators, integrators, and optimizers. These marketers know how to thrive in complexity, bring cross-functional teams together, and drive results in environments where scale, structure, and stakeholders rule.

You need marketers who:

• Think strategically but execute with discipline – They align tightly with business objectives and know how to manage large-scale initiatives with clarity and focus.

• Understand systems and process – From brand governance to multi-channel campaign orchestration, they know how to work within and improve established frameworks.

• Influence across functions – Great mature-stage marketers are skilled collaborators who can partner with product, legal, compliance, analytics, and executive teams to get things done.

• Elevate performance – They’re not just maintaining the status quo they’re finding new efficiencies, applying data rigor, and improving ROI across channels.

• Balance innovation with risk management – They push boundaries while respecting the guardrails that come with scale, reputation, and regulation.

Because not all marketers are wired for structure, process, and navigating matrixed environments. At this stage, you need leaders who can work with the machine and still make it move faster.

What the Best Marketers Have in Common

Regardless of the business maturity, the best marketers I’ve worked with share the same DNA:

• Entrepreneurial mindset

• Deep customer empathy

• Storytelling + data fluency

• Resourcefulness under constraints

• Ability to lead and execute

• Relentless curiosity

They don’t just “do marketing.” They think like founders or CEOs, constantly aligning their work with the bigger picture of where the company is headed. They obsess over how marketing drives real business outcomes: revenue growth, customer retention, product adoption, and long-term brand value.

They always ask: Will this move the needle for the business? Every decision is grounded in impact. They collaborate closely with product, sales, and leadership to co-create value, shape strategy and become a driving force behind company growth.

In short, the best marketers treat the business like it’s their own because that’s how they show up every day !

APPENDIX

Simplified summary of the full playbook below in table format