We still have slots, but it’s true, space is limited.

Two Silicon Valley legends, Aaref Hilaly, Bain Capital Ventures, and ​Gautam Gupta, Strata Capital, have agreed to join me and my co-host, Arjun Dev Arora, for an invite-only and founder-friendly event.

When and where? During TechCrunch Disrupt on Tuesday, October 28, in San Francisco.

Who else is going to be there? Click here to find out. (All the cool kids, of course.)

Founders, hiring your first head of marketing will be hard. And important.

Get it right, and you accelerate growth.

Get it wrong, and you burn precious time and money.

The title may be the same, but the person behind it can look very different depending on what your startup truly needs.

So how do you decide?

It will depend on the stage your business is at, the industry or area you are in, and the kind of team you have in place. Here’s my playbook, based on my experience of building and managing a successful go-to-market team at an early-stage startup.

Don’t just hire “a marketer” to help you “grow the business” in the abstract. Hire someone who can help close the most significant gap in your go-to-market right now.

Okay, that sounds like good advice. But what does that mean exactly?

Here are some examples:

If you have (some) product-market fit, but you don’t have enough leads and your revenue growth is slow, consider hiring a growth or performance marketer. This is the right solution for most mid-market SaaS companies.

If you're still trying to achieve product-market fit, consider hiring a product marketing professional to help refine your product strategy and work directly with your tech team to help guide product releases and strategy.

If your growth is primarily driven by partner networks or ecosystems, a community or partnerships marketer might be the right fit, as this approach is popular with many developer-focused platforms.

If you have a great sales team and sell to enterprises, a brand and communications leader can be the ideal person to elevate your reputation with large enterprises, warming them up for sales.

Above all, find someone willing to do the work, which is why the right hire isn’t about what’s impressive on paper. Do not get enamored with pedigree.

The goal is to match their superpower to your startup’s most urgent need.

In the early days, you don’t need a polished CMO who knows how to manage large teams and agencies.

You need a hands-on operator. And let’s be clear about precisely what this means.

Look for a candidate who can, for example, write and upload a blog post to Squarespace or WordPress, with graphics they created in Canva, and use AI to populate all SEO features. And when they don’t know how to do something, like edit the email sequences in HubSpot or migrate your website from one service to another, they know how to go on UpWork and find someone to help them get it done.

Think “task completor,” not “Asana task creator.”

The best early-stage marketers are often full-stack operators who can wear multiple hats until you’re ready to scale.

Ideally, you find a candidate who has lived through the process of building from scratch: no budget, no team, no brand awareness, and no existing playbook. And is looking to do it again. It’s rare, but it does happen.

The second best option to consider is talented up-and-comers who work at a marketing consultancy or agency and view this as their opportunity to break into what they call the client side, and work in the tech industry. In my experience, this is a much more realistic profile than holding out for a startup veteran.

The key is they need to know how to create action when there is no action

What to look for to evaluate for this:

Have they gone from zero to one? Look for someone who set up and grew a Substack newsletter, blog, or built a large social media account from scratch. Or they have run successful paid campaigns with a tiny budget. Perhaps they can write, design, and create amazing decks independently. They need to know how to start with nothing.

Are they a strong writer? Early on, your marketer must also be your copywriter, PR person, and brand voice. They need to write compelling social media hooks, landing pages, customer emails, and press pitches. Yes, AI will help, but they still need the skill to communicate a compelling value proposition for your company.

Can they stay calm and prioritize under pressure? In a startup, there will be ten things on fire and zero resources to fix them all. The right marketer doesn’t panic. They can keep a cool head and quickly separate smoke from flames, decide what actually matters today, and let the rest wait.

Are they adaptable? When your product strategy changes, or the GTM shifts, or the customer feedback surprises everyone, they must be able to scrap a campaign and start fresh without drama. FAANG employees and executives from large companies struggle with this because they are accustomed to meeting defined objectives.

Do you and the team like them? You’re going to spend a lot of time with this person, so it will help immensely if you like them and enjoy being around them. This was something I downplayed when I was younger, and I regretted it. I wish someone had told me (like Peter Thiel) to look for a team that I liked to be around a lot.

I see founders make these mistakes over and over again.

Why? I think the allure of the silver bullet hire that will solve everything is just too tempting to ignore. And candidates are more than happy to promise you the world during the interview process when they want the job.

Here are a few traps I see many founders fall into when hiring a head of marketing:

As a founder, you should always be thinking about recruiting. Finding top talent is challenging, which is why you want to be one step ahead, continuously expanding your network to include great people with whom you might want to work with.

Recruiting is so vital, I think you should aim to meet with someone once a week who might be a great future hire.

When recruiting for any key role, start by asking all your advisors, investors, accelerator classmates, and college friends who they could recommend.

You can also go to events and tech meetups.

I was once looking for a head of PR and thought I would attend the Silicon Valley PR Association’s MeetUp in Palo Alto to network and recruit. We ultimately hired the person who hosted the event and was a member of the association's board. Pretty smart, right? It worked out great.

I know there has been some pushback on these on social media. But I am a fan. It allows candidates to demonstrate their capabilities. Truth be told, my big break came because a startup took a chance and evaluated me based on my project.

However, if the candidate has a large body of work to review, this is overkill. True.

What’s really important is not to overthink this, for a head of marketing interview at an early-stage startup, you should ask them to create a 10-slide marketing plan. Let them know they are free to ask questions as they work on it. The experience should feel like you’re working together.

The best result is that they ask questions during the process and come back with something that identifies ideas you never considered. If that happens, bingo. You probably found the right person. If they half ass it, well…

I once had two candidates competing against each other on the same project for the same role. The exercise clearly demonstrated which candidate was better, and they went on to be very successful within the organization.

Now I know this might sound harsh, but in this day and age, if you’re hiring a head of marketing and they don’t have at least a few thousand followers on X and LinkedIn, plus maybe a Beehiiv or Substack they post on, even infrequently, how serious can they be about a tech career?

If you can attract a micro-influencer in your niche, that’s ideal.

If there is one thing I would prioritize above all else for a startup hire, it’s motivation. You want a candidate who is hungry and will stop at nothing to succeed.

On the Gregory and Paul Show, we break down the latest in startups, SaaS, AI, and whatever the internet is debating this week.

On this episode, Gregory and Paul welcome Tushar Kumar, private wealth advisor and co-founder of Twin Peaks Wealth Advisors. Tushar shares his founder journey, lessons from scaling to $500M AUM, and practical advice for tech professionals navigating equity compensation, IPOs, and acquisitions. The crew also dives (delves) into the hotly debated MIT report claiming 95% of enterprise AI pilots fail, and explores whether AI is creating efficiency—or killing jobs.

Watch episode 012 on YouTube →

Vibe Corps is not a course. It's micro-fractional consulting. (Yes, I invented the category.) Vibe Corps provides near-real-time feedback via Slack, and you’ll also receive the frameworks I've used to scale startups.

This means you can ask me as many questions as you'd like on Slack. (Just not on the weekend. I need that time to ride bikes.)

Send me materials to review, such as landing pages, blog posts, email sequences, newsletters, presentations, or sales call videos. Ask anything you want.

Additionally, you'll receive a 1-hour live session with me.

Frameworks included in Vibe Corps:

Ok, you’re in. So what does it cost?

It’s usually $699 but today is just $499 for 3 months. Because if you are a dedicated founder and you’re reading this on Labor Day, you’ll make a great client. You’re devoted, hardworking, and know the value of a good discount.

Use the code ‘laborday’ for $200 off and join the corps now.

I'm Gregory Kennedy, former creative director, 3X head of marketing, and founder of Vibe Your SaaS. I help early-stage startups build real momentum with strategic clarity, AI-driven execution, and zero BS. I love coffee. I love to ride a bike. And I love helping early-stage tech companies win.

Greogry Kennedy // Vibe Your SaaS // www.vbmrktr.com

Yeah, I know it’s Labor Day. That means summer is over, and it’s time to work. So here are some tunes about work, to rock, ummm… at work. Listen here →

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