Remote Creative Problem Solving Jobs in Chicago, IL

B2B Media Buyer / Creative Strategist (Limitless) Remote · US or Canada · Full-time · $120K–$150K OTE · 9am–6pm ET

Read this part first

This seat runs paid acquisition for our program: high-level B2B media on Meta, and the creative going into it. You run the ads AND you build the angles, hooks, and copy that make them work. Those aren't separate jobs here. A media buyer who can't talk creative is only half the picture, and so is a creative who can't run the account. We're looking for both, at a high level, in one person.

This is a senior seat. If you've been running serious B2B spend and building the creative behind it, we'd love to talk.

Who we are

Limitless is a coaching program for marketing agency owners. We teach agency founders how to scale.

#1 fastest-growing coaching program for marketing agencies. 225+ agencies joined us in the last 12 months. Built by two founders who've actually done what our students are trying to do.

Gill Valerio scaled his first agency from zero to $500K a month and exited in a multi-million dollar deal in three and a half years. Dave Pancham has run his agency for seven years, has been at multi-seven-figures for over five years steady, and his business is fully run by his team. Two founders, two paths, same destination.

What you'll own

Media buying — your primary. You run all paid media on Meta for our program: targeting, testing structure, pacing, every optimization decision. This is high-level B2B lead gen, not e-com, and you've done it before at real scale. You own the numbers. You know what changed, why it changed, and what you're doing about it before anyone has to ask. You diagnose at the concept level, is this angle dead or is it the hook, is the offer wrong or the persona too broad, because you're also the one who built the creative.

Creative strategy and copy. You develop the concepts, write the hooks, and script the funnel: ads, VSL, book-a-call page. Our funnel is VSL to book-a-call, and that's a hard creative problem on purpose. A B2B VSL has to hold a skeptical, sophisticated buyer through education before the offer shows up. The foundation under all of it is direct-response copywriting. If the message isn't dialed in, nothing else lands, no format, no targeting, no spend saves a weak message. You write the message that makes a cold agency owner stop and say yes.

Our market is a niche: agency owners. Every persona is an agency owner who needs what we teach, but for different reasons. One's stuck under a revenue ceiling. One's drowning in delivery and can't sell. One's profitable but has no system. Same buyer, different pain, each a different angle. The job isn't just writing ads, it's reading where the market's head is at, how aware they are of the problem and the solution, and meeting them there. Sometimes that means selling a better mechanism, sometimes it means selling an opportunity they didn't know existed. You research what makes them say yes and turn it into angles nobody's run yet. You won't edit or design, we have a team for that. You bring the angle, the copy, and the brief.

Organic, part of the same acquisition engine. Instagram organic and YouTube organic aren't a side project here, they're part of our client acquisition ecosystem, the same goal as paid, a different channel. Once you're in the creative, turning our coaching calls and winning angles into organic content and YouTube scripts is the same muscle pointed at another way to bring clients in. You'll help own that strategy and scripting too.

Coaching. You'll run a weekly group coaching call with our students, showing them what's working in our ads right now and helping them sharpen their own B2B strategy, and you'll be the one who steps in with feedback when they have questions along the way. You're not doing support and you're not on client calls. The reason you can do this is that you run this stuff yourself, you're the expert in the room.

Who you'll work with

You report to Dave and Gill, the founders. You'll work closely with both of us, this isn't a hand-off-and-disappear seat. You work alongside our editors and designers, who handle production. You don't manage clients and you don't sit in client calls. Your job is the work and the room.

Requirements

What you've done — both halves, both at a high level

Media buying:

• You've run B2B paid media at a high level, national campaigns, six figures a month in spend, hands-on, in the account making the calls.
• B2B lead gen specifically: agencies, coaching/info, or high-ticket services sold to businesses. This one really matters to us, B2B behaves nothing like e-com, and we need someone who already knows the difference.
• Deep on Meta. You read an account and know what the data is telling you without anyone translating it.

Creative:

• Direct-response copywriting is one of your strongest skills. You can write the message that makes a cold, skeptical B2B buyer pay attention, and prove it with copy that converted. VSLs, ads, book-a-call pages.
• A track record of original concepts and angles, not just variations of someone else's idea. You can name the work and what it produced.
• A genuine point of view on creative. You study the space, you know what's working right now and why, you have opinions about it, and you can brief it so the team builds what you pictured.

Both:

• You can explain why an ad works to someone less experienced without drowning them in jargon. That's the coaching test.
• Portfolio or work samples, we'd love to see the work.

Logistics

• Able to work 9am–6pm ET.
• Located in the US or Canada. Required, you work directly with our team.

Preferred (not required)

• Google Ads and YouTube Ads experience. We run Meta first, our students ask about Google, and we don't have an expert in-house. If you've done it, that counts.
• AI built into your workflow.
• Experience with organic content or growing an audience of your own.

Benefits

What you'll get

$120K–$150K OTE. Base plus performance. Full medical, dental, and vision. Paid time off. Fully remote. Direct access to the founders who've built real agencies and lived the exact path our students are on.

Benefits listed apply to US employees. Canada hires join as contractors paid in USD.

How to apply

Send your resume, a link to your portfolio or work samples, and answer these:

1. What's the most you've spent in a single account in a single month on B2B, and what did it produce?
   
2. Walk us through a winning angle you developed: the concept, why it worked, and how you knew it was the angle and not the offer or the audience.
   
3. Have you taught, trained, or coached other marketers? If so, where and what.
   

Shortlisted candidates do a paid trial project: take one of our offers and build the creative spine for it, a batch of distinct angles each speaking to a different reason an agency owner would need us, a VSL hook and opening, and a walkthrough of how you'd structure and read the account to know if you were right. We pay for your time, and it's the closest thing to the actual job you'll see in any interview.

This team is going somewhere. The only question is whether you're on it. If you're the one, you'll know it reading this. Apply, and let's find out.