We’re Hiring: Digital Strategist – Hybrid | Build, Lead, Grow with OMG

Build your book. Lead the team. Shape the future.

Location: Hybrid (East Coast preferred, near any OMG market and/or Colorado)
Type: Full-Time
Reports to: VP of Digital, Joe Paul

This is a front-row, hands-on growth role.

This is your chance to own a national client list, train local sales teams, and help lead a fast-growing digital agency that actually does things differently.

We’re O’Rourke Media Group — a family-owned, bootstrapped company that's been shaking up local media since 2018. We started with a few newspapers. Today we operate in eight states, 40 markets, run 58 hyper-local publications, and have built a full-service digital agency that’s delivering real results for over 15,000 businesses annually.

Now, we’re looking for someone who’s part closer, part coach, and fully obsessed with helping local businesses grow.

What You’ll Actually Do Here

Build and manage your own book of digital clients across the U.S.

Prospect for new business — actively identify, research, and pitch ideal client opportunities

Jump into sales meetings with our reps and help them close bigger, better deals

Join client meetings to help close new and incremental opportunities

Develop and pitch full-funnel campaigns across Google, Facebook, YouTube, CTV, and Programmatic

Sell not only digital, but our owned and operated print and local audiences — a differentiator few can match

Collaborate with the VP of Digital to grow our agency playbook

Deliver post-sale support and ensure long-term campaign success and client retention

Travel when needed to get face time with clients or support sales teams

What You Bring

Required:

You’ve sold digital before — and you’re good at it

Strong knowledge of paid digital platforms: Google, Meta, YouTube, CTV, Programmatic

Tools like GA4, SEMrush, and Facebook Ads Manager aren’t intimidating

Confident in prospecting, presenting, and closing digital campaigns

You like coaching others, and you don’t need your hand held

Bachelor's degree or equivalent experience

Preferred:

5+ years in digital or agency-side sales

Google and Meta certifications

Experience helping scale a local/regional digital agency

You’ve got ideas. You’ve got leadership chops. You want to shape something bigger

Why We’re Different

We’re not backed by private equity or a big holding company.

We don’t chase awards — we chase results.

We care about the people we hire, and we’re in this for the long game.

If you want a predictable 9-to-5 where you’re just selling what’s in a deck — this isn’t it.
But if you want to help build something, drive your own growth, and make a serious impact?
This is your shot.

What You Get

Write your own check – competitive base + commission with unlimited upside

Full benefits: medical, dental, vision, PTO, 401(k) with match

Hybrid flexibility – East Coast or Colorado preferred, near any of our OMG markets

Freedom to lead and room to grow – we promote from within

A team that cares about your ideas, your goals, and your success

To apply, send your resume to Caleb Anderson at canderson@orourkemediagroup.com.
Let’s build something great.

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