Remote - U.S. & Canada Only | Full-Time | OTE: $125,000-$150,000 USD (Base + Commission)

We're not hiring a Director to keep things moving. We're hiring a closer to change the game.

Level Agency is hiring a driven, strategic Director of Sales to lead high-value pursuits, deepen enterprise relationships, and accelerate our outbound strategy. This is a rare role for a senior seller who thrives on complexity, owns outcomes, and knows how to drive impact without waiting for permission.

You'll lead the charge on our most strategic accounts-referrals, RFPs, and high-value opportunities that demand precision, poise, and big-picture thinking. You'll also shape and scale a modern outbound engine-overseeing our Inbound Manager and SDR functions, and partnering with the CRO to expand into new markets with precision.

This Isn't for Everyone. We're building something rare: a place where growth, truth, and high performance go hand-in-hand.

You'll thrive here if:

You can close 6-7 figure deals without a net

You lead through influence, not authority

You think in strategies, not scripts

You've carried a quota and delivered real revenue

You're hungry-in the right stage of your career and ready to win

And you'll struggle here if:

You need layers of hierarchy to get things done

You're uncomfortable with executive visibility and ownership

You rely solely on a network, not sales craft

About Level Agency

We're an AI-powered performance marketing agency-built for precision, designed to scale, and powered by a scientific mindset. At Level, we blend strategy, media, creative, and machine intelligence to deliver outcomes that matter. Every time. At scale.

We've been named one of Pittsburgh's Best Places to Work and an Inc. 500 Fastest-Growing Company. Our clients span ecommerce, B2B, education, healthcare, and beyond. And our team? Fully remote, deeply collaborative, and relentlessly driven.

Your Role (and Impact)

As Director of Sales, you'll be at the forefront of our most critical growth efforts. You'll own the strategy and execution of our complex, high-stakes deals while shaping how Level goes to market through outbound and inbound channels. You will:

Lead the end-to-end sales process for strategic, high-value deals (referrals, RFPs, inbound)

Build deep relationships with C-level buyers and close transformative client engagements

Shape and scale a high-performing outbound function with the Inbound Manager and SDRs

Drive $3-5M in new business annually, with a clear line of sight to ROI

Operate with executive visibility and autonomy, collaborating directly with the CRO and senior leaders

Serve as the quarterback for internal sales pursuits, aligning cross-functional teams

Lead custom proposal efforts and RFP responses with clarity and strategic rigor

Engineer bespoke marketing solutions in collaboration with subject matter experts

Maintain a healthy, accurate pipeline and forecast with precision

Travel to client meetings, key conferences, and internal summits as needed

Requirements

You Bring:

10+ years of B2B sales experience, with 5+ years in enterprise or strategic selling

Track record of closing $1M+ deals without support

Fluent in high-stakes selling: RFPs, referrals, complex buyer journeys

Expertise in selling agency services (not just media or ad tech)

Hunger, presence, and polish to lead in the room-not just join it

Preferred Experience:

Familiarity with the Sandler Sales framework (or similar consultative methods)

Experience with CRM or creative services in addition to media

Prior oversight of SDR or outbound teams

AI Expectations

At Level, proficiency with AI tools is a core part of your role-not a nice-to-have. Your success in this position depends not only on your functional expertise, but also on your ability to actively integrate AI into how you work.

You are expected to:

Continuously experiment with tools like ChatGPT, Perplexity, and Claude to improve messaging, outreach, and efficiency

Share prompts, learnings, and workflows to elevate the broader team

Treat AI as a force multiplier for creativity and clarity, not a crutch

Embrace discomfort and iteration as you refine how AI supports your sales approach

Our Core Values

No Ego, All In

We don't do "that's not my job." We win together.

Better Every Day

We want the feedback-even when it stings.

Relentless for Results

Activity is nothing without outcomes.

Driven by Truth

We challenge assumptions and follow the data.

Benefits

Base salary + commission with On-Target Earnings (OTE) of $125,000-$150,000 USD depending on experience and qualifications.

Perks & Benefits:

Remote work from anywhere in the U.S.

Unlimited PTO to rest, recharge, and do your best work

12 weeks Paid Parental Leave

8 weeks Paid Family Leave

12 Paid Holidays + 2 Floating Holidays

Summer Fridays

Competitive Medical Plan Options

100% Employer-Paid Vision & Dental Insurance

Pet Insurance

401(k) with 3% Employer Contribution (100% vested)

Biannual Performance Reviews

Career Advancement Opportunities

Medical Travel Reimbursement

$100 Monthly WFH Stipend (paid quarterly)

In-Person & Virtual Company Events

Peer-to-Peer Recognition Programs

Concierge Support Services

Employee Assistance Program (EAP)

Remote-First

This is a remote role open to candidates located within the U.S & Canada. We are unable to sponsor visas at this time.

Level Is Built on Inclusion

We are committed to Diversity, Equity, Inclusion, and Belonging (DEIB). Level is proud to be an Equal Opportunity Employer. We prohibit discrimination and harassment of any kind and celebrate what makes you, you-regardless of race, gender identity, age, disability status, sexual orientation, or background.

Ready to Apply?

Click below and submit your resume. You'll also be asked a few thoughtful questions-take your time. We care more about your thinking than your pedigree.

Let's build something together.

Level.Agency

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