Director of Sales

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

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. 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.