Remote – U.S. & Canada Only | Full-Time | OTE: $125,000–$150,000 (Base + Commission)
GOOD ENOUGH ISN’T.
Level is the digital marketing agency for brands ready to shatter yesterday’s wins.
We help high-consideration, complex businesses grow faster using a connected system of paid media, SEO, creative, web, data, and AI-powered iteration. We don’t sell “campaigns.” We sell compounding performance—built through daily optimization, relentless testing, and truth-first decision making.
We’re not hiring a Director to keep deals moving.
We’re hiring a closer who can lead executive conversations, uncover the real problem, and sell the right solution across a full performance marketing stack.
The Role
Level Agency is hiring a driven, strategic Director of Sales to lead high-value pursuits, deepen enterprise relationships, and accelerate our outbound strategy. This role is for a senior seller who thrives in complexity, owns outcomes end-to-end, and knows how to win without waiting for permission.
You will lead the charge on our most strategic opportunities—referrals, inbound, and RFPs—and help shape a modern outbound engine alongside the CRO, including oversight and partnership with our Inbound Manager and SDR functions.
Important: This role requires someone who has sold for a digital marketing agency—not just media inventory, not just ad tech, not just software. You’ve sold integrated services and know how to build confidence in a multi-discipline approach.
What You’ll Sell
Our partners hire Level because our capabilities work together—and we evolve them as platforms change. You’ll be selling a performance marketing system that includes:
- Paid Media Planning & Buying (search, social, programmatic, etc.)
- SEO + AI Search Strategy
- Performance Creative & Content (hooks, iteration, production velocity)
- Web / Landing Page Development & Conversion Optimization
- CRM, Lifecycle, and Marketing Automation
- Data Science, Measurement, and Analytics
- Strategy & Consulting for high-consideration journeys
This role is best suited for someone who has previously sold across these disciplines and can confidently represent an integrated performance marketing solution.
Your Impact
As Director of Sales, you’ll own strategy + execution for complex, high-stakes deals while shaping how Level goes to market. You will:
- Lead the end-to-end sales process for strategic, high-value deals (inbound, referrals, RFPs)
- Build relationships with C-level buyers and close transformative client engagements
- Represent Level in Tier 1 rooms—credible, composed, and persuasive in executive conversations
- Translate ambiguous business problems into clear, board-level outcomes and scoped solutions
- Quarterback internal pursuits by aligning cross-functional experts (paid, SEO, creative, web, data)
- Lead custom proposals and RFP responses with sharp positioning and strategic rigor
- Maintain a healthy pipeline and forecast with precision and truth (no vibes-based CRM)
- Drive $3–5M in new business annually with clear visibility into ROI
- Travel to key client meetings, conferences, and internal summits as needed
This Isn’t for Everyone.
We’re building something rare: a place where growth, truth, and high performance go together.
You’ll thrive here if you:
- Have carried a quota and produced real revenue selling agency services
- Can close 6–7 figure deals with multi-stakeholder buyer groups
- Can confidently sell paid media + SEO + creative + web + analytics as one system
- Run executive discovery like a pro: crisp, consultative, and high-control (in a good way)
- Know how to sell outcomes without over scoping, and hold scope without getting “commoditized”
- Use AI to move faster and sharper—researching, messaging, prospecting, and preparing
- Want to win and want your work measured
You’ll struggle here if you:
- Need layers of hierarchy to get things done
- Rely only on your network and don’t have repeatable sales craft
- Have only sold one slice (e.g., “media only” / “SEO only”) and can’t sell integrated services
- Get uncomfortable when the conversation goes technical (measurement, web, SEO, creative tradeoffs)
- Can’t command attention in executive conversations or struggle to drive next steps
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
- Exceptional client-facing communication: you can run executive meetings, guide stakeholders, and keep momentum
- Natural charisma + gravitas: you’re someone clients want to talk to and trust quickly
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
- Experience selling into Tier 1/Tier 2 orgs with multi-stakeholder buyer groups
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
You bring:
- 10+ years of B2B sales experience, including 5+ years enterprise / strategic selling
- A track record of closing $1M+ deals (ideally agency services, not just software)
- Proven performance selling into complex journeys: RFPs, referrals, long cycles, multiple stakeholders
- Deep experience selling digital marketing agency services (paid + SEO + creative + web + data)
- Strong executive presence and client-facing clarity—you can run the meeting, not just attend it
- High accountability: you own pipeline reality, forecast accuracy, and deal momentum
Preferred:
- Sandler (or similar consultative framework) familiarity
- Experience overseeing or partnering closely with SDR/outbound functions
- Experience selling into Tier 1 / Tier 2 orgs with mature procurement and stakeholder complexity
- Ability to collaborate in scoping across media, SEO, creative, web, analytics, lifecycle
AI Expectations
At Level, AI proficiency is part of the job. Your success depends on using AI to increase output, clarity, and velocity.
You are expected to:
- Use tools like ChatGPT, Perplexity, Claude to improve messaging, research, personalization, and efficiency
- Share prompts and workflows that raise the team’s standard
- Treat AI as a force multiplier—not a shortcut
- Embrace iteration: test, learn, refine, repeat
Our Core Values
- No Ego, All In — 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, depending on experience and qualifications.
Perks & Benefits:
At Level, we support our people across the U.S. and Canada with benefits designed to promote flexibility, wellbeing, and long-term growth.
- Fully remote across the U.S. & Canada, plus monthly WFH stipend and Summer Fridays
- Generous time off, including unlimited PTO (U.S.), competitive vacation (Canada), and parental/family leave options
- Comprehensive health benefits, mental health support, and company-paid disability & life coverage
- Employer retirement contributions (401(k) in the U.S., RRSP match in Canada)
- Quarterly performance reviews and career advancement opportunities
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 DEIB. Level is proud to be an Equal Opportunity Employer.
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.
Leave yesterday behind. Build tomorrow with us.