Vice president of sales

This job posting is available in English and Canadian French. Please scroll down for the French version.

Cette offre d’emploi est disponible en anglais et en français (Canada). Veuillez faire défiler pour la version française.

Remote - U.S. & Canada Only | Full-Time

Compensation:

OTE $125,000 - $175,000 USD/CAD (Salary + Commission)

We’re Not Looking for Someone to Manage the Pipeline. We’re Looking for a Closer Who Can Shape It.

Level Agency is hiring a Vice President of Sales to lead complex pursuits, win high-value accounts, and build the sales systems that fuel our next stage of growth.

This is not a role for someone who needs a C-level executive to step in when the deal gets complicated. This is for a proven seller who can earn trust with senior decision-makers, lead a six- or seven-figure opportunity from first conversation through signed agreement, and coordinate the internal team required to win.

You’ll take ownership of Level’s most strategic opportunities, including executive referrals, high-potential prospects, RFPs, and “house accounts” that have traditionally gone directly to senior leadership. You’ll also oversee our inbound and SDR functions and shape our outbound strategy in partnership with the CRO.

You’ll sell sophisticated, customized marketing services to organizations with complex goals, multiple stakeholders, and high expectations. That means understanding the client’s business, asking better questions, assembling the right solution, navigating procurement and internal politics, and creating enough confidence for the buyer to move forward.

Success in this role means Level is consistently winning the right clients, our pipeline is healthy and credible, our sales team is operating with focus, and executives no longer need to quarterback every major opportunity.

This role reports directly to the Chief Revenue Officer.

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 have personally closed six- and seven-figure B2B services engagements.
• You know how to sell complex, customized solutions—not just software licenses or standardized packages.
• You understand how buyers in industries such as B2B, education, healthcare, financial services, ecommerce, and other considered-purchase categories make decisions.
• You can build credibility with executives, uncover the real business problem, and connect Level’s capabilities to outcomes that matter.
• You are comfortable owning the entire sales process, including qualification, discovery, solution development, proposals, negotiation, procurement, and close.
• You can lead internal teams through influence, create clarity, and keep a pursuit moving without formal authority over every contributor.
• You know how to balance hands-on selling with sales leadership, pipeline strategy, forecasting, coaching, and process improvement.
• You use data, technology, and AI to improve how you research accounts, prepare for meetings, develop solutions, and move opportunities forward.

And you’ll struggle here if:

• Your largest wins depended on an executive stepping in to lead the strategy, pitch, or negotiation.
• Your experience is limited to transactional sales, short sales cycles, or highly standardized products.
• You confuse a large pipeline with a strong pipeline.
• You avoid difficult qualification decisions or keep weak opportunities alive to protect your forecast.
• You rely on charisma without disciplined discovery, preparation, follow-through, and commercial judgment.
• You need direct authority to align people and move work forward.
• You are more interested in managing sellers than personally winning business.
• You treat AI as a novelty rather than a practical tool for improving sales performance.

About Level

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 B2B, education, healthcare, financial services, ecommerce, and more.

Your Role (and Impact)

As Vice President of Sales, you’ll own Level’s most strategic and complex revenue opportunities while helping lead the systems, people, and processes behind our broader sales function.

You’ll serve as the primary point of contact for high-stakes pursuits and lead the full sales process from qualification through negotiation and close. You’ll also oversee inbound and outbound functions, manage our Inbound Manager and SDR resources, and partner with the CRO to develop a modern, high-impact outbound strategy.

You’ll:

• Own Strategic Sales Execution: Lead the end-to-end sales process for high-value, high-complexity opportunities, including executive referrals, strategic prospects, RFPs, and high-potential accounts.
• Close Six- and Seven-Figure Services Engagements: Independently navigate complex buyer journeys, build consensus among multiple stakeholders, and close significant marketing services partnerships without relying on executive intervention.
• Lead Discovery and Qualification: Identify the business problem behind the request, assess fit, clarify decision criteria, understand the stakeholder landscape, and determine whether an opportunity deserves Level’s time and resources.
• Sell Level’s Service Lines: Connect client challenges to tailored solutions across performance media, creative, strategy, analytics, AI-enabled marketing, and related capabilities.
• Lead Solution Engineering: Partner with strategists, channel experts, creative leaders, analysts, and executives to develop solutions that are differentiated, commercially sound, and grounded in the client’s business goals.
• Own RFP and Proposal Development: Lead the strategy, positioning, coordination, writing, review, and delivery of RFP responses and proposals across your accounts.
• Navigate Complex Deals: Manage long sales cycles, multiple decision-makers, procurement requirements, budget constraints, legal reviews, competitive pressure, and shifting internal priorities.
• Lead Negotiation and Closing: Protect value, maintain momentum, resolve objections, and negotiate agreements that support successful, sustainable client relationships.
• Quarterback Internal Pursuit Teams: Establish roles, timelines, decision points, and next steps across cross-functional teams. Keep contributors aligned and hold the process together without depending on formal authority.
• Build Referral Relationships: Develop and strengthen relationships with referral partners, industry contacts, executives, current clients, and other sources of high-value opportunities.
• Lead Outbound Strategy: Develop, implement, and optimize outbound programs across email, calls, LinkedIn, events, account-based outreach, partnerships, and emerging channels.
• Oversee Inbound and SDR Functions: Provide direction, coaching, prioritization, and accountability across inbound and sales development activities.
• Improve Sales Infrastructure: Ensure Level has the right processes, messaging, tools, technology, data, and talent to support a high-performing sales function.
• Own Pipeline Health and Forecasting: Maintain accurate opportunity data, inspect deal quality, identify risk, create realistic forecasts, and provide senior leadership with clear visibility into expected revenue.
• Partner with the CRO: Work closely with Level’s Chief Revenue Officer to shape sales strategy, refine market focus, improve sales execution, and identify new growth opportunities.
• Contribute Beyond the Core: Depending on business needs, you may support industry events, strategic partnerships, sales hiring, compensation planning, enablement, team development, or other revenue initiatives.

Travel is required and may include client meetings, company events, pitches, conferences, and industry events. Occasional evening or weekend work may be required based on deal activity and business needs.

RequirementsMust-Haves

• 10+ years of complex B2B sales experience. You have built a career selling sophisticated solutions to organizations with multiple stakeholders and meaningful commercial risk.
• At least 5 years in enterprise or strategic sales. You understand long-cycle, high-value opportunities and know how to maintain momentum across extended buying processes.
• Proven six- and seven-figure closing experience. You can point to specific services engagements you personally sourced, shaped, negotiated, and closed.
• Relevant services sales experience. You have sold digital marketing, advertising, consulting, professional services, technology-enabled services, agency services, or similarly complex solutions.
• Experience selling to Level-like clients. You understand considered buyers in markets such as B2B, education, healthcare, financial services, ecommerce, or other industries where trust, expertise, measurable outcomes, and stakeholder alignment matter.
• Full-cycle sales ownership. You have managed deals from prospecting or referral through qualification, discovery, proposal, negotiation, procurement, and close.
• Strong discovery skills. You know how to move beyond surface-level requests, uncover business needs, evaluate urgency, identify decision dynamics, and shape the buying process.
• Executive presence. You can lead high-stakes conversations with senior executives, challenge assumptions appropriately, and build trust without overpromising.
• Customized solution selling experience. You know how to assemble tailored offerings with subject matter experts rather than relying on a fixed product or standard package.
• RFP and proposal leadership. You have led complex proposals and RFP responses that required positioning, coordination, customization, and strong written communication.
• Commercial and negotiation judgment. You can protect value, manage scope, work through objections, and negotiate agreements with confidence and professionalism.
• Leadership through influence. You can align cross-functional teams, create accountability, resolve friction, and drive decisions without relying solely on reporting lines.
• Sales leadership experience. You have experience coaching, directing, or managing inbound, outbound, SDR, business development, or sales team members.
• Pipeline and forecasting discipline. You use data and deal evidence—not optimism—to evaluate pipeline quality and forecast revenue.
• CRM fluency. You have strong working experience with HubSpot or a comparable CRM and consistently maintain accurate, useful sales data.
• Sandler knowledge. You have a working understanding of the Sandler Sales framework and can apply disciplined qualification and mutual decision-making principles.
• Bachelor’s degree. You hold a bachelor’s degree in Business, Marketing, Communications, or a related field.

Strong Preferences

• Digital marketing agency experience. You have sold services such as paid media, creative, analytics, strategy, lifecycle marketing, SEO, performance marketing, or integrated digital programs.
• Professional services experience. You understand how to sell expertise, people, process, and outcomes rather than a tangible product.
• Experience with complex client types. You have sold into regulated industries, matrixed organizations, founder-led companies, private equity-backed businesses, or other environments with complex decision structures.
• Existing referral network. You have trusted relationships with executives, investors, consultants, technology partners, or other sources of strategic opportunities.
• Outbound program experience. You have built or materially improved outbound systems, messaging, segmentation, team structure, technology, or performance.
• Account-based sales experience. You know how to coordinate personalized outreach and pursuit strategies across a defined set of high-value accounts.
• Experience hiring and developing sales talent. You have recruited, coached, evaluated, and made performance decisions involving sales or business development staff.
• Marketing fluency. You can credibly discuss performance media, creative strategy, measurement, customer acquisition, pipeline generation, conversion, and business growth with both clients and internal specialists.

AI Expectations

At Level, AI is a skillset—not a shortcut. In this role, AI fluency is not optional. You’ll be expected to use AI to improve the quality, speed, rigor, and leverage of how you sell.

You’ll be expected to:

• Use tools like ChatGPT, Claude, Perplexity, Gemini, Midjourney, and other AI platforms to improve account research, prospecting, discovery preparation, proposal development, competitive analysis, meeting follow-up, and sales planning.
• Build and document AI-assisted workflows that improve consistency and effectiveness across inbound, outbound, qualification, proposal development, and pipeline management.
• Use AI to synthesize industry information, company context, stakeholder priorities, call notes, account history, and opportunity risks.
• Experiment with AI-supported messaging, personalization, objection preparation, proposal structures, and pursuit strategies while maintaining strong human judgment.
• Create and share prompt libraries, sales workflows, use cases, and lessons that other team members can adopt and improve.
• Evaluate AI outputs critically and verify claims, insights, and recommendations before using them in client-facing work.
• Approach AI with an iterative mindset. The first prompt, message, or workflow is rarely the best one.
• AI is not a replacement for commercial judgment, preparation, relationship-building, or thoughtful selling. It is infrastructure that should make each of those capabilities stronger.

Our Core Values

• No Ego, All In: We don’t do “that’s not my job.” We win together, step in where needed, and care more about the outcome than the org chart.
• Better Every Day: We want the feedback—even when it stings. We test, learn, adapt, and keep raising the bar.
• Relentless for Results: Activity is nothing without outcomes. We care about the work that moves the business forward.
• Driven by Truth: We challenge assumptions, follow the data, and tell clients what they need to hear—not just what is easy to say.

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 role is open to U.S. and Canada residents and is fully remote. Travel is required and may include client meetings, company events, pitches, conferences, and industry events. Occasional evening or weekend work may be required based on deal activity and business needs.

We are unable to sponsor visas at this time.

Level Is Built on Inclusion

We are committed to diversity, equity, inclusion, and belonging. Level is proud to be an Equal Opportunity Employer—we celebrate what makes you, you.

Level Agency provides reasonable accommodations to applicants with disabilities during the recruitment process. If you require an accommodation, please let us know during your application or interview process.

Ready to Apply?

Click below to submit your resume. You’ll also answer a few thoughtful questions, so take your time.

We are looking for evidence—not sales theater. Tell us what you sold, who you sold it to, how you shaped the opportunity, and what you personally did to get the deal across the line.

We care more about your ability to build trust, navigate complexity, and close the right business than whether your career path has been perfectly linear.

Let’s build something together.

We use AI-assisted tools to support parts of our hiring process, including resume screening and interview note-taking or summarization. These tools support, but do not replace, human judgment. All hiring decisions are made by Level’s hiring team.