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. Requirements Must-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