Vice President of Sales

Level Agency

21d • $125,000 - $175,000 • Remote

About The Position

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.

Requirements

• 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.
• 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.

Nice To Haves

• 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.

Responsibilities

• Lead the end-to-end sales process for high-value, high-complexity opportunities, including executive referrals, strategic prospects, RFPs, and high-potential accounts.
• Independently navigate complex buyer journeys, build consensus among multiple stakeholders, and close significant marketing services partnerships without relying on executive intervention.
• 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.
• Connect client challenges to tailored solutions across performance media, creative, strategy, analytics, AI-enabled marketing, and related capabilities.
• 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.
• Lead the strategy, positioning, coordination, writing, review, and delivery of RFP responses and proposals across your accounts.
• Manage long sales cycles, multiple decision-makers, procurement requirements, budget constraints, legal reviews, competitive pressure, and shifting internal priorities.
• Protect value, maintain momentum, resolve objections, and negotiate agreements that support successful, sustainable client relationships.
• 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.
• Develop and strengthen relationships with referral partners, industry contacts, executives, current clients, and other sources of high-value opportunities.
• Develop, implement, and optimize outbound programs across email, calls, LinkedIn, events, account-based outreach, partnerships, and emerging channels.
• Provide direction, coaching, prioritization, and accountability across inbound and sales development activities.
• Ensure Level has the right processes, messaging, tools, technology, data, and talent to support a high-performing sales function.
• Maintain accurate opportunity data, inspect deal quality, identify risk, create realistic forecasts, and provide senior leadership with clear visibility into expected revenue.
• Work closely with Level’s Chief Revenue Officer to shape sales strategy, refine market focus, improve sales execution, and identify new growth opportunities.
• Depending on business needs, you may support industry events, strategic partnerships, sales hiring, compensation planning, enablement, team development, or other revenue initiatives.

Benefits

• Monthly WFH stipend
• Summer Fridays
• Generous time off, including unlimited PTO (U.S.), competitive vacation (Canada), and parental/family leave options
• Comprehensive health benefits
• Mental health support
• Company-paid disability & life coverage
• Employer retirement contributions (401(k) in the U.S., RRSP match in Canada)
• Quarterly performance reviews
• Career advancement opportunities

What This Job Offers

• Job Type: Full-time
• Career Level: Senior