Vice President of Sales

About the role

This role reports directly to the Chief Revenue Officer. This isn't 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.

Responsibilities

• 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

• Protect Value, Maintain Momentum, Resolve Objections, and Negotiate Agreements: 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

• Develop and Strengthen Relationships: Develop and strengthen relationships with referral partners, industry contacts, executives, current clients, and other sources of high-value opportunities

• Develop and Implement Outbound Programs: 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

• Maintain 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

Qualifications

• 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 have sold digital marketing, advertising, consulting, professional services, technology-enabled services, agency services, or similarly complex solutions

• 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

• You have full-cycle sales ownership

• You have managed deals from prospecting or referral through qualification, discovery, proposal, negotiation, procurement, and close

• You have 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

• You have executive presence

• You can lead high-stakes conversations with senior executives, challenge assumptions appropriately, and build trust without overpromising

• You have customized solution selling experience

• You have led complex proposals and RFP responses that required positioning, coordination, customization, and strong written communication

• You have commercial and negotiation judgment

• You can protect value, manage scope, work through objections, and negotiate agreements with confidence and professionalism

• You have leadership through influence

• You can align cross-functional teams, create accountability, resolve friction, and drive decisions without relying solely on reporting lines

• You have CRM fluency

• You have strong working experience with HubSpot or a comparable CRM and consistently maintain accurate, useful sales data

• You have Sandler knowledge

• You have a working understanding of the Sandler Sales framework and can apply disciplined qualification and mutual decision-making principles

• You have a bachelor's degree in Business, Marketing, Communications, or a related field

Skills

• Digital marketing agency experience

• Professional services experience

• Complex client types experience

• Account-based sales experience

• Experience hiring and developing sales talent

• Outbound program experience

• Pipeline and forecasting discipline

• CRM fluency

• Sandler knowledge

Benefits

Level is 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.

Pay

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

Schedule

Remote - U.S. & Canada Only