Vice President of Sales
$125k - $175k per yearCanada
- Remote job
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.
- 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.
- 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.
- 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.
- 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
- Prendre en charge l’exécution des ventes stratégiques : Diriger l’ensemble du processus de vente pour des occasions à forte valeur et grande complexité, notamment les recommandations de cadres, les prospects stratégiques, les appels d’offres et les comptes à fort potentiel.
- Conclure des mandats de services à six et sept chiffres : Naviguer de façon autonome dans des parcours d’achat complexes, créer un consensus entre plusieurs parties prenantes et conclure d’importants partenariats de services marketing sans dépendre de l’intervention de la direction.
- Diriger la découverte et la qualification : Déterminer le problème d’affaires derrière la demande, évaluer l’adéquation, clarifier les critères de décision, comprendre l’écosystème des parties prenantes et déterminer si une occasion mérite le temps et les ressources de Level.
- Vendre les lignes de services de Level : Relier les défis des clients à des solutions personnalisées en médias de performance, création, stratégie, analytique, marketing propulsé par l’IA et autres capacités connexes.
- Diriger la conception de solutions : Collaborer avec les stratèges, spécialistes de canaux, responsables de la création, analystes et membres de la direction afin d’élaborer des solutions différenciées, commercialement solides et ancrées dans les objectifs d’affaires du client.
- Prendre en charge les appels d’offres et les propositions : Diriger la stratégie, le positionnement, la coordination, la rédaction, la révision et la présentation des réponses aux appels d’offres et des propositions liées à vos comptes.
- Naviguer dans des ententes complexes : Gérer de longs cycles de vente, plusieurs décideurs et décideuses, les exigences d’approvisionnement, les contraintes budgétaires, les examens juridiques, la pression concurrentielle et les priorités internes changeantes.
- Diriger la négociation et la conclusion : Protéger la valeur, maintenir l’élan, répondre aux objections et négocier des ententes qui soutiennent des relations clients durables et fructueuses.
- Diriger les équipes internes responsables des démarches : Établir les rôles, les échéanciers, les points de décision et les prochaines étapes pour les équipes multidisciplinaires. Maintenir l’alignement des personnes contributrices et assurer la cohérence du processus sans dépendre d’une autorité formelle.
- Développer les relations de recommandation : Établir et renforcer les relations avec les partenaires de recommandation, les contacts de l’industrie, les cadres, les clients actuels et les autres sources d’occasions stratégiques.
- Diriger la stratégie de ventes sortantes : Élaborer, mettre en œuvre et optimiser des programmes de prospection par courriel, téléphone, LinkedIn, événements, comptes ciblés, partenariats et nouveaux canaux.
- Superviser les fonctions de ventes entrantes et de développement des ventes : Fournir de l’orientation, de l’accompagnement, des priorités et de la responsabilisation pour les activités de ventes entrantes et de développement des ventes.
- Améliorer l’infrastructure commerciale : Veiller à ce que Level dispose des bons processus, messages, outils, technologies, données et talents pour soutenir une fonction de vente performante.
- Prendre en charge la santé du pipeline et les prévisions : Maintenir des données exactes, évaluer la qualité des occasions, repérer les risques, produire des prévisions réalistes et donner à la haute direction une visibilité claire sur les revenus attendus.
- Collaborer avec le chef de la direction des revenus : Travailler étroitement avec le chef de la direction des revenus de Level pour façonner la stratégie de vente, préciser les marchés prioritaires, améliorer l’exécution et repérer de nouvelles occasions de croissance.
- Contribuer au-delà des responsabilités principales : Selon les besoins de l’entreprise, soutenir des événements de l’industrie, des partenariats stratégiques, l’embauche en vente, la planification de la rémunération, l’aide à la vente, le développement de l’équipe ou d’autres initiatives de revenus.
- Au moins 10 ans d’expérience en ventes B2B complexes. Vous avez bâti votre carrière en vendant des solutions sophistiquées à des organisations comptant plusieurs parties prenantes et comportant des enjeux commerciaux importants.
- Au moins 5 ans d’expérience en ventes stratégiques ou auprès de grandes entreprises. Vous comprenez les occasions à forte valeur et à cycle long et savez maintenir l’élan au fil de processus d’achat prolongés.
- Une expérience démontrée de conclusion d’ententes à six et sept chiffres. Vous pouvez fournir des exemples précis de mandats de services que vous avez personnellement trouvés, façonnés, négociés et conclus.
- Une expérience pertinente en vente de services. Vous avez vendu des services de marketing numérique, de publicité, de consultation, des services professionnels, des services technologiques, des services d’agence ou d’autres solutions de complexité comparable.
- Une expérience auprès de clients semblables à ceux de Level. Vous comprenez les acheteurs à processus réfléchi dans des secteurs comme le B2B, l’éducation, la santé, les services financiers, le commerce électronique ou d’autres industries où la confiance, l’expertise, les résultats mesurables et l’alignement des parties prenantes sont essentiels.
- Une prise en charge complète du cycle de vente. Vous avez géré des ententes de la prospection ou de la recommandation jusqu’à la qualification, la découverte, la proposition, la négociation, l’approvisionnement et la conclusion.
- De solides compétences en découverte. Vous savez aller au-delà des demandes de surface, découvrir les besoins d’affaires, évaluer l’urgence, comprendre les dynamiques décisionnelles et façonner le processus d’achat.
- Une présence auprès des cadres. Vous pouvez diriger des conversations à fort enjeu avec des membres de la haute direction, remettre les hypothèses en question de façon appropriée et établir la confiance sans faire de promesses excessives.
- Une expérience en vente de solutions personnalisées. Vous savez assembler des offres adaptées avec des spécialistes plutôt que de dépendre d’un produit fixe ou d’un forfait standard.
- Une expérience en direction d’appels d’offres et de propositions. Vous avez dirigé des propositions et des réponses complexes nécessitant du positionnement, de la coordination, de la personnalisation et de fortes aptitudes rédactionnelles.
- Un bon jugement commercial et de négociation. Vous pouvez protéger la valeur, gérer la portée, répondre aux objections et négocier des ententes avec assurance et professionnalisme.
- Du leadership par influence. Vous pouvez aligner des équipes multidisciplinaires, créer de la responsabilisation, résoudre les frictions et faire avancer les décisions sans dépendre uniquement des liens hiérarchiques.
- Une expérience en leadership commercial. Vous avez accompagné, dirigé ou géré des membres d’équipes de ventes entrantes, de ventes sortantes, de développement des ventes, de développement des affaires ou de vente.
- Une grande rigueur en gestion du pipeline et en prévisions. Vous utilisez les données et les faits liés aux occasions, plutôt que l’optimisme, pour évaluer la qualité du pipeline et prévoir les revenus.
- Une maîtrise des CRM. Vous possédez une solide expérience pratique avec HubSpot ou une plateforme comparable et maintenez des données commerciales exactes et utiles.
- Une connaissance de Sandler. Vous avez une compréhension pratique du cadre de vente Sandler et savez appliquer des principes rigoureux de qualification et de prise de décision mutuelle.
- Un baccalauréat. Vous détenez un baccalauréat en administration des affaires, en marketing, en communications ou dans un domaine connexe.
- Une expérience en agence de marketing numérique. Vous avez vendu des services comme les médias payants, la création, l’analytique, la stratégie, le marketing du cycle de vie, le référencement, le marketing de performance ou des programmes numériques intégrés.
- Une expérience en services professionnels. Vous comprenez comment vendre de l’expertise, des personnes, des processus et des résultats plutôt qu’un produit tangible.
- Une expérience avec des clients complexes. Vous avez vendu à des organisations de secteurs réglementés, à structure matricielle, dirigées par leurs fondateurs, soutenues par du capital-investissement ou évoluant dans d’autres contextes décisionnels complexes.
- Un réseau de recommandation existant. Vous entretenez des relations de confiance avec des cadres, des investisseurs, des consultants, des partenaires technologiques ou d’autres sources d’occasions stratégiques.
- Une expérience en programmes de prospection. Vous avez bâti ou amélioré de façon importante des systèmes, des messages, une segmentation, une structure d’équipe, des technologies ou des résultats de ventes sortantes.
- Une expérience en vente par comptes ciblés. Vous savez coordonner des stratégies personnalisées de prospection et de démarche auprès d’un groupe défini de comptes à forte valeur.
- Une expérience en embauche et en développement de talents commerciaux. Vous avez recruté, accompagné et évalué du personnel de vente ou de développement des affaires et avez pris des décisions relatives au rendement.
- Une bonne compréhension du marketing. Vous pouvez discuter de façon crédible des médias de performance, de la stratégie créative, de la mesure, de l’acquisition de clients, de la génération de pipeline, de la conversion et de la croissance avec les clients et les spécialistes internes.
- Utiliser des outils comme ChatGPT, Claude, Perplexity, Gemini, Midjourney et d’autres plateformes d’IA pour améliorer la recherche sur les comptes, la prospection, la préparation à la découverte, l’élaboration de propositions, l’analyse concurrentielle, le suivi des rencontres et la planification commerciale.
- Bâtir et documenter des processus assistés par l’IA qui améliorent la cohérence et l’efficacité des ventes entrantes, des ventes sortantes, de la qualification, de la conception de propositions et de la gestion du pipeline.
- Utiliser l’IA pour synthétiser l’information sur les secteurs, le contexte des entreprises, les priorités des parties prenantes, les notes d’appels, l’historique des comptes et les risques liés aux occasions.
- Expérimenter avec des messages, de la personnalisation, des réponses aux objections, des structures de propositions et des stratégies de démarche assistés par l’IA tout en conservant un solide jugement humain.
- Créer et partager des bibliothèques de requêtes, des processus de vente, des cas d’utilisation et des apprentissages que les autres membres de l’équipe peuvent adopter et améliorer.
- Évaluer de façon critique les résultats produits par l’IA et vérifier les affirmations, les constats et les recommandations avant de les utiliser dans du travail destiné aux clients.
- Adopter une approche itérative. La première requête, le premier message ou le premier processus est rarement le meilleur.
- L’IA ne remplace pas le jugement commercial, la préparation, le développement de relations ou la vente réfléchie. Elle constitue une infrastructure qui doit renforcer chacune de ces capacités.
- Télétravail complet aux États-Unis et au Canada, allocation mensuelle pour le travail à domicile et vendredis d’été
- Congés généreux, notamment des congés payés illimités aux États-Unis, des vacances concurrentielles au Canada et des options de congé parental et familial
- Régime complet d’assurance collective, soutien en santé mentale et assurance invalidité et vie payée par l’employeur
- Cotisations de l’employeur aux régimes de retraite, soit le 401(k) aux États-Unis et une contribution équivalente au REER au Canada
- Évaluations trimestrielles du rendement et possibilités d’avancement professionnel
Vacancy posted 5 hours ago
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...Job Responsibility: Job Posting : Vice President of Sales, Madero Location: Calgary, Edmonton, Saskatoon, Winnipeg (Flexible) Company: West Four Group of Companies Division: Madero West Four Group of Companies is a family-owned business, proudly comprising...Permanent employmentFull timeRelocationRelocation packageMonday to fridayFlexible hours- ...hardware-focused business into a recurring revenue SaaS-driven organization. To support this next chapter, Prosaris is seeking a Vice President, Sales to lead commercial growth and build a scalable sales function. The Role Reporting to the CEO, the Vice...Long term contractInternshipRemote workFlexible hours
- ...Responsibility: TandemLaunch is currently looking for a VP of Technical Sales for one of our portfolio companies specializing in hardware... ...continue to grow, they are seeking a passionate and driven Vice President of Technical Sales to join their team. We are looking for a...Full timeContract work
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