Senior Director of Sales | Directeur(trice) principal(e) des ventes

Job Description

Job DescriptionSalary:

Company Overview
Jesta I.S. is a leading supplier of ERP software for the apparel, footwear, and soft-goods industries. Our global client base includes many recognizable brands and continues to grow. We are seeking a Senior Director of Salesto join our Sales team in Montreal.

Position Summary

The Senior Director of Salesis responsible fordriving revenue growth and expandingJestasfootprint within the retail technology sector. This role leads the Sales organization and works closely with Marketing and other cross-functional partners to ensure cohesive, datadriven gotomarket execution. The Senior Director develops and implements strategic sales initiatives grounded in industry insights, customer needs, and retail trends. The ideal candidate brings over 10 years of progressive leadership experience in B2B enterprise sales, ideally within retail technology, SaaS, apparel, footwear, or related environments, combined with strong business acumen and a deep understanding of retail operations.

Responsibilities

Sales Strategy, Revenue Growth & New Logo Acquisition

• Develop and execute a comprehensive enterprise sales strategy to achieve revenue targets, expand market share, and drive net-new customer acquisition.
• Own the new logo strategy by defining priority segments, target accounts, and structured pursuit plans aligned with long-cycle enterprise sales cycles.
• Lead end-to-end enterprise pursuits, including discovery, executive alignment, value articulation, negotiations, and closing.
• Build and manage a disciplined, data-driven pipeline using CRM and analytics tools.
• Lead, coach, and scale a high-performing Sales team to exceed objectives.

Channel Partnerships & Ecosystem Expansion

• Develop and execute a partnership strategy across system integrators, consultancies, ISVs, and cloud/channel partners to generate qualified pipeline.
• Establish partner enablement frameworks including co-selling, joint positioning, referrals, and deal registration processes.
• Build strong executive and field-level partner relationships to position Jesta as a preferred platform.
• Expand strategic partnerships across North America, Europe, Asia, and other global markets, representing the company at key industry events.

Go-to-Market Alignment

• Partner with Marketing to align demand generation, messaging, and brand positioning with sales objectives.
• Contribute customer insights to value propositions and campaign strategies.
• Support product launches, events, digital programs, and thought-leadership initiatives that grow pipeline.

Channel Partnerships & Global Expansion

• Develop and expand strategic partnerships across North America, Europe, Asia, and other key markets.
• Lead partner enablement programs, co-selling initiatives, and joint go-to-market strategies.
• Represent the company at industry events, trade shows, and partner summits.

Market Intelligence & Competitive Strategy

• Lead market analysis and interpret industry trends to inform sales priorities.
• Collaborate with Product and Marketing on segmentation, pricing, and positioning.
• Influence product direction based on customer and competitive insights.
• Evaluate international expansion opportunities.

Sales Analytics, Forecasting & Budget Management

• Establish KPIs related to revenue growth, pipeline health, customer acquisition, and regional performance.
• Lead forecasting processes, analyzing enterprise sales cycles, renewal trends, and conversion metrics.
• Manage departmental budgets and resource allocation.
• Present performance updates and strategic recommendations to the executive team.
• Align sales execution with SaaS financial metrics such as CAC, CLTV, subscription models, and onboarding cycles.

Cross-Functional Leadership

• Collaborate with Product, Marketing, Operations, and Customer Success teams.
• Provide structured customer feedback to support product and service improvements.
• Promote alignment across departments to ensure cohesive customer engagement.

Qualifications

Education

• Bachelors degree in Business or a related field required. (MBA or relevant Masters degree preferred)

Experience

• Minimum 10 years of progressive leadership experience in enterprise B2B sales.
• Proven track record of driving revenue growth and expanding market share in complex enterprise environments.
• Experience in retail technology, enterprise SaaS, retail, wholesale, fashion, apparel, or related industries.
• Experience managing multi-region or global sales operations.
• Experience managing complex, cross-regional B2B enterprise sales cycles.

Business & Technical Expertise

• Strong business and financial acumen, including understanding of SaaS revenue models (subscription models, CAC, CLTV, onboarding cycles).
• Expertise in CRM platforms (e.g., HubSpotor equivalent), sales enablement tools, and analytics dashboards.
• Strong capabilities in pipeline management, forecasting, territory planning, and enterprise account strategy.
• Data-driven decision-maker with strong analytical abilities.

Leadership & Communication

• Demonstrated ability to lead, coach, and scale high-performing sales teams.
• Excellent communication, negotiation, and executive presentation skills.
• Proven ability to collaborate cross-functionally with Marketing, Product, Operations, and Customer Success teams.
• English proficiency (spoken and written): Required due to regular communication and negotiations with clients and partners in the United States and international markets.

Benefits

• Health coverage (medical, dental, disability, and life insurance)
• Wellness program (gym membership reimbursement)
• Professional growth (training platforms, career development fee subsidy, etc.)
• Company events
• Referral program
• Flexible schedule

Additional Information

• This is a hybrid role, 2 days working in the office in Montreal, QC is required. (remote work mode could be considered for exceptional candidates)
• We thank all applicants for their interest. However, only shortlisted candidates will be contacted.

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Prsentation de lentreprise

Jesta I.S. est un fournisseur de premier plan de logiciels ERP pour les industries de lhabillement, de la chaussure et des biens de consommation. Notre clientle mondiale comprend de nombreuses marques reconnues et ne cesse de crotre. Nous recherchons une Directeurtrice principale des ventes pour joindre lquipe Ventes Montral.

Rsum du poste

Lela Directeurtrice principale des ventes aura la responsabilit de stimuler la croissance des revenus et dlargir la prsence de Jesta dans le secteur des technologies pour le commerce de dtail. Ce rle dirige lorganisation des ventes et collabore troitement avec le Marketing et dautres partenaires interfonctionnels afin dassurer une excution cohrente et axe sur les donnes. Lela titulaire labore et met en uvre des initiatives stratgiques de vente fondes sur les connaissances sectorielles, les besoins clients et les tendances du commerce au dtail. Lela candidate idale possde plus de dix (10) ans dexprience progressive en leadership dans la vente B2B denvergure, de prfrence en technologies de dtail, SaaS, habillement, chaussure ou secteurs connexes, ainsi quune solide acuit commerciale et une comprhension approfondie des oprations de dtail.

Responsabilits

Stratgie commerciale, croissance des revenus et acquisition de nouveaux clients

• Dvelopper et excuter une stratgie de vente enterprise complte pour atteindre les objectifs de revenus, accrotre la part de march et gnrer des clients new logo .
• Prendre en charge la stratgie new logo : dfinir les segments prioritaires, comptes cibles et plans de poursuite structurs adapts aux cycles longs de vente enterprise.
• Mener les dmarches commerciales de bout en bout : dcouverte, alignement excutif, articulation de la valeur, ngociation et clture.
• Construire et grer un pipeline disciplin et ax sur les donnes laide dun CRM et doutils analytiques.
• Diriger, coacher et faire crotre une quipe de ventes performante pour dpasser les objectifs.

Partenariats canaux et expansion de lcosystme

• Concevoir et excuter une stratgie de partenariats (intgrateurs systme, cabinets-conseils, ISV, partenaires cloud/canal) pour gnrer un pipeline qualifi.
• tablir des cadres dactivation partenaires incluant co-vente, positionnement conjoint, rfrencements et enregistrement des transactions.
• Dvelopper des relations de confiance aux niveaux excutif et terrain pour positionner Jesta comme plateforme de choix.
• tendre les partenariats stratgiques travers lAmrique du Nord, lEurope, lAsie et dautres marchs globaux; reprsenter lentreprise lors dvnements sectoriels cls.

Alignement go-to-market

• Collaborer avec Marketing pour aligner la gnration de demande, les messages et le positionnement de la marque aux objectifs de vente.
• Apporter des insights clients pour enrichir les propositions de valeur et les campagnes.
• Soutenir les lancements produits, vnements, programmes numriques et initiatives de thought leadership qui alimentent le pipeline.

Intelligence de march et stratgie concurrentielle

• Piloter lanalyse de march et interprter les tendances pour orienter les priorits commerciales.
• Collaborer avec Produit et Marketing sur la segmentation, la tarification et le positionnement.
• Influencer lorientation produit partir des retours clients et des analyses concurrentielles.
• valuer les opportunits dexpansion internationale.

Analytique des ventes, prvisions et gestion budgtaire

• Dfinir les KPI lis la croissance des revenus, la sant du pipeline, lacquisition client et la performance rgionale.
• Piloter les processus de prvision, en analysant les cycles de vente enterprise, les tendances de renouvellement et les mtriques de conversion.
• Grer les budgets dpartementaux et lallocation des ressources.
• Prsenter les rsultats et recommandations stratgiques lquipe de direction.
• Aligner lexcution commerciale avec les mtriques financires SaaS (CAC, CLTV, modles dabonnement, cycles donboarding).

Leadership interfonctionnel

• Travailler en collaboration avec Produit, Marketing, Oprations et Customer Success.
• Fournir des retours clients structurs pour amliorer produits et services.
• Favoriser lalignement entre les dpartements pour assurer une exprience client cohrente.

Qualifications

Formation

• Baccalaurat en administration ou domaine connexe requis. (MBA ou matrise pertinente souhaite.)

Exprience

• Minimum dix (10) ans dexprience en leadership progressif en ventes B2B enterprise.
• Antcdents probants en croissance de revenus et en expansion de parts de march dans des environnements complexes.
• Exprience souhaite dans les technologies de dtail, SaaS, commerce de dtail/commerce de gros, mode, habillement ou secteurs lis.
• Exprience en gestion dquipes commerciales multi-rgionales ou internationales.
• Exprience dans la gestion de cycles de vente B2B enterprise complexes.

Comptences commerciales et techniques

• Solide acuit daffaires et financire, notamment comprhension des modles de revenus SaaS (abonnements, CAC, CLTV, cycles donboarding).
• Matrise de plateformes CRM (p. ex. HubSpot ou quivalent), outils dactivation commerciale et tableaux de bord analytiques.
• Comptences dmontres en gestion de pipeline, prvision, planification territoriale et stratgie de comptes enterprise.
• Prise de dcision base sur les donnes et fortes capacits analytiques.

Leadership et communication

• Aptitude dmontre diriger, coacher et dvelopper des quipes de vente performantes.
• Excellentes comptences en communication, ngociation et prsentations excutives.
• Capacit avre collaborer efficacement avec Marketing, Produit, Oprations et Customer Success.
• Connaissance de langlais (oral et crit) : requise en raison dchanges et de ngociations rguliers avec des clients et partenaires aux tats-Unis et sur des marchs internationaux.

Avantages

• Couverture sant (assurance mdicale, dentaire, invalidit et vie)
• Programme bien-tre (remboursement abonnement gym)
• Dveloppement professionnel (plateformes de formation, subvention frais de perfectionnement, etc.)
• vnements dentreprise
• Programme de recommandation
• Horaire flexible

Informations supplmentaires

• Ce poste est hybride : 2 jours par semaine au bureau Montral sont requis (un mode travail distance pourra tre considr pour des candidates exceptionnelles).
• Nous remercions toutes les personnes candidates pour leur intrt; seules les personnes slectionnes pour une entrevue seront contactes.