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

Jesta I.S.•Montreal, QC

117d•Hybrid

About The Position

The Senior Director of Sales is responsible for driving revenue growth and expanding Jesta’s footprint within the retail technology sector. This role leads the Sales organization and works closely with Marketing and other cross-functional partners to ensure cohesive, data‑driven go‑to‑market 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.

Requirements

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.
Strong business and financial acumen, including understanding of SaaS revenue models (subscription models, CAC, CLTV, onboarding cycles).
Expertise in CRM platforms (e.g., HubSpot or 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.
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 is required for international collaboration and global client engagement.

Nice To Haves

MBA or relevant Master’s degree preferred

Responsibilities

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.
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.
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.
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.
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.
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.
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.