Named Account Executive

Leadout Capital; Florida; Sur place; USD 150 000 - 190 000; Plein temps

Résumé du poste

Leadout Capital is seeking a Senior Enterprise Account Executive to lead Named Accounts in Puerto Rico, the Dominican Republic, and the Caribbean. You will manage senior client relationships, drive complex digital transformations, and cross-sell cloud solutions across top banks andConsumer goods players.

The ideal candidate has 10+ years of enterprise software sales, a native Puerto Rico network, and a proven history closing multi-million dollar deals while fluently operating in English and

Qualifications

• 10+ years of direct software/SaaS enterprise sales experience.
• Deep Puerto Rico territory knowledge.
• Native-level network in Puerto Rico's corporate landscape.
• Experience selling into Puerto Rican banking sector and major CPGs.
• Expertise in Challenger, Value Selling, Solution Selling.
• Quota overachievement of $2M+ annual targets.
• Fluency in English and Spanish (written and verbal).

Responsabilités

• Lead multi-year growth strategy across Named Accounts in Puerto Rico, DR, and Caribbean.
• Penetrate existing base, cross-sell cloud solutions, capture market share from competitors.
• Manage C-suite relationships with CEOs, CIOs, CFOs in banking and financial services.
• Orchestrate large enterprise technology transformation deals with long sales cycles.
• Collaborate with Solution Engineers and Services teams to build ROI-backed proposals.
• Maintain rigorous forecasting and territory planning to exceed revenue targets.

Connaissances

Enterprise software sales

C-level engagement

Forecasting & territory planning

Cross-functional collaboration

B2B sales excellence

Description du poste

We are seeking a high-performing, deeply experienced Senior Enterprise Account Executive to lead and expand our Named Accounts portfolio across Puerto Rico, the Dominican Republic, and the broader Caribbean region. In this role, you will be responsible for driving complex digital transformation initiatives, managing top-tier strategic relationships, and significantly expanding our technology footprint in key accounts. The ideal candidate is a Puerto Rico native or long-term resident with an established, high-level network across the local banking and commercial sectors, coupled with a proven track record of overachieving multi-million-dollar sales targets.

Key Responsibilities

• Territory & Named Account Leadership: Execute a multi-year growth strategy across high-value Named Accounts in Puerto Rico, the Dominican Republic, and the Caribbean.
• Footprint & Installed Base Expansion: Serve as a strategic catalyst to deeply penetrate our existing customer base, cross-sell complex cloud solutions, and capture market share from competitors.
• C-Suite Relationship Management: Act as a trusted advisor to C-level executives (CEOs, CIOs, CFOs, Heads of Business Units), particularly within Puerto Rico's top commercial banking and financial service institutions.
• Complex Business Development: Orchestrate large-scale, enterprise-wide technology transformation deals with long, multi-stakeholder sales cycles.
• Cross-Functional Collaboration: Partner effectively with Solution Engineers, Delivery/Services teams, Executive Sponsors, and Regional Partners to build compelling ROI-backed proposals and ensure post-sale execution.
• Pipeline & Operational Rigor: Maintain precise forecasting, territory planning, and opportunity management to consistently achieve and exceed annual revenue targets (ARR/ACV).

Qualifications & Required Experience

• Industry Experience & Track Record: 10+ years of direct software/SaaS enterprise sales experience, selling complex, high-value technology platforms and enterprise software solutions.
• Territory Expertise: Deep, firsthand commercial experience in Puerto Rico, with secondary expertise in the Dominican Republic and Caribbean enterprise markets.
• Local Executive Network: Native-level cultural understanding of Puerto Rico's corporate landscape, backed by an active, high-level contact network in the local business community.
• Financial Services & Retail/CPG Specialization: Proven success selling into the Puerto Rican banking sector (commercial/retail banks, credit unions, insurance) and major consumer goods conglomerates.
• Complex Enterprise Sales Mastery: Demonstrated expertise in consultative sales methodologies (e.g., Challenger, Value Selling, Solution Selling) with a history of closing complex, multi-cloud digital transformation deals.
• Quota Overachievement: Consistent, verifiable track record of reaching and exceeding sales quotas ($2M+ annual targets).
• Language Proficiency: Complete business fluency in English and Spanish (written and verbal).