Enterprise Sales Director

About the role

Five9 is seeking an Enterprise Sales Director to drive new business growth in the Portugal market. This role owns the end-to-end sales performance for large enterprise accounts in the contact center and customer experience category within Portugal. You will be responsible for identifying strategic opportunities, building executive-level relationships, and positioning Five9 as the critical platform for digital transformation initiatives. The hire will manage the full sales cycle, from complex discovery and stakeholder mapping through solution validation, negotiation, and final contract closure. Success in this position requires a deep understanding of cloud economics and the operational value of contact center automation for large organizations. You will work closely with internal stakeholders to align solutions with client business outcomes and long-term strategic goals. This role demands a proactive leader who can navigate multi-threaded buying committees and influence without direct authority. You will be measured on your ability to generate predictable pipeline, close high-value deals, and expand footprint within key accounts over time.

Key facts

What you'll do

• Lead the identification and qualification of new enterprise sales opportunities across Portugal, focusing on multi-million dollar deals in the contact center space.
• Architect and deliver compelling value propositions that demonstrate the financial and operational impact of migrating to a cloud contact center platform.
• Build and leverage executive-level sponsor relationships within target organizations to guide strategic decision-making and mitigate business risk.
• Conduct discovery sessions with economic buyers and influencers to define business challenges and map them to Five9's platform capabilities.
• Own the end-to-end negotiation of commercial terms, ensuring agreements align with both customer needs and Five9's strategic objectives.
• Collaborate with solutions engineering and professional services teams to develop tailored demonstrations and proof-of-concept scenarios.
• Analyze competitive positioning and customer sentiment to refine sales approaches and messaging on an ongoing basis.
• Track and report on pipeline health, win-loss patterns, and key metrics to enable data-driven adjustments to strategy.
• Partner with marketing to develop relevant content and case studies that accelerate engagement with in-market enterprise accounts.
• Mentor junior sales representatives on enterprise selling techniques, account planning, and stakeholder management best practices.
• Coordinate cross-functional input for technical assessments, security reviews, and pricing approvals to keep deals moving efficiently.
• Represent Five9 at industry events and strategic forums to elevate brand presence and generate new inbound interest.
• Translate complex product features into clear business benefits that resonate with C-level stakeholders across finance, operations, and customer experience functions.
• Establish a repeatable sales methodology for enterprise deals that emphasizes disciplined forecasting and rigorous opportunity assessment.

Requirements

• Demonstrated success in enterprise software sales, specifically within the contact center or CX industry, with a track record of selling complex, high-value solutions to large organizations.
• Proven ability to manage complex sales cycles and achieve quota consistently in a fast-paced, target-driven environment.
• Strong understanding of cloud-based solutions and their benefits for large businesses, including scalability, security, and total cost of ownership considerations.
• Excellent communication, presentation, and negotiation skills, with the ability to articulate technical concepts to non-technical decision-makers.
• Ability to work independently and as part of a broader sales organization, balancing personal accountability with collaboration across teams.
• Fluency in both English and Portuguese is required to communicate effectively with stakeholders at all levels in Portugal.
• Experience working with enterprise buying committees and influencing multiple stakeholders throughout the procurement process.
• A results-oriented mindset that includes strict adherence to forecasts, pipeline integrity, and accurate opportunity scoring.

Practical notes

This is a hybrid role based in Porto, Portugal, requiring a mix of in-office and remote work. Full-time engagement is expected, with availability during standard business hours for collaboration with global teams. Travel requirements are not specified in the source material, so candidates should be prepared for occasional in-person meetings with key accounts or internal stakeholders when necessary. No specific visa information or deadlines are provided in the source job description.