Regional Sales Director (Team Management)

As we aggressively scale our commercial footprint in APAC, we are seeking an experienced, high-caliber Regional Sales Director to lead our Enterprise sales Team in Singapore, Malaysia and Greater China Region. This is a pivotal leadership role for an emotionally intelligent, data-driven sales coach who thrives in a fast-paced environment and is passionate about building high-performing teams to exceed revenue and operational goals.

Responsibilities

Team Leadership & Coaching: Hire, mentor, and inspire a successful team of enterprise account executives; New Business Acquisition (Hunting): Drive strategic initiatives to penetrate the enterprise space, securing new logos and expanding OutSystems' market share; Executive Engagement & Strategic Selling: Map prospective accounts, engage high-level business discussions with senior executives; Deal Execution & Negotiation: Lead sales strategies, overcome complex objections, spearhead commercial negotiations; Account Expansion: Develop and execute strategic growth plans to upsell and upgrade existing customers; Value Demonstration: Communicate how prospective clients can capture measurable business value and envision their future with OutSystems; Cross-Functional Collaboration: Partner with Pre-Sales, Marketing, Partners/Alliances, and Customer Success teams

Requirements

Minimum of 12 years of quota-carrying B2B sales experience, with a proven track record of success selling into the enterprise segments within the software/SaaS industry; 4+ years of direct experience managing, coaching, and leading a quota-carrying, closing sales team to over-achievement; Strong leadership presence built on trust, emotional intelligence, and mutual respect; Deep understanding of cloud computing technologies, SaaS business drivers, enterprise IT ecosystems, and digital transformation trends; Exceptional interpersonal and communication skills; Expert-level capability in objection handling, risk mitigation, and sophisticated commercial negotiations; Data-driven mindset with the ability to leverage sales metrics and forecasting tools to drive predictable business growth; High level of professional integrity, solid time-management skills, and the ability to operate autonomously to execute regional business plans

Benefits

Real growth opportunities; Professional Development Fund; Internal Mobility Program; A global collective of world-class talent; Accessible, approachable mentors; Inclusive culture