Regional Sales Director (Team Management)

There are NO limits to your career: come shape the future and be part of a truly unique global culture at OutSystems!

About OutSystems

At OutSystems, we are accelerating digital transformation globally by empowering organizations to build enterprise-grade applications quickly and efficiently. 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.

Key Responsibilities

As the Regional Sales Director, you will be responsible for driving new business acquisition, expanding existing accounts, and cultivating a highly motivated team of full-cycle sales professionals.

• Team Leadership & Coaching: Hire, mentor, and inspire a successful team of enterprise account executives. Act as a dedicated coach to elevate individual performance, foster career growth, and retain top sales talent.

• New Business Acquisition (Hunting): Drive strategic initiatives to penetrate the enterprise space, securing new logos and expanding OutSystems' market share in those dedicated countries.

• Executive Engagement & Strategic Selling: Map prospective accounts (organizational structures, key stakeholders, and legacy technology ecosystems). Engage and orchestrate high-level business discussions with senior executives to align OutSystems’ value proposition with their corporate objectives.

• Deal Execution & Negotiation: Serve as a key executive point of contact for critical accounts. Lead sales strategies, overcome complex objections, and spearhead commercial negotiations to secure win-win outcomes.

• Account Expansion: Develop and execute strategic growth plans to upsell and upgrade existing customers as their digital transformation needs evolve.

• Value Demonstration: Effectively communicate—verbally, in writing, and through executive-level presentations/demonstrations—how prospective clients can capture measurable business value and envision their future with OutSystems.

• Cross-Functional Collaboration: Partner closely with Pre-Sales, Marketing, Partners/Alliances, and Customer Success teams to optimize regional sales execution and maximize customer success.

Qualifications & Requirements

We are seeking a results-oriented leader with a strong track record in enterprise/commercial IT sales and a people-first management philosophy.

• Sales Experience: 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.

• Leadership Experience: 4+ years of direct experience managing, coaching, and leading a quota-carrying, closing sales team to over-achievement.

• Leadership Style: Strong leadership presence built on trust, emotional intelligence, and mutual respect. A proven ability to attract, develop, and retain premier sales talent.

• Domain Expertise: Deep understanding of cloud computing technologies, SaaS business drivers, enterprise IT ecosystems, and digital transformation trends. Experience prospecting to IT decision-makers (CIOs, IT Directors) is required.

• Deal Management & Negotiation: Exceptional interpersonal and communication skills. Expert-level capability in objection handling, risk mitigation, and sophisticated commercial negotiations.

• Analytical Skills: Data-driven mindset with the ability to leverage sales metrics and forecasting tools to drive predictable business growth.

• Integrity & Autonomy: High level of professional integrity, solid time-management skills, and the ability to operate autonomously to execute regional business plans.

More about OutSystems

OutSystems is a leading AI Development Platform built for the enterprise. Global organizations trust OutSystems to rapidly build mission-critical apps and agents, modernize legacy processes with agentic systems, and govern their entire AI portfolio across complex regulatory environments, all on one unified platform.

As the future becomes agentic, our customers need us now more than ever. While AI has opened the door to extraordinary possibilities, most large organizations find themselves stuck on one side of the "enterprise gap" because AI by itself doesn't solve their complex use cases and business challenges. OutSystems bridges the "enterprise gap" by combining the speed of generative AI with a deterministic, enterprise-grade framework. We provide the tools for teams of any size to deliver high-quality, reliable AI solutions that drive real business impact.

We are looking for passionate, talented, and motivated people to join us as we empower organizations to build, deploy, and scale the next generation of enterprise software. While we are leading the charge into the agentic era, our mission is broader: we are the platform enterprise leaders trust to evolve their entire business, accelerating innovation through secure, governed human-AI collaboration. 

OutSystems is a global company, with more than 900k developer community members, 1,700 employees, more than 600 partners, and thousands of active customers in over 75 countries and across 21 industries. Founded in 2001, OutSystems now has offices in the United States, United Kingdom, the Netherlands, Portugal, Germany, the UAE, Japan, Hong Kong, Malaysia, Australia, India, and Singapore, and  includes a thriving, worldwide community of remote employees.

Our customers are some of the world's most recognizable brands across diverse industries— such as Toyota, Heineken, Bosch, KeyBank, and UCLA—who trust OutSystems to deliver ROI and transformational impact. 

Consistently recognized as a leader by top analyst firms Gartner, IDC and Forrester, OutSystems continues to shape the future of enterprise software development in the agentic era. We are proud to be named a leader in more than 100 categories on G2, including #1 in Customer Satisfaction in Enterprise Low Code Development, and most recently as a leader in AI Agent Building in the G2 Spring 2026 Reports. 

Working at OutSystems

Our culture is built on our core values of Trust, Customer Success, Innovation, and Alignment. We operate as one global OutSystems team, taking ownership to pursue our vision of being the AI platform enterprise leaders trust to build, secure, and evolve their most critical applications and systems.

What do we have to offer you?

• A company at the vanguard of the agentic revolution, where we don’t just react to AI innovation—we architect it. Joining OutSystems means stepping onto a high-growth rocket ship that combines the fearless agility of a startup with the sophisticated, global foundation of an enterprise powerhouse.

• Real growth opportunities. We don't just talk about development; we invest in it through structured programs designed to scale your expertise. Whether you are aiming for vertical progression, exploring lateral moves into new domains, or mastering specialized AI skills through our Professional Development Fund and Internal Mobility Program, we provide the resources to get you there.

• A global collective of world-class talent, where you’ll collaborate with enterprise software legends and sought-after thought leaders. At OutSystems, our industry experts aren't just visionaries—they are accessible, approachable mentors who are deeply invested in your growth as we architect the agentic future together.

OutSystems nurtures an inclusive culture where talented individuals from all backgrounds are empowered to learn, experiment and make an impact. . We believe that driving our next phase of growth requires the radical creativity that only comes from diverse perspectives. We are committed to building a team as global and diverse as the organizations we serve, ensuring every individual can perform to their full potential. As an equal opportunity employer, all qualified applicants receive equal consideration regardless of race, origin, religion, sex, sexual orientation, gender identity, disability, veteran status, or any other protected status.