Regional Sales Manager, Mid-Market (Commercial Segment)

Job title: Regional Sales Manager, Mid-Market (Commercial Segment)

About the Role Regional Sales Manager, Mid-Market (Commercial Segment) in Tokyo will lead OutSystems' Enterprise sales division in Japan, focusing on Automotive and Manufacturing sectors. This is a pivotal leadership role for a data-driven, emotionally intelligent sales coach who builds high-performing teams to exceed revenue and operational goals. The position is hybrid/office-based and requires native-level Japanese with business-level English to engage executives.

What You'll Do

• 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.
• Drive New Business Acquisition (Hunting): penetrate Mid-Market, secure new logos, and expand OutSystems' market share in Japan.
• Engage with senior executives through Executive Engagement & Strategic Selling: map accounts, stakeholders, and legacy tech ecosystems; lead high-level discussions to align value with objectives.
• Lead Deal Execution & Negotiation: serve as the executive point of contact for critical accounts; steer strategies, overcome objections, and close deals.
• Drive Account Expansion: develop and execute plans to upsell and upgrade existing customers as their digital transformation needs evolve.
• Demonstrate Value: clearly communicate how OutSystems delivers measurable business value through presentations and demos.
• Cross-Functional Collaboration: partner with Pre-Sales, Marketing, Partners/Alliances, and Customer Success to optimize regional sales and success.

What We're Looking For

• 8+ years of quota-carrying B2B sales experience in enterprise software/SaaS with a proven track record in Enterprise segments.
• 4+ years of direct leadership experience managing a quota-carrying sales team to above-target performance.
• Leadership style grounded in trust, emotional intelligence, and mutual respect; proven ability to attract, develop, and retain top talent in Japan.
• Deep domain expertise in cloud computing, SaaS economics, enterprise IT ecosystems, and digital transformation trends; experience prospecting IT decision-makers (CIOs, IT Directors).
• Strong deal management and negotiation skills; expert at objection handling and risk mitigation.
• Data-driven analytical mindset; proficient with forecasting tools to drive growth.
• High integrity, autonomy, and time-management; able to execute regional business plans.
• Language: Native or bilingual Japanese (written and spoken) with professional business etiquette; Working-level English to collaborate with APAC/global leadership.

Compensation & Benefits

• Competitive base salary with an attractive, performance-driven OTE.
• Social Insurance fully covered (Health Insurance, Employee's Pension, Employment Insurance, Industrial Accident Compensation Insurance).
• Flexi - Allowance.
• Generous annual paid leave, continuous leadership development programs, and a collaborative, globally-minded work environment.