Head of Sales

Head of Sales

Workforce Optimizer Pte Ltd · Singapore, Singapore (Hybrid) · Full-time · Posted 2026-09-22

Salary: SGD 120,000–180,000

Workplace: hybrid

Department: Sales and Marketing

Description

The Head of Sales will own and drive enterprise and public-sector revenue growth for Workforce Optimizer (WFO), a workforce management and optimisation SaaS platform serving healthcare, aviation, facilities management, hospitality, and large enterprises.

This is a player–coach role. The successful candidate will personally close strategic deals, build and coach a high-performing enterprise sales team, and establish a repeatable sales motion aligned with long procurement cycles, regulated environments, and complex solution selling.

Key Responsibilities

1. Revenue Ownership & Deal Closure

• Own new ARR and professional services revenue targets
• Personally lead and close large, complex enterprise and government deals

• Manage the full sales lifecycle:

• Discovery & value framing

• Executive presentations and demos
• Commercial structuring and pricing

• Contract, procurement, and legal negotiations

• Act as executive sponsor for strategic accounts

2. Sales Strategy & Go-To-Market

• Define and execute WFO’s enterprise go-to-market strategy
• Establish clear Ideal Customer Profiles (ICPs) and vertical focus
• Build and maintain a strong, qualified pipeline
• Drive account-based selling for key logos and lighthouse customers

3. Sales Team Leadership (Player–Coach)

• Recruit, onboard, and coach Enterprise Account Executives

• Develop sales capability in:

• Solution selling

• Value-based pricing

• Public-sector procurement

• Set clear sales targets, quotas, and performance expectations

• Conduct deal reviews and ensure pricing discipline

4. Sales Process & Playbook Ownership

• Create and continuously improve WFO’s sales playbook, including:

• Discovery frameworks

• Demo and pilot strategy

• Proposal and commercial models

• Ensure consistent and repeatable sales execution across the team

• Improve sales forecasting accuracy and pipeline hygiene

5. Market & Partner Engagement

• Represent WFO in:

• Customer executive briefings

• Industry events and conferences

• Strategic partner discussions

• Support partnerships with system integrators and technology partners where relevant

Requirements

Must-Have

• 10+ years of B2B sales experience, with at least:

• 5+ years in enterprise or public-sector SaaS sales

• Proven track record of closing:

• 6–7 figure enterprise or government contracts

• Strong experience selling:

• Complex, configurable software platforms

• Solutions involving integration, implementation, and services

• Hands-on experience navigating:

• Government procurement and tender processes

• Long sales cycles and multi-stakeholder decision making

• Experience managing and coaching senior sales professionals

Nice-to-Have (Strong Advantage)

• Experience selling into: Healthcare, aviation, logistics, or regulated industries
• Familiarity with: Workforce management, HR tech, or optimisation software
• Exposure to: SAP SuccessFactors, Workday, or enterprise ERP ecosystems
• Regional sales exposure (APAC)

Benefits

Competitive senior-level compensation, strong sales enablement, long-term growth incentives, and the opportunity to build and lead an enterprise SaaS sales function with real market impact.

• Hybrid work setup with flexibility to manage enterprise and public-sector engagements
• Sales enablement tools provided, including laptop, mobile, CRM, and demo environments
• Clear performance incentives, including accelerators and long-term growth opportunities
• High autonomy and visibility, with direct access to leadership and influence on GTM strategy

Apply

Apply at Workforce Optimizer Pte Ltd

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