Head of Sales

Workforce Optimizer - AI Enabled WFM; Singapore; Hybrid; SGD 180,000 - 280,000; Full time

Benefits offered by this job

Hybrid work setup

Sales enablement tools provided

Performance incentives

Autonomy and leadership access

Job summary

Workforce Optimizer - AI Enabled WFM seeks a Head of Sales to own enterprise and public-sector revenue growth. This player-coach role will directly close strategic deals while building and coaching a high-performing enterprise sales team. Expect long procurement cycles and complex solution selling in regulated environments.

You will shape GTM strategy, establish ICPs, and drive account-based selling for key logos and lighthouse customers, while maintaining a strong, repeatable sales motion.

Qualifications

• 10+ years of B2B sales experience.
• 5+ years in enterprise or public-sector SaaS sales.
• Proven track record closing 6-7 figure enterprise or government contracts.
• Experience selling complex configurable software platforms.
• Hands-on with government procurement and long sales cycles.
• Experience coaching senior sales professionals.

Responsibilities

• Own revenue ownership, targets, and deal closure.
• Lead and close large, complex enterprise and government deals.
• Manage full sales lifecycle: discovery, value framing, and pricing.
• Negotiate contracts, procurement, and legal terms.
• Coach Enterprise Account Executives and build a high-performing team.
• Define GTM strategy, ICPs, and vertical focus.
• Develop and maintain a qualified pipeline; drive ABM for key logos.

Skills

Enterprise sales

Public-sector sales

SaaS deals

Leadership

Deal negotiation

Job 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

• 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
• 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
• 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
• 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
• 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