HEAD OF SALES
Your Next Career Move:
This role is designed for enterprise revenue leaders, not transactional sellers.
We’ve been exclusively retained to scale the B2B Sales organization of a fast-growing, category-defining digital financial wellness platform serving leading local and multinational enterprises across the Philippines. The company partners with HR, Finance, and business leaders to deliver payroll-integrated, responsible financial solutions that directly impact employee wellbeing, productivity, and workforce stability.
As the Head of Sales, you will operate at a principal level, owning complex enterprise opportunities from origination through close, influencing executive decision-making, and shaping how large organizations adopt and scale financial wellness programs.
You will be trusted to run your territory with autonomy, judgment, and accountability.
📌 Enterprise Scope: Large, complex organizations; multi-stakeholder buying groups; long sales cycles
📌 Strategic Influence: Executive-level conversations that shape budget, policy, and workforce strategy
📌 Domain Advantage: Payroll, payroll-integrated, or HR-adjacent selling experience is a strong differentiator
This is a full-time, hybrid-enabled role for top-tier enterprise closers who consistently deliver in high-expectation, high-impact environments.
What You’ll Own:
Principal-Level Enterprise Revenue Ownership
Own a defined enterprise territory or segment, with full accountability for new logo acquisition, pipeline health, and revenue delivery.
Originate high-value enterprise opportunities through strategic prospecting, executive networking, referrals, and ecosystem partnerships.
Lead end-to-end enterprise sales cycles, discovery, solution design, commercial structuring, negotiation, and contract execution.
Exercise independent commercial judgment across deal qualification, pricing, risk assessment, and prioritization.
Deliver predictable revenue outcomes while maintaining disciplined forecasting and pipeline governance.
Executive Advisory & Strategic Value Selling
Engage CHROs, CFOs, Payroll Heads, and senior business leaders as a trusted advisor rather than a vendor.
Lead strategic conversations around workforce financial wellbeing, payroll-linked benefits, and measurable ROI.
Build compelling enterprise business cases that connect product capabilities to productivity, retention, cost control, and employee resilience.
Influence executive stakeholders across multiple functions and levels to drive alignment and consensus.
Complex Deal Leadership & Stakeholder Orchestration
Navigate sophisticated enterprise buying processes involving HR, Finance, Payroll, IT, Legal, Procurement, and Risk.
Anticipate and manage objections related to compliance, implementation complexity, data security, and organizational change.
Maintain deal momentum across extended sales cycles through structured stakeholder mapping, value reinforcement, and executive sponsorship.
Field Leadership & Cross-Functional Influence
Act as a senior voice from the field, providing feedback to Product, Marketing, and Leadership on buyer behavior, objections, and competitive dynamics.
Partner closely with Marketing and Product on enterprise GTM initiatives, pilot programs, and strategic accounts.
Ensure seamless handoff to Client Success and Operations, setting accurate expectations and driving long-term account success.
Contribute to improving sales playbooks, messaging, and enterprise deal standards.
Standards, Culture & Professional Maturity
Model enterprise-grade professionalism, ethical selling, and client stewardship.
Maintain strong self-management, accountability, and resilience in a high-performance environment.
What You Bring To The Table:
Enterprise Sales Expertise (Non-Negotiable)
8–12+ years of progressive B2B or enterprise sales experience, with at least 5+ years selling to enterprise or upper mid-market accounts.
Demonstrated success closing complex, multi-stakeholder deals with long sales cycles (3–9+ months).
Clear track record of new logo acquisition and consistent quota achievement in competitive environments.
Executive Presence & Commercial Judgment
Proven ability to engage and influence C-suite and senior functional leaders (HR, Finance, Payroll, Operations).
Strong financial and business acumen, with comfort discussing ROI, budgets, and commercial trade-offs.
Excellent executive communication skills, concise, credible, and outcomes-oriented.
Domain & Industry Advantage (Strongly Preferred)
Prior experience selling payroll software, payroll services, or payroll-integrated products.
Background in HR tech, workforce technology, financial wellness, fintech, or enterprise SaaS.
Familiarity with compliance-sensitive or regulated enterprise selling environments.
Ownership, Drive & Resilience
Self-directed, highly accountable seller who thrives with autonomy and responsibility.
Comfortable operating without heavy oversight, while maintaining strong alignment with leadership goals.
Persistent, resilient, and disciplined in managing complex enterprise pursuits.
Location & Schedule Flexibility
This is a full-time, remote-first, hybrid-enabled role for professionals based in Metro Manila.
The role requires comfort with:
Executive-level, in-person client meetings
High-stakes presentations and negotiations
On-demand collaboration with internal stakeholders
Being Manila-based enables close engagement with enterprise clients and leadership teams.
Your Future Starts Here. Are You Ready?
If you are a principal-level enterprise seller who thrives in complex environments, influences executive decisions, and consistently closes high-impact deals, this role offers the platform to shape a category and leave a measurable market footprint.
While we’d love to respond to every application, we’ll only be reaching out to shortlisted candidates. Thank you for your understanding and interest.
