Enterprise Sales Director, S&D

Accountabilities Represent the organization’s workforce-focused services and broader solution portfolio with strong commercial expertise, credibility, and executive presence.

Develop and execute strategic account plans for enterprise service and distribution prospects and clients, particularly organizations with large, distributed, multi-brand, and multi-site workforces.

Lead complex, end-to-end enterprise sales cycles, managing multiple stakeholders across Operations, HR, Finance, IT, and executive leadership.

Conduct consultative discovery to understand challenges such as high-volume hiring, seasonal workforce demand, compliance, labor costs, scheduling, employee engagement, union and non-union environments, and multi-jurisdiction requirements.

Translate customer challenges into compelling, quantified value propositions and business cases that demonstrate measurable business impact.

Coordinate internal consulting experts and strategic technology partners to develop solution scope, commercial proposals, business cases, and phased roadmaps.

Build relationships with partner and alliance organizations to identify and close joint enterprise opportunities.

Manage enterprise procurement, security, IT review, legal, contracting, and other commercial processes through successful deal completion.

Maintain rigorous opportunity management practices, including accurate forecasting, pipeline hygiene, CRM updates, and deal governance.

Develop and execute sales plans designed to exceed quarterly and annual revenue objectives.

Maintain pipeline coverage equivalent to approximately 3x the sales plan target.

Conduct regular business reviews to evaluate progress against sales objectives and refine account and territory strategies.

Build long-term strategic relationships with enterprise customers and partners while identifying opportunities to expand services over time.

Deliver a high standard of customer engagement by anticipating needs, providing proactive guidance, and consistently exceeding expectations.

Requirements

Minimum 7 years of experience in consultative sales, relationship management, solution selling, or a related enterprise sales discipline, with strong preference for experience serving enterprise service and distribution organizations.

Demonstrated success leading complex, multi-threaded enterprise opportunities involving multiple business and executive stakeholders.

Strong ability to influence decision-makers across Operations, HR, Finance, IT, and C-suite functions.

Experience selling services or technology designed to improve workforce outcomes at scale, such as HCM, workforce management, payroll, timekeeping, scheduling, compliance, or analytics solutions.

Proven experience working with resellers, ISVs, channel partners, strategic alliances, or technology ecosystems to develop and close joint opportunities.

Experience navigating enterprise procurement, security and IT reviews, legal requirements, contracting processes, and other complex buying environments.

Exceptional verbal, written, presentation, negotiation, and executive communication skills.

Strong consultative discovery and value-selling capabilities, with the ability to connect customer challenges to measurable business outcomes.

Highly self-directed and organized, with the ability to manage multiple complex opportunities and lengthy sales cycles simultaneously.

Strong commercial discipline and experience managing forecasts, pipelines, sales plans, and revenue targets.

Ability to work effectively in a fully remote environment while traveling as needed for enterprise customers and strategic partners.

Bachelor’s degree from an accredited university is preferred.

Benefits

Competitive salary with bonus potential.

Comprehensive benefits package.

Paid time off.

Flexible remote work environment.

Opportunity to play a high-impact role within a growing enterprise consulting and services portfolio.

Significant growth potential as the organization expands its solutions and market reach.

Opportunity to deepen expertise in UKG, workforce management, retail, hospitality, and enterprise services.

Exposure to complex enterprise customers, strategic technology partners, and senior executive stakeholders.

Collaborative environment with internal consulting, sales, and technology experts.

Opportunity to shape go-to-market strategies and influence how comprehensive workforce solutions are positioned and delivered.

How Jobgether works: We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team. We appreciate your interest and wish you the best!  Why Apply Through Jobgether? 

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