Senior Account Executive

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The Senior Account Executive (SAE) at Syssero is a strategic, quota-carrying sales leader responsible for driving new services revenue within a defined territory through disciplined pipeline development, executive engagement, and end-to-end deal ownership across the Workday ecosystem. The SAE builds, cultivates, and converts a high-quality pipeline of Workday end-client opportunities, consistently delivering against annual bookings targets while balancing revenue growth, margin integrity, and long-term client value.

This role owns the full sales lifecycle, from proactive market engagement and executive-level discovery through solution shaping, proposal development, negotiation, and close, ensuring that Syssero is positioned as a trusted advisor and that all engagements are competitively differentiated, commercially sound, and aligned with successful delivery outcomes. The SAE operates with a consultative, outcome-oriented approach, translating complex client needs into tailored service solutions across Workday HCM, Financials, Payroll, and Integrations.

The SAE serves as a key extension of the Workday field organization, leading and deepening relationships with assigned Workday Regional Sales Directors (RSDs) and their aligned Account Executives to drive joint go-to-market execution and co-sell success. In close partnership with Principal Sales Engineering, Alliances, and Services leadership, the SAE shapes winning deal strategies, validates solution feasibility, and ensures seamless alignment between sales commitments and delivery capabilities, leveraging Syssero’s unique differentiation as a firm staffed by former Workday end-clients.

Beyond core sales responsibilities, the SAE contributes to broader commercial strategy and cross-functional initiatives that enhance Syssero’s market position, sales effectiveness, and client experience. The role requires strong operational discipline, including accurate forecasting, CRM rigor, and pipeline analytics, to inform decision-making and ensure consistent execution.

The SAE partners with Sales leadership to define and achieve Quarterly Rocks aligned to both individual development and organizational growth priorities. Consistent achievement of these goals, along with sustained revenue performance, directly influences compensation, advancement opportunities, and long-term career progression within Syssero.

Other Duties: Please note this job description is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities that are required of the employee for this job. Duties, responsibilities and activities may change at any time with or without notice.

Territory Management & Pipeline Development

• Own and strategically lead a defined territory anchored in executive-level relationships with assigned Workday Regional Sales Directors (RSDs) and their aligned AEs, expanding influence across priority accounts and whitespace opportunities.
• Build, mature, and continuously optimize a high-quality pipeline with sufficient coverage to consistently exceed annual bookings targets across all Syssero offerings.
• Develop and drive a data-informed territory strategy that prioritizes high-value accounts, accelerates deal velocity, and aligns with Workday go-to-market motions.
• Maintain rigorous CRM discipline with real-time pipeline visibility, ensuring data integrity to support accurate forecasting and executive decision-making.
• Proactively assess pipeline health, conversion metrics, and deal risk, adjusting strategy in real time to ensure consistent quota attainment.

• Pipeline coverage ratio vs. individual quota
• CRM hygiene and completeness of opportunity records
• Territory plan quality and execution consistency
• Monthly and quarterly bookings vs. ramp and annual targets

Prospecting & Lead Generation

• Lead sophisticated, multi-channel prospecting strategies that combine digital outreach, executive networking, Workday ecosystem engagement, and co-sell motions to generate net-new pipeline.
• Engage senior client stakeholders to identify and shape demand for Workday optimization, implementation, and managed services across HCM, Payroll, Financials, and Integrations.
• Apply disciplined qualification frameworks to prioritize high-probability opportunities with clear business value, aligned stakeholders, and defined buying timelines.
• Position Syssero’s differentiated value (former Workday client-side expertise) to establish early credibility and accelerate access to decision-makers.
• Activate and expand partner-sourced opportunities by collaborating closely with Workday field teams to drive joint pipeline creation.

• Volume and quality of net-new pipeline created
• Lead-to-opportunity conversion rate
• Co-sell activity and Workday field engagement
• Prospecting consistency and outreach cadence

Discovery & Opportunity Qualification

• Lead executive-level discovery with cross-functional stakeholders (HR, Finance, IT, Operations) to uncover strategic priorities, transformation goals, and underlying business challenges.
• Utilize advanced consultative selling techniques to identify root-cause issues and align Syssero’s solutions to measurable business outcomes.
• Synthesize and document discovery insights into clear, actionable requirements that enable seamless transition to Sales Engineering and Services teams.
• Evaluate deal viability through rigorous assessment of stakeholder alignment, financial drivers, competitive landscape, and delivery risk.
• Engage Principal Sales Engineer early and strategically to strengthen solution fit, validate assumptions, and increase win probability.

• Quality and completeness of discovery documentation
• Opportunity win rate and stage progression velocity
• Sales Engineer and Services feedback on handoff readiness
• Reduction in late-stage scope changes or expectation mismatches

Proposal, Negotiation & Close

• Own end-to-end deal strategy and execution, leading the development of compelling, outcome-based proposals aligned to client priorities and Syssero delivery standards.
• Direct complex RFP/RFI responses and procurement processes with strategic positioning that differentiates Syssero in competitive environments.
• Lead commercial negotiations with senior client stakeholders, structuring engagements that optimize revenue, margin, and long-term client value.
• Navigate legal, procurement, and executive approval processes to remove barriers, maintain momentum, and drive timely close.
• Ensure all deal terms, scope, and booking details are accurately documented and positioned for successful downstream execution.

• Proposal-to-close conversion rate
• Average deal size and contract mix (LEAP/AMS vs. T&M)
• Accuracy of CRM contract records and booking documentation
• Client satisfaction and Services feedback at deal handoff

Collaboration & Internal Communication

• Operate as the quarterback of the deal team, ensuring alignment across Sales Engineering, Services, and Alliances throughout the sales lifecycle.
• Engage Services leadership proactively on complex or high-risk opportunities to validate delivery approach, mitigate risk, and ensure successful execution.
• Deepen and expand co-sell relationships within the Workday ecosystem, driving alignment with RSDs and AEs to influence joint pipeline and bookings.
• Deliver precise, executive-level pipeline reporting and forecasts, demonstrating consistency, transparency, and accuracy.
• Lead high-quality Sales-to-Services handoffs, ensuring full clarity on scope, client expectations, and success criteria.

• Pipeline forecast accuracy
• Timeliness and quality of STS handoff documentation
• Internal stakeholder feedback (Sales Engineer, Services, Alliances)
• Workday partnership activity and compliance

Market Knowledge & Professional Development

• Maintain deep expertise in Workday’s product suite, ecosystem, and roadmap, positioning Syssero as a strategic advisor in client conversations.
• Develop mastery of Syssero’s services, delivery methodology, and client outcomes to effectively articulate differentiated value.
• Represent Syssero in the market through active participation in Workday events, partner forums, and industry networks to build brand presence and generate demand.
• Demonstrate a commitment to continuous improvement through achievement of Quarterly Rocks and ongoing development of advanced sales capabilities.

• Demonstrated product and market knowledge in client conversations
• Completion rate of Quarterly Rocks
• Event participation and field engagement activity