Senior Account Executive

Syssero•Remote-NC, NC

32d

About The Position

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.

Requirements

Quota-carrying sales leader
Driving new services revenue within a defined territory
Disciplined pipeline development
Executive engagement
End-to-end deal ownership across the Workday ecosystem
Build, cultivate, and convert a high-quality pipeline of Workday end-client opportunities
Consistently deliver against annual bookings targets
Balance revenue growth, margin integrity, and long-term client value
Own the full sales lifecycle
Proactive market engagement
Executive-level discovery
Solution shaping
Proposal development
Negotiation
Close
Position Syssero as a trusted advisor
Competitively differentiated, commercially sound, and aligned with successful delivery outcomes
Consultative, outcome-oriented approach
Translate complex client needs into tailored service solutions across Workday HCM, Financials, Payroll, and Integrations
Serve as a key extension of the Workday field organization
Lead and deepen relationships with assigned Workday Regional Sales Directors (RSDs) and their aligned Account Executives
Drive joint go-to-market execution and co-sell success
Shape winning deal strategies
Validate solution feasibility
Ensure seamless alignment between sales commitments and delivery capabilities
Leverage Syssero’s unique differentiation as a firm staffed by former Workday end-clients
Contribute to broader commercial strategy and cross-functional initiatives
Enhance Syssero’s market position, sales effectiveness, and client experience
Strong operational discipline
Accurate forecasting
CRM rigor
Pipeline analytics
Inform decision-making and ensure consistent execution
Partner with Sales leadership to define and achieve Quarterly Rocks
Aligned to both individual development and organizational growth priorities
Consistent achievement of goals
Sustained revenue performance
Territory Management & Pipeline Development
Data-informed territory strategy
Prioritize high-value accounts
Accelerate deal velocity
Align with Workday go-to-market motions
Maintain rigorous CRM discipline
Real-time pipeline visibility
Data integrity
Accurate forecasting
Executive decision-making
Proactively assess pipeline health
Conversion metrics
Deal risk
Adjusting strategy in real time
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
Combine digital outreach, executive networking, Workday ecosystem engagement, and co-sell motions
Generate net-new pipeline
Engage senior client stakeholders
Identify and shape demand for Workday optimization, implementation, and managed services
Apply disciplined qualification frameworks
Prioritize high-probability opportunities
Clear business value
Aligned stakeholders
Defined buying timelines
Position Syssero’s differentiated value (former Workday client-side expertise)
Establish early credibility
Accelerate access to decision-makers
Activate and expand partner-sourced opportunities
Collaborate closely with Workday field teams
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)
Uncover strategic priorities, transformation goals, and underlying business challenges
Utilize advanced consultative selling techniques
Identify root-cause issues
Align Syssero’s solutions to measurable business outcomes
Synthesize and document discovery insights
Clear, actionable requirements
Seamless transition to Sales Engineering and Services teams
Evaluate deal viability
Rigorous assessment of stakeholder alignment, financial drivers, competitive landscape, and delivery risk
Engage Principal Sales Engineer early and strategically
Strengthen solution fit
Validate assumptions
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
Lead the development of compelling, outcome-based proposals
Aligned to client priorities and Syssero delivery standards
Direct complex RFP/RFI responses and procurement processes
Strategic positioning that differentiates Syssero in competitive environments
Lead commercial negotiations with senior client stakeholders
Structure engagements that optimize revenue, margin, and long-term client value
Navigate legal, procurement, and executive approval processes
Remove barriers
Maintain momentum
Drive timely close
Ensure all deal terms, scope, and booking details are accurately documented
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
Ensure alignment across Sales Engineering, Services, and Alliances throughout the sales lifecycle
Engage Services leadership proactively on complex or high-risk opportunities
Validate delivery approach
Mitigate risk
Ensure successful execution
Deepen and expand co-sell relationships within the Workday ecosystem
Drive alignment with RSDs and AEs
Influence joint pipeline and bookings
Deliver precise, executive-level pipeline reporting and forecasts
Demonstrate consistency, transparency, and accuracy
Lead high-quality Sales-to-Services handoffs
Ensure 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)
Market Knowledge & Professional Development
Maintain deep expertise in Workday’s product suite, ecosystem, and roadmap
Position Syssero as a strategic advisor in client conversations
Develop mastery of Syssero’s services, delivery methodology, and client outcomes
Effectively articulate differentiated value
Represent Syssero in the market
Active participation in Workday events, partner forums, and industry networks
Build brand presence and generate demand
Demonstrate a commitment to continuous improvement
Achievement of Quarterly Rocks
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

Nice To Haves

Former Workday client-side expertise

Responsibilities

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.
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.
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.
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.
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.
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.