Senior Sales Success Specialist

Summary

Join Smartsheet as a Sr Sales Success Specialist and play a pivotal role in optimizing sales outcomes, driving revenue growth, and ensuring operational excellence. You will support key accounts and territories throughout the sales cycle, partnering with the account team and cross-functional teams. Responsibilities include aligning with sales reps to support forecasting and pipeline management, analyzing sales pipelines to identify bottlenecks, optimizing deal strategies, monitoring deal performance, and reviewing customer licensing and purchasing patterns. You will also lead the resolution of deal-related challenges, share best practices, design strategies to streamline the sales process, and work cross-functionally with multiple internal departments. The role requires 3-5+ years of experience in a Deal Desk or Sales Operations role supporting a cloud/SAAS based go-to-market organization, strong analytical and communication skills, and proficiency in Salesforce and Salesforce CPQ. Smartsheet offers a comprehensive benefits package including fully paid health and life insurance, a monthly stipend, paid time off, parental leave, and professional development opportunities.

Requirements

• 3-5+ years experience in a Deal Desk or Sales Operations role, supporting a cloud/SAAS based go-to-market organization
• Demonstrated critical thinking: analyze complex deal issues, make decisions and solve problems self-sufficiently, without requiring ongoing direction setting
• Excellent interpersonal and customer oriented communication skills
• Able to prioritize workloads and effectively demonstrate time management in a fast-paced sales environment
• Knowledge of revenue recognition rules/requirements related to software and professional services
• Proficiency in Salesforce, Salesforce CPQ and Salesforce Reporting
• A proven track record to build strong and positive relationships with business partners across the organization
• Understanding of operational Quote-to-Cash business processes
• Exposure to contract negotiation/drafting, including Legal and SOX compliance

Responsibilities

• Align with sales reps, accounts and territories to support forecasting, pipeline management, and revenue-driving activities. Coordinate deal reviews with the account team
• Analyze sales pipelines to proactively identify potential bottlenecks, risks to closing deals, potential booking or approval issues or a negative customer experience
• Partner with the account team to optimize deal strategies, focusing on maximizing revenue opportunities
• Monitor deal performance and maintain data hygiene, including tracking kickbacks, usage reports, and other key account metrics
• Review and analyze customer licensing, product usage, and purchasing patterns to uncover upselling or cross-selling opportunities
• Lead the resolution of deal-related challenges by providing strategic guidance on complex structures and innovative solutions for non-standard requests
• Escalate specialized issues to appropriate departments for resolution and approval
• Share best practices with team members to enhance the quality and efficiency of support and contribute to the account knowledge base through creating SOPs and training
• Design and execute strategies to streamline the sales process and improve deal velocity with sales leadership input
• Work cross-functionally with multiple internal Departments (Deal Desk, Order Operations, Revenue Accounting, Operation Excellence, Finance Operations, Fulfillment, Legal, Professional Services, Tax)
• Support EOM, EOQ and EOY close to make sure all business closes on time

Benefits

• Fully paid Health & Life insurance for full-time employees and family members
• Monthly stipend to support your work and productivity
• Asociacion Solidarista with employee and employer contributions as well as potential alliances with entities such as universities, gyms, etc
• 12 days paid Vacation + Flexible Time Away Program
• 20 weeks fully paid Maternity Leave
• 12 weeks fully paid Paternity/Adoption Leave
• Personal paid Volunteer Day to support our community
• Opportunities for professional growth and development including access to Udemy online courses
• Company Funded Perks including a counseling membership and your own personal Smartsheet account
• Teleworking options from any registered location in Costa Rica (role specific)