We are looking for a Sr. Risk and Renewals Operations Manager to develop and manage a world-class customer renewal and risk management operation. You will focus on operationalizing churn mitigation and renewal excellence, taking high-level risk identification and commercial strategies and converting them into scalable, automated processes. Your objective is to move the organization toward a disciplined, proactive risk management motion and optimized renewal process that protects our global recurring revenue base.

You Will

• Standardize Renewal Journeys: Design and implement renewal paths based on customer value and complexity. This includes automating high-volume renewals and establishing workback schedules for enterprise-level accounts.
• Systematize Risk Workflows: Architect the CRM and Gainsight workflows necessary to move the organization toward 100 percent proactive risk identification at least 90 days prior to renewal.
• Manage Renewal Planning Rhythms: Develop and support the execution of renewal planning and forecasting rhythms. You will establish the recurring operational cadences needed to maintain visibility into the book of business and ensure proper accountability across Sales and Customer Success teams.
• Improve Forecasting Predictability: Own the weekly aggregation and formalization of the renewals forecast. You will drive the evolution of the reporting infrastructure that provides visibility into risk aging, engagement gaps, and forecast accuracy.
• Operationalize Mitigation Playbooks: Partner with leadership to design mitigation strategies. You will support the build-out of associated playbooks, enablement assets, and tracking mechanisms for the field.
• Enforce Commercial Policy: Support the development of commercial contract renewal standards and oversee adherence within Customer Success. You will ensure systems and processes are optimized to maximize successful on-time customer renewal.
• Continuous Process Improvement: Regularly audit and iterate on renewal processes to remove friction for our internal teams and our customers.

You Have

• 7+ years of experience in Renewals Operations, Sales Operations, or Commercial Risk Management in an Enterprise SaaS environment.
• Systems Thinking: Demonstrated ability to translate complex commercial policies into streamlined system workflows in Salesforce or Gainsight.
• Commercial Fluency: Strong understanding of SaaS contract mechanics, including multi-year terms, uplift caps, and termination logic.
• Analytical Discipline: Leverage retention data to diagnose root causes for cancellations and downgrades to design segmented, process-based mitigations.
• Collaboration Skills: Experience working cross-functionally with Legal, Finance, and Sales to formalize and scale commercial processes.

Smartsheet is seeking a Sr. Technical Support Operations Manager to focus on the operational architecture required to balance efficiency with a high-quality customer experience. You will be responsible for the tools and logic that dictate how we staff our teams, how we measure quality, and how we route technical issues. Your goal is to move the support organization toward a predictive, data-driven model that integrates technical signals into the broader customer retention strategy.

You Will

• Lead Strategic Roadmap Planning: Partner with the Technical Support senior leadership team to drive the development of quarterly roadmaps and prioritization planning for the technical support organization.
• Optimize Support Delivery Process: Own the technical lifecycle of the global support stack, including oversight of Workforce Management and Quality Assurance tools. You will lead the design of scoring rubrics and staffing logic to maintain service level targets across global time zones.
• Drive Demand and Capacity Planning: Build the support capacity models used for long-term headcount planning. You will use historical volume data and growth projections to predict future support demand and determine the optimal staffing requirements to meet business needs.
• Manage Routing and Tiering Logic: Manage the technical rules, definitions, and workflows that dictate how cases are segmented and routed. You will ensure that technical issues reach the correct internal tiers immediately to minimize resolution time and customer effort.
• Operationalize Support-to-Success Handoffs: Design and manage the workflows that pass account risks, expansion opportunities or training gaps identified in support tickets to the appropriate Sales or Customer Success teams. You will ensure these handoffs are automated and trackable.
• Automate Premium Entitlements: Manage the technical integration of appointment scheduling systems for premium offerings. You will define the logic that verifies a customer’s entitlement in Salesforce before allowing access to specialized support sessions.
• Establish Product Feedback Loops: Partner with Product and Engineering to formalize the process for surfacing the voice of the customer sentiment, technical friction points and common product issues. You will provide the data-driven insights needed to influence the product roadmap and reduce support volume at the source.

You Have

• 7+ years of experience in Technical Support Operations, Revenue Operations, or Business Operations in a SaaS environment.
• Systems Expertise: Proficiency with Salesforce Service Cloud and integrated operational tools such as WFM and QA platforms.
• Analytical Proficiency: Strong capability in capacity modeling and volume forecasting, with the ability to translate data into actionable staffing plans.
• Operational Discipline: A track record of formalizing messy processes into documented, repeatable workflows that scale globally.
• Collaboration Skills: Experience partnering with Support VPs and Directors to build systems that meet aggressive service level targets without increasing operational friction.

Smartsheet is seeking a Learning Experience Designer to join our team. As a LxDesigner, you'll put our employees’ knowledge above all else and have a passion for creating learning solutions. You'll work on a motivated, supportive team with ownership of our internal learning and development products. Graphic design and knowledge of human-computer interaction are essential, and, of course, becoming a certified Smartsheet user is important to your success. 

You will report to our Manager, Learning Experience.This role is eligible for remote work within Costa Rica. You  must reside in Costa Rica.  

You Will:

• Develop creative, customer-centric, performance-based training materials.
• Manage learning product development projects, including scoping, managing Subject Matter Experts (SMEs), and working with other departments.
• Work with our Customer Excellence teams and SMEs to create storyboards/scripts and production-ready content that meet employees' needs.
• Report on and communicate the results of educational content to cross-functional stakeholders.
• Stay current on new learning approaches, behavioral science, and technology, and apply that knowledge to our learning products.
• Become a Smartsheet product expert
• Be an Administrator for the Learning Management System (LMS). Maintain systems, create user profiles, create usage reports, publish SCORM, video, and other digital content etc.
• Other job duties as assigned.

You Have

• 5+ years of combined experience building engaging educational content in various modalities in consultation with your stakeholders.
• At least 2 years of experience creating educational content for SaaS. 
• Strong grasp of adult learning principles.
• Proficiency in Articulate Storyline, Articulate Rise, and Camtasia
• Experience with digital content creation using Adobe Creative Cloud.
• A portfolio of eLearning, video, and graphic design projects. The portfolio should reflect graphic design skills with a clean aesthetic.
• Experience using ID strategies to launch digital training
• Experience managing and reporting on all curriculum and assessment data
• LMS administration experience, including eLearning publishing and learning assessments.
• Basic knowledge of web development (HTML5, CSS, JavaScript) is preferred.

Perks & Benefits:

• Fully paid Health & Life insurance for full-time employees and family members
• Monthly stipend to support your work and productivity
• 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 LinkedIn Learning 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)