Remote Sr. Sales Success Specialist (Remote Eligible-Costa Rica)

For over 20 years, Smartsheet has helped people and teams achieve–well, anything. From seamless work management to smart, scalable solutions, we’ve always worked with flow. We’re building tools that empower teams to automate the manual, uncover insights, and scale smarter. But more than that, we’re creating space– space to think big, take action, and unlock the kind of work that truly matters. Because when challenge meets purpose, and passion turns into progress, that’s magic at work, and it’s what we show up for everyday.
Smartsheet is looking for an experienced Sr Sales Success Specialist to support the sales teams throughout the sales cycle.

In 2005, Smartsheet was founded on the idea that teams and millions of people worldwide deserve a better way to deliver their very best work. Today, we deliver a leading cloud-based platform for work execution, empowering organizations to plan, capture, track, automate, and report on work at scale, resulting in more efficient processes and better business outcomes.

You will report to our Manager, Sales Success located in the US. This role is eligible for remote work within Costa Rica. You must reside in Costa Rica.

You Will:

Aligned to a specific set of Accounts and/or Territories, the Sr Sales Success Specialist will provide support for monthly forecasting & sales transaction process

Attend forecast calls & actively review sales pipeline in Clari and corresponding deal information in Salesforce to anticipate potential booking issues or negative customer experience impact

Partner with account manager in managing and driving pipeline and revenue

Provides leadership & works to resolve potential deal issues during the negotiation process, giving guidance on complex deal structure, and deliver solutions for non-standard requests

Escalate specialized issues to appropriate partners for resolution and approval

Coordinate deal reviews with sales; support training, development, and compliance with operational policies

Analyze and review current customer licensing, products and usage and partner with the account manager to identify new revenue opportunities

Provide routine reporting and analysis on team operations & transaction metrics

Share best practices with team members to enhance the quality and efficiency of support and contribute to the knowledge base through creating SOPs and training

Contribute ideas and innovations to improve upon existing systems, work processes and procedures.

Work cross-functionally with multiple internal Departments (Deal Desk, Order Operations, Partner Support, Revenue Accounting, Finance Operations, Fulfillment [Provisioning], Legal, Customer Success, Sales, Professional Services, Tax).

Support EOM, EOQ and EOY close to make sure all business closes on time.

Other job duties as assigned.

You Have:

5-8+ years experience in a 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.

Knowledge of revenue recognition rules / requirements related to software / services.

Proficiency in 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 financial Governance.

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)

Get to Know Us:

At Smartsheet, your ideas are heard, your potential is supported, and your contributions have real impact. You’ll have the freedom to explore, push boundaries, and grow beyond your role. We welcome diverse perspectives and nontraditional paths—because we know that impact comes from individuals who care deeply and challenge thoughtfully. When you’re doing work that stretches you, excites you, and connects you to something bigger, that’s magic at work. Let’s build what’s next, together.

Equal Opportunity Employer:

Smartsheet is an Equal Opportunity (EEO) employer committed to fostering an inclusive environment with the best employees. It is our policy to provide equal employment opportunities to all qualified applicants in accordance with applicable laws in the US, UK, Australia, Germany, Costa Rica, Japan, Bulgaria, and India. All qualified applicants will receive consideration without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran or disabled status, or genetic information.

If there are preparations we can make to help ensure you have a comfortable and positive interview experience, please let us know.

LI-Remote