[All remote jobs](https://jobicy.com/jobs.md)[![Smartsheet logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/8b6103bd-221.jpg)](https://jobicy.com/company/smartsheet.md)[Smartsheet](https://jobicy.com/company/smartsheet.md) # Commercial Account Executive (Remote Eligible – Costa Rica) Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/smartsheet.md)ShareRemote from[Costa Rica](https://jobicy.com/job-region/costa-rica.md)SalaryUndisclosedDepartment[Sales](https://jobicy.com/categories/seller.md)EmploymentFull TimeExperienceDirectorPublished23 Oct 2026Apply before22 Nov 2026Listing views37Application actions1Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. Smartsheet is seeking a Commercial Account Executive to drive expansion and revenue growth across a portfolio of B2B accounts in Costa Rica. The role centers on consultative, solution-based selling, executive relationship management, pipeline development, forecasting, and complex deal execution. The successful candidate will apply MEDDICC, use Salesforce, Outreach, and Tableau, and partner closely with solution engineering and customer success teams. This is a remote, full-time sales role for a resilient technology seller with 1–3 years of progressive experience and strong English communication skills. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 4/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 4/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThe position requires ownership of complex B2B software sales cycles, reliable forecasting, and influence with C-level stakeholders. Success depends on consistently achieving targets while coordinating multiple internal and client-side decision-makers. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Market rate$50,000US market range (per year)$35k–$70k0$77k AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. No employer salary was disclosed. The yearly cadence and USD compensation estimates are inferred for a full-time Commercial Account Executive role based in Costa Rica; actual pay may vary by base-versus-variable commission structure, quota, experience, and local payroll practices. ## Core skills Skills and capabilities most closely associated with this opportunity. [B2B software sales](https://jobicy.com/jobs?search_keywords=B2B%20software%20sales.md)[Account management](https://jobicy.com/jobs?search_keywords=Account%20management.md)[Consultative selling](https://jobicy.com/jobs?search_keywords=Consultative%20selling.md)[MEDDICC](https://jobicy.com/jobs?search_keywords=MEDDICC.md)[Pipeline management](https://jobicy.com/jobs?search_keywords=Pipeline%20management.md)[Sales forecasting](https://jobicy.com/jobs?search_keywords=Sales%20forecasting.md)[Executive stakeholder management](https://jobicy.com/jobs?search_keywords=Executive%20stakeholder%20management.md)[Complex deal negotiation](https://jobicy.com/jobs?search_keywords=Complex%20deal%20negotiation.md)[Salesforce](https://jobicy.com/jobs?search_keywords=Salesforce.md)[Outreach](https://jobicy.com/jobs?search_keywords=Outreach.md)[Tableau](https://jobicy.com/jobs?search_keywords=Tableau.md)[Solution selling](https://jobicy.com/jobs?search_keywords=Solution%20selling.md)[Customer expansion](https://jobicy.com/jobs?search_keywords=Customer%20expansion.md)[English communication](https://jobicy.com/jobs?search_keywords=English%20communication.md) Sample interview questionsHow do you use MEDDICC to qualify a complex opportunity?I map each component early: measurable customer outcomes, the economic buyer, decision criteria and process, identified pain, internal champion, and competitive position. I use gaps in that map to plan discovery and reduce risk before forecasting the deal. Describe how you would identify expansion opportunities within an existing account. I would review usage patterns, business objectives, stakeholder changes, support themes, and upcoming initiatives. I would then validate the customer's priority through discovery and build a value-based proposal with the relevant internal teams. How do you create an accurate sales forecast? I maintain clear stage criteria, validate mutual next steps, assess decision process and champion strength, and record risks in the CRM. I distinguish committed opportunities from upside based on evidence rather than optimism. How would you engage a C-level buyer who is not yet convinced of the platform's value? I would lead with the executive's strategic priorities and quantify the operational or financial impact of the current problem. I would tailor the conversation to measurable outcomes, share relevant proof points, and align a concise path to a decision. Tell us about your approach to managing a difficult sales cycle with multiple stakeholders. I establish stakeholder roles, confirm decision criteria, and create a mutual action plan with dates and owners. I communicate consistently, bring in technical or customer-success partners when needed, and address objections directly while keeping the customer focused on desired outcomes. Opportunity details ## About this role. For over 20 years, Smartsheet has empowered teams to manage work seamlessly and scale solutions smarter. Now, in our most ambitious chapter yet, we are uniting human teams with AI agents. By orchestrating the work agents do best, automating manual tasks and uncovering insights at scale, we create the space for people to focus on what truly matters: judgment, creativity, and big thinking. That is magic at work, and it’s what we show up for every day. Smartsheet is empowering ambitious sales professionals to join our team as Account Executives. In this role, you’ll transcend traditional sales, becoming a trusted advisor and strategic partner to our customers. You’ll be at the forefront of driving significant revenue growth by managing and expanding relationships within a portfolio of accounts. This is your chance to leverage your strategic thinking and sales acumen to navigate complex deals and deliver transformative solutions that directly impact our clients’ success. At Smartsheet, we provide a leading cloud-based platform for work execution, enabling organizations to plan, capture, track, automate, and report on work at scale. We are committed to fostering a culture of trust and innovation, empowering our team to deliver exceptional value to our clients. This role is eligible for remote work within Costa Rica. You must reside in Costa Rica. You will: * Drive Strategic Growth: Exceed software and services sales targets by developing and executing strategic account plans for clients. * Cultivate Executive Relationships: Build and nurture strong relationships with C-level executives and key decision-makers, positioning Smartsheet as a strategic partner. * Navigate Complex Deals: Lead complex, solution-based sales cycles, aligning Smartsheet’s capabilities with clients’ strategic objectives and driving significant deal closures. * Proactive Opportunity Identification: Identify and capitalize on expansion opportunities within existing accounts, anticipating client needs and proactively offering tailored solutions. * Strategic Pipeline Management: Develop and maintain a robust sales pipeline, accurately forecasting revenue and leveraging data-driven insights to optimize sales strategies. * MEDDICC: Expertly apply MEDDICC qualification methodologies to ensure deal success and drive predictable revenue growth. * Cross-Functional Collaboration: Partner with internal and external stakeholders, including solution engineering and customer success teams, to deliver exceptional client experiences. * Sales Leadership: Embody the traits of an elite sales professional, serving as a mentor and role model for the team. * Other job duties as assigned. You have: * Proven Sales Expertise: 1-3 years of progressive sales experience, with a strong track record of success in the software or technology sector. * Strategic Account Management: Demonstrated ability to manage and expand relationships within accounts in a B2B environment. * Strategic Thinking and Problem-Solving: Ability to analyze complex client needs, develop strategic solutions, and navigate challenging sales cycles. * Professional Presence and Communication: Exceptional written and verbal communication skills, with the ability to effectively engage and influence C-level executives. B2 English Proficiency Level or higher. * Technical Acumen: Passion for technology and the ability to quickly grasp complex technical concepts. * Sales Tools Proficiency: Proficiency in CRM systems (Salesforce), sales engagement tools (Outreach), data visualization platforms (Tableau), and others as needed. * Resilience and Adaptability: Ability to thrive in a fast-paced environment, adapt to change, and overcome challenges. * Educational Background: Degree in Business Administration, Marketing, Sales, or a related field preferred, or equivalent sales experience. * Smartsheet Expertise: Deep understanding of the Smartsheet platform and advanced capabilities. * Complex Solution Sales: Proven ability to execute complex solution sales involving both software and services. Perks & 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 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, India, and Singapore. 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 Show more [Apply now >](https://jobicy.com/jobs/156650-commercial-account-executive-remote-eligible-costa-rica.md) > Annual salary information is not provided for this position. 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