Commercial Account Executive (Remote Eligible - Costa Rica)

Tech Sales Jobs; United States; Remote; USD 90,000 - 120,000; Full time

Benefits offered by this job

Fully paid Health & Life insurance for

Monthly stipend

Paid vacation + time away

Maternity/Paternity leave

LinkedIn Learning access

Professional growth opportunities

Teleworking options in CR

Job summary

Smartsheet is seeking an Commercial Account Executive (Remote Eligible - Costa Rica) to drive strategic growth and manage a portfolio of accounts from a remote setting in Costa Rica. You will build executive relationships, navigate complex deals, and apply MEDDICC methodologies to forecast and close opportunities, while collaborating with engineering and customer success teams to deliver exceptional value.

Ideal candidates bring 1–3 years in software sales, strong strategic thinking, and proven

Qualifications

• 1–3 years of progressive sales experience in software/tech.
• Experience managing B2B accounts.
• Strong written and verbal communication with C-levels.

Responsibilities

• Drive Strategic Growth: Exceed software and services sales targets by developing and executing strategic account plans.
• Cultivate Executive Relationships: Build and nurture relationships with C-level executives and key decision-makers.
• Navigate Complex Deals: Lead complex, solution-based sales cycles and drive significant deal closures.
• Proactive Opportunity Identification: Identify expansion opportunities within existing accounts and offer tailored solutions.
• Strategic Pipeline Management: Develop and maintain a robust sales pipeline and forecast revenue.
• MEDDICC: Apply MEDDICC to ensure deal success and growth.
• Cross-Functional Collaboration: Partner with solution engineering and customer success teams.
• Sales Leadership: Mentor and model elite sales behaviors.
• Other duties as assigned.

Skills

Sales experience

Strategic account mgmt

C-level engagement

Communication skills

Technical acumen

Education

Bachelor's degree in business or related field

Tools

Salesforce

Outreach

Tableau

Job description

Commercial Account Executive (Remote Eligible - Costa Rica)

Location: San Jose, CR

Department: Commercial Sales

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 possible alliances with entities such as universities, gyms, etc.
• 12 days paid Vacation + Flexible Time Away Program
• 20 weeks fully paid Maternity Leave12 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.