["Full-Time"]
Remote
SaaS
jobicy
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
Selling Motion
Sales Cycle
Enterprise
6–18 month cycles, complex multi-stakeholder deals
Prospecting
Channel / Partner
Sell through partners, resellers, or alliances
Buyer Persona
C-Suite
Selling to executive decision-makers
Territory
Named Accounts
Pre-assigned list of target companies
Requirements at a Glance
Typical Day — Account Executive
Estimates based on role type and selling motion — actual may vary by company.
Role Signals
Green Flags
Inherit existing accounts
Location flexibility
SaaS — Interview Intel
Typical Sales Cycle
30–90 days (SMB) · 3–9 months (Mid-Market) · 6–18 months (Enterprise)
Common Buyer Objections
- "We're locked into a contract with [competitor]"
- "We built something in-house already"
- "We don't have budget until next quarter"
- "Our team won't adopt another tool"
Key Industry Metrics
Hot Topics to Reference
- • AI-native product disruption
- • PLG vs sales-led motion debate
- • Vertical SaaS consolidation
- • Usage-based pricing models
Use these insights to speak the buyer's language in interviews.
Tags
Walk me through your discovery process.
Template questionHow do you handle a prospect who goes silent mid-deal?
Template questionTell me about your largest closed deal and the sales cycle.
Template questionHow do you build business cases for stakeholders?
Template questionDescribe a deal you lost and what you learned.
Template questionAs an Account Executive with Smartsheet, you'll own the entire revenue pipeline and be measured on quota attainment.
Expect to work with recurring revenue models where customer retention is as important as acquisition.
Remote positions in sales offer flexibility but require strong self-discipline and proactive communication with distributed teams.
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