Enterprise AI Sales Executive at Wonderful - Remote — Columbus
Traveler-Friendly Insight
Location & Remote Flexibility: This role is hinted as based in Bridgetown, Barbados. However, enterprise sales roles at high-growth AI/SaaS companies often carry significant flexibility for seasoned performers — especially when covering a regional territory. The job description mentions no explicit office requirement, which is a mild green flag for partial remote work, though enterprise sales typically requires in-person customer visits.
Timezone Considerations: Barbados operates on AST (UTC-4), which aligns well with North and South American business hours. Digital nomads based in the Americas — from Medellín to Miami — would find this timezone manageable without major schedule disruption.
Cost of Living Snapshot (relative to likely OTE):
- Bridgetown, Barbados: Higher cost of living for the Caribbean; rent for a 1BR can exceed $1,500/mo USD. Suitable if compensation is competitive.
- Medellín, Colombia: Much lower cost of living (~$800-1,200/mo), ideal if full remote is confirmed.
- Lisbon, Portugal: Mid-range (~$1,400-1,800/mo); Barbados Digital Nomad Visa could be an option for short stints.
Visa Note: Barbados offers a "Welcome Stamp" 12-month remote work visa, making it accessible for nomads if the employer supports remote arrangements. However, confirm whether this role requires residency in Barbados or simply regional availability before applying.
You'll lead and close high-stakes enterprise deals across the region, expand existing relationships, and create durable revenue streams with major organizations.
- Build and grow trusted relationships with CxOs, IT leaders, and Customer Service executives in large enterprises.
- Drive measurable growth within the accounts you own, turning them into long-term success stories.
- Expand Wonderful's footprint by opening new doors and landing fresh enterprise customers.
- Hit — and exceed — activity, pipeline, and revenue targets, setting the bar for sales excellence.
- Keep customer details sharp and actionable in Salesforce: use cases, purchase timelines, next steps, and forecasts.
- Sell on value, not features, using a solution-based approach that proves real business impact for customers.
- 7+ years of smashing sales quotas in SaaS or AI-driven solutions, consistently closing large, complex accounts with multi-stakeholder cycles.
- Exceptional communication, presentation, and negotiation skills.
- The ability to work independently, manage a sales pipeline, and prioritize effectively.
- Excellent English (written and spoken) plus fluency in local language.
- A passion for artificial intelligence and a "get-it-done" attitude.
- A "hunter" mentality with a track record of generating new leads and closing deals.
- A proven ability to navigate and win in early-stage, high-growth environments, staying sharp and effective with limited oversight.
- Strong relationships with CxOs and senior decision-makers at enterprise level with the credibility to open new doors fast.
- The skill to cut through tech jargon and turn technical capabilities into clear, compelling business value that makes executives lean in.
- Proven wins working hand-in-hand with System Integrators and Hyperscalers to drive joint success.
- Bachelor's Degree (or equivalent hustle and expertise).
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Frequently Asked Questions
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