Remote Regional Enterprise SaaS Account Executive

Go Icon; Chicago (IL); Hybrid; USD 125,000 - 135,000; Full time

Benefits offered by this job

Health, dental, and vision insurance

Unlimited PTO

401K with 4% employer match

Job summary

Go Icon is seeking a Regional Enterprise Account Executive to drive new business across the assigned region. The role manages the full sales cycle from qualified opportunity to close, with a quota of $1–1.5M ARR, reporting to the CEO.

The ideal candidate blends consultative selling with MEDDIC/Challenger methodologies and thrives in a growth-stage SaaS environment. Responsibilities include in-person discovery, tailored product demonstrations, security reviews, IT approvals, and negotiations.

Qualifications

• 5+ years of B2B SaaS sales, regional/senior account executive.
• Experience selling to operations buyers in senior living/healthcare/hospitality.
• Quota attainment of 100%+ for 2+ years.
• Closed $1M-$1.5M ARR annually.
• Win rate 35-45% on qualified opportunities.
• MEDDIC, SPIN, Challenger or similar sales methodologies.
• Navigate complex multi-stakeholder sales processes.
• CRM forecasting and pipeline hygiene; security/compliance discussions.

Responsibilities

• Achieve annual quota of $1-1.5M ARR (10-15 deals, $50-150K ACV).
• Manage complete sales cycle from discovery to closing.
• Conduct in-person discovery meetings to uncover pain and requirements.
• Deliver outcome-focused product demonstrations for stakeholders.
• Navigate security reviews, IT approvals, and procurement.
• Execute multi-threaded sales with multiple personas and decision makers.
• Negotiate terms within guidelines; maintain pipeline forecasting.
• Collaborate with Product Managers on technical validation.
• Coordinate with Customer Success on handoffs.
• Build pipeline in region and qualify inbound leads; outbound prospecting.

Skills

Enterprise SaaS sales

Quota attainment

Multi-stakeholder sales

MEDDIC/SPIN/Challenger

CRM forecasting

Security & compliance talks

In-person discovery

Negotiation skills

Education

Bachelor’s degree

Tools

Salesforce

PointClickCare

MatrixCare

Yardi Senior Living

Job description

Go Icon is seeking a Regional Enterprise Account Executive to drive new business across the assigned region. The role manages the full sales cycle from qualified opportunity to close, with a quota of $1–1.5M ARR, reporting to the CEO.

The ideal candidate blends consultative selling with MEDDIC/Challenger methodologies and thrives in a growth-stage SaaS environment. Responsibilities include in-person discovery, tailored product demonstrations, security reviews, IT approvals, and negotiations.