Regional Enterprise 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

About Go Icon

Go Icon is a leading SaaS platform modernizing resident engagement and activities management for senior living communities. With 2,000+ customers and strong growth, we're bringing on elite sales talent to accelerate our expansion.

We operate with urgency, ownership, and tenacity. We hire adults, expect high output, and measure ourselves by outcomes - not activity. We move quickly, learn aggressively, and keep ego out of the way.

Position Overview

We are seeking a Regional Enterprise Account Executive to drive new business revenue through a multi-step, detailed consultative sales cycle in assigned region. This sales team member role requires managing the full sales cycle from qualified opportunity to close, with an annual quota of $1-1.5M ARR. The role will initially report to the CEO.

Required Qualifications

Domain Knowledge (Required)

• Candidates must have direct experience selling enterprise software to operations buyers in one or more of the following verticals:
  • Senior living (Activity Directors, Life Enrichment Directors, Executive Directors)
  • Healthcare operations (home health, hospice, skilled nursing, behavioral health)
  • Hospitality operations (hotel management, restaurant operations, guest experience)
• Note: Experience selling exclusively to IT or technical buyers (CIOs, CTOs) does not meet this requirement.
• Minimum 5 years of B2B SaaS sales experience as a regional / senior account executive
• Consistent track record of 100%+ quota attainment for 2+ consecutive years
• Demonstrated history of closing $1M-$1.5M+ ARR annually
• Win rate of 35-45% on qualified opportunities
• Expertise in consultative sales methodologies (MEDDIC, SPIN, Challenger, or similar)
• Proven ability to navigate complex, multi-stakeholder sales processes
• Strong discovery, demonstration, and negotiation skills
• Experience with technical sales including security and compliance discussions
• Excellent CRM discipline and forecasting accuracy

SaaS Industry & Stage Experience

• Growth-stage SaaS company experience ($5-50M ARR)
• Vertical SaaS experience with industry-specific solutions
• Comfort with high autonomy and minimal oversight environments

Key Responsibilities

• Achieve annual quota of $1-1.5M ARR (10-15 deals, $50-150K ACV)
• Manage complete sales cycle: discovery, qualification, demonstration, negotiation, and closing
• Conduct in-person discovery meetings to uncover operational pain and business requirements
• Deliver compelling, outcome-focused product demonstrations tailored to stakeholder needs
• Navigate technical sales processes including security reviews, IT approvals, and procurement
• Execute consultative, multi-threaded sale with multiple personas and decision makers
• Negotiate commercial terms and pricing within established guidelines
• Maintain accurate pipeline forecasting and CRM hygiene
• Collaborate with Product Managers on technical validation and deep-dive sessions
• Coordinate with Customer Success on seamless customer handoffs

Region & Pipeline Management and Generation

• Build and maintain pipeline at 3x quota coverage ($3-4.5M)
• Qualify inbound leads and convert to sales opportunities
• Execute targeted outbound prospecting in assigned region

  Preferred Qualifications

  • Familiarity with senior living technology ecosystem (PointClickCare, MatrixCare, Yardi Senior Living)
  • Experience with EHR/ERP integrations and enterprise software implementations
  • Track record of building or partnering with Sales Engineer functions
  • Active participation in relevant industry associations (ASHA, Argentum, LeadingAge)
  • Bachelor’s degree from an accredited 4-year institution
  • Hunter mentality with bias toward new logo acquisition
  • Detailed-oriented, consultative selling to non-technical operations buyers
  • Executive presence and ability to engage C-suite stakeholders
  • Objection handling and competitive displacement
  • Self-direction and ability to thrive with minimal supervision
  • Resilience and persistence in face of rejection
  • High integrity and trust-building with customers
  • Variable Compensation: $125,000 - $135,000
  • Total OTE: $250,000 - $270,000
  • Commission Structure: Uncapped with accelerators at 100%+ quota attainment
  • Benefits: Comprehensive health, dental, and vision insurance, Unlimited PTO, 401K with 4% employer match
  • Remote with Travel (onsites at Chicago office)