Regional Enterprise Account Executive

Go Icon; Chicago, Northern (IL, KY); Hybride; USD 125 000 - 270 000; Plein temps

Avantages offerts par ce poste

Comprehensive health, dental, and 401K

Unlimited PTO

Remote with travel (Chicago office)

Résumé du poste

Go Icon, a leading SaaS platform for senior living and healthcare operations, seeks a Regional Enterprise Account Executive to drive $1-1.5M ARR in a multi-step consultative sales cycle. You will own the full sales cycle from qualified opportunity to close, working with multiple stakeholders and driving security/compliance discussions.

This role requires 5+ years of B2B SaaS sales, a history of achieving quota, and experience selling to operations buyers in senior living, healthcare, or

Qualifications

• Direct experience selling enterprise software to operations buyers in senior living, healthcare or hospitality operations
• Minimum 5 years of B2B SaaS sales as regional/senior account executive
• Consistent 100%+ quota attainment for 2+ years
• Closing $1M-$1.5M+ ARR annually
• Experience with security/compliance discussions and multiple stakeholders
• Strong discovery, demonstration, and negotiation skills
• Proven ability to navigate complex sales processes with CRM discipline

Responsabilités

• Achieve annual quota of $1-1.5M ARR (10-15 deals, $50-150K ACV)
• Manage complete sales cycle from discovery to close
• Conduct in-person discovery meetings to uncover operational pain
• Deliver tailored product demonstrations for stakeholders
• Navigate security reviews, IT approvals, and procurement
• Coordinate with Product and Customer Success for technical validation and handoffs
• Maintain accurate pipeline forecasting and CRM hygiene
• Build pipeline and account strategies across multi-site enterprises
• Attend events to generate regional pipeline

Connaissances

Enterprise software sales

B2B SaaS sales

Quota attainment

Multi-stakeholder selling

Consultative selling

Negotiation

CRM discipline

Security & compliance discussions

Forecasting accuracy

Discovery & demonstrations

Formation

Bachelor's degree

Outils

CRM (Salesforce)

ERP integrations

Description du poste

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
• Develop account strategies to succeed across multiple personas and decision makers within large enterprises (multi-site senior living organizations)
• Maintain regular communication cadence with active opportunities
• Attend networking events and conferences to generate pipeline

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)