Enterprise Account Executive

About the role

Rilla is a leading virtual ridealong software designed for outside sales professionals in industries such as home improvement, home builders, and property management. Our AI-powered system captures and analyzes conversations between sales reps and customers, providing insights to enhance sales effectiveness.

Responsibilities

• Run the full Enterprise cycle: outbound prospecting, multi-stakeholder discovery, tailored demos, ROI modeling, negotiations, and closing
• Sell directly to C-Suite, VPs, Directors, and operational leaders across field-heavy enterprises
• Lead multi-threaded, complex sales cycles with cross-functional support (Solutions, Product, SEs, CSMs)
• Develop deep expertise in multiple verticals and bring market intelligence back to the org
• Build playbooks and repeatable processes as one of the first Enterprise AEs on the team
• Forecast with precision while managing 10-15 active opportunities
• Establish Rilla as the category leader in every new vertical we open

Requirements

• 3-4+ years of Enterprise SaaS sales, consistently closing 7-8 figure ACVs
• Proven success selling into large, Fortune 1000 companies
• Strong technical fluency — comfortable demoing, discussing integrations, API/ workflow mapping, and partnering with technical stakeholders
• A true hunter mentality: evidence of consistent self-sourced pipeline generation and strong outbound muscle
• Operates with grit, speed, and obsession — thrives in high-growth, high-intensity environments
• Highly coachable, curious, and competitive
• Exceptional written and verbal communication skills — able to lead rooms of senior executives and command attention

Qualifications

• Exceptional written and verbal communication skills — able to lead rooms of senior executives and command attention

Skills

• Exceptional written and verbal communication skills — able to lead rooms of senior executives and command attention

Benefits

• Medical, dental, and vision insurance
• Breakfast, lunch, dinner, and snacks provided 6 days/week
• Gym membership
• Commuter benefits
• Relocation assistance
• Take-what-you-need PTO
• $1,000 annual learning & development stipend
• All necessary tech equipment
• Rent stipend for qualifying employees relocating to NYC

Pay

$200K - $300K base salary + bonus

Schedule

Full-time, remote with some in-person meetings in NYC