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Rilla builds the leading virtual ride-along software for outside sales and service teams. We’re bringing conversation intelligence out of Zoom and call centers into the field. We’re growing 20% month over month, with dozens of customers, including Fortune 500s. Now we’re building our Founding Enterprise Sales Team — the AEs who will define how Rilla enters new markets, closes our largest customers, and shapes the playbook for our next stage. This is a role for elite hunters: people who have closed 7-8 figure deals, immediately see where we win, and want to build something generational.
Job Responsibility:
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
What we offer:
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