Who We Are
Rilla’s the leading virtual ridealong software for outside sales. Think home improvement, home builders, property managers, and other sales people who talk to customers face to face.
Sales reps talk, our mobile app records their conversations, and our AI automatically transcribes and analyzes their conversations to help them improve their sales.
Our vision is to bring the power of conversation intelligence from the Zoom meeting and the call center to the more than 10M sales people who work offline.
We are one of the fastest growing startups in the world right now and in history.
We’re backed by Crystal Huang of Google Ventures, and Byron Deeter (one of the best investors of all time) from Bessemer Venture Partners, the top Cloud investor in the world.
And we’re a Cloud 100 Rising Star company.
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.
The Role
Rilla is growing quickly, and you’ll play a big part in opening up new markets and helping our customers fundamentally change their businesses. As an Enterprise Account Executive, you will help identify, engage, and close new business from strategic enterprise customers.
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.
What You’ll Do
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
What You Need
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
Do Not Work Here
Please don't join if you're not excited about:
Working ~70 hrs/week in person with some of the most ambitious people in NYC
Attempting to build a generational company, and the intensity required to do so
Benefits
Medical, dental, and vision insurance
Breakfast, lunch, dinner, and snacks provided 6 days/week
Wellness / Gym Benefits
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