Enterprise Account Executive

Rilla builds the leading virtual ride-along software for outside sales and service teams — HVAC, windows, roofing, solar, real estate, and every rep who sells face-to-face.

They talk. Our mobile app listens.
Our AI transcribes, analyzes, and transforms every conversation into insights that help teams sell more, faster.

We’re bringing conversation intelligence out of Zoom and call centers into the field — where 10M+ salespeople work offline.

And it's working.

We’re growing 20% month over month, with dozens of customers, including Fortune 500s.
We have 170%+ NRR, an NPS higher than the iPhone, we’re profitable, and we’re backed by Byron Deeter (Bessemer) — the #1 cloud investor globally.
We’re also a Cloud 100 Rising Star and one of the fastest-growing startups in history.

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

• 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