Why This Job is Featured on The SaaS Jobs
Rilla sits in a distinct part of the SaaS landscape: conversation intelligence applied to offline, field-based selling rather than desk-bound call centers. That focus brings enterprise SaaS patterns into industries where data capture and coaching have historically been uneven, creating a clear use case for AI-driven workflow change and measurable commercial impact.
From a SaaS career standpoint, the role maps to the parts of enterprise selling that tend to compound over time: multi-threading across stakeholders, translating product capabilities into ROI narratives, and navigating longer buying cycles with technical and operational counterparts. Building fluency in integrations, workflow mapping, and executive-level discovery is broadly transferable across modern B2B SaaS categories, particularly analytics, enablement, and AI applications.
This position is best suited to a sales professional who prefers owning outcomes end to end, from self-sourced pipeline through negotiation, and who is comfortable operating with limited playbook structure while helping shape one. It will fit someone motivated by complex deals, cross-functional collaboration with solutions and product partners, and a market where category definition is still being established.
The section above is editorial commentary from The SaaS Jobs, provided to help SaaS professionals understand the role in a broader industry context.
Job Description
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
