---
title: 'Director of Enterprise Sales at Rilla'
canonical: 'https://feeny.ai/job/director-of-enterprise-sales-rilla-new-york-hyp8gs97314z'
type: 'job'
last_seen: '2026-09-10'
---

# Director of Enterprise Sales at Rilla

- **Company:** Rilla
- **Location:** New York, NY
- **Compensation:** $160k–$200k
- **Employment:** full-time
- **Work type:** onsite
- **Posted:** 2026-06-17
- **Last confirmed live:** 2026-09-10
- **Apply:** https://jobs.ashbyhq.com/rilla/34ec488e-4dd1-4862-9e6f-9b0f73cc533f

## Job description

A Foundational Company Rilla builds the leading conversation intelligence software for offline commerce. Salespeople talk, our mobile app records the conversation, and our AI transcribes and analyzes it to make them better at their jobs. We’re bringing the technology of the 21st century’s most innovative companies to the more than 10 million salespeople who work face to face. We’ve grown from zero to $55M+ in ARR in four years, and we’re profitable. We sell to enterprises like The Home Depot, KKR, Neighborly, and PulteGroup. We’re backed by Google Ventures, Bessemer Venture Partners, Crew Capital, and Broom Ventures. We hire people with high agency and high urgency. We’re in-office because the best work happens when ambitious people are in the same room.

## The Role

This role is for someone who has done both. Closed at the top of the board and taken a team to numbers it had never touched. You know the difference between carrying a quota and building the engine that blows past one. Now you want to build and lead your own here.

- You want to pass on everything you've learned, build something real at a startup, and grow a team in your image. You're on the way up, with everything to prove, and you'll outwork anyone in the room.
- You get your hands dirty.
- You lead by example.
- At Rilla, leaders are second-class citizens. You work for your team, not the other way around. Your job is to clear their obstacles, make everyone around you better, and put them first.
- You hire great reps, coach them hard, and build a team that wins.

## What You'll Do

- Lead, grow, and develop a team of enterprise AEs. Set a high bar for pipeline, deal quality, and quota attainment, and coach the team hard to clear it.
- Design and own how enterprise sales runs at Rilla: the sales process, playbooks, and deal motions that turn complex, multi-stakeholder deals into predictable wins.
- Coach your reps into trusted advisors to enterprise buyers. Help them run long sales cycles, win over multiple stakeholders, get through procurement and security, and sell outcomes instead of features.
- Stay in the biggest deals yourself. Run the toughest closes alongside your reps and show them how it’s done.
- Own the forecast. Define the metrics that matter (pipeline coverage, win rate, cycle time, ACV, net new ARR) and build the pipeline reviews and accountability to move them.
- Be the clearest voice for what enterprise prospects need from the product. Turn what you hear in deals into sharp, prioritized feedback that shapes the Rilla roadmap.
- Partner across Marketing, SDRs, Customer Success, and Product to give buyers one seamless experience from first touch through close and expansion, and clear the internal friction that slows deals down.

## Who You Are

- A customer obsessive. You deeply care about delighting customers and solving their pains, not about vanity metrics.
- An infinite learner. You’re always looking to learn more and learn faster. You feel uneasy when you get complacent, and you’re constantly seeking discomfort.
- A team player. You love giving and receiving feedback, and learning and growing as a team.
- Unafraid of failure. You take risks. You see failure as an opportunity to learn, grow, and be better the next time. You’re excited by the unconventional.
- Extremely focused. You practice extreme focus in everything you do. You’re always prioritizing your time and resources for maximum efficiency.
- Our operating principle is that we try to run Rilla like a high speed reinforcement learner: a machine learning algorithm that plays a game a million times over and becomes invincible in a short amount of time.

## Skills & Requirements

- You put your team first, always. Their growth is the scoreboard you actually care about, and you’d trade your own spotlight for their wins every time.
- You’re a proven top enterprise closer. You carried a big number and beat it, again and again, winning complex, multi-stakeholder deals that other reps couldn’t.
- You’re ready to step into leadership and build a team, and you want to pass on the playbook that made you great.
- You know what great enterprise selling looks like and can develop it in others: coaching reps through long cycles, multiple stakeholders, procurement, and security reviews.
- You build trust with executives and the C-suite, and you can coach your reps to earn that same trust.
- You develop people intentionally: you invest in each rep’s growth, give direct feedback, and create the conditions for your team to do the best work of their careers.

Nice to Haves

- You were an early hire at a fast-growing startup.
- You’ve sold a behavior-change, coaching, or enablement product, where the win is getting a whole team to work differently, not just signing a contract.
- You’ve already mentored or coached reps on the side, and you want to do it for real.

## Benefits

- Medical, dental, and vision insurance
- 401(k) retirement plan
- Parental leave
- Fertility benefits
- Breakfast, lunch, dinner, and snacks 6 days a week in our NYC office
- Wellness / Gym Benefits
- Commuter benefits
- Relocation assistance to NYC
- Unlimited PTO (not accrual-based — take what you need)
- $1,000 annual learning and development stipend
- Tech equipment + unlimited Claude spend

## About Rilla

## Company Overview
- **One-liner**: Rilla provides an AI-powered coaching platform that records, transcribes, and analyzes in-person sales conversations to give managers 100% field visibility and accelerate rep performance.
- **Entity Type**: Private (Seed Stage – raised $3.9M total)
- **Headquarters**: New York, New York, United States
- **Founded**: 2019
- **Founders**: Sebastian Jimenez (CEO), Chris Martin (CTO, Co-Founder), Michael Castellanos (Chief Data Scientist, Co-Founder)

## Core Business
- **Primary industry**: AI-powered sales enablement and conversation intelligence for in-person sales teams.
- **Target customers**: B2B – field sales organizations in home services, home building, automotive, dental, senior living, multifamily, and other verticals where sales happen offline.
- **Mission statement**: *“Make the offline world as searchable as the web.”* The company aims to create the first living map of offline commerce.

## Products & Services
- **Rilla AI Coaching Platform**: A mobile app and web platform that records in-person sales conversations, then automatically transcribes, analyzes, and delivers coaching feedback. Managers can perform “virtual ridealongs” in minutes instead of hours. The AI adapts to each team’s sales process and best performers.

## Market Standing
- **Valuation/Market Cap**: Not disclosed (privately held).
- **Key Metric – Annual Revenue**: $25M–$50M (LinkedIn estimate, 2026).
- **Key Metric – Total Funding**: $3.9M across three seed rounds. Lead investor in latest round (Seed, Dec. 2022): **Crew Capital**.
- **Notable Investors/Partners**: Crew Capital; also 7 additional investors in the last round. Advisors include Filip Kaliszan (CEO & Founder of Verkada), Jim Kowalski (fmr Group VP North America, Oracle), Daniel Dines (CEO & Founder of UiPath), Nikolay Storonsky (CEO & Founder of Revolut), Steve Zahm (Cofounder of Procore).
- **Growth Signals**:
  - Headcount grew **64.5% YoY** to 108 employees.
  - Net revenue retention reported at **232%** (from careers page).
  - Average increase in close rates of **+40%** and average increase in ticket price of **+17%** for customers.
  - Trusted by thousands of sales teams in verticals like home improvement, home building, dental, and automotive.
  - Recently partnered with Neighborly (March 2026) to empower plumbers and HVAC technicians with AI.

## Competitive Advantages
- **Purpose-built for offline sales** – unlike generic conversation intelligence platforms, Rilla focuses exclusively on in-person field sales, capturing voice, location, and context.
- **Rapid onboarding** – claims setup in 1 hour 45 minutes.
- **Unprecedented visibility** – managers can review every rep’s appointment every day without being physically present.
- **High-performance coaching** – customers report 40–50% performance improvement within the first month, with reps achieving 627% monthly sales increases from instant feedback.

## Strategic Focus
- Continue dominating verticals with heavy offline commerce (home services, building, dental, automotive, senior living).
- Expand AI capabilities to serve more industries and deepen personalization of coaching.
- Build the “first living map of offline commerce” by indexing millions of in-person sales interactions.

## Why Work Here
- **Compensation**: 90th percentile of market rate; competitive salaries and equity.
- **Benefits**:
  - Full medical, dental, and vision coverage.
  - Unlimited PTO.
  - Free daily breakfast, lunch, dinner, and snacks.
  - Gym membership (fitness benefits).
  - Commuter benefits (fully covered transit/ride-shares).
  - Parental leave.
  - $1,000 annual learning stipend (courses, books, conferences).
  - Proximity stipend for employees near the office.
- **Culture & Work Environment**:
  - Values: Obsession, Speed, Simplicity, Fun.
  - Hybrid-friendly: New York HQ with a proximity stipend; also operates in Canada, Australia, Nigeria, UK, and Poland.
  - Company offsites twice a year (past trips: San Diego, Cape Cod, Palm Springs).
  - Leadership team includes former founders, D1 athletes, and top tech company alumni.
  - High-growth environment (22 active job postings as of mid-2026).
- **Engineering Culture**: Emphasis on building fast, solving hard problems, and pioneering AI for the real economy. Tech roles include Senior Software Engineer, Software Engineer (Platform & Applied AI).

## Sources
1. [Rilla Careers Page](https://www.rilla.com/careers)
2. [Rilla About Page](https://www.rilla.com/company/about)
3. [Rilla LinkedIn Profile](https://www.linkedin.com/company/rilla-co)
4. [Rilla Homepage](https://www.rilla.com/)

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