Director of Sales

Who we are

Rilla’s the leading virtual ridealong software for outside sales. Think solar, roofing, real estate, and other sales people who talk to customers face to face.

They 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’re growing 20% MoM, have dozens of customers including Fortune 500 companies, Net Revenue Retention above 150%, an NPS higher than the iPhone’s, and we are cash flow positive!

We are one of the fastest growing startups in the world right now and in history.

We’re backed by 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.

Who you are

• A customer obsessive. Someone who deeply cares about delighting customers and solving their pains, not about vanity metrics.

• An infinite learner. You are 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 not afraid of trying out unconventional ideas. You’re excited by the unconventional.

• Extremely focused. You practice extreme focus in everything you do. You’re always looking to prioritize your time and resources to 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.

The role

“Startup equals growth” - Paul Graham.

In our case, growth equals sales.

Since we started selling in 2022, we’ve been growing 89% MoM. It is still growing at 20% MoM after surpassing seven figures in annual recurring revenue.

We are growing insanely fast.

But still, we’re not growing quickly enough.

The main reason is we’ve only had one person doing all our sales.

Right now, we have so much demand for our product that we don’t have the time to close all of the leads coming through our pipeline.

Your job will be to help us grow faster. You will work alongside our CEO to help us build our first sales team.

You will hire, onboard, and train new reps consistently.

You will get your hands dirty.

You will hop on customer demos, do cold calls, and help us close key deals.

You will lead by example.

You will do whatever it takes to maximize the rate at which we spread the gospel of conversation intelligence for the physical world.

Day to day

• Own the entire revenue funnel, from prospecting to lead qualification, handoff to the account executives, and upselling from account managers

• Develop and implement a data-driven outbound sales strategy focused on prospecting and pipeline generation

• Build and manage a high-performing sales development team with a focus on coaching, mentoring, and skills development

• Establish and manage clear sales goals and quotas for the team

• Track and forecast sales performance and pipeline health

• Manage our customer success organization to drive net upsells.

Outcomes

1. Develop net new revenue to continue Rilla’s 20% MoM growth.

   1. Drive our lead generation strategy and significantly increase qualified leads entering the sales pipeline

   2. Build sales motions to meet prospects and customers at various points in their Rilla journey

   3. Drive our net dollar retention up by being in charge of the customer success organization, and helping us drive more growth with existing accounts.

2. Build and lead a high-performing sales organization

   1. Motivate, coach, and develop a diverse and talented team

   2. Scale the sales organization and strategy to meet our ambitious revenue goals

Skills & Requirements

• 5+ years of sales leadership

• Proven track record in evolving sales organization within a hypergrowth company

• Taking a revenue organization from 10M to at least $100M in ARR

• Built and executed winning inbound and outbound motions across all segments

• Expert in pipeline management: including forecasting, setting quotas, and optimizing the sales process for efficiency

• Experience in sales team leadership and growth; ability to hire and retain top talent

• Strong entrepreneurial mindset: drive high pace of execution in an ambiguous context

• Hyper competitive, low-ego with a strong drive to learn

• Excellent communication and presentation skills with high attention to detail

• Deep familiarity with Salesforce / Hubspot, Zoominfo, and SalesLoft

• Strong empathy for customers and passion for revenue and growth

Nice to haves

• You were an early hire at a fast growing startup

• You have experience in managing sales teams for software companies in the construction, or home improvement industry. Companies like BuilderTrend, BuildOps Service Titan, or Housecall Pro.

• You have experience managing sales teams for software companies that sell to non-tech industries. Companies like Flexport and Veeva for instance.