People Operations @ Rilla

Who We Are

Rilla's the leading virtual ridealong software for outside sales. Think home improvement, housebuilders, 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 analyses 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.

The Role

As a Sales Development Representative, you will be at the forefront of our growth efforts. Your main priority will be to help us evangelize the power of conversation intelligence to more companies that sell offline.

This role is for an exceptional person who happens to be interested in sales.

We don't care if you don't have sales experience. We care how driven you are.

Our team is built with D1 athletes from top universities across the country, former founders, and people who've demonstrated excellence in something demanding - banking, consulting, athletics, startups, coaching, anywhere grit and performance matter.

What You'll Do

• Own the top of the sales funnel, prospect, research, and engage new leads daily

• Book qualified meetings for AEs through cold calling, email, and LinkedIn outreach

• Reactivate cold leads and build pipeline from scratch

• Travel to industry conferences to engage prospects and book demos on the spot

• Follow up with inbound and conference leads through calls and email

• Become a genuine expert on our product, our customers, and how great salespeople sell

We Don't Just Hire Top Performers. We Build Them.

Sales coaching is not a side benefit at Rilla. It's the product. We build software that makes salespeople better, and we use it on ourselves. Every rep on our team is coached with the same tools we sell. Most companies say they care about your development. At Rilla, it's why we exist.

When you join as an SDR, you enroll in Rilla Sales Academy, a structured training program designed to take you from zero to enterprise rep:

• Foundations: Cold calling, prospecting, multi-threading, finding active leads

• Conversation skills: Opening sequences, discovery questions, active listening, mirroring

• Advanced selling: Demo storytelling, closing sequences, objection handling, next steps

When you graduate, you move to AE, then enterprise. Every single Account Executive at Rilla was promoted from the SDR pipeline.

We don't hire outside AEs. If you come here and perform, that's the path.

Who You Are

• A customer obsessive. Someone who deeply cares about delighting clients 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. In a weird way, you trick your brain into being excited when you fail because it means you get a new opportunity to learn more.

• Affinity for the unconventional. You get a kick out of rejecting conventional wisdom. And you're not afraid to try weird, crazy, and quite possibly stupid ideas.

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

Nice to Have

• Former or current D1 athlete - if you've won championships, even better

• Top percentile in something exceptional - academics, competitions, club leadership, anything that shows you operate at a high level

• You've sold something before - door knocking, summer job, side hustle, lemonade stand, doesn't matter. If you've had to convince someone to buy, that counts

Compensation & Benefits

• OTE: $70,000-$120,000 (base + commission)

• 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