Founding Sales Development Representative

Who We Are

Rilla’s the leading virtual ridealong software for outside sales. Think home improvement, housebuilders, 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 centre 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 Founding Sales Development Representative, you will be working directly with the UK Head of Sales to take Rilla from 0 to 1 in the UK & EMEA. This is a startup within a startup, with outsized responsibility and opportunity for growth. Your main priority will be to help us evangelise the power of AI sales coaching to more companies that sell offline.

While sales experience is a plus, it is not required. This role is for an exceptional person who happens to be interested in sales.

Our team is built with elite athletes from top universities across the world, 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 the Head of Sales 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 enrol in Rilla Sales Academy, a structured training programme 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

You graduate when the Head of Sales' calendar is full and we need you to step into the Account Executive role and start closing. If you perform, you will become an Account Executive by week 10-14. This is not a "two years as an SDR" role.

We don't hire outside AEs — every single AE at this company has been promoted from within.

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 prioritise your time and resources for maximum efficiency.

   

Nice to Have

• 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

• Former or current elite-level athlete — if you've competed nationally or won titles, even better

• Fluent or business proficient in European language(s)

Compensation & Benefits

• OTE: £90,000–£150,000 (base + commission)

• Daily meal stipend 6 days a week

• Private health insurance (medical and dental)

• Pension scheme

• Enhanced parental leave

• Fertility benefits

• Wellness / Gym Benefits

• Cycle to Work scheme

• Unlimited holiday (not accrual-based — take what you need)

• £750 annual learning and development stipend

• Tech equipment

Right to Work & Equal Opportunity

Applicants must have the existing right to work in the UK. We are unable to sponsor visas or provide work authorisation for this role. Rilla is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees — we welcome applications regardless of age, disability, gender identity, marital status, pregnancy or maternity, race, religion or belief, sex, or sexual orientation.