Why This Job is Featured on The SaaS Jobs
Rilla sits in a distinctive corner of SaaS: conversation intelligence built for offline, field based sales rather than call centers or video meetings. That focus reflects a broader SaaS trend of pushing AI workflows into historically analog industries like home services and property operations, where data capture and coaching have been harder to standardize.
For a SaaS sales professional, a Sales Development Manager remit here emphasizes the operational side of predictable revenue. The work naturally builds fluency in pipeline mechanics, outbound experimentation, and the instrumentation that makes SDR teams measurable, from QA cadences to forecasting hygiene. Managing hiring, onboarding, and coaching at meaningful team size also develops the leadership toolkit that transfers across SaaS go to market orgs, particularly where process and enablement need to mature alongside growth.
This role tends to suit someone who prefers being close to the work while still leading, with comfort moving between call reviews, performance management, and systems thinking. It also aligns with candidates who want their next step to be people leadership in SaaS, and who value environments where metrics, tooling, and iteration are central to how revenue teams improve.
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
Who we are
Rilla’s the leading virtual ridealong software for outside sales. Think home improvement, home builders, 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 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 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.
Who you are
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 natural leader. You take pride in giving and receiving feedback, and learning and growing as a leader of your 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.
We started Rilla in 2019 and have since grown to help over 3,500 customers, analyzed tens of millions of conversations, and raised a round from GV valuing Rilla at $800M after crossing eight figures in annual recurring revenue.
We are growing insanely fast.
But still, we’re not growing quickly enough.
One of the main reasons is we’ve only had one person directing our entire sales team.
With the number of fully ramped SDRs now dialing, having only one person running the team has started to become counterproductive.
Your job will be to help us grow faster and become a force multiplier. You will work alongside our Sales Leadership to help us grow our outbound revenue.
You will hire, onboard, and train new reps consistently.
You will get your hands dirty.
You will listen in on cold calls, run team meetings, and help the team increase hold rate, booking rate, and qualification rate.
Along with assisting your team by building running reports, keeping forecasts clean, and maintaining data integrity.
You will lead with experience.
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
Manage a high-performing sales development team (10+ people) with a focus on coaching, mentoring, and skills development
Implement and maintain a data-driven outbound sales strategy focused on prospecting and pipeline generation
Design performance management plans, QA cadence through call and email reviews, and provide cross-collaboration with our growth team to drive new business revenue
Establish and manage clear outbound sales goals and quotas for the team
Track and forecast sales performance and pipeline health
Provide out of the box thinking to follow the untravelled path and reach Rilla’s name to every corner of our ICP
Outcomes
Develop net new revenue to support Rilla’s continued growth
Own and evolve our demo-booking strategy to continue the growth of qualified, held demos entering the sales pipeline
Build and refine outbound sales cadences to properly qualify and fit-check prospects at different stages of the Rilla customer journey
Drive new business revenue by leading the sales development team and unlocking growth from new and untapped accounts
Maintain a high expectation bar expected of a top-tier sales team
Motivate, coach, and develop a diverse and talented team
Be comfortable with performance management of SDRs missing quota
Scale your sales team and strategy to meet our ambitious revenue goals
Skills & Requirements
Experience in sales team leadership and growth; ability to hire and retain top talent
Proven track record in evolving sales teams within a hyper-growth company
Expert in pipeline management: including forecasting, setting quotas, and optimizing the sales process for efficiency
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 modern SDR tooling like Hubspot, Orum, SalesLoft, and Zoominfo (Rocket Reach is a plus)
Strong empathy for customers and passion for revenue and growth
Nice to haves
Compensation
Benefits
Medical, dental, and vision insurance
Breakfast, lunch, dinner, and supplementary food and drink — 6x a week
Gym membership
Commuter benefits
Relocation assistance
Take what you need paid time off, not accrual-based
$1,000 stipend for learning and personal growth
Tech equipment
