What You'll DoPlan design & administration- Own the design and ongoing refinement of go-to-market commission plans across sales, renewals, expansion, and solutions engineering.
- Generate and distribute compensation agreements for signature.
- Calculate payouts accurately, and partner closely with payroll to ensure every rep is paid correctly and on time, in line with our payment cycle (currently quarterly).
- Establish and maintain the controls, systems, and operating rhythms that keep the program well governed, accurate, and auditable.
Analysis, strategy & tooling- Measure whether plans are working by tracking attainment, quota achievement, and how many reps are hitting target.
- Identify when plans are driving unintended behaviour and recommend adjustments to targets and mechanics.
- Recommend and help stand up the right commissions / sales-comp tooling. ROLLER runs the program without a dedicated comp tool today (just Salesforce), so you'll shape what we adopt.
- Use data to recommend changes to plan structure as the business evolves.
- Design scalable processes and workflows for the program, leveraging AI to cut down manual, repetitive work.
About You- You have a high appetite for Technology and AI and a natural curiosity for how it can transform your work. You're comfortable using AI tools to automate repetitive 'busy work,' freeing you up to focus on high-impact work.
- Around 7+ years of experience in go-to-market or sales commissions.
- A software / SaaS background, with a clear understanding of how compensation works in a software business.
- Experience building commission plans from the ground up, ideally at small-to-mid-size SaaS companies. If you've come from a larger company, you've also worked somewhere lean enough to build without ready-made infrastructure.
- A genuine blend of strategy and analysis. You design the plans and run the numbers behind them, rather than purely executing.
- Strong analytical and modelling skills, and confidence working across large data sets.
- A hands-on operator who digs into the details rather than working from 10,000 feet. A strong communicator who moves fast, adapts well, and can influence and manage stakeholders across regions and outside official reporting lines, from sales, finance, revenue ops, and payroll to leaders like the CRO and RVPs.
- A tertiary qualification in business, finance, or a related discipline is a plus, though hands-on experience matters most.
- Keen to grow, interested in expanding over time into broader compensation, including bonus, short-term incentives, equity, and benefits, as the role evolves.
We believe AI is a career-defining inflection point. ROLLER is a fast adopter of new technology like AI, and every team member is empowered to own their learning and use the latest tools to supercharge their impact. We're looking for candidates with the proficiency and curiosity to embrace AI and technology, not just as a technical skill, but as a core competency to help us achieve big goals.
Perks! You get to work on a category-leading product that customers love in a fun, high-growth industry - check our Capterra and G2 reviews.
ROLLER Recharge days to celebrate and recharge once we've hit our goals
Engage in our 'Vibe Tribe' - led by our team members; you can contribute to company-wide initiatives directly. Regular events and social activities, fundraising & cause-related campaigns... you name it. We're willing to make it happen!
♥ Team member Assistance Program to proactively support our team's health and wellbeing - access to coaching, education modules, weekly webinars, and more.
16 weeks paid Parental Leave for primary carers and 4 weeks paid Parental Leave for secondary carers
Work with a driven, fun, and switched-on team that likes to raise the bar in all we do.
Individual learning & development budget plus genuine career growth opportunities as we continue to expand!
