Head of Revenue Strategy & Operations

About this role

About ROLLER

ROLLER is not your average software-as-a-service company. With a global presence in over 30 countries, we're here to bring some excitement to the leisure and attractions industry and make a difference! Our mission is to help businesses operate smoothly and create fun and memorable guest experiences by providing seamless ticketing, point-of-sale, self-serve kiosks, memberships and digital waiver processes.

But here's the best part: our team. We're a group of 300+ highly passionate, enthusiastic, and down-to-earth professionals located all around the world who are all working together to build something truly remarkable. We're aiming high and believe that the possibilities are endless. As we continue to grow globally, we're excited to write our success story and have fun along the way.

We genuinely love what we do, and we're looking for like-minded people to join us on this amazing journey. If you're ready to be part of a dynamic team and make a real impact, come aboard, and let's create some unforgettable experiences together at ROLLER!

About the Role

ROLLER is seeking a highly strategic and execution-oriented Head of Revenue Strategy & Operations to join our Go-To-Market (GTM) leadership team. This role is responsible for architecting, operating, and continuously optimizing ROLLER’s GTM engine to drive efficient, predictable, and scalable bookings growth. You will partner closely with the CRO, CFO, Executive Leadership Team, and leaders across Marketing, Sales, Professional Services, Customer Success, Support, Partnerships, and Product. Acting as a primary business partner to Finance, you will ensure tight alignment between revenue strategy, financial planning, forecasting, and investment decisions.This role blends strategy, analytics, systems, and execution with direct ownership of ROLLER’s most critical cross-functional growth initiatives. You will define where and how ROLLER grows across segments, verticals, geographies, and channels, and mobilize the organization to execute.

What You’ll Do

• Own and evolve ROLLER’s GTM strategy, operating model, and organizational structure.

• Drive major cross-functional growth initiatives including outbound scale, integrated marketing campaigns, and new geography and vertical expansion.

• Serve as a core business partner to Finance, aligning GTM strategy with financial planning, budgets, and ROI.

• Own sales forecasting, pipeline inspection, scenario modeling, and forecast accuracy.

• Design and optimize sales territories, coverage models, and capacity planning.

• Lead sales compensation and incentive plan design.

• Lead annual and long-range GTM planning including headcount, ROI, and market prioritization.

• Build executive dashboards, KPIs, board materials, and QBR insights.

• Partner with IT to scale Salesforce and GTM systems.

• Drive operational efficiency, automation, and GTM operating cadence.

What We’re Looking For

• 10–12+ years of experience in Revenue Strategy, RevOps, Strategy & Operations, FP&A, or GTM leadership roles, including prior experience in Strategy Consulting and/or Investment Banking.

• Proven ownership of cross-functional GTM initiatives with measurable growth impact.

• Deep experience in sales forecasting, territory design, compensation planning, and GTM org design.

• Strong partnership experience with Finance and CFO organizations.

• Exceptional analytical, modeling, and executive communication skills.

• Strong systems orientation with hands-on Salesforce and BI experience.

• Experience leading high-performing, globally distributed teams.

Perks!

• You'll get to work on a category-leading product that customers love in a fun, high-growth industry! Check our Capterra and G2 reviews.

• 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!

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