Head of Revenue Strategy & Operations

ROLLER • San Francisco, CA

5d

About The Position

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.

Requirements

• 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.

Responsibilities

• 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.

Benefits

• 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.
• 4 ROLLER Recharge days per year (When we hit our goals each quarter, we take a well-earned day off together to relax, recharge, and celebrate our wins).
• 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!

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed
• Number of Employees: 101-250 employees