Sr. Manager, Sales Compensation & Strategy

WatchGuard Technologies, Inc.; Miami (FL); On-site; USD 140,000 - 190,000; Full time

Job summary

WatchGuard Technologies, Inc. in Miami seeks a Senior Manager, Sales Compensation Strategy to design, model, and execute global sales compensation programs.

You will partner with Sales, Marketing, Finance, and Revenue Operations to ensure incentive plans are financially sound, scalable, and aligned with company strategy. This high‑visibility role supports 200+ commission members and may build a team over time, with a focus on modernizing performance measurement and transitioning from a TCV‑based

Qualifications

• Deep expertise in designing and optimizing sales compensation programs for large, distributed teams.
• Strong financial modeling skills for cost, route‑to‑market, and M&A impact analysis.
• Proficiency with BI tools (Tableau and Power BI) for reporting and analysis.
• Ability to partner across Sales, Marketing, Finance and Revenue Operations.
• Excellent analytical, communication, and stakeholder management abilities.
• Comfort with ambiguity and driving process improvements in a fast‑moving environment.
• Familiarity with ARR‑based metrics and recurring‑revenue models preferred.

Responsibilities

• Lead planning, modeling, and execution of global sales compensation programs for 200+ employees.
• Analyze compensation plans for effectiveness, cost, and strategic alignment; propose improvements.
• Drive transition from TCV‑based to ARR‑based metrics and model impacts.
• Partner with FP&A and Sales on AOP processes including quota setting and capacity planning.
• Build financial models to evaluate routes to market, team structures, and M&A impact.
• Collaborate across Sales, Marketing, Finance, and Revenue Operations to align compensation strategy.
• Identify and close gaps in compensation governance and administration.
• Work with commissions teams to ensure accurate calculation and timely payout.

Skills

Sales compensation design

Financial modeling

Tableau

Power BI

Cross‑functional partnership

Analytical skills

ARR‑based metrics

Forecasting and quota planning

Tools

Tableau

Power BI

Job description

About the Position

The Senior Manager, Sales Compensation Strategy owns the design, modeling, and execution of WatchGuard's global sales compensation programs and serves as a strategic partner across the go-to-market organization. Reporting to the VP of Business Operations, this role sits at the intersection of Sales, Marketing, Finance, and Revenue Operations, ensuring our incentive plans are aligned with company strategy, financially sound, and built to scale.

This is a high-visibility individual contributor role supporting a global commission population of 200+ team members, with the potential to build out a team over time. A key early focus will be modernizing how we measure and reward performance, including leading the transition from a TCV-based to an ARR-based compensation framework.

A Day in the Life

No two days look quite the same in this role. One morning you might be deep in a model evaluating the cost and behavioral impact of moving a compensation plan from TCV to ARR; by the afternoon, you're partnering with Sales leadership and FP&A on quota setting for the upcoming Annual Operating Plan. You field a question from Revenue Operations about how a new route to market should be incentivized, refine a Power BI dashboard so leadership can see attainment at a glance, and flag a process gap in how commission agreements are administered. You move fluidly between strategic, big-picture modeling and the detailed, hands‑on work that keeps commissioned team members paid accurately and on time. Throughout, you act as the connective tissue between Operations, Finance, and the field, translating company strategy into compensation that drives the right outcomes.

Position Responsibilities

• Lead the planning, modeling, and execution of sales compensation programs across a global commission population of 200+ employees.
• Analyze current compensation plans for effectiveness, cost, and alignment with company objectives, and recommend improvements.
• Drive the transition of compensation structures from TCV‑based to ARR‑based metrics, including modeling the financial and behavioral impact of the change.
• Partner with FP&A and Sales leadership on the Annual Operating Plan (AOP) process, including quota setting, capacity planning, and cost modeling.
• Build financial models to evaluate new routes to market, sales team structures, and the compensation impact of M&A activity.
• Serve as a cross‑functional partner across Sales, Marketing, Finance, and Revenue Operations to ensure compensation strategy supports broader go‑to‑market goals.
• Identify and close process gaps in compensation planning, governance, and administration.
• Partner with the commissions team to operationalize approved plans, translating plan design into clear calculation logic, documentation, and payout processes so commissions are calculated accurately and paid on time.

Skills and Qualifications

• Deep expertise in sales compensation plan design, modeling, and execution for sizable, distributed sales teams.
• Strong financial modeling skills, including modeling new routes to market, team structures, and M&A impacts.
• Proficiency with Tableau and/or Power BI for reporting and analysis.
• Demonstrated ability to partner cross‑functionally across Sales, Marketing, Finance, and Revenue Operations.
• Excellent analytical, communication, and stakeholder‑management skills.
• Comfort operating with ambiguity and driving process improvements in a fast‑moving environment.
• Familiarity with ARR‑based metrics and recurring‑revenue business models preferred.
• Exposure to sales compensation platforms and FP&A/ERP systems preferred.

Experience

• 10+ years of experience in sales compensation, sales strategy, sales finance, or a closely related field.
• Track record of owning compensation programs for large, distributed commission populations.
• Experience supporting a B2B SaaS or recurring‑revenue business preferred.