Sales Operations Manager, Commissions

Guideline is seeking a Sales Operations Manager, Commissions to take ownership of our commissions process and make it a powerful driver of motivation and performance. In this role, you’ll redesign our end-to-end commissions system to be simpler, transparent, and scalable. You’ll be the go-to expert for monthly payout calculations, ensuring accuracy and accountability. Beyond commissions, you will own sales capacity modeling and analysis, providing Sales and Finance Leadership with critical insights to inform capacity and resource planning. Working cross-functionally, you’ll design innovative commission structures that align with the sales team's goals and inspire our sales team to perform at their best.

Our ideal candidate has a proven track record of redesigning and managing commission processes, ensuring accuracy, transparency, and alignment with business goals. They excel at delivering actionable, data-driven insights to stakeholders, driving sales optimization through capacity modeling and resource planning, and collaborating across teams to create innovative and motivating commission structures that enhance performance.

What You Will Do

• Redesign Commissions Processes: Overhaul the end-to-end sales commissions process to create a simpler, more transparent, and scalable system that aligns with business goals
• Own Payout Calculations: Take full accountability for accurate, timely, and compliant monthly commission payouts, ensuring clarity for all stakeholders
• Own Sales Capacity Modeling: Develop capacity models and analysis to guide leadership on resource allocation and role planning to ensure optimal sales team structure and productivity
• Drive Strategic Insights and Plan Design: Collaborate with Sales and Finance leadership to analyze commission trends, deliver actionable insights, and design data-driven, commission structures that motivate sales teams 
• Optimize Tools and Systems: Evaluate and enhance commission management tools and CRM integrations, streamlining processes for efficiency and scalability
• Leverage Technical Expertise: Work with complex data sets to build models, perform deep-dive analyses, and support commission plan optimization with advanced data techniques
• Ensure Compliance and Accuracy: Maintain rigorous documentation and processes to meet accounting and compliance standards while supporting leadership’s decision-making

What We’re Looking For

• Experience: 4+ years in a Sales Commissions Manager, Commissions Analyst, Deal Desk, or similar role at a high-growth B2B or SaaS company, with a proven track record of designing, managing, and administering commission plans across various roles.
• Expertise in commission tools (e.g., Spiff, CaptivateIQ, Xactly) and CRM platforms like Salesforce, with advanced Excel/Google Sheets skills for complex data analysis and modeling.
• Strong ability to analyze and interpret data, identify trends, and translate insights into actionable recommendations for leadership.
• Demonstrated success in redesigning and streamlining commission processes to improve scalability, transparency, and efficiency in high-growth environments.
• Experience creating commission plans that align with company objectives while motivating sales teams to achieve and exceed goals.
• Excellent interpersonal skills, with a proven ability to work closely with Sales, Finance, and cross-functional teams to drive alignment and solve complex problems.
• Rigorous focus on accuracy and compliance, ensuring calculations and payouts meet internal policies and accounting standards.
• Proactive mindset with the ability to manage competing priorities, identify opportunities for improvement, and take ownership of solutions.
• Exceptional written and verbal communication skills to explain commission plans, deliver insights, and provide clarity to stakeholders at all levels.

More About Guideline
Everyone should have a simple, affordable way to save for retirement. At Guideline, our plans are low cost and highly automated. This makes it easy for companies to offer a valuable benefit—and easy for people to invest in their financial future with confidence.
Compensation
At Guideline, we believe compensation should be fair and equitable. We take a data-driven approach to set our compensation bands; the successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, and work location. We are always evaluating our pay zones to be as competitive as possible, so keep in mind these may be subject to change in the future.

• Metro+:
• The base salary range for this position is $131,000-$146,000 annually.
• Metro:
• The base salary range for this position is $120,000-$135,000 annually.
• National:  
• The base salary range for this position is $120,000-$135,000 annually.

In addition to base salary, this position is eligible for equity in the form of Incentive Stock Options (ISOs). 

• Health
• Medical, dental, and vision insurance — We offer multiple plan options with varying company premium contributions
• Opt-out credit for waiving coverage
• Health Savings Account and Flexible Spending Account
• Company paid disability and life insurance
• Optional Voluntary life insurance
• Mental health benefit navigation with Rula for employees and dependents
• Parental Leave
• Paid parental leave for birthing and non-birthing parents
• Generous Time Off
• Flexible time off in addition to company holidays — We observe the NYSE Holiday Calendar
• 401(k) Plan
• We use our own platform and contribute 100% of employee contributions up to 5%
• Other Benefits
• 1-month paid Sabbatical after 5 years of employment
• Annual learning and development stipend — We reimburse approved professional development expenses, up to $750 per employee per year

Guideline provides equal employment opportunities to all employees and applicants for employment without regard to race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Pursuant to the San Francisco Fair Chance Ordinance, we will consider for employment qualified applicants with arrest and conviction records.  Additionally, Guideline participates in the E-Verify program in certain locations, as required by law.