Sales Operations Manager, Guideline
Commissions
$120-146k
Salary dependent on location and is eligible for equity in the form of Incentive Stock Options
Retirement plans for small business
Open for applications
Retirement plans for small business
201-500 employees
Open for applications
$120-146k
Salary dependent on location and is eligible for equity in the form of Incentive Stock Options
201-500 employees
Company mission
To help everyone arrive at a safe, secure retirement, whether they're a small business owner, an employee, or self-employed.
Role
Who you are
- 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
- Our ideal candidate has a proven track record of redesigning and managing commission processes, ensuring accuracy, transparency, and alignment with business goals
What the job involves
- 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
- 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
- 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
Our take
When businesses offer a 401(K) plan, a message is sent to employees and potential employees that their future is valued by their employer. However, small businesses are often left behind, being charged extortionate fees or ignored by 401(K) providers altogether, leaving many American families with no retirement savings and the potential of retiring into poverty.
Guideline spotted this oversight as an opportunity to jump in and offer small businesses an affordable 401(K). It generates income by charging each business a flat monthly fee per participant.
The company now manages retirement plans for hundreds of thousands of people in over 40,000 companies and has accumulated over $8 billion in assets under management. Benefits providers Intuit, Gusto, and Square all use Guideline as their 401(K) partners.
Freddie
Company Specialist at Welcome to the Jungle
Insights
-6% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Jun 2021
$200m
SERIES E
Jul 2020
$80m
SERIES D
Total funding: $339m
Company benefits
- Comprehensive medical, dental and vision plans—100% for employees, 70% for dependents
- Generous 401(k) match
- Paid time off + unlimited vacation days
- Paid parental leave
- Mental health coaching and therapy
- Learning and development stipend
- Cash referral bonus
- Commuter benefits
Company HQ
Downtown, Burlingame, CA
Leadership
Kevin Busque
(CEO)Majored in Computer Information Science at Fitchburg State University. Started out as an Advisory Unix Systems Administrator at IBM and then founded LinkedUp.net, an Open Source consulting company, in 1996. Acted as Chief Information Security Officer at the Institute for Health Metrics and was Director of IT at Humedica. Co-founded TaskRabbit in 2008, acting as its VP of Technology until 2015.
Mike Nelson
(CTO)Majored in Mechanical Engineering at the University of Southern Maine. Was Mobile Developer and CTO at TechStars-backed Accelgolf from 2007 to 2010. Joined SkillSlate as Rails Engineer and CTO, before being hired by TaskRabbit as Staff Engineer in 2012.
Jeremy Caballero
(Co-Founder & CPO)Started out as a Junior Programmer at Mail Boxes Etc. Worked as a Photographer and Videographer from 2007 to 2011, and then as a Freelance Digital Designer. Was Lead Designer at lifestyle adventure brand Targa Trophy before joining TargetSafety's UX team. Was made Lead Product Designer at TaskRabbit in 2012.
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