Associate, Sales Compensation Strategy and Operations

Toast•Boston, MA

1d•Hybrid

About The Position

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. Toast is looking for an Associate to support how we run and scale compensation for our sales organization. You'll work closely with the Sales Compensation Strategy & Operations Manager and partner with the Commissions and Territory teams from day one. You'll own opportunity credit adjustments, applying sales policy and rules of engagement to get crediting right, and you'll own quarterly MBO consolidation and reporting. Reps rely on getting paid accurately, so precision and judgment matter here. This role also has a builder side. Much of sales compensation work is still manual and reactive. You'll help redesign it into scalable, proactive processes using AI tools and automation. As you grow, you'll take on more analytical work: attainment reporting, quota analysis, and the insights Sales leaders use to make compensation decisions. About the GTM Strategy & Operations Team We’re a small, collaborative team that sits at the intersection of data, sales strategy, and go-to-market systems. Our work shapes how Toast’s sales org is structured, how territories and quotas are set, and how reps are paid. We move fast, stay close to the business, and take pride in building things that actually get used.

Requirements

0–2 years of experience in an analytical or operations role, such as sales ops, revenue ops, finance, payroll, business operations, or consulting
Strong Excel/Google Sheets skills and comfort working with large datasets
High attention to detail, with ownership of accuracy when deadlines are tight
Curiosity about AI tools and a habit of looking for a better way to do repetitive work
Clear written and verbal communication
A bias toward action and comfort with a fast-moving, high-volume environment
Experience with Salesforce (CRM) or similar systems or willing to learn quickly

Nice To Haves

Experience with sales compensation software (e.g. Xactly, CaptivateIQ, Spiff, Varicent)
Hands-on experience using AI tools to build workflows, automations, or reusable prompts
SQL fluency or experience with Snowflake, Sigma, or similar BI tools
Familiarity with sales compensation concepts like quotas, accelerators, crediting rules, and pay mix

Responsibilities

Manage a high volume of opportunity credit adjustments, applying sales policy and rules of engagement (ROE) to get crediting right, and escalate exceptions with a clear recommendation
Process recurring data loads throughout the month
Lead quarterly MBO (management by objectives) consolidation and reporting for sales managers, from collecting inputs to delivering final results
Be a trusted point of contact for sales leaders and reps on crediting questions, explaining decisions clearly and consistently
Design, build, and test AI-assisted workflows and automations, such as data cleanup and recurring reports, that cut manual effort on your projects
Help shift sales compensation from reactive to proactive by building automated checks and alerts that surface issues early
Write and maintain SOPs and sales comp policy documentation so processes are consistent, auditable, and not dependent on any one person
Spot repetitive work across the team and propose better ways to do it
Support monthly attainment reporting and leadership-facing decks
Help scale and elevate compensation reporting by standardizing recurring reports, improving dashboards, and automating manual refreshes
Support plan design and quota analysis, such as modeling scenarios and pulling data for Sales leadership recommendations
Partner with the Territory team to support the rollout of territory-based quotas, including data preparation, validation, and rep-level quota reporting