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Added 8 mins ago
Delivery Service Centre Analyst
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Toronto, ON · Greater Toronto Area, Canada
Full-time
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Added 10 mins ago
Contracts and Sourcing Analyst
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Full-time
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Gusto, Inc.

Sr. Sales Operations Analyst

Toronto, ON, Canada

Pay: Our cash compensation amount for this role is targeted at $100,000 - $120,000/yr in Scottsdale, $105,000 - $130,000/yr in Denver and Atlanta, $130,000 - $155,000/yr in San Francisco and New York, and $120,000 - $145,000 CAD/yr for Toronto.
Posting language: English
Posted: Oct 1, 2026

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Original job description

About Gusto

At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff - payroll, health insurance, 401(k)s, and HR - so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.

All full-time employees receive competitive base pay, benefits, and equity (RSUs) - because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy.

AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process.

About the Role

This is your chance to own one of the most technical, horizontal levers in GTM planning: building the scalable models and infrastructure that enable every route to market to grow efficiently. As Senior Sales Operations Analyst, you’ll partner with GTM leaders, Finance, Revenue Operations, and GTM Ops to develop and execute segmentation, book-of-business design, quota setting, and capacity planning. You’ll turn GTM strategy into concrete, automated models that determine how customers are segmented, how reps are staffed, and what they are held accountable for.

This role takes an end-to-end, platform-minded view across GTM motions, not just a single sales team. You’ll identify where manual work, fragmented logic, or inconsistent processes limit scale and build durable planning infrastructure that drives revenue outcomes as the business evolves. You’ll own the outcome: balanced books, defensible quotas tied to capacity, and scalable models that hold up under scrutiny.

About the Team

You'll sit within GTM Operations, working as the dedicated segmentation, book-of-business, and capacity planning owner for our Direct, Expansion, and Benefits sales teams. We think of ourselves as builders and problem solvers: we turn ambiguous planning questions into scalable, defensible models, and we hold the line on rigor even when the business is moving fast and priorities compete.

You'll work in close partnership with each organization's GTM leaders and their dedicated GTM Ops partners, leaning on their operational and business context, while you own building, defending, and maintaining the segmentation, book, quota, and headcount models that everyone plans against.

Here's what you'll do day-to-day

Segmentation & Book of Business

Own the design and ongoing maintenance of customer/account segmentation for Direct, Expansion, and Benefits sales, translating org-level segmentation strategy into concrete, rules-based models these teams can operate against.
Build and maintain balanced books of business across reps and teams, accounting for account potential, workload, geography, and product mix; own rebalancing when the business shifts (new hires, departures, territory changes, book splits).
Set and maintain clear, documented rules for account assignment, routing, and reclassification, and serve as the ruling authority when edge cases or disputes come up.
Partner with Sales, GTM Ops, and Systems & Tooling to ensure segmentation and book structures are reflected accurately in Salesforce and downstream systems.

Quota Setting

Own the end-to-end quota-setting process for Direct, Expansion, and Benefits: translating top-down revenue targets into bottoms-up, capacity-based quotas by rep, team, and segment.
Build and maintain the quota models and methodology, ensuring quotas are defensible, equitable across territories/books, and tightly tied to book-of-business design and headcount capacity.
Partner with RTM leaders, Finance, and Sales Compensation to align quotas with comp plans, revenue targets, and business priorities each planning cycle.
Own quota administration through the cycle: true-ups for territory or book changes, new-hire ramp adjustments, and mid-cycle corrections.

Headcount & Capacity Planning

Partner with GTM Ops & Finance on capacity planning for Direct, Expansion, and Benefits: modeling the headcount needed to cover segmented books and hit revenue targets, and identifying where the org is over- or under-staffed relative to opportunity.
Build the headcount models that inform hiring plans, partnering with RTM leaders and Finance on timing, sequencing, and prioritization of new roles.
Continuously monitor capacity against actual book size, productivity, and attrition, flagging gaps or imbalances before they become a problem.
Own scenario planning for headcount and territory changes (reorgs, new segments, M&A, product launches), modeling the impact before decisions are made.

Cross-functional Partnership & Communication

Partner closely with RTM leaders and their GTM Ops partners across Direct, Expansion, and Benefits to ensure segmentation, book, quota, and capacity decisions reflect real operational context, while retaining ownership of the outcome and the execution.
Work with GTM Ops, Finance, and Sales Compensation to stay aligned with org-wide segmentation frameworks, revenue targets, and comp design.
Communicate clearly and proactively with sales leadership on plan status, tradeoffs, and risk: you're the trusted authority on "how the books, quotas, and headcount are built and why."
Document methodology and decisions so segmentation, quota, and capacity models are transparent, auditable, and repeatable across planning cycles.

Here's what we're looking for

5+ years in Sales Ops, RevOps, or a similar analytical GTM role, with direct, hands-on experience owning segmentation, territory/book design, quota setting, or headcount/capacity planning; ideally in a fast-paced SaaS or fintech environment.
Proven ability to own outcomes and execution, not just analysis or recommendations: you're comfortable being the accountable owner when a quota, book, or headcount plan is challenged.
Strong sales process & tooling proficiency: you can build and audit account assignment/routing logic, manage territory and book structures, and build reporting that leaders trust.
Analytical depth; comfortable building and defending quantitative models (quota, capacity, segmentation) under time pressure.
Experience running planning processes on a recurring cadence (annual/quarterly quota setting, ongoing book rebalancing, headcount reviews) across multiple stakeholder groups.
Excellent written and verbal communication; you can defend a model's methodology to GTM leaders and senior sales leadership, and hold your ground when a decision is unpopular but correct.
A first-principles problem solver who can build a defensible model from ambiguous inputs and translate org-level strategy into concrete, rules-based execution.
A strong cross-functional partner, able to work closely with GTM leaders and GTM Ops peers without ceding ownership of the outcome.

Preferred Qualifications

Experience owning segmentation, book-of-business, or quota/capacity planning across multiple sales organizations or motions simultaneously (e.g., new business, expansion, and a distinct product line).
Experience in payroll, HR tech, benefits, or SMB SaaS go-to-market motions.
Experience partnering with Sales Compensation and Finance on quota-to-comp alignment.
Experience designing or improving account assignment/routing automation (e.g., lead-routing tools, rules engines).

Compensation

Our cash compensation amount for this role is targeted at $100,000 - $120,000/yr in Scottsdale, $105,000 - $130,000/yr in Denver and Atlanta, $130,000 - $155,000/yr in San Francisco and New York, and $120,000 - $145,000 CAD/yr for Toronto. Final offer amounts are determined by multiple factors including candidate experience and expertise and may vary from the amounts listed above.

Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale.

Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas.

When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees.

Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto.

Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you.

Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer.

Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.

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More about this job

Responsibilities

The Senior Sales Operations Analyst will build scalable models and infrastructure for segmentation, quota setting, and capacity planning to drive efficient go-to-market growth. You will partner with GTM leaders and Finance to translate strategy into automated, defensible models that optimize sales performance.

Requirements

Candidates must have 5+ years of experience in Sales Ops, RevOps, or similar analytical roles with hands-on expertise in territory design and quota setting. Strong proficiency in sales tooling, quantitative modeling, and cross-functional communication is required to succeed in this fast-paced environment.

Skills

Sales operations
Revenue operations
Segmentation
Book-of-business design
Quota setting
Capacity planning
Salesforce
Data modeling
Financial modeling
Strategic planning
Cross-functional leadership
Process automation
Analytical modeling
Territory management
SaaS
Fintech

Benefits

Competitive base pay
Equity
RSUs
Health insurance
401(k)s

Visa sponsorship

Not detected in the job text

Keywords

Sales Operations
RevOps
GTM Strategy
Segmentation
Quota Setting
Capacity Planning
Salesforce
SaaS
Fintech
Data Modeling
Territory Management
Account Assignment
Revenue Targets
Headcount Planning
Scenario Planning
Sales Compensation
Process Automation
Business Intelligence
Analytical Depth
Cross-functional Partnership

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