Senior Sales Operations Analyst

Gusto; Toronto; On-site; CAD 90,000 - 130,000; Full time

Benefits offered by this job

Gender-affirming care

Family care

Mental health resources

Medical, dental, and vision insurance

Free meals at office

Paid vacation, sick time, holidays

Job summary

Gusto is seeking a Senior Sales Operations Analyst to own segmentation, book-of-business design, quotas, and headcount planning across Direct, Expansion, and Benefits sales. You will build scalable models, partner with GTM, Finance, and Sales Compensation, and drive disciplined planning processes in a fast-paced SaaS environment.

You will translate GTM strategy into automated models, maintain governance, and ensure accurate reflections in Salesforce and related systems.

Qualifications

• 5+ years in Sales Ops, RevOps, or a similar analytical GTM role.
• Hands-on experience owning segmentation, territory/book design, quota setting, or headcount/capacity planning.
• Experience building scalable, defensible planning models in fast-paced SaaS or fintech environments.

Responsibilities

• Own the design and ongoing maintenance of customer segmentation for Direct, Expansion, and Benefits sales.
• Build and maintain balanced books of business across reps and teams.
• Set and maintain clear rules for account assignment, routing, and reclassification.
• Partner with Sales, GTM Ops, and Systems to ensure segmentation and book structures are reflected in Salesforce.
• Own the end-to-end quota-setting process for Direct, Expansion, and Benefits.
• Build headcount models and inform hiring plans.
• Monitor capacity against actual book size and flag gaps.
• Document methodology and decisions for transparency and auditability.

Skills

Segmentation design

Book-of-business design

Quota setting

Capacity planning

Cross-functional partnership

Salesforce tooling

Headcount modelling

GTM operations

Tools

Salesforce

Job description

• 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
• 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
• 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

Benefits

• Gender-affirming care and support
• Family care and support, including family planning and fertility benefits
• A variety of mental health resources
• Medical, dental, and vision insurance for employees and dependents
• Free meals and refreshments at the office (conversation and community is an added bonus!)
• Paid vacation, sick time, bereavement, and holidays, paid leaves, sabbatical, and more

A first-principles problem solver who can build a defensible model from ambiguous inputs and translate org-level strategy into concrete, rules-based executionA strong cross-functional partner, able to work closely with GTM leaders and GTM Ops peers without ceding ownership of the outcomeStrong sales process & tooling proficiency: you can build and audit account assignment/routing logic, manage territory and book structures, and build reporting that leaders trustProven 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 challengedExperience running planning processes on a recurring cadence (annual/quarterly quota setting, ongoing book rebalancing, headcount reviews) across multiple stakeholder groupsAnalytical depth; comfortable building and defending quantitative models (quota, capacity, segmentation) under time pressure5+ 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 environmentExcellent written and