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 Perks: 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

Perks

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

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📌 Senior Sales Operations Analyst (Winnipeg)
🏢 Gusto
📍 Winnipeg