About GustoAt 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. About GustoAt 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 Current 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.

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. About The TeamYou’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. 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. 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. Partner with RTM leaders, Finance, and Sales Compensation to align quotas with comp plans, revenue targets, and business priorities each planning cycle. 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.” 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; 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. 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. 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. Experience owning segmentation, book‑of‑business, or quota/capacity planning across multiple sales organizations or motions simultaneously (e.
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.

📌 Sr. Sales Operations Analyst (Winnipeg)
🏢 Gusto
📍 Winnipeg