Deal Desk Manager, Sentry

• 5+ years of experience in Deal Desk, Sales Operations, Revenue Operations, or a closely related function at a B2B SaaS company
• Hands-on experience with CPQ tools (Dealhub, Salesforce CPQ, MonetizeNow or similar) and a clear understanding of how quoting logic, product catalogs, and approval workflows are configured
• Comfortable in Salesforce; you know your way around objects, fields, and reports, and you can have a productive conversation with a Salesforce admin about what needs to change
• Experience handling the full deal lifecycle: quoting, redlines, order forms, and booking
• Strong analytical instincts, you can build a model or a report to answer a question, and you know which questions are worth asking
• A demonstrated habit of improving the processes you inherit, not just executing them
• Experience using AI tooling (Copilot, ChatGPT, or purpose-built RevOps tools) to accelerate deal review, summarization, or exception routing

Desirable

• Sentry's Revenue Operations team is built around three pillars — Analytics, GTM Technology, and Deal Desk — and we're hiring a Deal Desk Analyst to strengthen the third
• This isn't a role where you sit at the end of the sales process waiting for deals to land in your queue
• We want someone who is curious about why deals are structured the way they are, who spots inefficiencies before anyone else does, and who sees our CPQ and Salesforce environment as a system to be improved, not just operated
• You'll partner closely with our Senior Deal Desk Manager and together you'll be the team that keeps sales moving without the bottlenecks
• Your mandate is twofold: handle deals with speed and consistency, and help us automate and simplify the deal desk experience so that more and more of the routine work becomes self-service for reps
• This role is an opportunity to grow into a deep operator and systems thinker
• Own end-to-end processing of deals — including quote creation, discount review, order form generation, and approval routing — with minimal escalation and fast turnaround
• Partner with our Senior Deal Desk Manager to ensure coverage across the full deal portfolio so no single point of failure exists on the team
• Become an expert in our CPQ system and Salesforce integration– not just as a user, but as a critical voice for what should change. Document pain points, propose solutions, and work alongside our GTM Tech team to drive improvements
• Help design and implement self-service guardrails and automation that reduce the volume of deals requiring manual Deal Desk intervention, working toward a future where reps can handle standard deals entirely on their own
• Build and maintain deal desk playbooks, approval matrices, and process documentation that create consistency and reduce re-review
• Support pricing updates by ensuring that changes are reflected accurately and promptly in CPQ, and flagging downstream impacts before they become problems for sales
• Identify patterns across deal data — approval rates, exception types, deal velocity — and surface insights that inform policy and pricing decisions
• If you're someone who thrives on bringing order to chaos, who gets excited about eliminating the manual step that shouldn't exist in the first place, this is the job
• You'll Love This Job If You:
• Get frustrated by manual work that could be automated, and do something about it
• Can hold your own in a conversation with a sales rep pushing for a discount and with a systems engineer asking why a workflow is configured a certain way
• Like operating with autonomy while staying tightly coordinated with a small team
• Enjoy making things simple — the kind of simple that takes real work to build
• Believe that a good deal desk shouldn't be a bottleneck; it should make deals go faster
• Are energized by a company that is actively re-imagining processes as GTM technology is being re-invented. You want to be part of shaping what comes next, not just inheriting the status quo