Deal Desk Manager

About Sentry Software runs the world and the pace is faster than ever. Sentry helps developers fix errors and performance issues before users notice, so teams can spend less time firefighting and more time building. Trusted by 200,000+ organizations, Sentry is today’s application monitoring standard and our team is building its AI-native future. About the Role 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. 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. In This Role You Will 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. 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. Qualifications 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 analytic