Deal Desk Operations Lead

Triple Whale•New York, NY

12h•$110,000 - $135,000•Remote

About The Position

Triple Whale is moving quickly across renewals, customer migrations, credits, usage, discounts, approvals, billing workflows, and commercial exceptions. As these motions continue to scale, we have a meaningful opportunity to strengthen the Deal Desk processes, systems, and operating rules that help teams evaluate requests, manage approvals, coordinate renewals, and handle customer-specific exceptions. As the Deal Desk Operations Lead, you will assess the current Deal Desk motion, identify where workflows and systems can be simplified or improved, and bring more structure to how discounts, exceptions, approvals, renewals, credits, pauses, refunds, and billing-related requests are managed across the business. You will work closely with Pricing & Packaging, RevOps, Finance, Sales, CS, Renewals, Billing, Product, Internal Systems, and Revenue Enablement to improve and automate Deal Desk processes so teams can move faster with clearer approval paths, better visibility, stronger field guidance, and fewer manual handoffs. This is a highly cross-functional role for someone who can operate in ambiguity, build scalable process, support reps in the moment, and help Triple Whale evolve its quote-to-cash and commercial exception infrastructure.

Requirements

6+ years of experience in Deal Desk, Revenue Operations, Billing Operations, Sales Operations, Pricing Operations, SaaS Operations, or a similar GTM operations role.
Strong understanding of SaaS billing, subscriptions, renewals, discounting structures, credits, add-ons, quote-to-cash workflows, Deal Desk systems, and commercial approvals.
Experience diagnosing and improving Deal Desk, approval, renewal, billing exception, or quote-to-cash workflows
Experience supporting Sales, Account Management, CS, or Renewals teams on non-standard pricing, commercial terms, approvals, or deal structure.
Experience with HubSpot, Salesforce, Stripe, Chargebee, NetSuite, Ironclad, DocuSign, Jira, or Deal Desk / CPQ tooling.
Experience managing cross-functional workflows across Sales, CS, Renewals, Finance, RevOps, BizOps, Product, and/or internal systems teams.
Strong operational judgment around when to create process, when to simplify, and when to escalate.
Ability to turn ambiguous business needs into clear operating rules, workflows, and requirements.
Comfort working with billing systems, CRM systems, approval workflows, contracts, and internal tooling.
Strong attention to detail in workflows where accuracy, approvals, and customer impact matter.
Ability to build trust with commercial teams while still maintaining process discipline.
Strong communication skills and the ability to explain policy, process, and tradeoffs clearly.
Ability to create clear training materials, field guidance, enablement resources, and process documentation for internal teams.

Nice To Haves

Experience implementing, administering, or evaluating Deal Desk, CPQ, CLM, or approval workflow software.
Experience supporting operational changes tied to pricing, packaging, renewals, migrations, usage-based pricing, or billing workflows in a SaaS business.
Experience with customer migration projects, packaging transitions, or legacy plan cleanup.
Experience building discount reporting, approval dashboards, Deal Desk SLAs, or renewal operating cadences.
Baseline knowledge of ASC 606 and revenue recognition implications of discounts, credits, refunds, pauses, usage-based pricing, and contract modifications.
Familiarity with usage-based pricing, credits, AI usage, or add-on monetization.
Basic SQL or data-analysis comfort to investigate discrepancies and validate business logic.
Experience working in a fast-moving, high-growth environment where systems and processes are still being built.

Responsibilities

Assess the current Deal Desk motion across discounts, approvals, renewals, billing exceptions, credits, refunds, pauses, usage-based pricing, and commercial concessions. Identify gaps, simplify workflows, and create a more scalable process based on prior Deal Desk / RevOps experience.
Partner with Account Executives and Account Managers on non-standard deal structures, pricing guidance, discounting questions, customer-specific exceptions, and migration-related scenarios. Help reps navigate unusual commercial structures quickly and consistently, especially as Triple Whale continues to evolve packaging, usage, credits, and migration motions.
Maintain discount thresholds, approved ranges, approval requirements, escalation paths, and audit expectations so teams know what can be offered, when approval is required, and how exceptions should be handled.
Manage intake, routing, follow-up, and resolution for non-standard requests, including discounts, concessions, credits, refunds, pauses, billing exceptions, renewal exceptions, and customer-specific commercial terms.
Coordinate renewal timing, scheduling, handoffs, and operational follow-through so upcoming renewals are proactively managed and the right teams have visibility ahead of time.
Support customer migration by helping surface renewal timing, exception categories, discount implications, system requirements, and customer-specific review needs.
Help clarify how credits, recurring usage, add-ons, feature access, and billing-related requests should move through Deal Desk workflows, internal systems, and customer-facing handoffs.
Coordinate, design, and deliver training materials for internal teams and stakeholders. Partner with Revenue Enablement to lead operational trainings for the field, ensuring Sales, CS, Renewals, and other teams understand Deal Desk policies, approval paths, migration rules, discounting guidelines, and exception workflows.
Create leadership visibility into discount usage, exception trends, renewal status, migration progress, approval bottlenecks, system gaps, and areas where process needs refinement.
Partner with Sales, CS, Renewals, Finance, RevOps, Billing, Pricing & Packaging, Product, Internal Systems, Data, and Revenue Enablement to make sure Deal Desk workflows are understood, followed, and continuously improved.
Translate Deal Desk workflow requirements into clear tooling requirements for Internal Systems / Product and help evaluate whether Triple Whale should introduce a dedicated Deal Desk, CPQ, or approval workflow platform.