Head of Deal Desk

Attentive-posted 1 day ago
Full-time • Manager
1,001-5,000 employees
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As the Head of Deal Desk at Attentive, you will lead our end-to-end deal support function across Deal Strategy and Order Operations, ensuring our teams close business with speed, rigor, and the right commercial discipline. Reporting to the VP of Revenue Operations, you will be a critical partner to Sales Leadership, Finance, Legal, and GTM Operations, owning the operating rhythm, tools, and pricing governance that enable high-quality quoting and clean execution from quote to cash. You’ll help the business win strategically, while building scalable processes that improve forecast reliability, reduce friction, and strengthen margin and compliance over time.

  • Deal Strategy & Commercial Governance: Lead the team that supports new business and renewals through pricing guidance, negotiation support, and approval governance—ensuring consistency, fairness, and alignment to company objectives.
  • Commercial Architecture & Pricing Strategy: Be the chief architect of Attentive's pricing matrix, moving beyond guidelines to define the commercial trade-offs and key contract terms that drive sustainable business growth and enable us to win strategic clients. Own and evolve the pricing strategy, packaging, discounting guardrails, term strategy, and services policies, in deep partnership with Finance and Sales leadership.
  • Quote Approval & Deal Risk Management: Build a high-trust, high-rigor approval process that balances speed with discipline—identifying risk early (margin, legal/terms, services scope, non-standard concessions) and driving clear paths to resolution.
  • Order Operations & CPQ Excellence: Lead the team responsible for deal configuration, Salesforce/CPQ accuracy, and order processing—ensuring clean data, compliant bookings, and seamless handoffs into downstream teams.
  • Quote-to-Cash Process Improvement: Identify bottlenecks and failure points across quoting, contracting, booking, and handoff; implement scalable workflows, SLAs, and documentation that improve cycle time and reduce rework.
  • Cross-Functional Deal Leadership: Serve as the “hub” across Sales, CS, RevOps, Finance, Legal, Business Systems, and Implementation/Services to align on deal structure, approvals, and execution—especially for complex, strategic, or non-standard deals.
  • Team Leadership & Development: Lead a team of ~10 across Deal Strategy and Order Operations (including 2 people managers). Define the right org structure and assess current coverage and operating mode. Build an enablement and quality bar that scales with the business.
  • 6+ years of experience in Deal Desk, Revenue Operations, Sales Operations, Finance, or a related commercial role (B2B SaaS preferred), including people management experience.
  • Deep expertise in pricing/discounting governance, deal structuring, approvals, and negotiation support—especially across renewals and complex enterprise deals.
  • Strong operational command of Salesforce and CPQ (e.g., Salesforce CPQ or similar): configuration, process design, data quality, and workflow automation.
  • Exceptional cross-functional leadership skills: able to align Sales, Finance, Legal, and GTM teams through influence, crisp communication, and strong judgment.
  • Analytical and detail-oriented: comfortable using data to identify trends (discounting, approval volume, capacity) and to drive measurable improvements.
  • Clear, confident communicator who can translate complexity into practical guidance for reps and leaders, and can set a high bar for commercial discipline without defaulting to a bottleneck.
  • competitive perks and benefits, from health & wellness to equity
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