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Posted 5 months ago
Requirements and responsibilities
About the Role 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.What You’ll AccomplishDeal 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.Your Expertise6+ 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.Closing Description You'll get competitive perks and benefits, from health & wellness to equity, to help you bring your best self to work. For US based applicants:- The US base salary range for this full-time position is $190,000 - $240,000 annually + equity + benefits- Our salary ranges are determined by role, level and locationAttentive Company Values Default to Action - Move swiftly and with purposeBe One Unstoppable Team - Rally as each other’s championsChampion the Customer - Our success is defined by our customers' successAct Like an Owner - Take responsibility for Attentive’s successLearn more about AWAKE, Attentive’s collective of employee resource groups.Equal Opportunity & Accessibility At Attentive, we know that our Company's strength lies in the diversity of our employees. Attentive is an Equal Opportunity Employer and we welcome applicants from all backgrounds. Our policy is to provide equal employment opportunities for all employees, applicants and covered individuals regardless of protected characteristics. We prioritize and maintain a fair, inclusive and equitable workplace free from discrimination, harassment, and retaliation. Attentive is also committed to providing reasonable accommodations for candidates with disabilities. If you need any assistance or reasonable accommodations, please let your recruiter know.
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