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Head of Deal Desk

United States
Attentive® is the AI marketing platform for 1:1 personalization redefining the way brands and people connect. We’re the only marketing platform that combines powerful technology with human expertise to build authentic customer relationships. By unifying SMS, RCS, email, and push notifications, our AI-powered personalization engine delivers bespoke experiences that drive performance, revenue, and loyalty through real-time behavioral insights.
 
Recognized as the #1 provider in SMS Marketing by G2, Attentive partners with more than 8,000 customers across 70+ industries. Leading global brands like Crate and Barrel, Urban Outfitters, and Carter’s work with us to enable billions of interactions that power tens of billions in revenue for our customers.
 
With a distributed global workforce and employee hubs in New York City, San Francisco, London, and Sydney, Attentive’s team has been consistently recognized for its performance and culture. We’re proud to be included in Deloitte’s Fast 500 (four years running!), LinkedIn’s Top Startups, Forbes’ Cloud 100 (five years running!), and Inc.’s Best Workplaces.

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 Accomplish

  • 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.

Your Expertise

  • 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.

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 location
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Attentive Company Values
Default to Action - Move swiftly and with purpose
Be One Unstoppable Team - Rally as each other’s champions
Champion the Customer - Our success is defined by our customers' success
Act Like an Owner - Take responsibility for Attentive’s success
 
Learn more about AWAKE, Attentive’s collective of employee resource groups.
 
If you do not meet all the requirements listed here, we still encourage you to apply! No job description is perfect, and we may also have another opportunity that closely matches your skills and experience.
 
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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Our company values diversity. To ensure that we comply with reporting requirements and to learn more about how we can increase diversity in our candidate pool, we invite you to voluntarily provide demographic information in a confidential survey at the end of this application. Providing this information is optional. It will not be accessible or used in the hiring process, and has no effect on your opportunity for employment.

 

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