Director, Deal Desk

Showpad•Boston, MA

About The Position

Showpad is hiring a Director, Deal Desk to lead its global Deal Desk function within Revenue Operations. The role owns the strategy and standards for pricing, deal structuring, approvals, bookings, and the end-to-end quote-to-cash process. It leads a global team currently comprising three Deal Desk Analysts supporting North America, EMEA, and APAC, and is responsible for the team’s operating model, regional coverage, capacity planning, hiring, and development. The Director serves as a trusted commercial advisor to the CRO, CFO, regional sales executives, and Revenue Operations leadership. They personally guide Showpad’s most strategic and complex deals, balance revenue growth with margin and revenue quality, and provide clear recommendations on high-stakes commercial decisions. The role chairs the Value Pricing Board and owns the global discount approval framework and commercial policies. Following the Bigtincan merger, the Director will lead the design and implementation of a scalable commercial framework for the combined business, addressing legacy customer migrations, price books, contract terms, and quote-to-cash processes. The position is the executive business owner for quote-to-cash strategy and related systems, partnering with Finance, Legal, GTM Systems, Product Marketing, Sales, and Customer Operations to improve process quality, automation, booking accuracy, and cycle times. The role reports to the Vice President, Revenue Operations. It is based in the United States, with working overlap to support EMEA and periodic APAC deal activity. Occasional international travel and availability during month-, quarter-, and year-end close peaks are expected.

Requirements

10+ years of experience in B2B SaaS go-to-market organizations, with significant experience in Deal Desk, Revenue Operations, Sales Finance, or Pricing.
Proven experience advising C-level and senior sales and finance leaders and influencing decisions constructively under quarter-end pressure.
Deep experience structuring and negotiating complex enterprise SaaS deals, including multi-year, ramped, co-termed, multi-entity, and non-standard agreements.
Demonstrated ownership of a quote-to-cash or deal approval process at scale, including measurable process and systems transformation.
Experience chairing or leading an executive deal review or pricing approval forum.
Experience supporting a global sales organization across multiple regions and time zones, including North America and EMEA.
Strong working knowledge of ASC 606 / IFRS 15 and the effect of contract terms on bookings and revenue.
Strong analytical and financial acumen, including the ability to form and defend a clear view using imperfect data.
Strong working knowledge of Salesforce opportunities, quotes, products, and price books.
Experience with CPQ platforms such as Salesforce CPQ / Revenue Cloud, DealHub, or equivalent, including approval workflow design and business requirements.
Advanced deal modeling capability, including discount analysis, multi-year economics, and margin and cash impact.
Expert grasp of SaaS commercial metrics, including ARR, ACV, TCV, NRR, GRR, discount, and price realization.
Executive presence, credibility, composure, and ability to deliver unwelcome decisions while maintaining relationships.
Strategic commercial judgment balancing deal wins with margin, revenue quality, and long-term value.
Complex problem-solving skills, including developing clear options and recommendations for ambiguous, high-stakes issues.
People leadership, coaching, and accountability skills.
Ability to influence without authority across Sales, Finance, Legal, Product, and Systems.
Composure and pace under month-, quarter-, and year-end pressure.
Transformation mindset focused on simplifying, standardizing, and automating processes.
Bachelor’s degree in business, finance, economics, or equivalent practical experience.
Based in the United States, with working overlap sufficient to support EMEA sales leadership and periodic APAC deal activity.
Availability during month-, quarter-, and year-end close peaks.

Nice To Haves

Experience shaping SaaS pricing and packaging strategy, including list price changes and new packaging launches.
Experience leading commercial integration in a post-merger environment with multiple heritage customer bases, price books, and systems.
Exposure to APAC commercial practices and contracting.
Experience with reseller, partner, or channel deal structures.
Background in a private-equity-backed business with value-creation accountability.
Experience with contract lifecycle management tools such as DocuSign CLM, Ironclad, or equivalent.
Experience with billing and subscription management platforms such as NetSuite, Zuora, or equivalent.
Experience with QuickSight, Power BI, Tableau, or equivalent.
Experience with revenue intelligence platforms such as Gong or Clari.
MBA or advanced degree.
Salesforce CPQ or Revenue Cloud certification.
Pricing or finance certification, such as CPP or CMA.

Responsibilities

Set the vision, strategy, standards, and operating model for the global Deal Desk function.
Lead, coach, and develop the Deal Desk team, including regional coverage, capacity planning, hiring, and talent development.
Establish service levels for quote turnaround, approvals, and order processing, and ensure the team meets them, including during close periods.
Create a tiered engagement model that prioritizes strategic, high-value, and time-sensitive deals while minimizing friction for standard deals.
Advise the CRO, CFO, regional sales leaders, and Revenue Operations leadership on deal strategy, pricing, and commercial risk.
Shape regional deal pipelines and prepare with sales leaders for quarter-end and complex opportunities.
Frame high-stakes commercial decisions with options, economics, risks, and a clear recommendation for executive resolution.
Represent Deal Desk in forecast calls, QBRs, and annual planning, providing data-backed insight into deal quality, discounting, and commercial risk.
Personally lead the structuring of strategic, complex, and non-standard new-logo, expansion, renewal, and multi-year deals.
Resolve complex commercial issues involving customer migrations, legacy terms and price books, at-risk renewals, competitive displacements, multi-entity or multi-currency agreements, and channel structures.
Develop deal structures that support winning business while protecting margin, revenue quality, and long-term customer value.
Partner with Legal on non-standard commercial terms and establish the acceptable commercial position.
Serve as the final escalation point for deal-level disputes among Sales, Finance, and Legal.
Chair the Value Pricing Board and own its charter, membership, cadence, decision rights, and decision documentation.
Ensure Value Pricing Board submissions include deal economics, discount rationale, competitive context, risk assessment, and a Deal Desk recommendation.
Own and evolve the global discount approval matrix, delegation of authority, and commercial policy framework.
Use Board outcomes to refine policy, strengthen guardrails, and reduce unnecessary executive escalations.
Own end-to-end quote-to-cash strategy, covering quote creation and approval, contract execution, booking, provisioning, invoicing, and renewal.
Lead quote-to-cash redesign for the combined Showpad and Bigtincan business, identifying bottlenecks, manual work, and control gaps and delivering a transformation roadmap.
Act as executive business owner for CPQ, approval workflows, contract management, and billing integrations, partnering with GTM Systems on requirements, priorities, and adoption.
Ensure bookings are accurate, complete, and audit-ready, working with Finance and Accounting on ASC 606 / IFRS 15 considerations and revenue recognition.
Improve handoffs among Sales, Deal Desk, Finance, Legal, and Customer Success so sold products and terms are correctly provisioned, billed, and recognized.
Reduce quote-to-cash cycle time and booking errors, and report progress to Revenue Operations and executive leadership.
Partner with the CRO, CFO, and VP of Revenue Operations on pricing strategy, list pricing, packaging, discount guardrails, and renewal uplift policy.
Provide deal-level evidence for pricing decisions, including discount trends, win/loss by price point, deal size and mix, price realization, and regional and segment variation.
Partner with Product Marketing and Finance to ensure new products and packaging are quotable, approvable, and bookable at launch.
Identify pricing leakage and commercial friction and present quantified recommendations for improvement.
Own rollout decisions and commit capacity when global pricing changes require reprioritization across Finance, Legal, and GTM Systems.
Deliver executive reporting on discounting, deal velocity, approval cycle time, non-standard terms, and price realization.
Partner with Sales and Customer Operations to support forecast accuracy and with Finance to reconcile bookings each period.
Lead change management for pricing, policy, and process updates, communicating clearly and early to affected stakeholders.
Champion automation, simplification, and documented, auditable, scalable processes.
Ensure the Deal Desk team is fully staffed, engaged, developing, and has clear career paths and regional coverage without single points of failure.