Director, Deal Strategy Operations

About the Role

The best deals don't happen by accident. They're designed.

As Director, Deal Strategy & Operations, you'll build and lead the function that shapes how Abnormal structures, approves, and closes its most important enterprise deals. Reporting to Ted Noble, VP of GTM Operations, you'll own two connected capabilities. The first is Deal Strategy, where you'll partner with sellers and leadership to design commercial structures for high-value enterprise customers that meet what the customer needs and stay within the guardrails that keep our business healthy. The second is Deal Desk, where you'll run the day-to-day engine of deal intake, approvals, non-standard terms, and related CRM data quality. This is a builder's role for someone who wants to help make Abnormal the #1 AI-native company: you'll take an AI-first approach to quoting, field guidance, approvals, and policy, so the field gets fast, confident answers and the business gets consistent, well-governed deals.

The opportunity is growing quickly. Abnormal closed FY26 at roughly $380M in ARR, growing about 50% year over year, with more than 5,000 customers and over 30% of the Fortune 500 trusting us to protect their people. As we expand from email security into a broader behavioral AI platform, our deals are getting bigger and more complex: multi-product bundles, enterprise license agreements, and multi-year structures. You'll make sure every one of those deals is built to win today and to grow with the customer over time.

What You Will Do

• Lead Deal Strategy for strategic enterprise deals. Partner with Account Executives, sales leaders, and executives to design commercial structures for high-value opportunities, including multi-product bundles, enterprise license agreements, multi-year terms, and expansion and renewals.
• Balance customer needs with business guardrails. Translate what customers are asking for into structures that protect margin, revenue quality, and long-term value, and bring clear recommendations to leadership when a deal needs an exception.
• Own Deal Desk operations. Run day-to-day deal intake and approvals, keeping deals moving quickly through the right reviewers with clear service levels, especially at quarter close.
• Validate non-standard terms. Review and resolve non-standard pricing, payment, billing, and contractual requests, working closely with Finance, Order Management and Legal to apply policy consistently.
• Make CRM data trustworthy. Ensure deal approvals, business justifications, and associated data in Salesforce is accurate and complete.
• Build AI-first deal systems. Design how AI and agentic workflows support quoting, field guidance, deal approvals, and policy questions, so sellers can self-serve routine answers and your team can focus on the deals that need human judgment. Set the standard that AI speeds things up without weakening accuracy, auditability, or policy compliance.
• Shape the future of quoting. Partner with Revenue Systems on the design of our next-generation quoting and approval experience, including CPQ, approval workflows, and pricing and packaging changes as new products launch.
• Write and maintain deal policy. Own the playbooks, approval matrices, and deal guidelines that the field relies on, and keep them current as our products, pricing, and markets evolve.
• Enable the field. Equip sellers and sales leaders with the guidance, tools, and training to structure better deals on their own, across every region and segment using an AI first approach.
• Build and lead the team. Hire, develop, and lead a high-performing team of deal strategy and deal desk professionals, with a focus on scaling through systems rather than headcount alone.
• Be a trusted cross-functional partner. Work hand in hand with Sales, Finance, Legal, Revenue Systems, Product, and Order Management to keep the full deal lifecycle connected from first quote to booked revenue.

Must Haves

• 8+ years of experience in deal desk, deal strategy, revenue operations, or commercial finance at a high-growth B2B SaaS company, with at least 3 years leading teams.
• Proven track record structuring complex enterprise deals, including multi-product, multi-year, and enterprise license agreements, in the six- and seven-figure ARR range.
• Deep understanding of SaaS deal economics, including discounting, pricing and packaging, payment terms, bookings policy, and the revenue recognition implications of different structures.
• Hands-on experience with Salesforce and CPQ quoting and approval workflows, plus a strong commitment to CRM data quality.
• Experience designing or rebuilding deal approval processes, policies, and service levels that hold up at scale and under quarter-end pressure.
• Demonstrated experience applying AI and automation to deal workflows, with sound judgment about where it helps and where human review is required.
• Strong partnership with Finance, Order Management and Legal, and the credibility to influence senior sales leaders and say no constructively when a deal doesn't fit.
• Exceptional communication skills, with the ability to turn complex commercial tradeoffs into clear recommendations.

Nice to Haves

• Experience with tools in our ecosystem, such as SpotDraft, Maxio, NetSuite, Gong, Snowflake, and Sigma.
• Experience leading or contributing to a CPQ implementation or replacement.
• Background in cybersecurity or another technical, enterprise-focused category.
• Experience supporting global deal operations across EMEA and APJ.