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Salary: USD 204,000 - 240,000 / annual
Abnormal AI is seeking a Director of Deal Strategy & Operations to build and lead the function that shapes how the company structures, approves, and closes its most important enterprise deals. Reporting to the VP of GTM Operations, you will own two connected capabilities: Deal Strategy and Deal Desk.
In Deal Strategy, you will partner with sellers and leadership to design commercial structures for high-value enterprise customers that balance customer needs with business guardrails, including multi-product bundles, enterprise license agreements, and multi-year terms. You will translate customer requests into structures that protect margin, revenue quality, and long-term value, and bring clear recommendations to leadership when deals require exceptions.
In Deal Desk operations, you will run day-to-day deal intake, approvals, and non-standard term reviews, keeping deals moving quickly through the right reviewers with clear service levels, especially at quarter close. You will work closely with Finance, Order Management, and Legal to apply policy consistently and ensure deal approvals and associated Salesforce data are accurate and complete.
Key responsibilities include: designing AI-first deal systems and quoting workflows that enable sellers to self-serve routine answers while your team focuses on deals requiring human judgment; partnering with Revenue Systems on next-generation CPQ and approval workflows; writing and maintaining deal policies, playbooks, and approval matrices; equipping the field with guidance, tools, and training to structure better deals; and building and leading a high-performing team of deal strategy and deal desk professionals.
Abnormal closed FY26 at approximately $380M in ARR, growing about 50% year-over-year, with over 5,000 customers and more than 30% of the Fortune 500 trusting the company to protect their people. As the company expands from email security into a broader behavioral AI platform, deals are becoming increasingly complex, requiring sophisticated structuring and governance.
You will be a trusted cross-functional partner working 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.
**Requirements:**
- 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 revenue recognition implications
- Hands-on experience with Salesforce and CPQ quoting and approval workflows, plus 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, with credibility to influence senior sales leaders and say no constructively
- Exceptional communication skills, with ability to turn complex commercial tradeoffs into clear recommendations
**Nice to Haves:**
- Experience with 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
