Director, Deal Strategy

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Hiring Remotely in Boston, MA, USA
Remote or Hybrid
Artificial Intelligence • Cloud • Information Technology • Sales • Security • Software • Cybersecurity
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The Role
Director, Deal Strategy
The Director of Deal Strategy is responsible for managing and optimizing the proposals, RFP's, deal structuring, and contract approval process to ensure efficiency, compliance, and profitability. This leadership role involves collaborating with sales, product, finance, legal, and operations teams to drive deal velocity, enforce pricing strategies, and streamline the sales cycle.
In this role, you will own:
  • Deal Structuring & Approval Process
    • Lead the deal pursuit function, which includes proposal management, order management and deal desk providing strategic guidance on deal structuring, pricing models, and contract terms.
    • Ensure all deals comply with company policies, revenue recognition guidelines, and financial targets.
    • Act as a key liaison between sales, product, finance, and legal teams to facilitate deal approvals and mitigate risks.
    • Oversee and improve approval workflows to ensure timely processing and contract execution.
  • Pricing Strategy & Compliance
    • Enforce pricing strategies that align with corporate goals and market dynamics.
    • Work with finance and product teams to evaluate discounting structures and margin optimization.
    • Ensure pricing policies comply with legal, regulatory, and internal governance requirements.
    • Monitor and analyze competitive pricing trends and recommend pricing adjustments as needed.
  • Operational Efficiency & Process Optimization
    • Continuously optimize tools, automation, and best practices to improve deal desk efficiency and accuracy.
    • Lead process standardization efforts to enhance scalability and deal execution speed.
    • Define and track key performance indicators (KPIs) related to deal cycle time, approval rates, and revenue impact.
    • Provide training and support to sales teams on deal desk processes, systems, tools and best practices.
  • Cross-Functional Collaboration & Leadership
    • Partner with sales leadership to strategize on high-value or complex deals.
    • Collaborate with legal to refine contract templates and approval requirements.
    • Work with finance to align deal structures with revenue recognition principles.
    • Lead, mentor, and develop a team of deal desk analysts and specialists.

The skills you'll bring include:
  • Bachelor's degree in Business, Finance, or a related field (MBA preferred).
  • 8+ years of experience in deal desk, sales operations, finance, or a related function, with at least 3+ years in a leadership role.
  • Strong understanding of SaaS/software pricing models, revenue recognition principles, and contract negotiation.
  • Experience working with CRM and CPQ tools (Salesforce, Apttus, etc.).
  • Excellent analytical, problem-solving, and decision-making skills.
  • Strong leadership and team management abilities.
  • Effective communication and stakeholder management skills.
  • Ability to thrive in a fast-paced, high-growth environment.

We know that the best ideas and solutions come from multi-dimensional teams. That's because these teams reflect a variety of backgrounds and professional experiences. If you are excited about this role and feel your experience can make an impact, please don't be shy - apply today.
About Rapid7
Rapid7 (NASDAQ: RPD) helps organizations across the globe protect what matters most so innovation can thrive in an increasingly connected world. Our comprehensive technology, services, and community-focused research simplify the complex for security teams, helping them reduce vulnerabilities, monitor for malicious behavior, be in 10 places at once, and shut down attacks. We're on a mission to make security solutions easier to use and access so we can bring safety and resilience to more people. With more than 10,000 customers across 140+ countries, Rapid7 is a leader in cybersecurity that has earned numerous industry accolades and recognition for our technology and culture.
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All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, age, national origin, disability, protected veteran status or any other status protected by applicable national, federal, state or local law.

What the Team is Saying

Cathal
Aparna
Ali
David Boffa
Ronan McKinless
Pete Rubio
Shilan Aliyal
Rohit Sharma
Ronan McKinless
Rajeev Sharma
Corey Thomas
Rajeev Sharma
Prasad Vidhate
Rapid 7
Matthew Cappello
Rajeev Sharma
Wael Mohamed
Rajeev Sharma
Alex Pratt
Maria Loughrey

Rapid7 Compensation & Benefits Highlights

  • Inclusive Benefits Coverage Health plans include transgender‑inclusive care, abortion‑travel support, neurodiversity coverage, and mental‑health resources. Inclusive offerings are further extended with options like pet insurance.
  • Leave & Time Off Breadth Policies feature unlimited PTO and unlimited sick leave in the U.S., paid volunteer time, company holidays, and global recharge days. Hybrid‑first flexibility and wellness days reinforce time‑off support.
  • Equity Value & Accessibility Many roles include company equity/RSUs and access to an Employee Stock Purchase Plan, broadening ownership participation. Feedback suggests stock plans are a standout component of total rewards.

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The Company
HQ: Boston, MA
2,400 Employees
Year Founded: 2000

What We Do

At Rapid7, our vision is to create a secure digital world for our customers, our industry, and our communities. We do this by harnessing our collective expertise and passion to challenge what’s possible and drive extraordinary impact. We’re building a dynamic and collaborative workplace where new ideas are welcome. Protecting 11,000+ customers against bad actors and threats means we’re continuing to push the envelope - just like we’ve been doing for the past 20 years. If you’re ready to solve some of the toughest challenges in cybersecurity, we’re ready to help you take command of your career. Join us.

Why Work With Us

With our products, research, and open source communities, we’re building a secure digital future for everyone. This means constantly learning and evolving in an industry that’s anything but stagnant. You’ll be faced with tough challenges, and given the support to find creative solutions that drive our business, and your career forward.

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Rapid7 Offices

Hybrid Workspace

Employees engage in a combination of remote and on-site work.

Our default working model is hybrid, with employees working three days per week in the office. This approach underpins our commitment to flexibility and adaptability while supporting our dedication to development, teamwork and customer purpose.

Typical time on-site: 3 days a week
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