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Running a Deal Desk on Ironclad

August 14, 2023 5 min read
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My name is Nick Thompson, and I am the Senior Manager of Deal Desk at Ironclad. Deal Desk is a strategic and operational function focused on collaborating with the sales team on executing non-standard transactions. These non-standard transactions could vary in any number of ways, but most frequently include custom commercial terms and conditions, custom pricing and packaging, or custom licensing structures.

Taking a Seat at the Deal Desk

I started my first Deal Desk role at AppDynamics in 2017. AppDynamics had just been through an acquisition with Cisco, and the next three and a half years were filled with exciting and unique opportunities to scale AppDynamics revenue growth. After AppDynamics, I went to DataRobot as Chief of Staff of the Legal and Deal Strategy & Operations teams. At both companies, the mission and value of the Deal Desk function was to structure custom transactions that resulted in ideal outcomes for the company and the customer, to partner with Sales in supporting revenue growth and retention, and to maintain a high degree of data integrity in our bookings and contracts. This mission certainly came with challenges:

  • Creating an auditable system of record for conversations about deals and non-standard approvals as each company continued to grow. Without that system of record, the internal contracting experience also suffered, creating confusion about the status of a deal as it navigated cross-functional conversations and approvals.
    Building an end-to-end process that accelerates the close of revenue while maintaining proper internal guardrails. Often, the end-to-end process and guardrails exist across multiple systems that are implemented and managed by different teams, which creates additional complexity.
  • Enabling the sales organization on process- and system-related changes and improvements to create a truly low-touch, self-service experience. Without strong enablement, the lack of clarity on execution can result in deals slowing down or even deals lost.

An Ironclad Discovery

While at DataRobot, we identified the need for a contract lifecycle management (CLM) solution. We ran an evaluation that validated Ironclad as the best fit based on its product capability and its ability to scale with our business. I collaborated with a few members of our internal team and the Ironclad team in implementing Ironclad, with a primary focus on building a repository for executed contracts and agreements. It was my first in-depth exposure to Ironclad, and it left me very impressed. It became clear that functions like Deal Desk, Order Operations, and Licensing could benefit immensely from the use of Ironclad not only as a system of record, but as a system that could help to manage complex approvals for commonly requested commercial terms.

Upon learning of the open role at Ironclad, I immediately knew that it was a great opportunity to work within a top-notch organization and with a very powerful product. After getting hired as Ironclad’s first–and only!–full-time Deal Desk operator, my foremost priority was to not only leverage Ironclad to accelerate our GTM motion while maintaining the necessary approval guardrails, but to do so in a thoughtful and scalable way that would not require significant staffing investments within the team.

Designing Ironclad’s Deal Desk in Phases

At Ironclad, I have had the benefit of collaborating on the project, dubbed the Deal Desk Design Initiative, with our talented teams in Sales, Legal, GTM Systems, Finance, Revenue Accounting, Customer Success, and Monetization.

Phase I

This part of the initiative required the creation of a true standard operating procedure and Deal Desk playbook. We had several cross-functional discussions to determine which requests are always acceptable, which requests require situational review/approval for each team, and which requests could not be accommodated.

By aligning on situational approvals, we were able to accelerate deal cycles by advising the sales team and giving clear guidance on available commercial options. The introduction of the Deal Desk playbook was paramount, as it created a consistent method for drafting commonly requested custom language on Order Forms. A strong standard operating procedure and Deal Desk playbook also allowed us to set an internal cadence for reviewing trends in requests and determining if we would like to introduce or remove approvals based on a given month or quarter.

Phase II

The next phase has centered on utilizing Ironclad to enforce the dynamic commercial approvals outlined in the Deal Desk playbook, as well as building a streamlined contracting experience for new, upsell, and renewal business. Approvals that used to require Deal Desk to draft and send emails to various functions at peak times like month- or quarter-end now involve little touch by Deal Desk, automatic email notifications to each team where approval is needed, and an activity feed for each deal where each conversation is centrally captured.

As a Deal Desk team of one, it allows me to quickly identify and assess deals requiring Deal Desk review, understand any background/context behind a request, and operate confidently knowing that the other cross-functional teams are able to do the same.

activity feed in ironclad CLM headshot

Through the ongoing focus and collaboration of the Deal Desk Design Initiative, we have:

  • Successfully automated and streamlined many of the previous pain points that existed in our end-to-end Order Form generation and negotiation processes.
  • Built a system of record that uses Salesforce CPQ for discounting approvals and Ironclad for negotiation of all non-standard commercial terms.
  • Utilized Ironclad to capture automated conditional approvals of these non-standard commercial terms from cross-functional teams all across the organization, ensuring that each Order Form is fully reviewed, accurate, and approved before execution.
  • Launched a consistent end-to-end experience for our new, upsell, and renewal business, creating a standard operating procedure for all phases of the customer lifecycle.

Empowering Solo Deal Desk Teams

The impacts of the Deal Desk Design Initiative have been immense. These improvements have helped me to sleep well at night knowing that I will not have to personally juggle hundreds of email threads and look back on archived conversations about deals years from now to understand previously executed contracts. From a contracting experience perspective, our sales team now has to answer only five questions to launch an Order Form workflow. On top of that, they have access to request frequent non-standard terms and automatically engage the necessary cross-functional approvers, all while knowing the status of their deal on the workflow. This allows me to focus on structuring and executing truly strategic transactions, and know that our use of Ironclad will continue to support the growth of our business in a time where there are more workflows being launched and more signature packets being sent every day.

By the Numbers

For those curious for more specifics about how Ironclad can scale the efficiency of Deal Desk:

  • 1 New Business / Add-On Business Order Form workflow built in Ironclad
  • 1 Renewal Order Form workflow built in Ironclad
  • Dynamic commercial terms and approvals built in Ironclad:
    • Price Locks, Payment Terms, Custom Payment Schedules, Options to Buy, Template Adjustments, Implementation/Success Plans, Custom SOWs, Cancel and Replacements, Auto-Renewals, Quarterly True-Ups, Term Lengths, Logo Rights, Publicity and Marketing Language.
  • Dynamic cross-functional approval groups:
    • Legal, Finance, Revenue Accounting, Customer Success, Services Sales, Sales Management.

The Next Phase

There is always more for Deal Desk to build, streamline, and support. With Phases I and II in the rear view mirror, there are many exciting opportunities ahead for Deal Desk to partner with teams across our organization and to maximize the metrics that are critical to our business through deal strategy. It is an exciting time to be at Ironclad, and to be a user of Ironclad!



Ironclad is not a law firm, and this post does not constitute or contain legal advice. To evaluate the accuracy, sufficiency, or reliability of the ideas and guidance reflected here, or the applicability of these materials to your business, you should consult with a licensed attorney. Use of and access to any of the resources contained within Ironclad’s site do not create an attorney-client relationship between the user and Ironclad.



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Nick Thompson is Ironclad’s Senior Deal Desk Manager. He enjoys working on process improvements, strategizing about deals, playing tennis, and traveling.