Five Years on the Deal Desk at Adobe, Box, and Otter.ai
The operating years that made the platforms possible.
Apttus/Conga (2020 – 2021)
Jon's Deal Desk career began at Apttus (later rebranded Conga), where he joined the enterprise renewal team as a contractor during COVID. The work was entirely manual: calculating pricing uplifts in Excel, structuring existing customer renewals, and assembling order forms through copy-paste into Word documents for approval and execution. There was no automation, no CPQ, and no margin for error on contracts that governed enterprise software relationships worth significant annual recurring revenue.
It was unglamorous work, but it was foundational. Doing the job manually, before ever touching a CPQ tool, meant understanding exactly what the automation was supposed to replace and why. Every hour spent in Excel building renewal calculations by hand became institutional knowledge that no amount of Salesforce CPQ training could replicate. The frustration of that process was also the first seed of what would eventually become a career-long instinct for building better tools.
Box (2021 – 2023)
At Box, Jon managed enterprise, mid-market, and SMB deals across the West region and Australia. The role spanned the full deal lifecycle: advising sales on deal structure, securing C-level approvals for complex pricing exceptions, and managing product and pricing migrations for existing Box customers. Net-new, expansion, renewal, and ramp deals all ran through his desk, giving him broad exposure to how enterprise software deals are structured across every stage of the customer relationship.
Otter.ai (2023)
Jon joined Otter.ai as the company's first and only Deal Desk hire, building the function from scratch. He owned everything: RFP responses, security questionnaires, approval matrix design, discount and promotion governance, legal language library management with outside counsel, pricing recommendations, order form creation, billing and invoicing, subscription management, and a full billing platform migration from Stripe to Zuora. The breadth of this role (one person, zero precedent, every deal) sharpened his instinct for building systems that work without organizational support around them.
Adobe (Aug 2023 – Oct 2025)
Jon ran the Deal Desk for Frame.io, a recent Adobe acquisition operating with separate revenue processes and sales infrastructure from the broader Adobe organization. The mandate was clear and constrained: close Frame.io deals to Adobe's quality standards without adding tooling, introducing complex workflows, or drawing on Adobe's central engineering or revenue resources. Operating effectively as a startup within a public enterprise company, Jon made consequential pricing and deal structure decisions with limited organizational support, handling net-new, expansion, migration, and renewal motions across a high-volume pipeline.
What This Experience Teaches
Five years on the Deal Desk builds a deep understanding of how enterprise software actually gets sold. It teaches pricing psychology: why certain discount structures work and others create perverse incentives. It teaches discount governance: how to balance sales flexibility with margin protection. It teaches multi-year contract structuring: how to model ramp deals, co-term agreements, and renewal pricing that protects long-term revenue. It teaches renewal optimization: how to structure initial deals so that renewals are straightforward rather than adversarial.
More importantly, it teaches the difference between what data sales teams actually need and what CRM dashboards show them. Most internal tools fail because they are built by people who have never done the job those tools are supposed to support. They optimize for data collection rather than workflow efficiency. They add fields instead of removing steps. They look good in demos but create friction in daily use.
Why It Matters for Product
The best product managers for revenue tools are people who have lived the revenue workflow. Jon does not need to interview sales reps to understand the problem; he was the one experiencing it. He does not need a discovery phase to map out approval chains; he built and maintained them. He does not need user research to understand what a quote document should look like; he has reviewed thousands of them.
Five years on the Deal Desk means the problem space was already deeply understood before the first conversation happened. The discovery phase for the CPQ was accelerated, not skipped: comparing third-party vendors, conducting end user research, and validating requirements against real workflows. But the approval chain logic wasn't abstract. The edge cases weren't surprises. The gap between what CPQ tools promise and what sales teams actually need wasn't a hypothesis; it was lived experience. That's the advantage domain expertise gives you when you sit down to build. The CPQ shipped in 50 days.