Sr. Pricing Operations Manager

Amazing Career Moments Happen Here

Transforming the insurance industry is ambitious, we know. That’s why at Applied, we’re building a team that shows up every day ready to learn, willing to try new things, and driven to deliver innovative software and services that make us indispensable to our customers – all within a culture built on values that make us indispensable to each other too. With 40+ years of experience in the insurtech game, we’re not just redefining what’s achievable, we’re creating a place where amazing career moments are made possible.

We’re searching for a Sr. Pricing Operations Manager to join our Sales Operations team in a hybrid setting from our Chicago office (2 days per week). To keep us headed in the right direction, we’re looking for people who understand winning is a team sport, who value and seek to learn from our team’s diverse experiences and backgrounds, who welcome a challenge and take risks in the pursuit of creating better outcomes for our customers, and who can, at any given time, step back to laugh and have some fun.

• Deal Desk Leadership & Optimization: Architect, launch, and lead the Applied Systems Deal Desk function, serving as the primary business partner for the Sales organization on complex, non-standard, and high-value deals. Ensure all approved pricing, discounting, and deal structures are operationalized and can be accurately reported and forecasted.
• Pricing Project Program Management: Be the ‘Quarterback’ for key pricing initiatives, partnering with Revenue Operations, Finance, IT, Sales Enablement, and/or Legal Departments to define requirements for, and drive the evolution of, our GTM systems stack and overall process design.
• Strategic Deal Structuring: Serve as a trusted advisor to GTM teams, providing expert guidance on alternative contract options, creative deal structuring, and value propositioning to help drive deal closure.
• Enterprise Deal Modeling: Develop, evaluate, and implement sophisticated pricing and financial models for multi‑year, high‑value enterprise agreements. Collaborate with key stakeholders to structure custom deals that align with customer needs while maximizing long‑term revenue (ARR) and profitability.
• Promotion & Discounting Governance: Design, implement, and govern the company‑wide discounting and promotion framework. Establish and maintain clear policies, approval matrices, and exception‑handling processes to ensure pricing integrity and margin protection.
• Annual Price Uplift: Partner with FP&A, sales, and executive stakeholders to align on our approach to annual price increases.

• 8‑12+ years of progressive experience in Deal Desk, Revenue Operations, Sales Operations, or Pricing, within a B2B SaaS or subscription‑based technology company.
• 3‑5+ years of experience in a senior, strategic, or people management capacity, with a proven ability to lead and influence cross‑functional teams.
• Expert‑level, demonstrable mastery of Microsoft Excel is essential. This includes building complex, multi‑dependent financial models from scratch, using advanced formulas, pivot tables, and data analysis functions.
• Proven track record of success in building, scaling, and managing a Deal Desk or "price desk" function.
• Deep expertise in structuring complex, multi‑product enterprise deals and the associated financial modeling (e.g., LTV, margin analysis, ARR impact).
• Strong grasp of financial and business metrics (e.g., LTV, CAC, margin analysis, ARR, and MRR) and how pricing and deal decisions impact the overall business strategy.
• Experience with multiple B2B SaaS pricing models (e.g., subscription tiers, usage‑based, "value‑based") is highly desirable.
• Understanding of GTM systems and quote‑to‑cash workflows and CRM (e.g., Salesforce) and CPQ platforms.
• Ability to work from our Chicago office 2 days per week (Monday and Wednesday).

We know that talent comes from all backgrounds and experience levels. We encourage military members and their spouses as well as candidates without a degree or a background in tech to apply!

A culture that values who…