Senior Deal Desk Analyst (Sales Operations)

Location: Hybrid in Chicago or Boston, United States; based within commuting distance of a hub and working in person three days per week.

Salary: $93,000–$110,000 per year plus equity.

Company

hirify.global is an intelligent platform for travel and spend management, automating travel bookings, expenses, invoice processing, and related manual work for more than 12,000 companies.

What you will do

• Support North America Sales through SMB, mid-market, and enterprise deals from quote to signature.
• Structure and price complex and non-standard deals, apply discounting rules, manage approvals, and escalate exceptions with recommendations.
• Review quotes, order forms, contract terms, and redlines for accuracy, compliance, commercial risk, and revenue-recognition considerations.
• Partner with Sales leaders, Account Executives, Legal, Finance, and Sales Operations to unblock deals and maintain deal velocity.
• Run workflows in Salesforce and CPQ or quoting tools, and support reporting on SLAs, deal velocity, and policy adherence.
• Contribute to process improvement, automation, and AI initiatives, including testing new tools and workflows.

Requirements

• Typically 4+ years of experience in deal desk, sales operations, or commercial operations in B2B SaaS, ideally supporting both mid-market and enterprise deals.
• Strong knowledge of pricing, discounting, and deal structuring, with sound commercial judgment and confidence making recommendations.
• Experience reviewing contract terms and redlines and knowing when to escalate issues to Legal or Finance.
• Hands-on experience with Salesforce and CPQ or quoting tools.
• Strong communication and stakeholder-management skills across Sales, Legal, and Finance.
• Excellent attention to detail and organization in a fast-paced, high-volume environment.
• Ownership and curiosity about using automation and AI to accelerate deal execution.
• English is the official language at the office; submit the application materials in English.

Culture & Benefits

• IRL-first hybrid work with in-person collaboration three days per week.
• 20 vacation days, 12 public holidays, paid parental leave, and a four-week paid sabbatical after five years.
• Medical, dental, vision, HSA, life and disability insurance, wellbeing support, and a 401(k) with company matching.
• Equity ownership, pet-insurance discounts, annual events, and 16 paid volunteering hours per year.
• Up to 20 Work from Anywhere days per year and relocation support to company hubs.
• AI-enabled tools are used across functions to reduce manual work and improve productivity.

Hiring process

• Submit an updated portfolio and/or resume.
• Submit the resume in English.