Senior Deal Desk Analyst - US

Perk•Chicago, IL
•$93,000 - $110,000•Hybrid

About The Position

Perk is hiring a Senior Deal Desk Analyst to support its North America sales team. The role is a senior individual-contributor position and serves as a commercial partner to Sales leaders and Account Executives, helping structure, price, and close deals across SMB, mid-market, and enterprise opportunities. The analyst works independently on complex and non-standard deals, makes judgment calls within pricing and approval guardrails, and helps improve Deal Desk operations as the company scales, including through automation and AI initiatives. The role reports to the Deal Desk Team Manager and collaborates closely with Sales, Finance, Legal, and Sales Operations. It uses CRM and CPQ tools such as Salesforce to manage deal workflows, reviews quotes and contract materials, supports approvals and reporting, and helps maintain accuracy, compliance, and deal velocity. The position is based within commuting distance of Perk hubs and follows an in-person working approach three days per week.

Requirements

  • Typically 4 or more 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.
  • Comfort reviewing contract terms and redlines and knowing when to escalate matters to Legal or Finance.
  • Hands-on experience with Salesforce and CPQ or quoting tools.
  • Strong communication and stakeholder-management skills, including the ability to work across Sales, Legal, and Finance.
  • Excellent attention to detail and the ability to stay organized in a fast-paced, high-volume environment.
  • Strong sense of ownership and curiosity about using automation and AI to make deal execution faster.
  • Ability to work within commuting distance of a Perk hub and work in person three days per week.

Nice To Haves

  • Experience supporting both mid-market and enterprise deals.

Responsibilities

  • Serve as the main Deal Desk contact for North America Sales and support deals from quote through signature across SMB, mid-market, and enterprise opportunities.
  • Structure and price complex and non-standard deals while balancing commercial risk with deal velocity.
  • Apply pricing and discounting guidelines, manage non-standard pricing approvals, and escalate exceptions with a clear recommendation.
  • Review quotes, order forms, and contract terms for accuracy and compliance; act as the first line of defence on non-standard terms and redlines before involving Legal or Finance.
  • Handle tickets and approvals accurately and promptly to keep deals moving through the pipeline.
  • Partner with Sales Executives, Regional Team Leads, and Sales leadership to unblock deals and advise on commercial structure.
  • Collaborate with Legal, Finance, and Sales Operations to resolve issues, considering revenue recognition and business risk on non-standard deals.
  • Communicate clearly across time zones, set expectations, and represent Deal Desk as a trusted partner.
  • Share knowledge with colleagues and support newer analysts as needed.
  • Use CRM and CPQ tooling, such as Salesforce, to manage deal workflows and identify opportunities to reduce manual effort.
  • Contribute to process improvement, automation, and AI initiatives, including testing new tools and workflows.
  • Support reporting and governance for SLAs, deal velocity, and policy adherence.

Benefits

  • Competitive compensation and equity ownership in Perk.
  • 20 vacation days and 12 public holidays.
  • Choice of three medical plans, with company contributions and an HSA when enrolling in an HDHP medical plan.
  • Dental and vision plans, and a Wellhub gym subscription from the start date.
  • Life and disability policies from the start date, with options for voluntary buy-up coverage.
  • 401(k) plan with company matching contributions.
  • Partner discounts on pet insurance.
  • Company events, including an annual summer party.
  • Spring Health wellbeing support, including 12 therapy sessions and 12 coaching sessions for employees and loved ones.
  • 12–16 weeks of paid parental leave.
  • 16 paid volunteer hours per year.
  • Up to 20 Work from Anywhere days per year.
  • A four-week fully paid sabbatical after five years.
  • Relocation support to move to one of the company's hubs.
© 2026 Teal Labs, Inc
Privacy PolicyTerms of Service