Senior Deal Desk Analyst

Perk • Full-time • Chicago, IL, US • $93k - $110k / year • 1d ago

About the Role

Perk's Deal Desk is becoming a strategic function: one that shapes how our Sales organisation structures, prices, and closes its deals. We're investing in that transformation now, with a growing focus on automation and AI to take manual work out of deal execution.

We're hiring a Senior Deal Desk Analyst to support our North America sales team. You'll be the go-to commercial partner for Sales leaders and Account Executives in the region, helping them structure, price, and close deals quickly and with confidence. You'll report to the Deal Desk Team Manager and work closely with Sales, Finance, Legal, and Sales Operations.

This is a senior individual contributor role. You'll work independently on complex and non-standard deals, make sound judgement calls within pricing and approval guardrails, and help us improve how the Deal Desk operates as we scale.

What You'll Do

Support North America deals end to end

Act as the main Deal Desk contact for North America Sales, supporting deals from quote to signature across SMB, mid-market and enterprise opportunities.
Structure and price complex and non-standard deals, 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, and act as the first line of defence on non-standard terms and redlines before involving Legal or Finance.
Keep deals moving through the pipeline with accurate, timely handling of tickets and approvals.

Partner with the business

Work closely 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 quickly and consider revenue recognition and business risk on non-standard deals.
Be a trusted, credible voice for Deal Desk across time zones, communicating clearly and setting expectations.
Share knowledge with colleagues on the team, including supporting newer analysts as needed.

Help us improve how Deal Desk works

Use our CRM and CPQ tooling (such as Salesforce) to run deal workflows, and flag where manual effort can be reduced.
Contribute to process improvement, automation, and AI initiatives led by the Deal Desk Team Manager, including testing new tools and workflows.
Support reporting and governance on SLAs, deal velocity, and policy adherence.

What success looks like

Accuracy, compliance, and SLA adherence across your deals.
Faster, smoother deal cycles for North America Sales.
Trust and positive collaboration with Sales, Legal, and Finance partners.
Improvements that reduce manual work for the team.

What We're Looking For

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 good commercial judgement and the confidence to make recommendations.
Comfort reviewing contract terms and redlines, and knowing when to escalate to Legal or Finance.
Hands-on experience with Salesforce and CPQ or quoting tools.
Strong communication and stakeholder management skills, with the ability to work across Sales, Legal, and Finance.
Excellent attention to detail and the ability to stay organised in a fast-paced, high-volume environment.
A strong sense of ownership and curiosity about automation and AI to make deal execution faster.

Compensation

Compensation for this role is a combination of salary and stock options. The anticipated base salary range is $93,000 - $110,000 per year. Actual compensation may vary based on specific qualifications, experience, and other job-related factors.

Benefits

Receive competitive compensation and equity ownership in Perk
Rest and recharge with our generous allocation of 20 vacation days and 12 public holidays
Enjoy the flexibility of three medical plans to choose from, with company contributions and an HSA when enrolling in an HDHP medical plan
Take control of your physical health with additional comprehensive benefit plans, covering dental, vision, and Wellhub’s gym subscription from your start date
Rest assured that you’re covered by life and disability policies from your start date, with options to add extra protection through voluntary buy-up plans
Plan for your future with our 401(k) plan with company matching contributions
Care for your furry friends through partner discounts on pet insurance
Join our unforgettable Perk events, including our spectacular annual summer party
Always feel supported with Spring Health, our market-leading wellbeing partner, providing fast, comprehensive access to 12x therapy and 12x coaching sessions for you and your loved ones
Focus on your family with 12-16 weeks’ paid parental leave
Contribute to your community with 16 paid hours per year to spend volunteering for your dearest charitable causes
Broaden your horizons with up to 20 "Work from Anywhere" days per year
Follow your passions and take a four-week, fully paid sabbatical once you reach 5 years
Let us help you move to one of our hubs with relocation support