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Deal Desk Specialist

| Chicago

About Showpad

Showpad is the leading sales enablement platform for the modern seller. Showpad’s all-in-one platform empowers sales and marketing teams to engage buyers through industry-leading training and coaching software and innovative sales content and engagement solutions. 

At Showpad, personalities and cultures connect across oceans to create something extraordinary. As a top 10 software company in the Inc. 5,000 Europe list, Showpad is changing the game when it comes to sales enablement. Our employees create the engagement and impact that drives our success as we expand globally.

In the morning, we’re drinking San Francisco cold brew coffee with a side of Portland doughnuts – English scones for afternoon tea, and in the evening we’re toasting success with Belgian tripel Westmalle to a Chicago house tune.

About the position

The Deal Desk Specialist will provide guidance on complex deal structures and support the execution of proper process while ensuring business and operational compliance. You will provide feedback to help drive enhancements to the quote-to-cash processes and policies to increase sales velocity and improve operational efficiencies. You will influence and drive strong working relationships with the sales teams and Showpad’s internal back office functions.

This role is a hybrid of traditional jobs in sales operations, finance, and administration and is crucial to supporting the explosive growth of the Showpad team. The candidate should be familiar with how software companies go-to-market in order to align with the responsibilities of different roles (e.g. sales development reps, account executives, specialists, product overlays, customer success, etc.) and be prepared to work in a fast-paced, collaborative team environment.

Key responsibilities as a Deal Desk Specialist at Showpad

  • Serve as a trusted advisor to field sales on pricing, product configuration, and business terms to drive agreement closure
  • Manage the end-to-end deal review process and proper execution of required materials
  • Ensure compliance with published sales and business approval policies and serve as an escalation point to business partners for quote-to-cash operations
  • Act as the primary liaison with all cross-functional business partners involved in the order process to facilitate closure
  • Build productive relationships and feedback loops with Legal, Finance, Sales, Customer Success teams to drive efficiencies
  • Review, research and approve pricing requests
  • Manage discount and gross margins
  • Develop and share best practices and ensure standardization across GEOs
  • Coordinate non-standard requests and be able to navigate through complex business processes and policies
  • Review and verify incoming deals for accuracy, including but not limited to: confirming contract terms, contact and billing information, pricing, business policies, and existing legal agreements/pre-existing terms

Skills and Qualifications we are looking for

  • Bachelor’s Degree in Business, Finance, Economics, or a related discipline
  • 1-3 years experience as a financial analyst, sales operations specialist, and/or experience supporting a complex Sales organization
  • Strong background in Salesforce.com, Excel, and CPQ/Quote-to-Cash Processes
  • Involvement with licensing and pricing programs at the enterprise level would be ideal
  • Strong change management skills and experience with a rapidly changing business environment and ongoing operational improvements
  • Strong analytical, accounting, and advanced Excel skills

Nice To Haves

  • Experience within high-tech industry, SaaS business models & needs
  • Knowledge or experience with billing systems/ERPs (such as NetSuite)
  • Experience and understanding of Software Revenue Recognition

What you can expect from Showpad

Focus on Impact and Growth

We are building the future in sales and marketing where every sales person is successful. As an international scale-up, we aim for yearly double digit growth that opens many opportunities. We want people who thrive in a fast-paced, performance-driven company, who are not afraid to stretch themselves in a fun environment, and focus on impact and growth.

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Technology we use

  • Sales & Marketing
    • WordpressCMS
    • SageCRM
    • SalesforceCRM
    • MarketoLead Gen


Centrally located in the Loop and easily accessible for all commuters with tons of options for lunch.

An Insider's view of Showpad

What’s the vibe like in the office?

The vibe in our Chicago office is unlike any other startup I've ever been a part of. Everyone is smart, humble and effective. Even though we are all busy, everyone is always willing to offer help or guidance - even if it outside of their wheelhouse. We all genuinely enjoy each other's company and want to see our teammates succeed.


Office Manager

How do you collaborate with other teams in the company?

Collaboration is absolutely key for my team, since we’re tasked with bringing many different groups together. And as an international organization, we’re building relationships not only across departments, but across the world too. The key for us is to show how we provide value and prove how our collaboration impacts both revenue and culture.


Head of Global Business Development and Alliances

What is your vision for the company?

We’re building the future of sales & marketing success, by empowering sales & marketing teams to sell the way buyers want to buy. We’re delivering a better buyer experience, intelligent sales content and an analytics-powered platform that’s smarter than traditional sales enablement.


President & COO

What are Showpad Perks + Benefits

Open office floor plan
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Wellness Programs
Retirement & Stock Options Benefits
Child Care & Parental Leave Benefits
Generous Parental Leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Volunteer Time
Perks & Discounts
Beer on Tap
Casual Dress
Commuter Benefits
Company Outings
Some Meals Provided
Happy Hours
Fitness Subsidies
Professional Development Benefits
Diversity Program
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