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System Operations 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 System Operations Specialist supports Showpad by supervising, curating, and maintaining key internal systems. This energetic and resourceful individual will be responsible for not just administering but also communicating and collaborating with internal stakeholders related to the systems of responsibility. You will operate as the Subject Matter Expert for questions or improvement efforts and a key resource for driving best practice utilization.

The role will interact and collaborate with cross-functional teams to survey their needs to enhance the system as well as to manage system enhancement requests. The position is expected to raise sales efficiency, sales productivity and monitor process compliance by means of consulting with the sales force and implementing best practice sales processes.

If you are excited about helping build new capabilities to support Showpad’s growth and bring a customer service outlook and passion to evolve daily operational systems and tools this could be the perfect fit.

Key responsibilities as a System Operations Specialist at Showpad

  • Be a resource and collaborative partner for end users across the Showpad organization
  • Proactively monitors and strives to maintain high levels of quality, accuracy, and process consistency in the systems of responsibility
  • Monitor system adoption and ensure effective implementation of strategies and tactics
  • Develop key performance metrics and dashboards that focus on performance drivers
  • Create and run reports, manage user permissions, and troubleshoot system issues
  • Partner with cross-functional teams on process, tracking and administration
  • Proactively identify opportunities for improvement
  • Escalate problems promptly to the correct audience(s)
  • Remain calm when under pressure from end users

Skills and qualifications we are looking for

  • Bachelor’s Degree
  • 3+ years of work experience, preferably with some time spent in Operations, Systems Management or Business Management
  • Understanding of the SaaS space and internal processes & systems used
  • Experience with tools like Salesforce, Google Suite, Outreach is preferred
  • Demonstrated communication skills for both internal customer and management audiences
  • Ability to excel in a fast growing/fast paced environment, delivering accuracy while managing to deadlines where adaptability is imperative
  • Positive, high-energy attitude, independent, and takes ownership of all tasks from start to finish
  • Acute attention to detail
  • Data-driven with a commitment to process improvement. Passion for process and experience scaling processes with an aptitude for working with data, e.g. Salesforce Reports and Dashboards, Microsoft Excel and/or Google Sheets experience
  • Consistently operate in an attitude of partnership and collaboration. Develop strong relationships in all organizations and promote Showpad’s core values
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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

Eat lunch together
Open office floor plan
Unconscious bias training
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
Stocked Kitchen
Some Meals Provided
Happy Hours
Fitness Subsidies
Professional Development Benefits
Job Training & Conferences
Diversity Program
Promote from within
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