Director of Customer Success and Strategy

| Remote
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About UPshow: 

UPshow is a rapidly growing SaaS company providing innovative solutions to the Hospitality, Health Care and Fitness industries.  Company growth has averaged 70% over the last several years.  UPshow completed a $14M cash raise in the second half of 2020.

UPshow is the leading innovator in digital signage for businesses. UPshow increases customer engagement with interactive TV and mobile software, creating a unique in-venue network to advertise to and entertain customers. We offer a three-in-one platform that provides: entertainment options, engagement solutions and a management suite to measure results. By using these tools, businesses can increase revenue; influence customer and employee behavior; and become more efficient. Our clients range from healthcare providers, to restaurant groups,  to nationwide gyms — all looking to reach their customers with the right messages at the right time. Founded in 2015, UPshow now reaches audiences in thousands businesses around the world. UPshow has been named one of Chicago's Best Places to Work and one of American's Fastest Growing Companies on Inc. 5000. 



About the Role:

The Director of Customer Success and Strategy will lead UPshow’s Customer Success team; be a significant factor in driving rapid revenue growth for our enterprise customers and collaborate closely with UPshow’s leadership team.  In addition to leading the Success Team, the individual will be designing and delivering sophisticated strategic plans/programs for our enterprise customers.

The Director of Customer Success and Strategy should provide a blend of: strategic counsel; industry acumen; innovation, detail-orientation; technical prowess and leadership / management skills..  



  • Collaborate with prospective and named customers to understand their strategic goals and objectives
  • Provide suggestive strategies and solutions that many times will not be exactly what the customer asks for, rather they will be based upon the intellectual capital and industry expertise that you possess. 
  • Develop ROI based models that support the value driven by the UPshow solution. (e.g increased revenues per transaction, more frequent visits and increase in new customer acquisition) 
  • Create tailored Account Plans and business reviews that provide clear feedback on progress to goals and objectives
  • Actively communicate product updates and relevant features to customers in order to set expectations and manage their experience.
  • Cultivate and develop close working relationships with Executives and other key stakeholders
  • Discover customer pain points and advocate for them internally by providing strategic direction to the product management team
  • Lead strategic growth opportunities 
  • Lead cross-functionally to drive customer success, including Renewals & Expansion, Sales, Product, and others, to improve the customer experience
  • Drive alignment with CS, Sales, and Product by defining up-sell strategy and focus on retention
  • Build and lead a world-class Customer Success team: 
    • Recruit and develop a high performing team
    • Foster collaboration within the UPshow team and across our customer base
    • Drive operational practices to track the performance of the Customer Success team
    • Deliver transformational leadership to motivate and engage the Customer Success team
    • Be an inspirational leader by challenging and maximizing the strengths of the team
  • Work closely with the CRO and the President, SVP of Customer Success to align on strategies, renewal forecasting, and account opportunities
  • Drive customer outcomes, product adoption, and customer experience
  • Address escalated customer issues with speed and urgency, orchestrating resources across the company as appropriate
  • Influence future lifetime value through higher product adoption and customer satisfaction


  • Bachelor’s degree in Business or related field; MBA preferred
  • 7+ years of Customer Success, Account Management, or Sales experience
  • Proven track record selling to and building relationships with C-level executives
  • Excellent communication and presentation skills
  • Advertising Agency, Creative Agency or SaaS experience is a plus


Benefits and Perks: 

  • Competitive Compensation + Commission
  • Stock Options
  • Medical, dental, vision, life, and short-term disability insurance
  • Professional Development Programs
  • Access to senior management and mentoring opportunities
  • Employee Recognition Program
  • Unlimited PTO
  • Parental Leave
  • 401k Match
  • Pre-tax Transportation
  • Summer Fridays
  • Employee Assistance Program
  • Work from Anywhere policy, to respond to an ever-changing work climate
  • Virtual Social Events including Team Wins and Highlights from the Month, Cultural and Diversity Spotlights, and Happy Hours

This is a chance for you to join a challenging and inspiring environment where you will have the possibility to make a daily impact. Every day you will work alongside helpful and down-to-earth colleagues who are dedicated and ambitious. Together we create an innovative environment that drives UPshow forward. If you are the right person for the role you will be part of a fantastic journey in a dynamic, high-growth business.

We look forward to your application.

UPshow is an equal opportunity workplace and an affirmative action employer. 

We are always committed to equal employment opportunities regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity, or Veteran status. Discrimination is not welcome on the basis of any other status protected by the laws or regulations in the locations where we work.

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Technology we use

  • Engineering
  • Product
  • Sales & Marketing
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    • PHPLanguages
    • Google AnalyticsAnalytics
    • SEMRushAnalytics
    • IllustratorDesign
    • PhotoshopDesign
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    • TrelloManagement
    • HubSpotCRM
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    • SalesforceCRM
    • MailChimpEmail
    • IntercomEmail
    • MandrillEmail
    • RapportiveLead Gen


Our office is in the heart of the loop surrounded by plenty of great bars and restaurants. Plus, our office is easily accessible by CTA/Metra.

An Insider's view of UPshow

What’s the vibe like in the office?

Imagine a fan club for your favorite team or hobby - that's what it's like in our office. Every person in the office is so enthusiastic about what they do, and deeply invested in the success of the company. Our energy is infectious: if you've never looked forward to coming into work before, that will quickly change when you join the UPshow team


Content Marketing Specialist

How do you collaborate with other teams in the company?

Working on the product team, collaboration is an important part of my job. Whether it's working with the CS team to ensure we address customer issues or getting ahead of a new feature to help the sales team hit their goal, I work with other teams to better understand our customer needs in order to make a better product.


Product Manager

How do your team's ideas influence the company's direction?

Our creative team is incredibly influential when it comes to the UPshow brand and product. Our product designers are reinventing how content appears on our screens with motion design, while making it easier for customers to schedule entertainment and promotions with UX/UI. Campaigns and brand assets are built by our marketing designers each day.


Chief Creative Officer

What are UPshow Perks + Benefits

Volunteer in local community
Employees are encouraged to suggest different organizations to work with and support throughout the year.
Friends outside of work
Eat lunch together
Intracompany committees
TeamUP, a committee of volunteer employees, comes together weekly to work on D&I, development, events and other initiatives that create the culture we are so proud of.
Daily stand up
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Open office floor plan
Diversity manifesto
Mean gender pay gap below 10%
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Our dental plan covers 50% of premiums.
Vision Benefits
The vision benefits plan covers annual eye exams with $150 for glasses and contact lenses.
Health Insurance Benefits
UPshow's health insurance policy covers 50% of premiums.
Life Insurance
Team workouts
With a discounted rate at Chicago Athletic Clubs and fitness customers all around the city, our team never hesitates to sweat it out together.
Mental Health Benefits
Retirement & Stock Options Benefits
401(K) Matching
Company Equity
UPshow offers stock options through its employee equity plan, including a 4-year vesting schedule with a 1-year cliff.
Performance Bonus
UPshow's performance bonus plan awards employees when they meet targets set by their direct manager.
Child Care & Parental Leave Benefits
Generous Parental Leave
Flexible Work Schedule
Remote Work Program
Family Medical Leave
Return-to-work program post parental leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Generous PTO
UPshow offers unlimited paid time off.
Paid Holidays
Paid Sick Days
Our unlimited paid time off policy includes sick days.
Perks & Discounts
Beer on Tap
Casual Dress
Commuter Benefits
Company Outings
Whether it's visiting a customer venue, getting creative with offsite brainstorms, or celebrating a milestone out on the town, Team UPshow works hard and plays hard.
Stocked Kitchen
Healthy snacks? Comfort food? Multiple flavors of LaCroix? Whatever your preference, our kitchen always has something to keep you going. 
Some Meals Provided
We provide catered lunch from some the best spots in the city during our monthly UPshow and Tell.
Happy Hours
Unwind with the team and enjoy a cold bottle of beer, seltzer, or ginger ale during our Friday happy hour.
Pet Friendly
UPshow has been called the Most Pet Friendly company in Chicago! If your pet is friendly and well-behaved, we welcome them as a part of our team. Check out some of our office pets on our Instagram!
Professional Development Benefits
Job Training & Conferences
Diversity Program
Lunch and learns
We host a monthly UPshow and Tell where employees gather to share their interests and passions outside of work. Lunches are catered by local hot spots.
Cross functional training encouraged
Promote from within
Mentorship program
Continuing Education stipend
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