Head of Customer Success - Enterprise Regional

About the Role

As a Manager of Customer Success Management, you will play a critical role in ensuring merchant success. This role is going to be split between leading a team focused on optimizing operational health (including a combination of operational efficiency, customer experience, and financial health), and enabling and driving revenue growth by supporting upselling and cross‑selling efforts working hand‑to‑hand with Client Partners, Account Management Managers and Heads of Segment, to analyze merchant performance, identify operational pain points, and develop tailored solutions to merchants.

Your role will be a co‑orchestrator of our Enterprise Partnerships, ensuring their ongoing success.

What You'll Do

Lead a team of Customer Success Managers, ensuring the timely and accurate monitoring of merchant operational health, driving product adoption, executing on agreed plans, ensuring customer retention and expansion, and guiding them in the right direction to effectively identify and solve potential issues.

Co‑own and manage relationships with key restaurant brands, developing and executing the strategy to achieve quarterly and annual growth goals.

Drive revenue growth by identifying upselling and cross‑selling opportunities, expanding product adoption and communicating the value of our newest products with a lens of creativity to differentiate our offering.

Analyze performance metrics to identify growth opportunities and present data‑driven recommendations to help partners optimize their performance.

Employ critical thinking and creative problem‑solving skills to navigate relationships and difficult partner conversations performance.

Build strong relationships with senior stakeholders and key decision‑makers both internally and externally.

Handle the big picture and the tiny details. You are organized, timely and ensure nothing gets missed; you are also attuned to high‑level strategy and consistently come up with new ways to add value to existing partnerships.

Partner with cross‑functional teams. Be the voice of the customer and effectively navigate internal processes with partners from various teams such as Product, Marketing, Operations, Legal, Finance, etc.

Basic Qualifications

• A minimum of 8+ years of relevant experience in strategic sales or account management with Enterprise clients (preferably in a tech, SaaS, advertising or retail media company).

• Bachelor's degree in Economics, Finance, Business Administration, or a related field.

• Excellent communication and interpersonal skills, with the ability to effectively collaborate with internal and external stakeholders.

• Creative thinker with a passion for problem‑solving and driving innovation.

• Ability to thrive in a fast‑paced and constantly evolving environment, with a proactive and results‑driven mindset.

• Proven track record of driving revenue growth and achieving targets.

• Basic proficiency in SQL, with the ability to adjust and refine queries as needed.

Preferred Qualifications

• Excellent listening, communication and relationship‑building abilities. Experience managing high‑value relationships and influence stakeholders, securing buy‑in with senior external partners.

• Proficiency in negotiation, forecasting, and problem‑solving skills. Experience selling into or partnering with large, complex enterprise brands and organizations.

• Organizational skills — you'll need to prioritize ongoing processes and projects simultaneously.

• Data‑driven decision mentality and sound business judgment through strong analytical thinking. Ability to translate data into insights and consult on core business objectives.

• Track record of building and executing strategic sales/marketing plans (quarterly – annual).

• Ability to work cross‑functionally and manage multiple stakeholders.

• Speed, resourcefulness, and a go‑getter mentality. You are comfortable working in a fast‑paced environment and navigating ambiguity.

• Experience with CRM and analytics tools (e.g., Salesforce).

• Proficiency in Microsoft Excel, Google Sheets, and reporting tools for data analysis.

For Chicago, IL-based roles:
The base salary range for this role is USD $136,000 per year - USD…