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Lead - Customer Success Manager

Job in Virginia Beach, Virginia, 23453, USA
Listing for: Checkmate
Full Time position
Listed on 2026-06-17
Job specializations:
  • IT/Tech
  • Customer Service/HelpDesk
Salary/Wage Range or Industry Benchmark: 100000 - 110000 USD Yearly USD 100000.00 110000.00 YEAR
Job Description & How to Apply Below

About Checkmate

Checkmate is a restaurant technology solution provider that has continually evolved over time. We started in 2017 by integrating 3rd party platforms into the POS systems of restaurants, including Grub Hub, Uber Eats, Door Dash, Postmates, Caviar, and Amazon. Over the years we have expanded our portfolio to include first‑party ordering solutions (web, app, kiosks, catering) and recently launched three new products:
Digital Menu Boards, Phone Ordering AI, and Drive‑thru AI. We form a core part of the restaurant technology ecosystem and are continually adding digital solutions for brands to increase sales.

Our revolutionary enterprise menu management system, Everyware, unlocks the potential of menus and how they can be customized for each digital channel. Today we power digital ordering solutions for some of the largest brands in the world.

We have been called the "north star of vendors" because we believe technology is a tool that serves customers, not the whole of it. Service is a big component of what we provide, and every team member values ownership and drive. We are applying AI to our products and experimenting at scale to determine what works for clients, and we use ML to analyze and productize our massive data.

Each individual makes a difference and contributes a valuable role. Join us if you have ownership and drive.

Role Overview

The Lead – Customer Success Manager is responsible for supporting the successful onboarding, engagement, and retention of superbrand and/or enterprise clients. The role focuses on proactively building strong client relationships, understanding their needs, and ensuring they receive maximum value from the company’s products and services. The Lead will work closely with cross‑functional teams to provide excellent client service, assist with issue resolution, and identify growth opportunities.

100% Remote

$100,000 – $110,000

What You’ll Do Client Relationship Management
  • Serve as the primary point of contact for superbrand and/or enterprise clients, addressing inquiries, resolving issues, and offering proactive solutions.
  • Build and maintain strong relationships with key stakeholders at client organizations, ensuring they are up to speed with the company’s product offerings.
  • Monitor client satisfaction and ensure that their needs are consistently met.
  • Assist with onboarding new clients, ensuring they are set up for long‑term success.
Client Support and Issue Resolution
  • Act as the primary POC for the Brand(s) assigned, working closely with the Customer Support Team to track open issues and provide updates on escalated issues. Internal escalation occurs proactively if SLA requirements cannot be met.
  • Collaborate with internal teams, such as product, support, and operations, to troubleshoot and resolve client concerns.
  • Monitor client satisfaction levels and elevate concerns to senior team members when necessary.
Product and Service Education
  • Provide clients with product demonstrations, training, and best practices to maximize product usage.
  • Assist in creating client resources such as guides, FAQs, and tutorials.
  • Stay informed about product updates and communicate relevant changes to clients.
Client Retention and Growth
  • Develop strategies to improve client satisfaction and retention, ensuring clients achieve their business goals.
  • Conduct or prepare regular business reviews and meetings with clients to identify opportunities for further collaboration. Work with the Account Management Team to identify opportunities to enhance client engagement and encourage adoption of additional products or services.
  • Gather and analyze client feedback, sharing insights with the broader team to improve products and services.
Reporting and Documentation
  • Track account performance, generating reports and insights for clients and internal teams.
  • Use data to assess the success of the client journey and suggest improvements for future client transitions.
Qualifications
  • Bachelor’s degree in Business Administration, Management, or a related field (or equivalent experience).
  • 4+ years of experience in client‑facing roles within SaaS, with experience in onboarding and relationship management.
  • Ability to…
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