Checkmate (itsacheckmate.com)

HQ
New York
Total Offices: 5
299 Total Employees
Year Founded: 2016

Checkmate (itsacheckmate.com) Benefits Overview

Compensation + Benefits

Offers 401(K)

Offers life insurance

Offers disability insurance

Offers dental insurance

Offers health insurance

Offers Health Savings Account (HSA)

Offers Flexible Spending Account (FSA)

Offers vision insurance

Provides family medical leave

Offers generous parental leave

Offers employee discounts

Work-Life Balance + Wellbeing

Offers company-sponsored outings

Offers an Employee Assistance Program (EAP)

Offers generous PTO

Provides paid sick days

Provides military leave

Provides paid holidays

Provides bereavement leave

Offers unpaid extended leave

Career Growth + Development

Provides customized development tracks

Job training & conferences

Company Culture

Offers a remote work program

Offers diversity-based Employee Resource Groups

2 Days AgoSaved
Remote
United States
Artificial Intelligence • Food • Software
Leads Checkmate’s global post-sale operations organization across onboarding, menu management, and technical account management. Owns service strategy, customer satisfaction, operational metrics, enterprise escalations, onboarding outcomes, process standardization, and team performance. Partners with Sales, Product, and Engineering to resolve systemic issues, improve product capabilities, reduce churn, and scale workflows through automation and AI-driven analytics. Acts as a strategic operational partner to the CEO.
11 Days AgoSaved
Remote
United States
Artificial Intelligence • Food • Software
Leads globally distributed software engineering teams, setting technical strategy, architecture, delivery processes, and engineering standards for AWS-based SaaS products. Partners with Product, Data Analytics, and Customer Success, develops engineering talent, manages vendors, drives continuous improvement, and promotes AI-assisted development practices. The role requires extensive software engineering and executive leadership experience, Ruby on Rails and asynchronous architecture expertise, AWS scalability knowledge, and experience managing remote global teams.