Checkmate Restaurant Technology

Online ordering integrations platform for restaurants

VP Operations

Customer SuccessConfirmed live in the last 24 hours

Full-timeRemote in USANo salary listed

About the Job

Requirements

A bachelor's degree in Business, Computer Science, or a related field is required.
At least 10 years of progressive operational leadership experience in a technology or SaaS environment is required, ideally in restaurant technology, food technology, or e-commerce delivery platforms.
Demonstrated success leading cross-functional and multi-region teams, specifically managing organizations based in the United States and India, is required.
Strong technical aptitude and experience interfacing with Engineering, Product, and Technical Account Management teams to drive technical issue resolution and product feedback loops are required.
Experience in direct executive-level customer communication, crisis management, and service performance improvement is required.
A proven track record of using operational metrics such as CSAT, SLAs, and time-to-onboard to hold teams accountable and improve business performance is required.
A proven track record of operational leadership in high-growth, mid-sized SaaS environments, such as scaled startups or scale-ups, is required.
Business acumen and emotional maturity, including comfort challenging the status quo, offering independent viewpoints, and making authoritative, data-driven decisions, are required.
An entrepreneurial, proactive, vision-driven mindset and the ability to lead transformational change, foster innovation, and work in a dynamic, fast-paced environment are required.
Strong project management skills and the ability to prioritize and manage multiple projects simultaneously are required.
Strong organizational skills and the ability to identify systemic issues in complex organizations and build lasting, scalable solutions are required.

Responsibilities

Define, establish, and execute the operational strategy for Checkmate’s post-sale service organization.
Directly lead, mentor, and scale an established global team of approximately 25 or more people across the United States and India, fostering accountability, excellence, and continuous improvement.
Optimize operational processes and workflows across onboarding and menu management teams to improve efficiency, speed, and consistency.
Own post-sale customer satisfaction, service delivery metrics, and operational performance standards.
Serve as an executive sponsor and escalation point for key customers, resolving complex issues and maintaining client relationships.
Drive operational strategies to enhance customer retention, reduce onboarding time-to-value, and ensure service continuity.
Use AI-driven analytics to identify churn risks, anticipate customer friction, and improve resolution times.
Build agents and workflow automations across the operations function to improve efficiency.
Oversee Technical Account Management to ensure technical alignment between customer workflows and Checkmate’s product capabilities.
Partner with Engineering and Product leadership to turn customer feedback and operational friction points into scalable product features and technical resolutions.
Lead cross-departmental operational initiatives and high-priority work as a strategic partner to the CEO.
Switch between strategic planning and hands-on problem-solving to diagnose and resolve systemic execution gaps.
Act as the primary contact for customer escalations, resolve enterprise account issues, restore client confidence, and shield executive leadership from escalations.
Directly oversee onboarding for high-stakes enterprise clients, ensuring rapid time-to-value and high-touch service delivery.
Drive alignment across Sales, Product, Engineering, and Support to resolve root-cause operational bottlenecks across post-sale boundaries.
Design, implement, and enforce standardized, scalable operational playbooks and promote process compliance and operational rigor across global teams.
Mentor and coach frontline and managerial staff through structured follow-ups, reinforcing performance and accountability.
Establish feedback loops between post-sale operations and product development to accelerate defect resolution and improve the platform.
Relay account-expansion opportunities to the go-to-market team.

Desired Qualifications

Experience in restaurant technology, food technology, or e-commerce delivery platforms is ideally preferred.

VP, Operations

Checkmate · United States (Remote) · Full-time · Posted 2026-10-23

Workplace: remote

Department: Customer Support

Description

The VP, Operations will be responsible for leading and transforming Checkmate’s post-sale operations, bridging the gap between customer expectations, technical performance, and product execution. As a member of our Executive Leadership Team, this highly visible role will manage an established, global team of professionals across onboarding, menu management, and technical account management based in the USA and India.

Define, establish, and execute the operational strategy for Checkmate’s post-sale service organization.
Directly lead, mentor, and scale an established global team (~25+ people across the US and India), fostering a culture of accountability, excellence, and continuous improvement.
Optimize operational processes and workflows across onboarding and menu management teams to drive efficiency, speed, and consistency.
Own post-sale customer satisfaction (CSAT), service delivery metrics, and operational performance standards.
Serve as an executive sponsor and escalation point for key customers, stepping in to resolve complex issues and maintain strong client relationships.
Drive operational strategies that enhance customer retention, reduce time-to-value during onboarding, and ensure seamless service continuity.
Utilize AI-driven analytics to proactively identify churn risks, anticipate customer friction, and improve resolution times.
Build agents and workflow automations across the operations function to gain efficiencies.
Oversee Technical Account Management functions to ensure technical alignment between customer workflows and Checkmate's product capabilities.
Partner directly with Engineering and Product leadership to translate customer feedback and operational friction points into scalable product features and technical resolutions.
Act as a strategic "right-hand" leader to the CEO, taking full ownership of cross-departmental operational initiatives and high-priority miscellany to streamline executive focus.
Transition between high-level strategic planning and hands-on, tactical problem-solving ("diving into the weeds") to diagnose and resolve systemic execution gaps.
Serve as the ultimate point of contact for customer escalations, effectively resolving enterprise account issues, restoring client confidence, and insulating executive leadership.
Directly oversee the onboarding of high-stakes, marquee enterprise clients, ensuring rapid time-to-value and high-touch service delivery.
Drive cross-departmental alignment across Sales, Product, Engineering, and Support to solve root-cause operational bottlenecks that span beyond post-sale boundaries.
Design, implement, and enforce standardized, scalable operational playbooks, instilling a culture of process compliance and operational rigor across global teams.
Mentor and coach frontline and managerial staff through structured follow-ups, enforcing high performance and accountability in a respectful, professional manner.
Establish clear feedback loops between post-sale operations and product development to accelerate defect resolution and drive continuous platform improvement. In addition to relaying growth opportunities of account expansions to our GTM team.

Requirements

Bachelor's degree in Business, Computer Science, or a related field.
10+ years of progressive operational leadership experience in a tech/SaaS environment, ideally within restaurant tech, foodtech, or e-commerce delivery platforms.
Demonstrated success leading cross-functional and multi-region teams (specifically managing US and India-based organizations).
Strong technical aptitude and background interfacing with Engineering, Product, and Technical Account Management teams to drive technical issue resolution and product feedback loops.
Experience in direct, executive-level customer communication, crisis management, and service performance improvement.
Proven track record of leveraging operational metrics (CSAT, SLAs, time-to-onboard) to hold teams accountable and elevate overall business performance.
Proven track record of operational leadership within high-growth, mid-sized SaaS environments (scaled startups/scale-ups).
High degree of business acumen and emotional maturity; comfortable challenging the status quo, offering independent viewpoints, and making authoritative, data-driven decisions.
A true entrepreneurial drive with a proactive, vision-driven mindset capable of leading transformational change, fostering innovation, and thriving in dynamic, fast-paced environment.
Strong project management skills, with the ability to prioritize and manage multiple projects simultaneously.
Superior organizational skills with a proven capacity to isolate core systemic issues within complex organizations and build lasting, scalable solutions. Be our root-cause problem solver!

Benefits

Health Care Plan (Medical, Dental, Vision)
Retirement Plan (401k)
Life Insurance (Basic, Voluntary, AD&D)
Flexible Paid Time Off
Family Leave (Maternity, Paternity)
Short-Term & Long-Term Disability
Work from Home

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About the Company

Checkmate Restaurant Technology

Online ordering integrations platform for restaurants

ItsaCheckmate provides ordering technology for restaurants by connecting and coordinating multiple online ordering channels to reach more guests while keeping operations simple for staff. The platform runs on a marketplace with 130+ integrations, allowing restaurants to add features or channels with a few clicks, and it partners with delivery services like DoorDash Drive, Relay, and Uber Direct, plus catering features with intuitive controls and seamless payments. Its broad, easily expandable integration set and mix of delivery and catering options help small local eateries scale up to large brands with less complexity. The goal is to improve the online ordering experience for both customers and restaurant staff by offering scalable, customizable solutions that expand guest access and drive revenue.

Company size: 201-500
Company stage: Series A
Total funding: $3M
Headquarters: New York City, New York
Founded: 2016

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