Checkmate Jobs

The Vice President, 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.

We are seeking a high-accountability, decisive, and hands-on operational leader who thrives in a fast-paced environment. The ideal candidate possesses the agility to alternate fluidly between high-level strategic planning and deep-dive problem-solving, with the business acumen to build scalable processes, drive cross-departmental alignment, and handle enterprise clients with ease.

• 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