VP, Operations

This is a fully remote position, open to applicants in United States.

📋 Description

• Define, establish, and implement the operational strategy for Checkmate’s post-sale service division.

• Lead, mentor, and expand an existing global team of approximately 25 individuals across the US and India, fostering a culture centered on accountability, excellence, and continuous enhancement.

• Streamline operational processes and workflows across onboarding and menu management teams to enhance efficiency, speed, and consistency.

• Take ownership of post-sale customer satisfaction (CSAT), service delivery metrics, and operational performance standards.

• Act as an executive sponsor and escalation point for key clients, intervening to resolve intricate issues and maintain robust client relationships.

• Propel operational strategies that boost customer retention, minimize time-to-value during onboarding, and ensure uninterrupted service delivery.

• Leverage AI-driven analytics to proactively detect churn risks, foresee customer friction, and enhance resolution times.

• Create agent and workflow automations within the operations function to achieve efficiencies.

• Supervise Technical Account Management functions to guarantee technical alignment between customer workflows and Checkmate's product capabilities.

• Collaborate closely with Engineering and Product leadership to convert customer feedback and operational friction points into scalable product features and technical solutions.

• Serve as a strategic "right-hand" leader to the CEO, taking full responsibility for cross-departmental operational initiatives and high-priority tasks to streamline executive focus.

• Transition seamlessly between high-level strategic planning and hands-on, tactical problem-solving to identify and address systemic execution gaps.

• Function as the primary contact for customer escalations, effectively resolving enterprise account challenges, restoring client trust, and shielding executive leadership.

• Directly manage the onboarding of high-stakes, marquee enterprise clients, ensuring swift time-to-value and high-touch service delivery.

• Promote cross-departmental alignment among Sales, Product, Engineering, and Support to address root-cause operational bottlenecks that extend beyond post-sale boundaries.

• Design, implement, and uphold standardized, scalable operational playbooks, cultivating a culture of process compliance and operational rigor across global teams.

• Mentor and guide frontline and managerial staff through structured follow-ups, promoting high performance and accountability with respect and professionalism.

• Establish clear feedback loops between post-sale operations and product development to expedite defect resolution and support continuous platform improvement while communicating growth opportunities for account expansions to our GTM team.

⛳️ Requirements

• Bachelor's degree in Business, Computer Science, or a related discipline.

• Over 10 years of progressive operational leadership experience in a tech/SaaS setting, preferably within restaurant tech, foodtech, or e-commerce delivery platforms.

• Proven success in leading cross-functional and multi-regional teams, specifically managing US and India-based organizations.

• Strong technical aptitude and experience collaborating with Engineering, Product, and Technical Account Management teams to facilitate technical issue resolution and product feedback loops.

• Experience in direct, executive-level customer communication, crisis management, and enhancing service performance.

• Demonstrated ability to utilize operational metrics (CSAT, SLAs, time-to-onboard) to hold teams accountable and uplift overall business performance.

• Established track record of operational leadership within high-growth, mid-sized SaaS environments, such as scaled startups or scale-ups.

• High level of business acumen and emotional intelligence; comfortable challenging the status quo, presenting independent viewpoints, and making authoritative, data-driven decisions.

• A genuine entrepreneurial spirit with a proactive, vision-driven mindset capable of spearheading transformational change, fostering innovation, and excelling in a dynamic, fast-paced environment.

• Excellent project management skills, with the capability to prioritize and handle multiple projects concurrently.

• Exceptional organizational abilities with a proven capacity to identify core systemic issues within complex organizations and develop lasting, scalable solutions. Become 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