About Checkmate
Checkmate is a restaurant technology solution provider that has continually evolved over time. We started in 2017 by integrating 3rd party platforms to the POS systems of restaurants. At that time, there were multiple 3rd party platforms like GrubHub, UberEats, DoorDash, Postmates, Caviar, and even Amazon!
This was the photograph that started it all!
We have since then continually evolved to add multiple products to our portfolio, the primary ones being first party ordering solutions like web and app ordering, kiosks and catering. We have now recently moved into three new exciting products: Digital Menu Boards, Phone Ordering AI and Drive thru AI. We form a very core part of the restaurant technology ecosystem, and are continually adding more and more digital solutions for the restaurant brands to increase their sales.
Our revolutionary enterprise menu management system, Everyware, truly unlocks the potential of menus and how it can be customized for each individual digital channel. As you can see, this is a company that continually evolves and adapts and today we are powering digital ordering solutions for some of the largest brands in the world.
We have been called the "north star of vendors" as we truly believe that technology is just a method by which we service the customers, it does not form the entirety of it. Service is a big component of what we provide to our customers, which is inherently believed by every single team member here. We are doing a lot of exciting things, including application of AI in our products and systems, using experimentation at scale to determine what works for our clients and ML to analyze and productize the massive amount of data we have. Each individual here makes a difference and has a valuable contribution. Key traits here are ownership and drive. Join us if you think you have them.
About the Role:
As a Technical Product Manager (Senior/Principal) in Voice AI, you will be a leader in the product direction and execution of Checkmate’s next-generation agentic Voice AI platform. This role drives the product strategy, feature roadmap, and operational rigor behind the systems that power real-time drive-thru automation at scale and will soon be present at some of the largest QSR brands in the US. You will partner closely and work directly with the C suite to translate business goals into actionable product strategies, ensuring the platform’s market relevance, adaptability, and long-term growth and scalability. You will guide the development of systems that leverage LLMs and Generative AI technologies, oversee the integration of production-grade features, and champion product standards that support a rapidly expanding customer footprint. This role requires a hands-on product leader, who loves getting into the details of the customer experience, capable of shaping both the technology and the teams responsible for delivering it.
In this role, you will be considered the primary driver of all the major development tasks. This role comes with a lot of responsibility and authority to be able to execute at a very high level. As a Principal Product Manager in Voice AI, you will be seen as one of the leaders in the Voice AI org and will be responsible for driving the day to day tactical tasks as well as working with the leadership to formulate the medium to long term strategy. There will be immense support from various parts of the org.
100% Remote
Salary $225,000 - $250,000
Essential Job Functions
- Translate product vision into clear, actionable roadmaps and delivery plans for Voice AI solutions in the restaurant industry.
- Gather and prioritize requirements from customers, internal stakeholders, and market research.
- Use data insights, user feedback, and industry trends to identify opportunities and define impactful product features.
- Define, scope, and launch features that improve AI accuracy, expand coverage, and enhance operational performance.
- Set KPIs and success metrics, monitor performance, and adjust priorities based on data insights.
- Rapidly prototype and build proof-of-concepts to validate ideas before full-scale development.
- Work with engineering and data science to test and iterate on conversational AI capabilities.
- Conduct competitive analysis and stay ahead of trends in LLMs, speech recognition, and conversational AI.
- Manage timelines, dependencies, and trade-offs to ensure successful product launches.
- Continuously refine the product based on performance metrics and customer feedback.
- Take true ownership of the product, and drive to not just implementation but beyond.
Requirements
- 8+ years of product management experience, ideally in AI, SaaS, or conversational/voice technology products.
- Hands-on technical skills with the ability to rapidly prototype and build proof-of-concepts using tools such as Python or similar, and leverage LLMs to design, experiment with, and validate new features.
- Demonstrated experience working with LLMs, speech recognition/synthesis, and conversational AI systems.
- Strong data-driven mindset with the ability to interpret analytics, extract actionable insights, and use them to inform product strategy
- Proven track record of defining KPIs, measuring outcomes, and using data to guide product direction and prioritization.
- Exceptional ability to collaborate cross-functionally with engineering, data science, design, and customer-facing teams to deliver impactful solutions.
- Solid understanding of UX principles for conversational interfaces and the skill to translate user needs into intuitive product experiences.
- Excellent communication, organizational, and stakeholder management skills, with the ability to influence and align diverse teams.
- The candidate should be comfortable working in the US shift till 5 pm EST and must have a remote setup to work with their own system/device.
- Nice-to-have: experience in restaurant technology, call center automation, or real-time audio streaming.
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
- Training & Development
- Work From Home
- Stock Option Plan
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What We Do
Checkmate empowers enterprise restaurant brands with powerful ordering solutions and hands-on support. Our scalable technology enables restaurants to drive sales across channels, including custom websites, apps, kiosks, catering, third-party marketplaces, voice AI, and more. With seamless integrations, smarter analytics, and 24/7 service, Checkmate helps brands conquer their digital goals. Restaurants can launch unique ordering experiences, centrally manage menus, recapture revenue, leverage customer data, and continually adapt with new integrations. Regardless of how you want to grow, Checkmate has the tools and guidance to power, manage, and evolve your digital business.
