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VP Engineering and R&D - AI Startup

July 29, 2026

Are you a technology leader who is not only passionate about AI but is also excited to be at the forefront of solving one of the most challenging problems that have plagued IT for years and could result in organizations becoming highly challenged or possibly extinct as digital transformation sweeps every sector? Are you looking for a role with the opportunity to: - Execute core research in AI knowledge management that leads to patentable technologies? - Take an idea from research to a commercially successful cloud-based enterprise software product? - Build a solution that will have a meaningful impact on one-third of the US economy - both for-profit and not-for-profit organizations? Are you seeking the potential to: - Be the first to bring a unique combination of AI and data management to the market? - Work with experienced, successful Silicon Valley entrepreneurs with 4X startup experience leading to IPO and acquisition exits? - Be mentored by a team of research advisors known in the industry as thought leaders? - Participate in a Silicon Valley-style equity opportunity within a venture with the potential for significant value creation? - Work with a company built around a remote model before COVID-19 made it a requirement? - Give back to your community through a 1-1-1 philanthropic model as pioneered by Marc Benioff’s Salesforce? The Essentials: - Master or Ph.D. in Computer Science, Mathematics, Physics, Engineering, Statistics, Operation Research or other equivalent quantitative fields - Experience in AI with a demonstrated understanding of expert systems, knowledge management, and digital assistants - Experience managing a team of data scientists and AI researchers and engineers using Agile methodologies and tools - Previous startup experience with a proven track record of leading teams that drive innovation and deliver products in a fast-paced, high-energy environment - Excited to work with new technologies and approaches - Experience working within an SBIR NSF (Small Business Innovation Research - National Science Foundation) Program grant award model Responsibilities: - Get to know our customer (or know them already) and use that empathy to inform shaping the product’s vision and requirements and building an exceptional product - Serve as a thought leader and technology strategy driver along with the CEO and Co-Founders to make decisions on the product technology architecture including building block components - with a preference for open source technologies - Build, build, build - especially in the early days, you will be rolling up your sleeves and writing code, from core platform to fixing bugs - Help form a top-performing team of talented and responsible software engineers, data scientists and product designers, and provide them the freedom to be creative and innovative - Lead product engineering including research and development of unique proprietary and patentable intellectual property that yields competitive advantages - Embody the company’s culture and mission by fostering a culture that is passionate about building awesome products that deliver measurable value and a customer experience that delights - Evangelize the company’s technology vision, roadmap and capabilities with customers, investors, employees, and other stakeholders - Stay current on technology advances in the field of AI - especially digital assistants, knowledge engineering, data-driven reasoning, expert systems - and in the field of data management - including column databases and other advanced decision analytics technologies All your information will be kept confidential according to EEO guidelines. C-PLan.IT is an early stage startup on a mission to enable mid-market organizations to measure and maximize value from IT investments. We are building an AI Digital Assistant delivered as-a service in real time to support IT investment decision making and value optimization. Unlike competitive solutions that focus on cost or asset management only C-Plan.IT specializes in IT investment management with a particular focus on digital transformation objectives. The benefits of using C-Plan.IT increase as the platform’s membership grows toward the bold goal of becoming the world’s largest IT investment platform with $100B annual IT investments under management across 2000 organizations in the next 10 years. Privately funded, we are a fully remote company with a 100% distributed team allowing us to hire the best people regardless of where they are located.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...