Discover Dollar:
At Discover Dollar, we're on a mission to uncover the hidden revenue that's been slipping through the cracks of large enterprises. We use AI to spot overpayments, pricing errors, and revenue leakages that most companies don't even know exist. Think of us as financial detectives—using cutting-edge tech like Natural Language Processing (NLP) and Generative AI to analyze millions of documents and billions in spend data.
Who Leads us?
Subu Rao isn’t your typical corporate exec. He’s the brains behind Discover Dollar’s AI-first platform that has helped Fortune 500 giants recover over $1 billion in overpayments. What started as a one-person company has grown under his leadership into a trusted partner for some of the world’s biggest enterprises.
From being named the youngest CEO featured in The CEO Magazine to building award-winning GenAI tech (recognized by SAP and NASSCOM), Subu has consistently stayed ahead of the curve. In 2025, Discover Dollar was named a Microsoft “AI First Mover” and recognized by Satya Nadella himself for pushing the boundaries of enterprise AI. Subu moves fast, thinks deep, and mentors generously. If you love solving hard problems and want a ringside seat at the cutting edge of AI and enterprise innovation, you’ll love working with Subu.
Our Impact and Growth
Proven Results
We've already helped Fortune 500 companies like Target, AbInBev, save millions—often delivering results in a matter of weeks. Our secret sauce? Fast, accurate, and scalable solutions that deliver a minimum of 4x ROI.
We're not just about tech—we're about making sure businesses can unlock real value, optimize cash flow, and improve their bottom lines.
Future Vision
But we're not stopping there. As a fast-growing startup, we're scaling up rapidly, building new tools, expanding into new regions, and always looking for innovative ways to help our clients stay ahead.
So, if you're ready to be part of a high-energy, high-impact team that's changing the way businesses manage financial processes, Discover Dollar is the place for you.
Join us in shaping the future of AI-driven financial recovery, and let's discover hidden dollars together!
Chief of Staff Opportunity
Discover Dollar is experiencing rapid growth and is looking for a dynamic Chief of Staff to work directly with the CEO and the leadership team. This role offers the opportunity to have an immediate and significant impact by driving strategic initiatives, optimizing organizational processes, and providing strong executive support. The ideal candidate will be someone who thrives in building structure from scratch, enjoys wearing multiple hats, and has a hands-on approach to execution. The candidate should be able to bring order to chaos and have a strong focus on optimizing processes and productivity across teams.
We're looking for a candidate who is quick to learn, adaptable, and can transition seamlessly between different tasks. You should have a passion for setting up systems and processes from the ground up and be comfortable managing legal due diligence, investor relations, and cross-functional team coordination. You'll be expected to manage high-priority projects, ensure timely execution, and act as a trusted advisor to the CEO.
Key Responsibilities
- Founder's Office Leadership: Build and manage the Founder's Office (FO), ensuring that it provides the necessary structure, processes, and systems to enable the CEO and leadership team to operate efficiently. The role will involve setting up tools, project management frameworks, and systems to improve operations and decision-making.
- Strategic Initiative Management: Oversee business initiatives, from development to execution, under the guidance of the CEO. Ensure alignment of initiatives across teams, track progress, and ensure timely completion of projects with measurable results.
- Cross-functional Coordination: Serve as the point of contact between the CEO and various departments. Streamline communication and ensure key objectives are being met across functions. Work closely with senior leaders to facilitate efficient collaboration and decision-making.
- Governance & Organizational Structuring: Assist the CEO in refining the organization's structure, helping to fill knowledge or skills gaps, and optimizing processes for increased productivity. Focus on setting clear organizational goals, ensuring alignment with business objectives, and creating accountability across teams.
- Investor Relations & Legal Due Diligence: Support the CEO with investor communications and manage legal due diligence processes. Maintain strong relationships with key stakeholders, including investors, and provide timely updates on business performance and strategic initiatives.
- Dynamic Problem-Solving & Execution: Given the ever-evolving nature of the business, this role requires someone with a versatile skill set who is comfortable shifting gears between tasks and projects. You will take ownership of ad-hoc tasks that require quick learning and execution, ensuring seamless operation in a fast-paced environment.
- Project Management: Own the implementation of project management tools, ensuring they are used effectively across the organization. Set up tracking and reporting systems to measure the progress of strategic projects and improve operational efficiency.
Required Skills & Qualifications
- Versatile Skillset: Ability to juggle multiple tasks, demonstrate flexibility, and wear multiple hats. The ideal candidate will be able to quickly learn and execute on new initiatives with little oversight.
- Strong Analytical and Communication Skills: Excellent written and verbal communication skills, able to distill complex information into concise summaries for the CEO. Ability to manage and synthesize large amounts of information across teams and stakeholders.
- Operational Excellence: A proven track record in process optimization, improving organizational efficiency, and driving productivity. Experience with project management tools and techniques to manage cross-functional teams.
- Stakeholder Management: Ability to engage effectively with senior executives, investors, and internal teams, establishing strong relationships and ensuring alignment with the CEO's vision and business objectives.
- Investor Relations & Legal Due Diligence: Experience in managing investor relations and legal processes, supporting high-stakes decision-making, and liaising between different stakeholders.
- Tool Savviness: Proficiency in using project management tools such as Airtable, Notion, and other dashboarding tools for tracking and reporting progress.
Preferred Qualifications
- Bachelor's degree or MBA (or equivalent experience) in Business Administration or a related field.
- Prior Experience: Ideal candidates will have experience in a Chief of Staff, Entrepreneur-in-Residence, or Founder's Office role, understanding the dynamic, multi-faceted nature of such positions. Experience in managing day-to-day operations within fast-paced, high-growth startup environments is highly preferred.
- This is a senior-level position, and we're looking for candidates with 4+ years of relevant experience.
Additional Requirements
Global Work Hours: As the CEO will be managing teams between the US and India, flexibility to work with at least 4 hours of overlap with US time zones is essential.
