Chief of Staff - AI Native bootstrapped startup

What You Will Work On
*STRATEGY & ANNUAL PLANNING *

• Lead the annual and quarterly planning process end-to-end: setting the framework, aligning leadership, tracking execution, and running the operating reviews that hold the organisation accountable
• Build the business cases that sit behind major decisions on new markets, pricing, product investments, and strategic partnerships
• Synthesise performance data into a clear point of view on what is working, what is not, and what needs to change. Not just a report of the numbers

FINANCE & BUSINESS ANALYTICS

• Own financial modelling for strategic decisions including unit economics, scenario planning, and investment cases, built from scratch and not inherited from a template
• Maintain the operating metrics framework the leadership team uses to run the business, and ensure it stays honest as the company scales
• Support fundraising preparation, investor updates, and due diligence processes directly alongside the founders

EXTERNAL & INVESTOR RELATIONS

• Prepare board materials, investor communications, and quarterly updates drafted to a standard where they go out with minimal revision
• Support the founders in strategic conversations with investors, partners, and customers where a prepared, analytical second voice adds value

AI EFFICIENCY & ORG-WIDE INITIATIVES

• Identify and drive AI efficiency initiatives across functions, from automating internal workflows to reducing operational overhead at scale
• Own cross-functional projects that cut across teams and require someone with the authority and context to drive them to completion
• Develop experimental MVPs, both internal tools and early-stage product concepts, working closely with the product and engineering teams to move from idea to something testable quickly

Who We Are Looking For
QUALIFICATIONS

• Top-tier MBA or Chartered Accountant with Big Four Articleship experience. Either is a strong foundation for this role
• 3 to 6 years of total experience, with a meaningful stint in management consulting, investment banking, or a strategy function
• At least 2 years of direct exposure to founders or senior leadership in a high-growth startup. You understand what it means to operate at that pace and with that level of accountability
• Familiarity with SaaS business models and GTM metrics is an advantage

COMPETENCIES

• Structured thinking and financial rigour. You can build a model from scratch, identify the assumptions that drive the answer, and present a clear recommendation without being asked to simplify it
• Enabling others to succeed. You measure your own effectiveness by whether the teams around you have what they need to hit their goals, not by how much you personally own
• Intellectual curiosity. You ask the second and third question, you read beyond what is required, and you are genuinely interested in understanding how the business works at every level
• Comfort with shifting priorities. You do not need a complete brief to get started, and you do not lose momentum when the scope changes
• Self-directed. You identify what needs to be done, pick it up, and follow through without waiting to be managed
• Written and verbal communication that is precise and direct. You can prepare a board-ready document and hold a room with equal confidence

Why This Role, Why Now

• A direct working relationship with founders backed by Girish Mathrubootham, Lakshmi Narayanan, and Mithun Sacheti. The access and perspective that comes with that is genuinely rare at this stage
• Enterprise customers across three continents, a platform that works, and AI capabilities that are already live and going deeper. You are joining at the most interesting part of the journey
• This is a fast-track role. The expectation is that the right person grows into a leadership position within the company
• A culture built on passion over experience. We care more about how much you want to solve the problem than how conventional your path here was
• Competitive compensation with meaningful ESOPs

Note: Apply only through the Wellfound platform. Applications via LinkedIn will not be considered.

Only shortlisted candidates will be contacted within 12–24 hours. If you don’t hear from us, please consider your application not shortlisted.