Chief Executive Officer

CannyFlyerDPIIT Recognised Startup  •  NVIDIA Inception Programme MemberRoleChief Executive Officer (CEO)LocationDelhi NCR / Hybrid (India)Experience10+ years, with early-stage leadershipEducationMBA preferred (IIM / ISB / Tier-1 equivalent or international)Reports ToBoard of Directors / Co-FoundersEngagement2–3 month paid trial period; equity vests post-confirmationAbout CannyFlyerCannyFlyer is a travel-tech startup that reimagines how Indians book flights through a demand-aggregation model. Solo travellers register pre-travel intent on specific routes and dates. Once a cohort of sufficient demand is formed, airlines privately quote fares against a ceiling price — a model CannyFlyer terms private yield matching — and travellers are matched at the best available fare without the airlines ever compromising their pricing integrity.Unlike traditional OTAs that aggregate supply, CannyFlyer aggregates demand — creating a fundamentally differentiated relationship between the platform and the airline. Airlines retain PNR ownership. CannyFlyer earns revenue through an annual membership fee and a per-ticket platform fee.The company is backed by DPIIT recognition and is a member of NVIDIA's Inception Programme. CannyFlyer is currently preparing for its first institutional raise, with an active airline pipeline spanning major domestic carriers across key metro and Tier-2 corridors.The OpportunityCannyFlyer is at an inflection point: demand-side traction has been established with hundreds of travel intents across multiple dated route groups, airline relationships are in active progress, and the company is preparing to close its first institutional round.The founding team — led by IIT Delhi, NSUT, and IIIT alumni — is looking for a CEO to take the reins of the company and lead it through its most critical phase: LOI signing with airline partners, fundraising close, and operational scaling. The CEO will be the primary decision-maker and the person the co-founders and BD team look to for direction.This is not a 'professional manager' role. This is a founder-equivalent leadership position for someone who has been in the trenches of early-stage company building and wants to own a genuinely novel model in a large market.What You Will Own1. Fundraising & Investor RelationsOwn the first institutional raise end-to-end — from investor conversations through to closeBuild and maintain relationships with angel investors, micro-VCs, and travel/fintech-focused fundsReview, understand, and defend the company's financial model and unit economics with institutional-grade rigourSet up governance structures (board, cap table, investor reporting) as the company scales2. Airline Business DevelopmentLead — and personally own — high-stakes conversations with airline commercial and revenue management teamsDrive LOI signing with priority airline partners across the domestic networkMaintain the company's 'private yield matching' positioning in all airline-facing interactions with absolute disciplineNegotiate commercial terms, settlement structures, and PNR workflows with airline counterparts3. Company Operations & Team LeadershipSet direction, priorities, and accountability for the cross-functional team (tech, BD, marketing, legal, finance)Lead hiring for critical roles as the company scales post-raiseManage relationships with key technology and distribution partners4. Stakeholder ManagementMaintain a productive working relationship with the founding team and the founding partner in his board capacityRepresent CannyFlyer externally — media, industry events, government/regulatory engagementKeep the board and co-founders aligned with regular, structured reportingWhat We're Looking ForNon-NegotiablesPrior experience closing an institutional or angel round as a founder or lead executive — not peripheral involvement, actual ownership of the closeA network of investors you can reach directly and credibly activate within 90 days of joiningDemonstrated 0→1 track record: signed early customers, partners, or commercial deals personally — not via a team you delegated toHigh-stakes relationship management with large institutional counterparts (airlines, banks, corporates, or government)Capital efficiency instincts — comfort operating with lean resources and making every rupee countBasic financial literacy: ability to independently read a startup financial model, stress-test assumptions, and assess whether projections are realistic — you don't need to build models, but you must be able to interrogate oneStrongly PreferredMBA from a Tier-1 institution (IIM A/B/C/L, ISB, XLRI, FMS, or international equivalent)10–15 years of experience, including at least one early-stage company leadership role (co-founder, founding team, or first executive hire)Exposure to travel-tech, marketplace, or fintech business models — understanding of PNR flows, fare structures, or aggregator ecosystems is a meaningful advantageExperience working with or selling to airlines, airports, or GDS/aggregator ecosystemsFamiliarity with Indian startup legal instruments and compliance frameworksPersonal AttributesAble to earn the trust of a technical founding team quickly — high EQ, no egoComfortable being a working executive, not just a strategic figureheadPrecise communicator — especially in writing; airline and investor materials require controlled, disciplined languageMission-oriented: believes in what CannyFlyer is doing, not just the résumé additionWhat Good Looks Like in Year 1First institutional round closed within 90 days of joiningLOIs signed with at least 2 airline partners within 6 monthsPilot cohort operations launched on priority routesCore team (tech, BD, ops) in place and operating with clear accountabilityA clear, defensible view on the company's financial trajectory — gaps identified, assumptions validated, and investor narrative tightenedTrial Period & Equity StructureWe believe the best way to build a lasting leadership relationship is to earn it — on both sides. We're therefore structured this engagement as follows:Months 1–3: Paid trial period. The CEO operates in full leadership capacity — owning decisions, leading conversations, and driving outcomes — but without an equity grant. This period is about mutual assessment: you learning the company deeply, us seeing how you operate under real conditions.Post-trial confirmation: Upon mutual agreement at the end of the trial period, a formal appointment is made and the equity package is structured and granted. Vesting terms will be agreed at the time of confirmation.Cash compensation during the trial is real and agreed upfront — this is not an unpaid internship. Equity simply follows demonstrated fit rather than preceding it.We are transparent about this structure upfront because we want candidates who are confident enough in their own abilities to embrace it, not candidates who need an equity commitment before they've shown what they can do.A Candid Note on FitCannyFlyer is not right for everyone at this stage. We want to be upfront:If you've only been part of fundraises, not led them — this role will be harder than expectedIf you need a large team and budget to operate effectively — we're pre-scale, and that's by designIf you're not comfortable sitting across from an airline commercial director and holding your ground on positioning and terms — the BD work will be a mismatchIf the equity-heavy (post-trial) compensation structure doesn't excite you — the cash will be below market at this stageIf those constraints feel like the right challenge, this is a rare chance to lead a genuinely differentiated model in the largest aviation market in the world by growth rate.How to ApplyIf this role resonates, send the following to samarth@cannyflyer.com:Your résuméA brief note (not a template cover letter) on what specifically excites you about CannyFlyer — the model, the market, the stage, or something else entirely. We read these carefully. Find us at CannyFlyer.comShortlisted candidates will be contacted for an interview with the founding team. There are no assignments or case exercises — just a real conversation about your background, how you think, and whether there's a fit on both sides.We aim to move quickly and expect to make a decision within 25–30 days of the role going live.