Engineering Leader | CTO | VP / Director of Engineering

Mayank Kumar Gupta

Engineering leader with seven years running the whole engineering function of a SaaS and AI product company.

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Projects
84
Skills
94
Stories
19
Since
2019

Timeline

  1. Jun 2019 – Feb 2020Full Stack Engineer · Smarter.Codes
    2019
    SEO analysis platformKeyword Country research productMedical-device monitoring for hospitals
  2. Feb 2020 – Dec 2021Program Manager · Smarter.Codes
    2020
    Paid trading community platformMarket-analysis tool for a market-intelligence firmAddress-directory crawling estateCloud estate managementInternal proposal management
    2021
    TalkingDB document question-answeringOmnichannel agent inboxKray.AI search and document assistantLive sales-call assistantCompany-location extraction at web scaleSupplement ingredient datasetInternal starter codebases and CI/CDEngineering recruitment pipelineKanban board exploration
  3. Dec 2021 – PresentChief Technology Officer · Smarter.Codes
    2022
    NLX entity-extraction APIJaya.ai proof of conceptWhatsApp conversation serviceObjective.Earth public catalogueConsumer tee-time alerting productNutrition Label grocery analysisInternal time and office toolingInternal operations deskConsulting business-development deskInternal engineering rulebookInternal engineering estateSales enablement deskHybrid.Chat marketing engineering
    2023
    Regulatory medical-writing platformWord add-in for regulated documentationSales chatbot for a commercial printerChatbot for a financial-advisory appHelp-centre chatbot for an HR software vendorChat-controlled IoT scopingHybrid.Chat conversational platformHybrid.Chat product backlogChatbot for a construction-trade marketplaceE-commerce search for a mechanical-seal manufacturerKray store rolloutsSite search and chatbot for an industrial-caster manufacturerSignup funnel for a clinical-documentation productAssistant for tax professionalsHospitality forecasting for hotel groupsLanding-page generator for foundersMulti-tenant SaaS for salon ownersRental-listing change monitoringRPA for merchant statement processingPayment-proof review for a P2P crypto marketplaceRetail shopping automationPrompt-driven video editingMooring-inspection workbook normalisationRecruitment campaign automation for a solar installerProduct design groupPeople operations trackRequirement-engineering trackerCompany website estateHybrid.Chat product designHybrid.Chat website
    2024
    AI Course WriterDocCraft generation engineDocInsight extraction APIMedical-writing platform archiveAI storefront conceptKray AI product searchJob-seeker portalSales assistance for a sales-performance vendorGovernment form-filling automationMaintenance-record reconciliation for shippingPersonalised go-to-market landing pagesProduct design housekeepingInternal lead scoring
    2025
    Learn-by-creating search suggestionsIngredient-panel photo extractionMakerz.Network learning platform
    2026
    Banking document chatbotProduct search for a fastener distributorIndustrial fastener marketplace

Skills 94

Engineering27

Commercial4

Cloud and Platform22

Leadership7

Domains4

AI19

Architecture11

Projects 84

Document AI8 Walk this district

AI Course Writer

2024–2026

Generates long structured documents by filling a template's placeholders from source documents, built for an external training-material business.

Read In the world

Conversational AI12 Walk this district

Search & commerce12 Walk this district

Product & SaaS12 Walk this district

Data & crawling7 Walk this district

Automation10 Walk this district

Platform & internal23 Walk this district

Stories 19

Decisions8

High availability for a bot runtime that insisted on being in memoryThe platform ran multi-container with state surviving restarts, and the design documented its failure modes, including those the fix introduced.2021 · Hybrid.Chat conversational platformWanting to build it in house and buying insteadWe shipped on the vendor, and the recorded trade-off made later customisation questions easy to answer.2023 · Hybrid.Chat conversational platformTaking a component out of the stack instead of adding oneThe dependency and its rollback logic came out, leaving the backend with a single store of record.2023 · Omnichannel agent inboxOne model for everyone, or one per customerThe partitioned design went forward, with the loss of cross-fleet questions accepted openly.2024 · Kray.AI search and document assistantFinding out what the cloud bill was actually forPruning followed the inventory instead of guesswork, and the sweep set the order of what to stop.2026 · Consulting business-development deskA port that turned out not to be a portThe order of work changed without changing the plan, and client-specific code stayed out of the generic package.2026 · TalkingDB document question-answeringTaking services away instead of adding themFewer services to deploy, fewer cross-service failures to trace, and each remaining split could be defended individually.2025 · Consulting business-development deskReading the bill before optimising the modelCost fell sharply with no change to models or outputs.2025 · Consulting business-development desk

Incidents and lessons3

A cache that remembered the failuresFailed runs stopped affecting later ones, a retry became a real retry, and the written root cause let the team review it.2026 · Regulatory medical-writing platformTables that arrived in the client's document as raw markupThe whole class of defect went away, not just the three reported instances.2026 · Regulatory medical-writing platformCredentials in git history, and rotating keys was not enoughThe repositories moved with secrets removed from every commit, and another file with hardcoded credentials was flagged for cleanup.2026 · TalkingDB document question-answering

People6

Making architecture decisions arguable instead of announcedThe practice carried across projects and became what new decisions arrive with, so decisions can be reviewed on their reasoning.2023 · Consulting business-development deskA hiring process that does not depend on me being in the roomThe format became how the round runs, and the shadow-to-lead path grew the pool of interviewers.2026 · Engineering recruitment pipelineA one out of five, written so the candidate could act on itThe rejection was reviewable rather than a bare verdict, and the panel's differing views were visible to decision makers.2026 · Engineering recruitment pipelineAsking what onboarding was supposed to produceOnboarding ran against a stated target and a first-value date, and the checklist was reused.2024 · Regulatory medical-writing platformTreating a tee-time booking as a reservation systemThe product launched on schedule to its user base, with the concurrency design in place before contention arrived.2022 · Consumer tee-time alerting productOverturning a hiring verdict by doing the review myselfThe decision changed on the merits, and the reviewer could see which points I accepted, setting the expectation that recommendations are examined.2026 · Consulting business-development desk

Influence2

Holding back an accuracy number that would have looked greatThe inflated figure never reached a customer-facing claim, and benchmark results are now reviewed against a sheet before approval.2026 · TalkingDB document question-answeringBeing asked to pull a date forward, and naming the real constraintThe conversation moved from when it can be done to which trade-offs we accept, with the task breakdown as shared evidence.2026 · TalkingDB document question-answering

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