Mayank Kumar Gupta

Engineering Leader | CTO | VP / Director of Engineering

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

Roles

Chief Technology Officer, Smarter.Codes, Dec 2021 – Present
Program Manager, Smarter.Codes, Feb 2020 – Dec 2021
Full Stack Engineer, Smarter.Codes, Jun 2019 – Feb 2020

Projects

TalkingDB document question-answering — A question-answering engine that rebuilds each customer document as its section tree and fetches only the sections a question needs.
NLX entity-extraction API — Natural-language API that returns entities, facts and a parse tree from domain-specific text such as ingredient declarations and medical supply descriptions.
Regulatory medical-writing platform — A platform that drafts regulatory documents for clinical trials from source evidence, built for a pharmaceutical documentation firm and its sponsors.
Word add-in for regulated documentation — Microsoft Word add-in that keeps documents in step with SharePoint copies, for a firm in regulated medical and clinical documentation.
AI Course Writer — Generates long structured documents by filling a template's placeholders from source documents, built for an external training-material business.
DocCraft generation engine — A document generation engine that fills Word templates from structured data, used mainly for estate-planning paperwork.
DocInsight extraction API — An API that takes several PDF documents in a single request and returns a spreadsheet of the facts extracted from them.
Medical-writing platform archive — A document-authoring product that fills medical writers' templates from a sponsor's own source documents, with redaction of confidential detail.
Document AI chatbot tracker — A tracker for a document-focused AI chatbot project.
Omnichannel agent inbox — A shared agent inbox where support teams answer customers from WhatsApp, email, Telegram or a custom API in one queue.
Jaya.ai proof of concept — A proof of concept where a chatbot interviews a visitor and a document fills itself in as they answer.
WhatsApp conversation service — An internal service that lets other software hold WhatsApp conversations through an API with postback delivery.
Sales chatbot for a commercial printer — A sales chatbot for a commercial printer that qualifies pricing enquiries and hands the shop a complete brief.
Chatbot for a financial-advisory app — A chatbot for a financial advisory web app that answers visitors, serves members from their profile and collects planner data.
Help-centre chatbot for an HR software vendor — A help-centre chatbot answering product questions for an HR software vendor's users from its own documentation.
Chat-controlled IoT scoping — Scoping sketch for controlling a Raspberry Pi from a chat product via a code-writing chatbot, a code editor or Blockly.
Hybrid.Chat conversational platform — Hosted self-serve platform where businesses build chatbots from visual blocks and deploy them on web, WhatsApp and Mattermost with human handover.
Hybrid.Chat product backlog — Product backlog for an omnichannel inbox merging chat, WhatsApp, email, API and voice conversations into one queue per business.
Chatbot for a construction-trade marketplace — A chatbot for a United States construction-trade marketplace, delivered from scratch to the client's requirements and designs.
Banking document chatbot — A chatbot that answers banking customers' questions from the bank's own FAQ documents using retrieval-augmented generation.
SERP feature exploration — Exploration of search-results page features: product cards, contextual snippets and combined variations of the same product.
SEO analysis platform — SEO analysis product that crawls a customer site, analyses its pages and turns findings into assignable tasks for marketing teams.
Keyword Country research product — A keyword research product that expands one seed phrase into a large, tagged keyword set with search-volume data.
Kray.AI search and document assistant — An AI search and document-assistant platform sold as Kray.AI, with a WooCommerce plugin and a demo store.
E-commerce search for a mechanical-seal manufacturer — Graph-backed e-commerce search over a mechanical-seal catalogue, for customers and staff finding parts by nomenclature, type or compatibility.
Kray store rollouts — Work that puts Kray, an AI e-commerce search product, into real stores: a store cloner, demo store and grocery rollouts.
Site search and chatbot for an industrial-caster manufacturer — AI site search and chatbot for a caster manufacturer's e-commerce site, delivered under the Kray.ai product name.
AI storefront concept — A plan for an online mall of industrial suppliers that refers trade buyers on to each supplier's own site.
Kray AI product search — An AI product search for e-commerce stores that replaces the store's keyword search with intent and specification matching.
Learn-by-creating search suggestions — Search suggestions that stay consistent regardless of how fast the user types.
Product search for a fastener distributor — A product search for a stainless-steel fastener distributor that understands buyers' abbreviations and thread standards.
Industrial fastener marketplace — Online marketplace for industrial fasteners with a single canonical product catalogue and competing seller offers, so trade buyers can compare prices.
Medical-device monitoring for hospitals — Monitoring and remote-access system for hospital medical devices: live dashboards and alerts for staff, browser-based remote access for service engineers.
Paid trading community platform — A paid community for stock traders: a membership site plus a chat server with in-conversation price charts.
Live sales-call assistant — A sales-enablement product that sits beside a live video meeting and shows reps cue cards, persona and sales stage.
Objective.Earth public catalogue — A public, editable wiki cataloguing environmental and social problems, their proposed solutions and the projects addressing them.
Consumer tee-time alerting product — A consumer alerting product that notifies golfers the moment a booked-out tee time frees up, built for a US tee-time business.
Signup funnel for a clinical-documentation product — A signup funnel taking a medical clinic from a marketing-site form to a signed contract, payment and sales record.
Assistant for tax professionals — Chat assistant for US tax professionals that answers from a curated knowledge base and reads uploaded individual tax returns to suggest strategies.
Hospitality forecasting for hotel groups — A hotel product where guests record food preferences by QR code so kitchens can predict breakfast demand and cut waste.
Landing-page generator for founders — Web tool that turns a founder's answers about their idea into a written business report for the founder and advisers.
Multi-tenant SaaS for salon owners — Multi-tenant software for salon owners, built for a client in Saudi Arabia: storefront, bookings, payments and white-label domains.
Job-seeker portal — A portal where job seekers set targeting, browse jobs and internships, and auto-apply, built for a client.
Sales assistance for a sales-performance vendor — Sales-assistance software for a sales-performance vendor's reps: voice and camera task capture, business-card scanning, and prospect research reports.
Market-analysis tool for a market-intelligence firm — A tool that shows who competes for a market in chosen locations and how visible each competitor is, for a market-intelligence firm.
Address-directory crawling estate — Crawling and address-extraction system that builds a directory of the physical locations of internet businesses from public web pages.
Company-location extraction at web scale — A web-scale crawler that finds a company's office address from its hostname, built for an external client.
Supplement ingredient dataset — A knowledge base of supplement ingredients and synonyms plus a recogniser that finds them in free-text product listings, for an outside client.
Nutrition Label grocery analysis — An internal product analysing ingredients across an online grocery catalogue, explaining each ingredient to shoppers.
Rental-listing change monitoring — A scraper that watches rental listings every hour and posts new properties into the client's system, scoped as a pre-sales demonstration.
Ingredient-panel photo extraction — A shopping aid that reads the ingredients panel from a phone photo and returns a structured ingredient list.
RPA practice tracker — A tracker project for the company's robotic process automation work.
RPA for merchant statement processing — Automation that downloads and processes monthly merchant statements from a payment gateway for a merchant-payments client.
Payment-proof review for a P2P crypto marketplace — A service that classifies payment-proof images on a peer-to-peer bitcoin marketplace and returns the key text line by line.
Retail shopping automation — A bot that shops on a major online retailer through a cloud browser, placing orders without a person at the keyboard.
Prompt-driven video editing — Text-prompt video editing for a client: users describe a style and get an edited video back.
Mooring-inspection workbook normalisation — Automation that turns inconsistent per-vessel mooring-inspection spreadsheets into rows a shipping client's database accepts.
Recruitment campaign automation for a solar installer — Chrome extension plus middleware and tagged video player showing a solar installer's recruiters who watched campaign videos and how much.
Government form-filling automation — A conversational proof of concept where a robot fills a government driving-licence renewal form while the citizen watches.
Maintenance-record reconciliation for shipping — Matches a ship's old maintenance jobs to its new system's jobs despite differing names, descriptions and duration formats.
Personalised go-to-market landing pages — Personalised sales landing pages for a sales-performance software company, one per prospect, with embedded video and viewing metrics.
Space management tracker — A project tracker for space management work.
Engineering hiring and enablement — Internal hiring funnel, competency ladder and appraisal cycle that bring engineers in and develop them, run mostly in Asana.
Cloud estate management — Smarter.Codes' internal effort to audit its cloud servers and cut hosting cost.
Internal proposal management — Internal software that watches freelance marketplaces and social networks for worthwhile opportunities, plus a writer that drafts grounded cover letters.
Internal starter codebases and CI/CD — Internal starter codebases and CI/CD tooling so new company projects skip setting up delivery from scratch.
Engineering recruitment pipeline — Internal engineering hiring pipeline at Smarter.Codes, run as one thread per open position with async tests before live interviews.
Kanban board exploration — An exploration of building a kanban board several ways so the implementations could be compared.
Internal time and office tooling — An internal time-tracking tool that logs hours against organisation-chart nodes, with a cross-platform desktop client that works offline.
Internal operations desk — An internal operations desk handling equipment, tool accounts, time tracking, invoices and interview logistics for Smarter.Codes staff.
Consulting business-development desk — Smarter.Codes' internal desk that qualifies, estimates, prices and proposes consulting jobs, bridging business development and delivery teams.
Internal engineering rulebook — Smarter.Codes' internal rulebook: each engineering, HR, design and management guideline written as its own citable tracker issue.
Internal engineering estate — Smarter.Codes' internal estate: a MediaWiki and Wikibase documentation portal, public website and engineering consoles used by staff.
Sales enablement desk — An internal desk where sales sends client technical questions and an engineer returns a written answer for the proposal.
Hybrid.Chat marketing engineering — Engineering support for Smarter.Codes' own marketing team, covering its websites, hosting and product pricing pages.
Product design group — The company's internal design group, running design sprints and producing design material for client engagements and proposals.
People operations track — Smarter.Codes' internal HR and learning track.
Requirement-engineering tracker — A tracker project for commercial requirement-engineering work.
Company website estate — Smarter.Codes' in-house software estate behind its public site: crawler, automation framework, natural-language stack and chatbots.
Hybrid.Chat product design — Design work testing demand for a chatbot product by building polished screens and marketing pages for it.
Hybrid.Chat website — A tracker project for the Hybrid.Chat product website.
Product design housekeeping — A small board an internal product design team used to track its own weekly housekeeping.
Internal lead scoring — Internal sales tool that scores freelance job leads and writes priorities from Urgent to Low back to the CRM.
Makerz.Network learning platform — An internal learning platform that ties training modules to real work artifacts, validated section by section.

Skills

Engineering Strategy, Organisational Scaling, Hiring and Technical Evaluation, Career Ladders, Delivery Management, Mentoring, Cross-functional Leadership, Distributed Systems, SaaS Architecture, Microservices, Event-Driven Architecture, C4 Modelling, Architecture Decision Records, LLMs, Agentic AI, RAG, Azure OpenAI, OpenAI API, LangChain, Prompt Engineering, Document Intelligence, Vector Search, NLP / NER, AI Evals, Guardrails, Multi-Agent Systems, GraphRAG, AWS, Azure, GCP, Kubernetes, Docker, Terraform, CI/CD, Observability, SRE, Java, Python, JavaScript/TypeScript, Node.js, React, SQL & NoSQL, Proposals and Pricing, Cost Modelling, SOWs, Client Engagement, Legal AI, Healthcare AI, Finance AI, Regulated Medical Writing, GitLab CI, Shell, Docker Compose, npm, Automated Testing, Sass, PHP, CSS, pip, Bitbucket Pipelines, HTML, Helm, Make, Dart, MongoDB, FastAPI, Redis, Maven, GitHub Actions, Elasticsearch, Pydantic, GraphQL, Code Quality, Prisma, Express, Nginx, Embeddings, PDF Processing, OCR, API Design, Message Queue Design, Multi-Tenancy, Infrastructure Provisioning, Function Calling, Agent Orchestration, Token Management, Rate Limiting, Asynchronous Processing, Fault Tolerance, Schema Design, Full-Text Search, Caching Strategies, Data Validation, Web Scraping

Stories

Making architecture decisions arguable instead of announced
High availability for a bot runtime that insisted on being in memory
Wanting to build it in house and buying instead
Taking a component out of the stack instead of adding one
One model for everyone, or one per customer
A cache that remembered the failures
Tables that arrived in the client's document as raw markup
Credentials in git history, and rotating keys was not enough
Holding back an accuracy number that would have looked great
A hiring process that does not depend on me being in the room
A one out of five, written so the candidate could act on it
Finding out what the cloud bill was actually for
Being asked to pull a date forward, and naming the real constraint
A port that turned out not to be a port
Asking what onboarding was supposed to produce
Treating a tee-time booking as a reservation system
Overturning a hiring verdict by doing the review myself
Taking services away instead of adding them
Reading the bill before optimising the model

Skills and work as text