Your team's knowledge, one question away
Tricky Wombat connects your docs, drives, and conversations into a single AI search layer built for small, close-knit teams. Ask a question in plain language. Get the answer your colleague would have given you.

Built with industry leaders
Elusive Knowledge
The knowledge exists. Finding it is the problem.
Small teams don't have an information problem. They have a retrieval problem. The vendor analysis is in a Google Doc somewhere. The decision about the API vendor happened in a thread three weeks ago. The current spec has four versions across two drives and nobody renamed any of them.
Everyone on the team knows these things exist. Nobody has time to dig for them, and nobody wants to interrupt the one person who remembers where everything lives. The result is that people either waste time searching or make decisions without the context they already own.
Tricky Wombat closes that gap. It connects your data sources, understands what your team is actually asking for, and returns direct answers instead of ranked document lists.

How It Works
Context First - Better answers are won before the model ever responds
Tricky Wombat is built on a simple idea: the quality of an answer is determined before the model produces a single token. Most teams treat AI search as a model problem. We treat it as a context problem.
That means controlling what reaches the model, how it is selected, how it is prepared, and whether it is actually relevant to the question being asked. When context is right, answers become more accurate, more useful, and easier to trust.
Clarify the real question
Your team asks shorthand questions with shared context baked in. A factual lookup needs different retrieval than a comparison across twenty documents. Tricky Wombat classifies the question type so the right strategy runs first.
Retrieve the most relevant information
More documents in the context window makes answers worse, not better. Retrieval uses hybrid search and reranking to return fewer, higher-quality sources. The goal is precision, not volume.
Assemble context for this question
Retrieved documents are compressed, structured, and scoped to the task. Stale content, redundant passages, and noise are stripped out. The model gets what it needs for this question and nothing else.
Generate against defined quality rules
Rules are set before the model runs: cite sources, stay within the evidence, flag uncertainty. The model does not guess what a good answer looks like. The pipeline defines it.
Score the result and improve the pipeline
Each answer is scored for faithfulness, relevance, and completeness. Results that fall short are caught before your team sees them. Over time, scoring tunes retrieval, context assembly, and ranking. The system gets sharper with use.


Team Directed Search
Search that understands how your team thinks
Generic enterprise search tools rank results for a broad audience. They don't know that when your team says "the dashboard proposal" there's only one document that phrase could mean.
Tricky Wombat's AI pipeline groups related information the way your team already organizes it: by project, by client, by decision. GraphRAG maps relationships between documents so a question about a client proposal also surfaces the related SOW, the pricing thread, and the revision history. Agglomerative clustering keeps related content together rather than scattering it across ten result pages.
The result is answers drawn from the right cluster of your data, not a keyword-matched list you sift through yourself.
Fully sourced5s answers
Fast responses to questions = customer/employee satisfaction
Regain1.8hrs/day
Increase employee productivity by recovering time lost searching
Live in2Days
Connect your data and start asking questions. It's that easy
Enterprise Security
Your data is protected at every layer
Encryption at
Every Layer
AES-256 encryption at rest across S3, DynamoDB, and Pinecone. TLS 1.2 in transit. Automatic HTTPS via Vercel.
Enterprise Vendor
Audited Infrastructure
Every service in the stack is independently SOC 2 Type II certified. DynamoDB is ISO 27001 and HIPAA-eligible. Pinecone is GDPR-ready.
Zero Training on
Your Data
No component of the pipeline trains on your data by default. Your information is used to answer your queries and nothing else.
Vanta-Managed
Compliance
SOC 2 Type II and ISO 27001 certification in progress, managed through Vanta's continuous compliance monitoring platform.
SOC 2 in Progress
In progress via Vanta
ISO 27001
In progress via Vanta
AES-256 Encrypted
Data encrypted at rest
TLS 1.2 in Transit
Data encrypted in motion
Zero Data Retention
Your data stays yours
Built on AWS
Enterprise-grade infrastructure
Integrations provided by Apache
Make productivity easier with 1,000+ Integrations
We use Apache Tika to provide more than 1000 data connectors.

Testimonials
Real teams. Real results
“My audience explores fresh content across all of my media in real time, without me having to think about it. ”

Chip Conley
Founder of MEA & Joie de Vivre Hotels, Strategic Advisor to Airbnb
“I explore my content, synthesize new ideas, and expand my strategic voice using Tricky Wombat.”

Ron Nakamoto
Founder of True Wealth Mentorship, Certified Financial Planner, Workshop Facilitator
Different Questions
Different questions get different answers
A factual lookup ("What's our current AWS spend?") and a synthesis question ("Summarize the last three client feedback sessions") need different retrieval strategies. Most search tools treat them the same way.
Tricky Wombat's question categorization identifies the type of question being asked and routes it to the retrieval method most likely to return an accurate response. A factual question gets precision retrieval from the most current source. A synthesis question pulls from multiple documents and assembles a coherent summary. Automated prompt rewriting refines vague queries behind the scenes so the system retrieves what the user meant, not just what they typed.
Your team doesn't need to learn query syntax or think about how to phrase things. The system adapts to them.

Each team is different. Build AI search that is as unique as your small team
Your team has its own documents, terminology, and workflows, and the answers your people need are buried inside that specific information.
But enterprise search tools are built to scale for everyone, not to work for anyone in particular.
Tricky Wombat builds a context pipeline around your actual data, so every answer reflects how your team works, what your documents say, and what your people are really asking.
HOVER TO EXPLORE

Your project. Your data. Not everyone else's
Your project. Your data. Not everyone else's
- Small teams don't need search results from the entire organization. They need the one answer that moves their project forward today.
- They run on tight timelines with specific deliverables, and the information they need lives across project plans, meeting notes, shared drives, and Slack threads.
- A focused knowledge base scoped to your project surfaces your documents, your decisions, and your deadlines without forcing your team to filter through everything else first.

Every decision starts with the right information
Every decision starts with the right information
- Product teams make decisions based on user feedback, feature requests, and research scattered across Slack threads, support tickets, and meeting notes.
- The insight that should shape the next sprint exists in the data. It has never been in the same place twice.

Precise questions deserve precise answers
Precise questions deserve precise answers
- Engineers ask specific questions about specific systems.
- The answer is buried in a 1,000-page manual or spread across three different documents that reference each other.
- A focused knowledge base finds the right answer across those documents instead of returning the first paragraph that mentions the keyword.

Stop being everyone's human search engine
Stop being everyone's human search engine
- Your team fields questions from leadership and other departments every week, and the answers require pulling from multiple sources, documents, and conversations that only your team fully understands.
- The VP asks for a status update. Another department needs to know your timeline. A quarterly review needs your numbers.Every one of these requests pulls someone off their actual work.
- A focused knowledge base lets your team answer up and across the organization without stopping work to become the search engine for everyone else.
Everything You Want to Know
Frequently Asked Questions
Every enterprise AI search evaluation raises the same questions.
- Which vendor fits my company?
- Does the technology actually work against real data?
- Why does one architecture produce better answers than another?
These are the questions we hear most, and the answers reflect how we think about the problem: context determines answer quality, not the model, not the number of connectors, not the size of the vendor's logo.
Take a look at the questions. Pick one and explore a little further. We've answered each one the way we'd answer it in a first conversation.
Tricky Wombat works with companies of any size that need better answers from their data. The platform performs especially well for companies in the 500 to 2,000 employee range, where data fragmentation is real but the big enterprise vendors treat you as an afterthought. Most AI search vendors optimize for Fortune 500 accounts spending mid-seven figures annually. Companies below that threshold get generic configurations, deprioritized support, and a spot as customer 4,312 on a renewal list.
Tech-forward larger organizations that want a more hands-on, context-first approach are a strong fit too. So are small but nimble teams inside large companies that need to solve a specific search problem without waiting for an enterprise-wide procurement cycle.
The difference is the relationship. TW builds the context pipeline around your specific data structures, query patterns, and organizational needs regardless of headcount. The people who built the product are the same people configuring your system. That level of direct engagement is the point, whether you are a 500-person company, a 5,000-person organization, or a 20-person team inside one.
Tricky Wombat's infrastructure is built on services that meet enterprise security standards at every layer of the stack.
Your documents and source data are stored in AWS S3 with server-side AES-256 encryption at rest and TLS encryption in transit. Metadata and application state live in DynamoDB, which provides the same encryption standards within AWS's SOC 2 Type II, ISO 27001, and HIPAA-eligible environment. Vector embeddings used for semantic search are stored in Pinecone, which is SOC 2 Type II certified, GDPR-ready, and HIPAA compliant, with AES-256 encryption at rest and TLS 1.2 in transit. The application layer runs on Vercel, which provides automatic HTTPS, DDoS protection, and SOC 2 Type II compliance.
No component of the pipeline trains on your data. Your information is used to answer your queries and nothing else. Access controls follow the permissions your organization already has in place, so users only see results from documents they are authorized to access.
The short version: your data is encrypted everywhere it sits and everywhere it moves. The services that store it are independently audited. And none of it is used for anything other than finding better answers for your team.
Large vendors offer long lists of connectors (most of which are irrelevant to any given customer), big implementation teams, and brand recognition that makes procurement comfortable. Their architecture is designed to solve a generic problem at scale. Your implementation gets the same configuration as every other customer.
That tradeoff has a cost. A connector that links to a data source is not the same as a connector that understands how to ingest, chunk, and prepare that data for accurate retrieval. Most companies use a fraction of the connectors available to them, and the ones they do use still produce shallow indexing, silent truncation of large files, and missed industry-specific context. When a platform is built to serve thousands of companies simultaneously, it optimizes for breadth over depth. The pattern is consistent: scaling the business does not scale the answer quality.
Tricky Wombat builds the context pipeline around your specific data structures, query patterns, and organizational needs. The platform runs on AWS with Vercel, the same enterprise-grade infrastructure that large vendors use, and the same infrastructure that scales instantly and meets the standards your organization requires.
The difference is what sits on top of that infrastructure. The people who built the product are the same people configuring your system. Implementation decisions happen in days, not weeks. When you identify a capability gap, that conversation goes directly to the people who can act on it. You are not a ticket in a queue. You are a partner with direct access to the team that built the system.
We connect to standard enterprise data sources including cloud storage, document management systems, internal wikis, and communication platforms. The platform is built on AWS with Vercel, uses Apache Tika to connect to over 1,000 different file types for text and metadata extraction (including PDF, Microsoft Office: DOC, XLS, PPT), HTML, Image files (PNG. JPG, TIFF, GIF), OCR, Audio (MP3, WAV), Video (MP4, Quicktime) (see Apache Tika Supported Document Formats for a full list) and scales with your data volume.
Connection is the easy part. Where most vendors fail is what happens after connection. Silent truncation of large files without signaling errors. Images and diagrams stripped instead of understood. Stale indexes that serve answers from last week's crawl while your data changed yesterday.
Tricky Wombat’s data layer monitors connected sources continuously. When a document changes, the pipeline re-processes it. When a new document appears, it enters the index without waiting for a scheduled crawl.
The ingestion system handles the cases other platforms handle badly or not at all: a 40 MB regulatory filing where the answer sits on page 800, handwritten details on a scanned document, or a footnote that references another manual entirely.
Your context layer reflects your organization right now, not the last time a crawl ran.
Most enterprise AI search evaluations run on demo data with scripted queries. That tells you what the product looks like. It does not tell you whether it works against your actual information.
Tricky Wombat runs a pilot against your real data, your actual queries, and your team's workflow before you commit to anything. The question worth asking during an evaluation is not "how many companies use this?" The question is "how well does this work against my data, my queries, and my team's actual workflow?"
We are confident enough in that answer to let you test it. If you are evaluating us alongside vendors with bigger websites and longer customer lists, you should.
Start a conversation, describe the problem, and we will tell you whether the fit is worth both sides' time.
Most enterprise AI search vendors require a sales-led evaluation, a scoping process, a multi-week implementation, and months of interaction data before the system starts producing useful relevance. A fully integrated deployment with a large vendor can take anywhere from 30 days to several months depending on data complexity, permission mapping, and integration depth. Some platforms need dedicated developer time for configuration, and the ML models behind them do not improve until they have accumulated enough usage data to learn from.
Tricky Wombat works differently. Connect your data sources and start asking questions. The context pipeline begins working immediately because it does not depend on months of behavioral data to produce relevant answers. The architecture is built to understand your documents, rank them correctly, and assemble focused context from the first query.
A typical engagement starts with a direct conversation about your data and your problem. From there, Tricky Wombat connects to your sources, ingests and indexes your documents, and gives your team a working system they can test against real queries.
Every customer gets white-glove onboarding. The people who built the platform are the same people running your setup, answering your questions, and tuning the pipeline to your data. The same way a Four Seasons remembers how you take your coffee, we learn your data structures, your query patterns, and your team's actual workflow. That level of attention stays with you. There is no implementation team handoff, no multi-week scoping phase, and no waiting for the system to "learn" before it becomes useful.
See how it works with your data
Connect a data source, ask a question, and see what Tricky Wombat finds. One call. No commitment required.
Book a 20-minute fit callEnterprise search without the enterprise price.
Plans start at $25/seat.