AI Tools for Sell-Side Investment Banking

Investment banking is undergoing a dramatic change, driven by artificial intelligence tools that are revolutionizing how deals get done. Gone are the days of junior bankers spending countless hours on repetitive tasks - AI is now shouldering much of this burden, allowing banking professionals to focus on what truly matters: strategy, client relationships, and deal execution.

AI-powered assistants are streamlining everything from market research to pitchbook creation. These tools can generate complex reports and client communications with minimal manual input, freeing bankers to focus on high-value activities. Generative AI is significantly accelerating workflows by automating routine tasks, allowing more deals to be processed with the same resources.

But it's not just about automation - AI is enhancing the quality and depth of analysis across the board. From conducting thorough due diligence to providing actionable insights, these tools are complementing your expertise. They're helping bankers work smarter, not just faster.

This guide explores several AI-driven tools that investment banking professionals, particularly those at boutique firms, can leverage to transform their client pitching, onboarding, and deal marketing processes. We'll examine each tool's capabilities and strengths, with a focus on practical applications in sell-side tasks. You'll discover how combining these tools can dramatically accelerate the deal process, and we'll introduce specialized solutions like Deliverables AI that are tailored specifically for investment bankers looking to harness AI's power.

What to Expect

Throughout this guide, we'll:

Compare various AI tools and their specific applications in investment banking
Highlight key benefits, including time savings and workflow optimizations
Provide practical recommendations for integrating these tools into your daily work
Share real-world examples of how these tools can transform deal execution
Introduce specialized solutions designed specifically for investment banking workflows

Whether you're a seasoned banker looking to modernize your practice or a junior professional seeking to maximize your efficiency, this guide will show you how AI can become your competitive advantage in today's evolving market.

Note: This guide reflects capabilities and tools available as of early 2025, with a focus on practical applications in investment banking workflows.

Perplexity AI: Your Real-Time Research Assistant

Think of Perplexity as your always-on research analyst. It's an intelligent search engine that doesn't just find information – it understands what you're looking for and delivers concise, relevant answers with sources to back them up. What sets it apart is its ability to parse through current information and deliver real-time insights with citations you can trust.

How It Shines in Banking Work

When you're in the thick of client pitching or document preparation, Perplexity becomes invaluable. Imagine you need quick facts about M&A activity in the fintech sector – instead of spending an hour digging through various websites, you can ask Perplexity directly and get an immediate, sourced answer. This is particularly useful when:

Gathering market statistics for pitch decks
Finding recent transaction comparables
Verifying industry trends for Confidential Information Memoranda (CIMs)
Doing quick background checks on potential clients or competitors

During client onboarding, you can rapidly pull together background information about a client's industry or competitive landscape, making your strategy meetings more informed and productive. The tool's real strength lies in its speed and reliability – you get the confidence of verified information without the time sink of traditional research.

A word of caution: Perplexity is only as good as its sources. We have found that it often references sources that are not up to date, of questionable quality, or are not relevant to the question.

Google Deep Research: Your Strategic Analysis Partner

Google's Deep Research takes a different approach (called "Deep Research AI" by many in the industry now). Available through Google's Gemini, it not only gathers information but synthesizes it into meaningful insights. When you pose a complex query, Deep Research doesn't just search – it creates a research plan, executes it systematically, and delivers a comprehensive report with key findings and direct links to sources.

For want of a better description, it is like a version of Perplexity that spends a lot more time thinking, planning, and reading before it makes it much longer answer. It is a more thoughtful, thorough version of Perplexity, that takes its time before responding.

Making Complex Research Simple

Let's say you're preparing a pitch for a healthcare tech client. Instead of spending days gathering market intelligence, you could ask Gemini + Deep Research to "analyze the key growth drivers, recent M&A deals, and competitive landscape in healthcare AI startups." Within minutes, you'll get a detailed report covering all these aspects, complete with verifiable sources.

The tool really shines when you need:

In-depth market analysis for pitch materials
Comprehensive industry overviews for CIMs
Understanding emerging trends affecting your client's sector
Building out the "Industry Overview" section of your documents

The output isn't just a collection of facts – it's a structured analysis that can form the backbone of your client materials. According to industry data, this type of AI-powered research can compress what used to be days of work into mere hours, allowing deal teams to focus on higher-value activities.

Real-World Application

Consider this scenario: You've just landed a meeting with a potential client in the renewable energy sector. Instead of scrambling to gather background information, you can:

Use Deep Research to generate a comprehensive overview of the renewables market
Get up to speed on recent deals and valuations in the space
Identify key trends and growth drivers to reference in your pitch
Back up every point with credible sources

The result? You walk into the meeting with deep industry knowledge and concrete data points, all gathered in a fraction of the traditional time.

What makes Deep Research particularly valuable is its ability to tackle multi-faceted questions. When you need to understand complex market dynamics or interconnected trends, it can piece together information from various sources to give you a complete picture. This isn't just faster than traditional research – it often uncovers connections and insights that might have been missed in manual research.

Similarly to Perplexity, Deep Research is only as good as its sources. We have found that it often references sources that are not up to date, of questionable quality, or are not relevant to the question. Always verify the sources and use your own judgement.

ChatGPT Pro: Your Content Creation Powerhouse

If you're familiar with ChatGPT, you know it's already a powerful tool for writing and analysis. But the Pro version, especially with its new Deep Research mode, takes things to another level. It's an analyst and copywriter rolled into one, capable of both deep research and polished content creation.

The Deep Research Advantage

What makes ChatGPT Pro's Deep Research mode special is its ability to act as an autonomous research agent. Give it a complex prompt like "Survey the recent trends in renewable energy M&A and summarize the outlook," and it'll spend several minutes searching the web, analyzing reports, and producing a detailed analysis that reads like it came from a seasoned professional. The output is a much longer answer than you would get from the regular ChatGPT.

Practical Applications in Banking

In day-to-day banking work, ChatGPT Pro proves its worth in countless ways:

For Client Pitching:

Draft compelling executive summaries that capture your client's unique value proposition
Create detailed buyer profiles with recent acquisition history and strategic fit analysis
Generate industry overviews that combine market data with strategic insights

For Document Preparation:

Transform bullet points into polished investment highlights
Convert technical jargon into clear, compelling narratives
Draft responses to buyer questions during due diligence

The real game-changer is how it handles complex tasks. Industry data suggests that using AI tools like ChatGPT can reduce document preparation time by up to 70%. Instead of spending hours crafting the perfect paragraph about market positioning, you can have ChatGPT generate several versions and pick the best one – or combine elements from different versions to create exactly what you need.

We could also see this being used to produce marketing assets such as in-depth industry reports, which are a great way to stand out from the crowd and add value for clients. Indeed, the first draft of this post was produced using ChatGPT Pro and then edited by hand. And - from first hand experience - we would add that, like Perplexity and Gemini, ChatGPT Pro is only as good as its sources. We have found that it often references sources that are not up to date, of questionable quality, or are not relevant to the question. Always verify the sources and use your own judgement.

Claude: Your Document Analysis Expert

Claude, by Anthropic, is an extremely capable model that brings an enormous capacity to handle large documents combined with sophisticated analysis capabilities. With its ability to process up to 200,000 tokens (roughly 150-200 pages) at once, it's like having a junior banker who can read and understand entire data rooms in minutes.

Why Claude Stands Out

The key advantage of Claude is its ability to maintain context across large amounts of information. Whether you're feeding it financial statements, legal documents, or entire pitch books, Claude can:

Process and analyze extensive documents in one go
Maintain consistency across long-form content
Extract key insights while preserving important details
Understand and interpret charts and graphs within documents

Claude is also known for its ability to write in a more human-like way than other AI models. This can be a great asset when you need to draft a document that reads naturally.

Real Investment Banking Applications

Here's where Claude really shines:

During Due Diligence:

Feed it an entire data room and ask for key findings or red flags
Have it summarize multiple financial reports while highlighting trends
Extract relevant information from lengthy contracts or technical documents

For Document Creation:

Write and refine entire sections of CIMs while maintaining consistency
Review complete pitch decks for messaging alignment
Generate comprehensive executive summaries that tie together multiple data sources

For Quality Control:

Review documents for internal consistency
Cross-reference facts and figures across multiple sections
Ensure messaging remains aligned throughout long documents

The practical impact is significant. Instead of having junior bankers spend days reading through documents, Claude can process everything quickly and highlight what matters most. This means your team can focus on analyzing the insights rather than just gathering them.

A Day in the Life Example

Imagine you're starting work on a new sell-side mandate. You receive a folder with:

100 pages of financial statements
50 pages of market research
30 pages of technical product documentation
20 pages of customer contracts

Instead of diving into each document separately, you can feed everything to Claude and ask for:

A summary of key financial metrics and trends
Major market opportunities identified in the research
Key product differentiators
Notable terms or restrictions in customer contracts

Within minutes, you have a comprehensive overview that would have taken days to compile manually. More importantly, Claude can then help draft these insights into various sections of your CIM or pitch deck, maintaining consistency and accuracy throughout.

Poe: Your AI Model Command Center

Think of Poe as your Swiss Army knife for AI tools. It's a platform that gives you access to multiple AI models (including ChatGPT, Gemini, Claude and even DeepSeek R1) in one clean interface. Instead of jumping between different websites and apps, you can switch between AI assistants as easily as switching between chat conversations.

Why Bankers Love It

The real value of Poe lies in its flexibility and comparison capabilities. You might find that:

GPT-4 writes the most sophisticated investment highlights
Claude excels at analyzing long documents
Another model might be best for quick market research

With Poe, you can leverage each model's strengths without the hassle of managing multiple applications. It's particularly useful when you want to:

Compare different AI responses to the same prompt
Use specialized models for specific tasks
Quickly switch between different types of analysis

Practical Applications

Let's say you're drafting a critical section of a CIM. You could:

Get a first draft from GPT-4
Have Claude review it for consistency with earlier sections
Use another model to polish the language
Compare all versions to pick the best elements of each

This kind of AI model comparison might seem like overkill, but when you're working on high-stakes documents, having multiple perspectives can be invaluable.

NotebookLM: Your Personal Deal Room Assistant

NotebookLM takes a different approach to AI assistance. Instead of working with general knowledge, it becomes an expert in your specific sources. Its perfectly memorizes every web page or YouTube video you've shared and can answer any question about them instantly.

What Makes It Special

The key difference is that NotebookLM grounds all its responses in your uploaded documents. This means:

You can curate your own sources and share them with the AI
Every answer comes directly from your source materials
It has a nifty "audio summary" feature that produces short podcasts based on your sources

Banking Use Cases

NotebookLM really shines during:

Deal Preparation:

Upload all client materials and quickly extract key information
Find specific details across multiple documents instantly
Generate summaries (including audio summaries) that you know are based on actual client data

Due Diligence:

Analyze large sets of client documents for key insights
Cross-reference information across multiple sources
Quickly find answers to specific questions within vast documentation

Document Creation:

Draft sections of pitch books using verified client information
Ensure accuracy of client descriptions and claims
Create fact-based market positioning statements

Grain: Your Meeting Memory Bank

If you've ever wished you could perfectly remember every detail from every client call, Grain is your solution. It's an AI-powered meeting recorder and analyzer that turns your conversations into searchable, shareable content.

Key Features in Practice

When you're running client calls or management presentations, Grain:

Records and transcribes everything automatically
Creates AI-generated summaries of key points
Lets you easily clip and share important moments
Provides a searchable database of all meeting content

Real Banking Benefits

The practical impact on your workflow is significant:

During Client Meetings:

Focus on the conversation instead of taking notes
Create perfect records of every client statement
Easily share key moments with your team
Never miss important details

For Deal Documentation:

Pull exact quotes for CIMs and pitch books
Create accurate meeting summaries in minutes
Build comprehensive Q&A logs from buyer calls
Maintain detailed records of all client interactions

At Deliverables, we have found that transcripts from client calls are a great input for generating CIMs and pitch books. There are many similar services out there, but Grain is particularly good at this and is SOC 2 compliant to ensure security and confidentiality.

Wispr Flow: Your Voice-to-Document Accelerator

Sometimes speaking is faster than typing, and that's where Wispr Flow comes in. It's an AI-powered dictation tool that turns your spoken words into polished written content, claiming to be up to three times faster than typing.

When to Use It

Wispr Flow is particularly valuable when:

You're brainstorming ideas for a pitch
You need to draft quick emails or memos
You're reviewing documents and want to add comments
You're multitasking and can't type
You're tired of typing after a long day

Banking Applications

Consider these scenarios:

Quick Content Creation:

Dictate initial drafts of CIM sections while reviewing materials
Speak out email responses between meetings
Create meeting summaries while they're fresh in your mind
Draft presentation talking points on the go

Document Review:

Voice-annotate documents during review
Dictate feedback on draft materials
Create revision notes while reading

The beauty of Wispr Flow is that it maintains your natural writing style while capturing your thoughts at speaking speed. This can be a game-changer during crunch times when you need to produce content quickly but don't want to sacrifice quality.

While Wispr Flow runs on their private cloud and the data is encrypted during transit and at rest, you may want to check their security practices before using it.

Key Benefits for Investment Banking Users

Let's talk about what these AI tools can actually do for you and your team in practical terms. The benefits go way beyond just saving time – though that alone is pretty impressive.

Transforming Your Time Management

The most immediate impact you'll notice is how much time these tools save you. Tasks that used to eat up your entire day can now be handled in a fraction of the time. Here's what that looks like in practice:

Time Savings in Action

That market overview section that used to take half your day? AI can draft it in minutes, leaving you time to focus on the analysis that really matters
No more spending hours transcribing meeting notes – Grain handles that automatically
Instead of manually updating countless market data slides, AI tools can pull and format the data quickly

Industry data shows that these tools can reduce deal preparation time by up to 70%. Think about what that means: work that used to take a week might now take just two days. For boutique banks especially, this means being able to handle more mandates without burning out your team.

The Ripple Effect

When you're spending less time on routine tasks, you can:

Take on more deals without increasing headcount
Spend more time on strategic thinking and client relationships
Respond to client requests faster
Give junior bankers more time for meaningful analysis instead of grunt work

Quality and Consistency Improvements

Time savings are great, but what about quality? This is where AI tools really shine – they help produce more accurate, consistent work across your entire deal process.

How AI Enhances Accuracy

AI doesn't get tired or make typos after a long day
Tools like Claude can cross-reference information across entire documents instantly
Multiple AI models can check each other's work through platforms like Poe
Every fact can be verified with sources through tools like Perplexity

Real-World Impact

Imagine you're working on a CIM. Instead of worrying whether the growth rate mentioned on page 5 matches what's in the financial section, you can have AI tools verify consistency across the entire document. They'll catch:

Mismatched numbers
Inconsistent terminology
Varying descriptions of the same concept
Missing cross-references

Focusing on What Really Matters

Perhaps the biggest benefit is how these tools free you up to focus on the high-value aspects of banking that truly require human judgment and expertise.

What You Can Do More Of

Strategic thinking about positioning and deal structure
Building and maintaining client relationships
Conducting thoughtful valuation analysis
Developing creative solutions to complex problems
Mentoring junior team members

What AI Handles

Initial research and data gathering
First drafts of documents
Meeting transcription and summarization
Fact-checking and consistency reviews
Basic Q&A during due diligence

Practical Workflow Integration

The real magic happens when you integrate these tools into your daily workflow. Here's how that might look:

Morning Prep

Use Deep Research to gather overnight market updates
Have Claude summarize any new client documents
Let Grain create summaries of yesterday's calls
Use Wispr Flow to dictate your to-do list while reviewing materials

Deal Work

Use AI to draft initial sections of pitch books and CIMs
Have different AI models review and refine each other's work
Use NotebookLM to quickly find specific information in client documents
Let AI handle first-pass responses to buyer questions

Team Collaboration

Share AI-generated meeting summaries with the team
Use AI to ensure consistency across different team members' work
Leverage AI for quick fact-checking during internal reviews
Create AI-assisted status updates and progress reports

Scaling Your Capabilities

For boutique and middle-market banks, these tools effectively give you the capabilities of a much larger team. You can:

Handle more deals simultaneously
Respond to clients faster
Produce higher-quality work consistently
Compete with larger banks on execution

According to industry data, banks using AI tools can process substantially more deals with the same resources. This isn't about replacing bankers – it's about making each banker more effective.

The Bottom Line

The combination of these AI tools creates a force multiplier for your team. You get:

Dramatic time savings on routine tasks
More consistent, accurate work product
Faster response times to client requests
More time for strategic thinking and client relationships
The ability to handle a larger deal flow without burning out

These tools are most effective when they're supporting skilled bankers who know how to leverage them properly. They're not replacing your judgment – they're freeing you up to use that judgment more effectively.

Deliverables.ai: Your AI-Powered Deal Room

Deliverables.ai is a specialized tool that takes the best features of the AI tools we've discussed and puts them together in a single, easy-to-use platform. It's like having a team of expert analysts at your fingertips, ready to help you with any task.

Get a demo of Deliverables.ai to try it out.