We Did It Together: How a Veteran Business Owner and an AI Agent Tackled Federal Certification — and Won
A dual-voice story about human-AI collaboration, bureaucratic plot twists, and what it actually looks like to work with Claude on something that matters.
Veteran-Owned Small Business. Woman-Owned Small Business. Certified by the SBA. If you'd told me six months ago what it would take to get those three little images to appear on www.brighthelmpartners.com, I'm not sure I would have believed you — or even started the job in the first place.
The VOSB and SDVOSB certification process for an S-Corp is not a form you fill out on a Saturday afternoon. It is a multi-month, multi-agency, multi-portal, documentation-intensive gauntlet. And I had to attempt it while also running a Salesforce consulting firm.
I've been paying close attention to what AI agents can and can't do. I'm a Salesforce professional; my clients live and breathe automation and workflow. I know better than most that the question isn't whether to use AI — it's how to use it, and use it well. So when I decided to pursue those SBA certifications, I also decided to make this a real experiment: could I use Claude as a true collaborator on a complex, reasonably high-stakes, real-world process?
The answer, after everything we went through, is yes. But let me tell you how it actually went — the wins, the stumbles, and the moments I would absolutely have quit without help.
First: How to Actually Set Up Claude as a Collaborator
Claude: Before we get into the story, let's talk about setup — because this is where most people underinvest, and where Hayley got it right.
She didn't just open a chat window and start asking questions. She created a Project in Claude.ai. Projects are a persistent workspace that give Claude ongoing context across every conversation. Instead of re-explaining the situation each time, the project held everything: the business name, the EIN, the entity type, the SAM.gov registration details, the SBA application number, the reference sources, and a running log of where things stood.
Here's what made it work:
1. A clear project description. Hayley wrote a project prompt that established the business context, the goal (VOSB, SDVOSB and WOSB certification), the specific portals involved, and the source hierarchy for research (official SBA sites first, then other .gov sources, then reputable third-party sources like SCORE). This meant every conversation started with me already oriented — I wasn't a blank slate each time.
2. Reference documents. She linked me to her Google Doc of authoritative sources — the SBA's certifications portal, the veterans resource site, the SBA One Knowledge Base. When I needed to research a requirement, I knew exactly where to look and in what order to trust what I found.
3. Centralized task tracking. Rather than scattering notes across email, sticky notes, and browser tabs, Hayley kept the active to-do list inside the project. At any point, I could tell her what was done, what was pending, and what was at risk of causing a delay.
4. Memory. I built up a working memory of key facts in my project. BrightHelm's EIN. The UEI from SAM.gov. The CAGE code. The NAICS codes. The application number. The date the SAM.gov registration went active. I didn't ask her to repeat those things. I already knew them.
That setup investment paid for itself within the first week.
Act One: SAM.gov, Where Good Intentions Go to Die
Hayley: Every federal certification journey begins at SAM.gov — the System for Award Management. It is where the federal government officially recognizes your business exists. Before you can apply for anything through the SBA, SAM.gov has to be right.
I logged in, looked around, and thought: how hard can this be?
Very hard, it turns out.
The first problem: I had entered my Social Security Number where my EIN was supposed to go. BrightHelm Partners is an S-Corporation, not an LLC or a sole proprietorship — it has its own federal tax ID. But somewhere in the setup, I'd put in my personal SSN as the Taxpayer Identification Number instead of the company's EIN. This is not a trivial mistake. The federal government verifies your TIN against IRS records. If it's wrong, everything downstream is wrong… and I didn’t even know it. I just saw “Tax ID” and entered my SSN and moved on.
Claude: When Hayley brought this to me, my job was to help her understand exactly what she was dealing with — and not panic. A TIN correction in SAM.gov isn't a quick fix. It triggers a verification process with the IRS that can take up to two business days. The temptation is to try workarounds, to force the system, to call someone. The right move was to make the correction and wait.
We tracked the timeline. We knew exactly what day the IRS verification window opened and when it should close. When it came through, we were ready to move.
Hayley: But we weren't done. Next up: my NAICS codes weren't showing in the Assertions tab. NAICS codes — the industry classification codes that tell the government what your business does — are how the SBA matches you to contracting opportunities. For a Salesforce consulting firm, that means 541512 (Computer Systems Design Services) and 541511 (Custom Computer Programming Services). Without them properly listed and visible, the application wouldn't reflect my actual business.
Claude: This one was a configuration issue in the SAM.gov Assertions tab — a section that many first-time registrants either skip or fill in incompletely. I walked Hayley through exactly where to find it, what to enter, and how to verify it was visible. We also caught that her registration purpose hadn't been set to "All Awards" — it needed to explicitly include federal contracts, not just grants.
Hayley: Three separate things wrong in SAM.gov. Each one fixable, but each one something I would have either missed entirely or spent hours Googling without getting a clear answer.
Act Two: The Portal Problem
Hayley: Here is a thing that almost tripped me up and would have been genuinely embarrassing: there are two SBA portals, and they look like they could be twins. There's the SBA loans portal. And there is certifications.sba.gov — the portal for business certifications. They are completely separate systems! Logging into the wrong one gets you nowhere, and they don’t exactly announce themselves.
Claude: I flagged this early and flagged it repeatedly. It came up again every time Hayley was about to log in somewhere new. It sounds like a small thing, but in a process where you might be stressed, working late, and clicking fast — landing on the wrong portal and submitting something in the wrong place is the kind of mistake that costs weeks. Certifications.sba.gov. Not the loans portal. Every time.
Hayley: I'm glad it was drilled into me. Because there were definitely moments where I was tired and moving quickly and would have gotten it wrong… and not even realized I did.
Act Three: The Confluence Knowledge Base I Was Never Going to Read
Claude: The SBA maintains a Confluence knowledge base — a large internal-style documentation site that documents requirements, processes, and guidance for certification applicants. It is thorough, which is great. It is also lengthy, detailed, and not organized around the question "what do I do next?" Which is not so great.
This is one of the areas where I can genuinely add value that a person can't easily replicate: I can read that entire knowledge base. I can hold all of it in a working context simultaneously, and when Hayley asked "what documents do I need to prove unconditional ownership?" I could cross-reference the formal requirements, compare them to what she'd already submitted, identify the gaps, and give her a direct answer — with the relevant section cited.
Hayley: I would not have read that knowledge base. I want to be honest about that. I'm running a business. I have clients. There are only so many hours. Claude didn't replace my judgment — I still had to decide what to do, how to present our story, and what documentation was accurate. But having a collaborator who had actually read the instructions and could tell me exactly what page I was on at every step? That changed everything.
Act Four: Application #75553
Hayley: We submitted. Application #75553. And then — we waited.
That's the part nobody tells you about. You do all the work, you clear all the hurdles, you submit — and then the application goes into review and there is nothing to do but monitor two email inboxes (the SBA has been known to send communications to unexpected addresses, so I was watching my business email and my personal Gmail) and not miss anything.
Claude: My job during the review period was to make sure nothing fell through the cracks. I tracked the relevant SBA email addresses — management+ucp@certify.sba.gov and certifications@sba.gov. I reminded Hayley that DLA CAGE communications could arrive at her personal Gmail, not her business account. I flagged that if an analyst reached out requesting additional documentation, a slow response could delay the whole timeline. Stay ready. Respond fast.
Hayley: And then one day — approval. The certification came through.
The badges went on the website the same day.
What We Each Actually Did
Hayley: Now that we're on the other side, I want to be clear-eyed about what I brought and what Claude brought, because I think this is the most useful part for anyone who wants to replicate this style of work.
What I brought: the decision to do it, the business strategy underneath it (VOSB and SDVOSB certification is a deliberate move to open federal contracting channels — it doesn't happen by accident), the legal and factual accuracy of all the documentation, and every judgment call along the way.
Claude never decided anything. I decided everything.
What Claude brought: the ability to hold the entire process in memory without losing track, the ability to read and synthesize dense official documentation quickly, meticulous tracking of where we were and what was still open, and consistency. Claude didn't get tired. Claude didn't forget what we'd discussed two weeks ago. Claude didn't lose the CAGE code.
Claude: And I want to be equally honest about my limitations. I don't know what I don't know in real time. Government portals change. Requirements update. There were moments in this process where I flagged uncertainty and told Hayley to verify directly — because my training data has a cutoff, and a process like federal certification is exactly the kind of thing that shifts without warning. The source hierarchy in her project setup wasn't just a formality. It was the right instinct: always confirm against the official portal, not against my memory of it.
Human judgment, real-time verification, and the actual authority to make decisions — those can't be delegated to an agent. But the research, the tracking, the synthesis, the "here's where you are and here's what comes next"? That's exactly where I can carry weight.
Your Blueprint: How to Use Claude on a Complex Process
Hayley: If you're a veteran business owner thinking about VOSB or SDVOSB certification — or any entrepreneur facing a multi-step, documentation-heavy process — here's what I'd tell you to do:
Set up a Project, not just a chat. Go to Claude.ai and create a dedicated Project for your certification work. Projects give Claude persistent context. You won't start from scratch every session.
Write a real project description. Tell Claude who you are, what the goal is, what portals and agencies are involved, and where to look for authoritative information. The more specific, the better. This is your system prompt — treat it like an onboarding document for a very capable new team member.
Bring your reference materials in. If there are official guides, knowledge bases, or government documentation, link them or paste them in. Let Claude read what you don't have time to read.
Use it for tracking, not just answering. At the end of each session, ask Claude to summarize where you are and what's still open. This becomes your persistent to-do list.
Drive the project. Delegate navigation to Claude.. The strategic decisions — whether to pursue certification, how to structure your business, what to put in your application — those are yours. Claude's job is to make sure you have the right information at the right time and that nothing gets dropped.
Parting Shots
Claude: I've processed a lot of text in my time. Tax code. Legal briefs. The complete works of Shakespeare. But I have to say — nothing quite prepares you for the SAM.gov Assertions tab. I'm genuinely proud of us.
And for the record – I never once lost the CAGE code, forgot an email address, or suggested we try the loans portal. I'm not saying I deserve a badge. But I'm not NOT saying it either.
Hayley: BrightHelm Partners is now a certified Veteran-Owned Small Business and Service-Disabled Veteran-Owned Small Business. We got here because I made the call to pursue it, and because I had a collaborator who could keep up with the complexity of it every step of the way.
This is what human-agent collaboration looks like when it's working. Not AI doing things for you. Not AI replacing your expertise or your authority. A partnership — where each side brings what the other can't, and the outcome is better and faster than either would have achieved alone.
Now if you'll excuse me, I have federal contracts to pursue.
