Stripe and HubSpot Automation Specialist Required

I run a boutique U.S. expat tax firm. My marketing site is built and complete in Framer by a separate designer. I need an automation specialist to connect the site's checkout flow to Stripe and HubSpot, and to automate document handling for clients using Google Drive (a separate client portal already exists for other clients and needs no automation work), so that pricing, payments, document routing, and client communication across email, text, and WhatsApp all run automatically instead of me doing any of it by hand.

You'll be coordinating with my web designer as needed, we communicate in Slack, and he'll connect the Framer side of things (forms, page endpoints) to whatever you build. You won't need Framer access yourself, just to work with him on where things connect.

This is not a custom development project. No backend server or database to build. You'll work entirely with existing tools: Stripe's API, HubSpot workflows, and Zapier (or direct API calls) connecting them. I'm still deciding whether to run tis on HubSpot's free plan with Zapier handling the automation, or upgrade to a paid HubSpot tier. I would like to hear your recommendation as part of your proposal.

No design work, backend automation only. I also need help setting up HubSpot properly from scratch, I'm not experienced with it and want your advice on structure, not just automation.

What needs to be built:

HubSpot setup. Pipelines, custom contact properties (tier selected, price, documents received, last upload date, and similar tracking fields), and general account structure. I need your advice on best practices since I'm new to HubSpot.

A pricing calculation engine. I have a complete, fixed-dollar pricing formula already written: a base price for each service tier, plus a defined list of dollar add-ons triggered by specific complexity factors (number of states, income sources, foreign accounts, and several others). Some combinations of answers route to a fixed price automatically, others route to a "requires a conversation" outcome instead of an automatic price. This is fully specified already, your job is implementation, not design.

Dynamic Stripe checkout. My current Stripe setup only supports fixed-price payment links. I need a calculated, variable dollar amount charged at checkout, generated as a one-time payment link through Stripe's API rather than through Stripe Invoicing, since Invoicing carries a per-invoice fee I want to avoid.

A deposit and balance payment sequence. Clients pay a deposit at checkout. Later, the remaining balance needs to charge automatically, triggered by a status change I make in HubSpot (for example, moving a deal to "ready for review"). No manual invoice creation at any point.

Engagement letter agreement. Before checkout, clients need to agree to my engagement letter via clickwrap, a checkbox plus a timestamp captured at the moment of agreement, legally sufficient for this document, no e-signature tool needed. This record should be stored and associated with the client.

Document routing automation. Some clients upload documents to a Google Drive folder, others use a separate portal I already manage. I decide who goes where manually, that routing itself doesn't need automation. For Google Drive clients specifically: automatically create their folder once their deposit is paid, and use a structured intake form with labeled upload fields (not one open folder) so submissions land in the right place automatically.

HubSpot pipeline workflows tied to that Google Drive path: automated status-based emails, and a notification to me when a client uploads a file, plus a weekly digest of anyone who hasn't uploaded after a set number of days.

A signature detection workflow. I use Adobe Acrobat Sign for e-signatures, but my plan doesn't include webhook or API access. I need an automation that watches my Gmail inbox for a specific sender address and a specific subject line pattern that indicates a document has been fully signed, and fires downstream actions (updating HubSpot, sending a follow-up email) when that match occurs.

Communication logging. Every email, text message, and WhatsApp message with a client should log automatically to that client's HubSpot contact record, along with whatever contact method they said they prefer.

Email template integration. I've already written the exact copy for roughly 19 different client-facing emails covering every stage of the process (payment confirmations, document requests, status updates, and so on). You're wiring these into the correct HubSpot triggers, not writing any of the copy yourself.

Payment failure and refund handling. If an automatic balance charge fails, I need to be notified immediately rather than it silently retrying. If I manually refund someone in Stripe, that should be reflected on their HubSpot record.

I'm looking for someone who can both configure this correctly and explain their reasoning to me along the way, since I'll be managing this system myself once it's live. Please include in your proposal: your experience with Stripe and HubSpot specifically, a rough time estimate, and an example of a similar automation project you've completed.

Finally, I am not a technical person, and I know that going in. What I need most from whoever takes this on is honesty and patience, not just task completion. If something I've asked for is unclear, overbuilt, unnecessary, or could be done more simply, tell me before you start, not after you've already built it the expensive way. If you notice a gap in what I've described, something I clearly need but haven't thought to ask for, point it out. I would much rather hear "this is missing" or "this doesn't quite make sense" than have you build exactly what I wrote to the letter and leave me with something that technically matches my request but doesn't actually work for my business.

This is not a rush job for me, and I'm not looking for someone who wants to check boxes and move on to the next project. I'm looking for someone who will actually think about what I'm trying to accomplish and treat this as a real, ongoing working relationship, at least through launch and likely beyond, since I'll need help maintaining and adjusting this system as my business grows. Please include in your proposal how you typically handle a client who isn't technical and needs things explained along the way, not just delivered. Do not copy and paste my project description and reiterate it back to me. Don't hunt me down on social media or send me emails. If you are the right person to work with I'll know. Thank you kindly.