AI Success Plan

"I don't want to say mindless work, but it's really important because, Lord forbid, I forget to enter a receipt. If I could just create a bill, specify what job it's for, and then maybe AI could just plug it into our expenses on Jobber. That'd be amazing."Britnie Escalante, HR & Admin

Form: Headless automation. Receipts still arrive by email, but to 1 address.

#	Step	Who	Software
1	Receive the receipt or vendor bill	Britnie	Email, paper
2	Rename and file it	Britnie	Google Drive (receipts & bills folder)
3	Route the vendor bill for review	William	Email
4	Create the bill; attach the invoice so Sergey can see what it's for	Britnie	QuickBooks
5	Find the job and enter the expense	Britnie	Jobber
6	Review & pay	Sergey	QuickBooks

• The same receipt gets handled in 3 places. That's ~1 to 1.5 hrs/wk.
• Entering the job expense in Jobber is easily missed.
• Reimbursements get tracked by Britnie typing [PAY] in front of the filename & Sergey deleting it by hand once he's paid. That becomes a status the system owns.

#	Step	Who touches it
1	Receipt or bill lands at a shared email alias, or gets uploaded	Person sends
2	AI reads it & routes to 1 of 3 paths: already-paid receipt (file only), vendor bill (file + QuickBooks bill), employee reimbursement (file + flag for Zelle)	Automatic
3	Renamed & filed into the monthly Drive folder the bookkeeper reconciles from	Automatic
4	Vendor bill created in QuickBooks with the document attached	Automatic
5	Job suggested from vendor, date & schedule, expense posted for job costing	Automatic
6	Notification email: done, or flagged for review	Automatic
7	Weekly payment run	Sergey reviews & pays

Receipts just need to be sent once, no more double entries, Will doesn't need to approve in the middle of the process, and Jobber stops missing expenses.

QuickBooks Online, Google Drive, Jobber.

• Can reimbursements be booked as QuickBooks bills with the employee as a vendor?
• Should AI match receipts to card transactions & categorize them?

"There's a lot of legwork that goes into making sure that we have the right information in the invoice. [...] I spend like the last 45 minutes to an hour on invoicing every day."Britnie Escalante, HR & Admin

Form: Headless automation. Fires when a job closes in Jobber. Britnie reviews a finished draft in QuickBooks instead of building one from scratch.

#	Step	Who	Software
1	Review completed work	Britnie	Jobber
2	Match against the signed proposal; check for scope changes	Britnie	Jobber, HubSpot
3	Find the billing or invoicing note; for new clients, confirm the billing contact	Britnie	HubSpot
4	Create the invoice	Britnie	QuickBooks
5	Log the invoice number	Britnie	Master timesheet (Sheets)
6	Trigger the review request	Britnie	GatherUp
7	Upload to portals where required	Britnie	Client vendor portals

• 4 systems read & cross-checked by hand on every invoice: Jobber, HubSpot, QuickBooks & the master timesheet. 45 to 60 min/day, 5 to 15 min per invoice.
• Terms & sales-rep attribution and the invoice number get retyped every time.

#	Step	Who touches it
1	Job marked Closed in Jobber	Automatic trigger
2	Job matched to its HubSpot record; signed proposal checked against the Jobber description, scope differences flagged	Britnie resolves flags
3	Draft invoice built in QuickBooks: billing contact, terms, sales rep, service date, description, site address, product category	Automatic
4	Review & send	Britnie
5	Invoice number written to the master timesheet	Automatic
6	GatherUp review request fires on send, except on deposit invoices	Automatic
7	Client vendor portal upload	Britnie

• Britnie reviews invoices rather than assembling each one across 4 tabs.
• Terms & rep attribution come from the signed proposal instead of memory.
• The master timesheet stays current without re-entry.

Jobber, HubSpot, QuickBooks Online, Google Sheets, GatherUp.

• The QuickBooks product & service category list.
• How deposit invoices get flagged, so GatherUp correctly skips them.

"I actually never close this tab because otherwise I would just reopen it every week and it's easier to just press refresh. [...] This pretty much stays permanently as a minimized tab on my computer."Zander Cohn, Marketing (on the data sources behind the weekly dashboard)

Form: Dashboard & reminders. The numbers pull themselves on a schedule and land in one place, with history.

• Monthly KSIs take Sergey ~5 hrs/month, plus weekly KPIs.
• Zander's weekly dashboard & scoreboard pull from 8 to 10 sources: ~1.5 hrs/wk, plus ~1 hr on the sitemap.

#	Step	Who touches it
1	Data pulls on a schedule from every source with an API: QuickBooks, HubSpot, Jobber, Google Sheets, GA4, Search Console, Google Ads & the rest	Automatic. Sources with no API still need manual entry
2	Calculations run; this period compared against history & against target	Automatic
3	Saved B2B conversion view, no re-filtering	Automatic
4	Anything off trend or off target gets flagged	Human reviews the flags
5	Marketing dashboard & company scoreboard populate	Zander reviews
6	Sitemap regenerates on publish	Automatic
7	Finished numbers read & acted on	Sergey interprets & decides

Connectors may not exist out of the box in ChatGPT for most platforms. Also, a prompt still needs someone to run it.

The team is never behind on reports and data, and no more manual time goes into hunting down data that can be pulled instantly with an API.

Any source with an API (QuickBooks, HubSpot, Jobber, Google Sheets, GA4, Search Console, Semrush, PageSpeed Insights & Google Ads). LinkedIn Ads & SiteDocs stay manual.

"I have to do it on the weekends, which kind of sucks [...] because I have to allocate this two hours on weekends [...] to calculate what's our productivity on jobs."Sergey Kucher, Owner

"If only we can use the time sheet, the master time sheet, I could just have one place to enter the data instead of having to do both [...] it's just like a double task."Britnie Escalante, HR & Admin

Form: Headless automation. Hours sync themselves between Workforce, the master timesheet & Jobber. Techs keep clocking in exactly as they do now.

#	Step	Who	Software
1	Clock in / out	Field techs	QuickBooks Workforce
2	Pull hours per employee per day	Britnie	QuickBooks Workforce
3	Enter hours into the master timesheet; split multi-job days by estimated effort	Britnie	Google Sheets (master timesheet)
4	Find each job and re-enter the same hours	Britnie	Jobber
5	Chase and fix missed clock-ins	Britnie, Sergey	Workforce, Sheets
6	Weekend productivity analysis: hours vs. work completed, by project	Sergey	Sheets, Jobber

• The same hours get entered twice, for every tech, every week. ~2.5 hrs/wk of Britnie's time, mostly cross-checking Workforce, Jobber, and the Sheet.
• Days with multiple jobs get split with educated guesses.
• Missed clock-ins hold up everything downstream.
• Sergey spends 2-3 hrs of his weekend on the productivity analysis.

• Option A, automate what exists. Daily sync of Workforce hours into the master timesheet & Jobber, splits calculated, anomalies flagged. Weekly analysis assembled before the weekend. Keeps all 3 platforms in sync.
• Option B, consolidate first (recommended). Clock in & out in Jobber, push to Workforce for payroll & to Sheets. Workforce still handles overtime & custom pay periods.

The Sheet is doing 3 jobs today: invoice tracking, hour splitting, and productivity analysis.

#	Step	Who touches it
1	Techs clock in & out	On QuickBooks Workforce
2	Hours sync to the master timesheet & to Jobber	Automatic
3	Multi-job days split by revenue	Deterministic. Britnie confirms flagged outliers only
4	Missing or anomalous entries flagged the same day by email	Britnie follows up
5	Hours, job costs & backlog assembled before the weekend, outliers flagged	Sergey reviews & decides

Percent-complete on multi-stage projects stays Sergey's call.

Britnie enters nothing twice, Sergey's weekend analysis becomes a quick review, and missed clock-ins get flagged the next day instead of at the end of the week.

QuickBooks Workforce (API), Jobber (API), Google Sheets (API).

"This is one of the bottlenecks right now, because we do have opportunities. It's not like we're [...] struggling to get business. It's just more of [...] processing them quickly enough and getting them proposals so they can approve it [...] and schedule the projects."Sergey Kucher, Owner

"I joined the company about maybe six months ago [...]. And I still do not know how to price most things [...]."Ed Balta, Project Estimator

Form: Custom application. Real software with its own interface, built on Sergey's existing calculation logic.

Pro	Pro++
Takeoff sheet upload, pricing logic set up & editable, calc app for the top 3-4 services, proposal generation	Everything in Pro, plus AI-drafted scope descriptions, AI price benchmarking with suggestions, & all services including B2C
~6-8 wks	~8-10 wks

Pro covers steps 4, 6, 7 & 9 for the top 3-4 services. The entire new flow is Pro++.

• The calc sheets are detailed but extremely hard to use. There are separate calc sheets for each service, but Ed can only do window cleaning.
• Ed needs to map window dimensions to S/M/L sizes on every single project.
• Job descriptions get written by hand, cleaned in ChatGPT, then reviewed again by Sergey.
• Sergey reviews 6 to 8 B2B estimates a week, taking ~2-4 hrs/wk. He tracks his own estimating time as a KSI because he wants it to come down.

#	Step	Who touches it
1-3	Pre-research, site visit, visual takeoff	Estimator
4	Takeoff export ingested; square footage mapped to sizes automatically	Automatic
5	Scope description drafted from the HubSpot scope of work, routed to the right service rows	Estimator with AI assistance
6	One tool covering B2B & B2C across all services, on Sergey's existing logic, with required fields prompted before a step can advance	Estimators enter
7	Estimate moves to review inside the tool, leadership notified it's ready	Automatic
8	Review of a consistent, pre-validated estimate with flags: price per sq ft against market for property type & size, materials cost benchmark, missing equipment check	Sergey with AI assistance
9	Proposal generated from the finished estimate	CSR sends

• Ed & the CSRs can price services only Sergey can price today.
• Sergey reviews instead of building, and reviews something already checked.
• More estimates go out, which is the actual revenue constraint.

Square Takeoff, HubSpot, the existing Excel calc sheets & Sergey's formulas, the proposal template.

In jobs won, not hours saved. RayAccess needs to send about $1M of proposals a month across 24-32 proposals, so the average is ~$31K. At a 30% close rate & the 15% margin target, each extra job won is worth ~$4.7K. Pro pays for itself after about 4 extra jobs, roughly 2 more proposals a month for 6 months. Pro++ takes about 5.

"The thing that [...] is the most weekly repetitive all the time thing [...] is the blog post and social media post creation."Zander Cohn, Marketing

"If you can create a structured system [...] I think it's a great idea. It will actually help us to be very consistent with our SEO strategy."Sergey Kucher, Owner

Form: Assistant (Claude skill). Zander drives it himself, step by step. Nothing runs in the background and there's no new platform to adopt.

Option 1: skill only	Option 2: full build
The Claude skill for topics, drafts, Claude Design prompts & social versions. Zander formats & publishes in WordPress himself	Everything in Option 1, plus WordPress integration (formatting, images placed, meta fields) & image generation beyond Claude Design

• 1 blog post & 1 social post every week, produced end to end. 3-6 hrs each.
• ~20% of that is hunting for usable job-site photos: 2 to 4 hrs/wk.
• ~20% goes to editing an SEO article that's already being written by AI.
• ~30% goes to WordPress updates & back-end formatting.

#	Step	Who touches it
1	Topic suggested from recently completed jobs, seasonality & search data	Zander chooses
2	Photos pulled from the tagged asset library for that job	Zander confirms
3	Case studies only: draft built from Jobber job notes & photos first, so the interview only fills gaps	Zander interviews staff
4	Draft written in RayAccess's voice	Zander edits
5	Claude Design prompt generated for the article & social creative	Zander runs it
6	Formatted for WordPress with images placed & meta fields filled	Zander reviews & publishes
7	Social versions generated from the finished post	Zander approves

Zander saves lots of time, photos stop taking so long to find, and the weekly cadence for SEO is much easier to keep up.

WordPress, the asset library, Jobber job notes (API), Claude.

"So it's (the collections SOP) really intricate. And honestly, we don't do this because it's just nobody has time for it. We have 31, which is horrible. [...] Usually we don't let it get that bad, but it's just a time thing."Britnie Escalante, HR & Admin

Form: Headless automation with email notification. A daily contact list and created QuickBooks tasks.

• 31 invoices outstanding at the time of the interview, & DSO sits at ~20 days.
• The SOP has 6 escalation stages, and it's very hard to ensure they all happen.
• Every call starts by hunting for context across QuickBooks tabs.

Daily, the new system will sweep QuickBooks for notes, incorporate the SOPs, and send an email notification to those responsible for collections that includes a daily contact list.

The escalation SOP actually runs, because the system tracks the stage, and Britnie can hand collections to Esmeralda.

QuickBooks (invoices, customers, AR aging, notes), HubSpot, email.

"Somebody's COI, W-9 or agreement is expiring in August. [...] time sensitive, but it's important. [...] It's just hard to have time to go in and look through the things when I have fires to put out."Britnie Escalante, HR & Admin

Form: Dashboard & reminders. An add-on to the same reminder engine as collections.

• Subcontractor COIs, W-9s, contractor agreements, workers' comp, licenses & certs get collected by email and tracked by hand across Drive & Monday.
• Annual renewal chasing irritates subs, who often feel they just sent it.

#	Step	Who touches it
1	Document uploaded or arrives by email, expiry date read off it	Britnie uploads
2	Status board per sub & per employee: complete, missing or expired	Automatic
3	Reminder & request email drafted 30 days before expiry	Britnie sends

Nothing expires quietly.

Google Drive, email.

"You're going to be my [...] control tower slash diagnostics motherboard."William Brauer, CEO

Form: Dashboard & reminders. A morning brief plus a compliance view. It reads the structured data the other 8 areas create.

Will's stated target is to close 2026 checking this first thing in the morning.

• 50+ SOPs written in 4 months, with no way to measure whether they're followed outside the field.
• Eduardo audits field SOPs & safety manually. Nobody audits the admin side at all.
• Problems get found reactively, through conversation, rather than surfaced.

Problems get surfaced daily to leadership instead of discovered.

Jobber, HubSpot, CallRail, Google Calendar (APIs). SiteDocs to verify.