Meet Operations Ollie
Your New Favorite Employee
Ollie is your 24/7 AI assistant for client communication, scheduling, reviews, follow-up, payment, forms, contracts and more.
Ollie is the BEST employee you’ve ever had. No time off, sick days, raises, benefits, taxes, payroll, interviews, resumes or performance reviews.
Ollie(s) learn on their own, but also take your feedback seriously. They work 365/24/7 and you can "hire" as many Ollies as you want for the price of one.
Automation, efficiency, and tech you can trust—
built by humans who actually get business.
Whether you run a health practice, style hair, repair appliances, show homes or build pools — you are the expert at what you do.
We're here to make sure your business runs as smoothly as your craft and ensure The Satisfaction Trifecta...
Clients/Patients <-> Business Owners <-> Ollie
At Upside Guide, we optimize the entire customer journey — from the first call to final payment.
The Back End of Your Horse 🐎
The real business horsepower lives in the systems you don’t see.
Your Business
Ollie’s AI-Powered Move
📞 Missed a Call?
💬 FAQs on Repeat?
📅 Tired of Manual Scheduling?
⭐ More Reviews?
💰 Get Paid?
📑 Paperwork Chaos?
👩💻 All Messages, One Inbox
🧠 Learns & Improves
🛠️ Custom Workflows
🛠️ "Ollie" Not Right for Your Biz?
→ Ollie sends an instant text follow-up so no lead is lost.
→ Ollie answers your most common customer questions 24/7.
→ Ollie books & confirms appointments — no back & forth.
→ Ollie politely follows up to collect glowing testimonials.
→ Ollie sends invoices, payment links and automates follow-ups.
→ Organized Ollie delivers contracts, forms, waivers automatically
→ FB, WhatsApp, live chat, email, text — Ollie keeps it all in one view.
→ Train Ollie & tweak as you go. He never forgets & doesn’t call in sick.
→ Ollie handles your unique flow: spa, home repair, salon, dental ++.
→ No problem! How about Roofer Rex, Doc Holly Day, Accountant Ava or...?
Hear Ollie in Action
Click to Listen to Ollie Chatting
👑 Beauty in the Front. Brains in the Back.
Where others glamorize the hustle, we honor the horsepower.
We’re not here to dabble—we’re here to build better businesses from the inside out.
When your systems run with power, everything else follows.
At Upside Guide, we don’t just smile for the parade—we drive it.
🎸 Ollie’s Jam: The Rhythm That Joins It All Together
Your business already knows the tune. Ollie just lays down a steady beat—quietly keeping everything in sync, so your days run smoother & your nights stay yours.
Immediate Text to Missed Calls
Answers Calls - LiveChat
Online WebChat
Books Appointments
Call recordings & transcripts
Automated Review Requests
Automated Review Replies
Central Inbox - Text, Email, FB Mssgr, What's App +. One app for all.
Invoice/Payment/Billing
Forms, Contracts
Ollie adapts to YOUR Business - he learns FAST and is easily edited/improved
Contact Management/CRM - emails, text, coupons, birthday messages ++
Before AI, there was instinct.
From Fortune 500s to first-time founders,
Melissa’s ops expertise left a mark.
Don’t take our word for it—take theirs.
“We grew lightning fast, and left systems & processes on the back burner a bit too long. Melissa is the rare kind of strategist who speaks process and people fluently. Our tangled workflows became streamlined systems, our market valuation skyrocketed and thanks, in part, to her hard work, we got to ring the NASDAQ opening bell."
—General Manager
Vital Stream
"She tackles operational messes like a freight train—but always with empathy and style. Sales, Ops, Tech & Clients all trust her instantly, and it’s easy to see why.”
—Product Manager
Armstrong World Industries
"Working with Melissa was a masterclass in clarity and execution. She made complex plans feel achievable, and her commitment was off the charts."
—Business Plan Client
Melissa didn’t just teach Excel—she elevated our entire workflow. She’s tech-savvy, patient, and always ten steps ahead.”
—Manager, Condé Nast
Basic
$ 29/m
Top features
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Advanced
$ 49/m
most popular
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Professional
$ 99/m
Top features
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About Upside Guide
🐎 ‘The Hindquarters Advantage’
“If I were a Halloween costume, I’d be the back end of the horse.
Not flashy—but it’s what drives the force, balance and direction. That’s operations.”
—Melissa, Founder, Back-End Badass at Upside Guide
At Upside Guide, we believe operational excellence is the real sexy. With over 30 years of experience and a deep love for systems, workflows, and back-end brilliance, we help businesses run smarter—so every front-end effort propels you further.
We make every dollar—on leads, ads, tools and time—work harder and smarter by ensuring your operations hum with precision.
Led by founder Melissa, a lifelong operations strategist and unapologetic back-end-of-the-horse thinker, Upside Guide blends old-school excellence with next-gen AI automation.
We’re not a marketing agency dabbling in tech. We’re operational experts who know: no ad campaign can outrun a broken process or poor customer experience. We don’t start with noise—we start with structure. Then, we amplify.
When your operations run like a dream, the upside takes care of itself.
Choose Your Operations Ollie
Basic
$4.99
/month
1 exclusive episode per month
Access to subscribers stream
Exclusive monthly Q&A
Access to Facebook community
Pro
$9.99
/month
All of Silver benefits +
Free access to annual events
Access to guides & resources
Exclusive stickers and merch
Premium
$39.99
/month
All of Gold benefits +
Become an official sponsor
Exclusive badge on community
Early access to all episodes
Contact
Free up your time & money while increasing sales & creating happy clients!
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Spam FREE Zone - We Hate it More Than You Do:)
Ollie & Your Clients
Immediate Text Back to Missed Calls
Website Live Chat
Books Appointments
Call recordings & transcripts
Auto Review Requests
Auto Review Responses
Ollie & You
Central Inbox - Text, Email, FB Mssgr, What's App ++ (one app for all)
Invoice, Payment, Billing, Forms, Contracts
Customize Ollie to YOUR Business
Upside Guide
30+ years Ops, Business & Efficiency
25+ yrs technology
Expertise in multiple industries (Hospitals & Docs to Wood Flooring & everything in between)
P&L, Finance, Operations, Systems, Consulting ++
Let Ollie "WOW" You Today!!
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