Upside Guide
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.
The BEST employee you've ever had—no time off, sick days, raises or benefits.
Ollie(s) learn on their own and consistently integrate your feedback. They work 365/24/7 and you can "hire" as many Ollies as you want for the price of one.
24/7 Available
Self-Learning AI
Instant Setup
Hi, I'm Ollie!
Ready to transform your business operations and give you more time to focus on what you do best.
Automation, Efficiency and Tech you can Trust
Built by humans who actually get business.
We optimize the entire customer journey from first call to final payment.
Missed call? Auto text customer immediately
One inbox for all platforms: email, SMS, chat forms
FAQs Answered
Follow-ups & reminders handled 24/7
Personalized messages with your brand voice
No missed messages, ever
AI-powered appointment booking
Calendar sync across platforms
Custom availability rules per service or team
Built-in buffers, confirmations & and reminders
Automated review requests
Smart routing to Google, Yelp ++
Negative feedback filters and alerts
Showcase top reviews on your site
Forms, contracts, e-signatures
Automated invoices, secure payment links
No-code customization for every vertical
Ollie adapts to your tone, preferences & workflows
Feedback loops refines responses & behavior
Your personality - Ollie, Lawyer Lou, Roofer Rex, Doc Holly Day ++
No coding - plug & play
The horsepower behind your business: automation, clarity, scale
Seamless backend systems that feel human
Built to grow with you
One Ollie, infinite possibilities
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.
The BEST employee you've ever had—no time off, sick days, raises, or benefits needed.
Ollie(s) learn on their own and consistently integrate your feedback. They work 365/24/7 and you can "hire" as many Ollies as you want for the price of one.
About Upside Guide
We're not just another tech company - we’re here to build better businesses from the inside out.
We understand the real challenges business owners face, because we've been there.
At Upside Guide, we don’t smile & wave for the parade—we drive it.
Whether you run a health practice, style hair, repair appliances, show homes or build pools — you are the expert at what you do.
We optimize the entire customer journey ensuring satisfaction for:
Clients/Patients ↔ Business Owners ↔ Ollie.
We handle all the business operations so you can focus on your craft and what you love doing most.
Our AI is built by business people who actually get business, ensuring practical solutions that work in the real world.
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.
Led by founder Melissa, a lifelong operations strategist and unapologetic back-end-of-the-horse thinker, we blend old-school excellence with next-gen AI automation to make every dollar—from leads and ads to tools and time—work harder and smarter.
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.
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
Choose Your Operations Ollie
PRO
$ 797 month
or
$7970 year
Mid-tier plan for growing law firms.
Lite Plan ++
Review Bot
Payment Bot
Scheduling Integration
Branded Onboarding
SMS + Automation Workflows Included
ELITE
$ 997 month
or
$9970 year
Premium automation suite for established law firms.
Pro Plan ++
CRM sync
Webhook Triggers
Custom Persona Logic (Injury Ian, Justice Judy)
Contact Upside Guide & Ollie
Name
xx
Phone Number
Business URL
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 ++
Your AI-Driven Operations Partner
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6586 W Atlantic Ave, Unit #2195, Delray Beach, FL 33446 | 561.782.1050 | info (at) upsideguide.com