On-demand expert support for your online business systems
delivered via Voxer, without the Zoom calls, the waiting, or the tech overwhelm.
Unlimited Voxer Access · Unlimited reviews
Let's be honest -
You Shouldn't Have to Google Your Way Through Your Own Business.
"I know I need to fix this, but I don't know where to start."
"Every time I try to figure it out, I fall down a YouTube rabbit hole."
"I've posted in the Facebook group. I got AI answers that were not helpful."
"I just need someone to tell me the answer — fast."
"I've sent a support ticket and I'm still waiting."
Here's the thing: your business issues don't wait for your next strategy call.
They show up at 9pm when you're trying to launch.
They pop up mid-campaign when everything matters most.
They come up when you're out of office and NEED something solved.
And while we are being honest, AI isn't helping...
Ask Jess puts an expert in your pocket —
so when something breaks, confuses you, or just needs a second opinion, you're never on your own
What is Ask Jess
Part support. Part strategy. All systems.
Ask Jess is a voice and text based support program for online business owners who are done Googling, done waiting, and done figuring out their tech alone. You get direct access to a certified systems expert — via Voxer. You didn't get into this to figure out the tech behind the scenes.
It's not just answering questions. It's building the kind of clarity and confidence in your systems that actually moves your business forward.
What you get...
Unlimited Private Voxer Access
Direct line to me — for you and up to 2 team members. Ask anything, any time. Responses within 24 hours on business days (usually way faster). No more waiting on hold or searching forums.
Unlimited System Reviews
Funnels, automations, email sequences, landing pages — send them over whenever you need fresh eyes. No caps, no "you've used your review for this month." Unlimited means unlimited.
Personalized Loom Walkthroughs
Sometimes a voice note isn't enough. When you need a visual, I'll record a step-by-step Loom just for you — showing you exactly what to do and where to click.
Up to 2 Team Members Included
Bring your VA, OBM, or tech person into the Voxer channel at no extra cost. Additional team members can be added for a small fee.
Discounts on All Pineapple Relations Services
Need something built while you're in the program? Active Ask Jess members get a 20% discount on done-for-you services and VIP Days.
Your choices...
Every plan includes the same full access
More commitment just means a better monthly rate
MONTHLY
$396/Month
Unlimited Voxer access
Unlimited system reviews
Personalized Loom videos
Troubleshooting support
Discounts on Done For You services from Pineapple Relations
YEARLY
$330/Month
$3960 total - two months free!
Unlimited Voxer access
Unlimited system reviews
Personalized Loom videos
Troubleshooting support
Discounts on Done For You services from Pineapple Relations
Is this the right fit?
THIS IS FOR YOU IF:
You're actively running an online business
You have systems in place but need support optimizing them
You want fast answers without scheduling a call
You're tired of Googling and getting lost
The last time you asked AI you went down a 2 day rabbit hole
You want an expert who actually knows your business
You're ready to stop winging your tech
THIS IS NOT FOR YOU IF
You haven't started building your systems yet
You want someone to do the work for you
You're not willing to implement feedback
You need a full-time tech team member
You're looking for a one-time fix only
You'll be up and running in no time.
Sign up
Pick monthly or annual. Process and then you're good to go...
Complete the quick onboarding form
Tell me about your business, your tech stack, and what you're working on. I'll learn your world fast.
Join me on Voxer
Download the free app (takes 1 minute), and I'll set up your private channel. Your support starts immediately.
Send me anything
Questions, reviews, glitches, second opinions, anything that's blocking you. I'll respond within 24 hours on business days, usually faster.
Watch your systems actually work
No more chaosWatch your systems actually work
No more chaos. No more guessing. Just clear, working systems, and the confidence that someone's in your corner.
Cancel Anytime
Ready to go out on your own? I'm doing backflips of joy for you - just let me know and I'll cancel your access effective your next billing date.
I've got you!
Real results from business owners, just like you...
"She is very responsive and is always willing to make a video to show you how — which has been very helpful for me as a hands-on learner!"
"She is very responsive and is always willing to make a video to show you how — which has been very helpful for me as a hands-on learner!"
Jessica with Pineapple Relations has been the missing link I've been looking for to streamline my email marketing. 12/10 recommend.
OH HI! I'm Jess
I didn't start in tech. I started in restaurants, where I learned how to make people feel calm, understood, and taken care of. Turns out that translates perfectly to helping business owners navigate systems that feel overwhelming.
I'm a Funnel Gorgeous Certified Master Marketer, Double Systeme.io Certified, Kartra Certified Business Consultant & Technical Expert. But more importantly, I'm someone who built all of this from scratch without a tech background and figured it out through hundreds (okay, thousands) of hours of trial and error.
Today I work with online business owners who are smart, successful, and completely done with tech drama. I'm the person they call when something breaks, when they're not sure if their funnel is actually working, or when they just need someone who gets it — fast.
Away from the keyboard and screens, I'm a huge foodie, amateur coffee snob, wanna be pro traveler and cat mamma to Bruce, the coolest crankiest, Russian Blue around
I speak plain English, not tech gibberish. And your wins are genuinely my wins.
You might be wondering...
What is Voxer?
Voxer is an app available for mobile and desktop with Push to Talk, walkie talkie, communication. It allows us to send live voice, text and photos. It works just like text messaging.
Do I have to pay for Voxer?
Nope — Voxer is free. There's a paid version at around $50/year but you don't need it to participate in 'Ask Jess'
What does "unlimited reviews" actually mean?
Exactly what it says. Send me your landing pages, email sequences, funnel flows, automations, as many as you need, via the review form, whenever you need. No monthly caps.
How fast will you respond?
My promise is within 24 hours on business days, and honestly, usually much faster than that. You're not waiting days to get unstuck.
Can I add more team members?
Up to 2 team members are included in every plan. Additional team members can be added for a $50/per member per month. I'll invoice you separately for additional team members.
What's the cancellation policy?
Just let me know, there's no contract - when you're ready to go out on your own just send me a message and let me know, I'll cancel you effective your next billing date. You'll keep access until then. You're welcome back at anytime.
Will my pricing change?
Not as long as you're an active client. If you cancel and comeback later you'll get current pricing.
Wings are for planes, birds, and chickens.
Stop winging it when it comes to your business systems.
Pick your timeline, join Voxer, and have an expert in your pocket — starting today.
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