Free Technology Roadmap Review

Every organization hits a ceiling. Let's find yours.

A 45-minute review with prpl pineapple, plus a written summary in 3 business days. You'll leave knowing what's holding the roof down and the first crack in it.

250+ organizations advisedNo sales pitchYour summary to keep

“Not just as a vendor, but as a true partner invested in our success.”

Whitney Dove, PhD · CEO, Ellipsis Education
Step 1 of 2

Which ceiling are you hitting?

Pick one. Not sure is a fine answer.

Free · No sales pitch · Summary in 3 business days · NDA on request

Which ceiling are you hitting?

Different ceilings. Same cause.

Growth exposes what leadership never had time to build. The review starts with the ceiling you feel.

Revenue ceiling · Businesses

The same number, year after year.

No matter how hard the team works.

We look at
Where growth stalls: handoffs, tools no one owns, decisions made on gut feel.
This is us
Mission ceiling · Nonprofits + churches

Held hostage by your own limits.

Nonprofits and churches whose systems should work as hard as their teams do.

We look at
What's holding the mission back: systems, staff capacity, donor and member data.
This is us
Exit ceiling · Sale or succession

You can't sell or step back.

Because everything still runs through you.

We look at
What a buyer, a board or your C-suite will uncover: undocumented processes, messy data, key-person risk. How we prepare owners for an exit.
This is us

Not sure? Pick "Not sure." Naming it is part of the review.

What we look at

We look underneath the ceiling.

PeopleWho owns what, who decides, and who's carrying too much.
StrategyWhere you're going in 12, 24 and 36 months, and whether the plan gets you there.
SystemsThe tools you pay for, the ones you use, and the gap between them.
DataWhether you can see what's happening, and whether you trust what you see.
How it works

Five steps. No surprises.

  1. RequestTwo minutes. Tell us about your organization and the ceiling you feel.
  2. PrepWe review your Technology Readiness Check (if you took it), website and public information, so we arrive with a point of view.
  3. The call45 minutes on video. Where you want to go, what's in the way, and what we see.
  4. Your summaryWithin 3 business days: your ceiling, named, and three moves for the next 90 days.
  5. Follow-upA 15-minute check-in a week later. What is inspected is respected.
Request my free review
What you walk away with

A summary you can act on, even if you never hire us.

One to two pages. Your ceiling, named. A red, yellow or green read on people, strategy, systems and data. Three moves for the next 90 days. Our recommendation for a 12-, 24- or 36-month roadmap and what it would cost.

Technology Roadmap Review: Sample Org

Your ceiling

Revenue: growth stalls at handoffs between sales and service.

What's holding the roof down
PeopleRed
StrategyYellow
SystemsYellow
DataGreen
Three moves for the next 90 days

1. Name an owner for the CRM. 2. Retire two unused tools. 3. Put three numbers on a monthly dashboard.

Recommendation: Advanced, 24-month roadmap.

Jay Cordova, Co-Owner of prpl pineapple
Who you'll meet

You'll talk to the people who do the work.

I started around 10 years old, helping my dad with the technical side of his newspaper outside Chicago. Since then I've built and architected hundreds of systems, and I've watched dozens of them die after delivery because no one owned them. That's why the review starts with people, not software.

I've also been the buyer, sitting in someone else's data, deciding what it was worth. So when I tell you what's holding you back, it's because I've looked. Kaylin and I lead prpl pineapple together, with a team that stays until yours owns it.

Jay Cordova · Co-Owner, prpl pineapple

Good fit, not a fit

We'll be honest with you.

Good fit if you
  • Have hit a ceiling and want to know why
  • Can bring the person who makes the final call
  • Want a plan your team can actually follow
  • Want decisions made on data, not gut feel
Not a fit if you
  • Want someone to pick software for you and leave
  • Want a report to file away, not a plan to run
  • Aren't ready to name an owner for the work
  • Need emergency IT support today (start with a rescue plan)
Proof

Leaders who broke through.

“When we faced the challenge of operating within legacy systems that no one on our current team fully understood, prpl stepped in.”

Whitney Dove, PhD · CEO, Ellipsis Education

“prpl’s approach goes beyond just technical execution—they bring a creative and strategic mindset.”

Mike Kelly · Managing Partner, DeveloperTown

“Partnering with prpl pineapple has been the best decision.”

Haeli Smith · Public Relations Lead, Valley Professionals Community Health Center
After the review

Every roadmap comes with a dashboard and a tracker your team will actually use.

Every plan is a fixed price that includes your first year. After that, Keep-Live is month to month. The free review confirms which plan fits, or whether you need one at all.

Starter12-month plan

Find your direction.

$6,000

Fixed price, Year 1 included

For organizations that can name the ceiling and need a clear first step.

RevenueFind the one fix that gets growth moving.
MissionStop the systems that drain staff and volunteers.
ExitSee what a buyer or successor would see first.
  • 5-editor tracker
  • Quarterly check-ins
  • One-page summary for your leadership or board
  • Monthly dashboard, 3–4 key measures
  • 12-month roadmap with owners

Keep-Live $100/mo from month 13, with a yearly check-in

Full 12-month plan: $6,000 total

Delivered in 3–4 weeks

Start with a free review
Recommended
Advanced24-month plan

Fix what's underneath.

$12,000

Fixed price, Year 1 included

For organizations that keep hitting the same ceiling, year after year.

RevenueFix the handoffs, tools and data that keep the number flat.
MissionFree your team to serve instead of managing tools.
ExitClean up processes and data before anyone looks.
  • 15-editor tracker
  • Quarterly reviews, all 24 months
  • Deck for your board, investors or leadership team
  • Weekly dashboard, 3–5 sources
  • 24-month roadmap + architecture

Keep-Live $400/mo from month 13, with quarterly reviews

Full 24-month plan: $16,800 total

Delivered in 6–8 weeks

Start with a free review
Complete36-month plan

Run it like it's built to last.

$24,000

Fixed price, Year 1 included

For organizations planning the next three years, whatever the next season holds.

RevenueA three-year plan your leaders can run and measure.
MissionA three-year plan your board and budget can stand behind.
ExitAn organization that runs without you, ready to sell or hand off.
  • 50+ editor tracker
  • Quarterly reviews, all 36 months
  • Risk readout for your board, buyers or successor
  • Daily dashboard, 6–9 sources
  • 36-month roadmap + budget plan

Keep-Live $1,000/mo from month 13, with quarterly reviews and a yearly budget and roadmap refresh

Full 36-month plan: $48,000 total

Delivered in 10–12 weeks

Start with a free review
Keep it liveYear 1 is included. From month 13, Keep-Live keeps your dashboard, tracker and data connections running, plus the reviews listed for your plan. Cancel anytime. Your roadmap stays yours.
Move up a tierChoose the next tier and what you paid counts toward the upgrade.
Have us lead itWant someone to lead the work? Our fractional CTO, CIO and CDO leadership picks up where the roadmap ends, and your roadmap fee counts toward it.

Fixed scope. Fixed price. No surprises. Not sure which fits? Start with the free review →

Questions

Before you request.

Is it really free?

Yes. The call and the written summary cost nothing.

Is it a sales call?

No. We don't pitch on the call. If you want help, we talk about it after you've read your summary.

Who should attend?

The person who makes the final decision (owner, executive director or senior pastor), plus your operations or IT lead if you have one.

We already have an IT provider. Is this still for us?

Yes. We look at direction and ownership, not who answers the help desk.

What should I prepare?

Nothing required. The Technology Readiness Check helps us arrive with more, and an existing roadmap or tool list is welcome.

What is Keep-Live?

It keeps the dashboard, tracker and data connections we build for you running, updated and supported, plus the reviews in your plan. Year one is included in every plan. From month 13 it’s $100 a month on Starter (with a yearly check-in), $400 on Advanced (with quarterly reviews) or $1,000 on Complete (with quarterly reviews and a yearly budget and roadmap refresh). Cancel anytime. Your roadmap stays yours.

Will you sign an NDA?

Yes, before the call if you ask.

Free Technology Roadmap Review

Ready to find your ceiling?

When you work with us, you get what you pay for, and we do what we said we would do.

Request my free review 
Technology Roadmap Review: Sample Org
Prepared for the Executive Director · prpl pineapple

YOUR CEILING
Mission: the team spends its week keeping systems alive instead of serving people.

WHAT'S HOLDING THE ROOF DOWN
People     Red      No one owns the donor database; one staff member holds every login.
Strategy   Yellow   A plan exists, but it lives in one person's head.
Systems    Yellow   Four tools do the work of one; two are paid for and unused.
Data       Green    Giving data is clean; program data is not yet tracked.

THE FIRST CRACK
Name an owner for the donor database and move every login to one shared vault.

THREE MOVES FOR THE NEXT 90 DAYS (with or without us)
1. Assign a database owner, by end of month.
2. Cancel the two unused tools, by next quarter.
3. Put three numbers leadership will watch on a monthly dashboard.

OUR RECOMMENDATION
Starter, a 12-month roadmap. Delivered in 3–4 weeks.

What is inspected is respected. We'll check in a week from today.

Request my free review →
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