Pineapples is the technology partner mid-market PE operating partners, CFOs, and CEOs call when the stakes are real — pre-acquisition assessments, post-merger integration, and fractional CTO engagements that translate technology decisions into business outcomes.
The 7-section checklist we run for PE operating partners and mid-market acquirers — the findings that translate directly into the deal model, the integration plan, and the value-creation roadmap.
Latest insights
Pre-acquisition diligence, post-merger integration, fractional-CTO playbooks — written for the operating partners, CFOs, and CEOs who own the decision.
Most M&A technology diligence focuses on the stack. The deals that fail focus on everything except whether the technology team can execute the integration plan. Here's the assessment framework that separates successful acquisitions from expensive regrets.
Read articleA practical guide to digital transformation consulting for mid-market companies — how to modernize operations, reduce costs, and scale without enterprise-level budgets.
Read articleMost post-merger technology integrations blow past timeline and budget. Here is what non-technical executives need to know before they greenlight a platform consolidation plan.
Read articleEngagements
Fixed-fee diligence on the front end. Predictable monthly retainer for ongoing CTO leverage. Sprint-priced builds when the work is real software. Pause or cancel any month.
Pre-acquisition · 10-day fixed fee
The 7-section assessment we run for PE operating partners and mid-market acquirers. Findings translate directly into the deal model — leadership execution, knowledge concentration, integration surface area, and the deal-thesis alignment most diligence skips.
Owner-led. No hand-off tax.
What's included
Ongoing · Monthly retainer
Owner-led technology leadership for mid-market companies and PE portfolio companies between full-time CTO hires. Same operator, predictable monthly cadence, no rotating contractors.
Owner-led. No hand-off tax.
What's included
Custom builds · Sprint-priced
When the work is real software — modernization, integration, or net-new product. Bi-weekly sprints, AI-native development, the same operators on-tools start to finish.
Owner-led. No hand-off tax.
What's included
Selected work
Pineapples ships work that holds up under board review, integration deadlines, and acquirer scrutiny. A few examples below — full case studies on request.
Telecom · Streaming
Unified $3M React Native investment into one codebase serving web, iOS, and Android
AT&T had $3M committed to a React Native mobile app and a separate 50-person web team maintaining a parallel codebase. We migrated to Expo + react-native-web, retired the duplicate web stack, and delivered one platform across all surfaces — without a rewrite.
2 → 1
Codebases consolidated
~50 FTE
Engineering org reduction
3 months
Timeline
Private Equity · Tech Diligence
Pre-acquisition technology assessment that reset the deal model on a $45M SaaS target
Diligence surfaced an undocumented payment-reconciliation module owned by a single engineer who had given notice, plus a framework two majors behind that wedged the integration plan. Findings translated into a $2.3M remediation line item the deal model originally missed.
10 days
Diligence window
$2.3M
Risk surfaced before close
+9 months
Integration timeline correction
Consumer · Family services
Built and shipped the platform that ZNest used to grow into a national footprint
Owner-led engineering partnership across the platform lifecycle. Same team that built v1 still ships features today — no rebuilds, no rotating contractors, no hand-off tax.
Multi-year
Engagement length
React Native + Web
Stack
Direct
Founder feedback
Why Pineapples
We are not a staffing firm. The same operator who runs your diligence reads your board report every month. Our work has to hold up — under acquirer scrutiny, integration deadlines, and the next quarter's value-creation plan.
Anthony reads your status report. No project-manager intermediary, no offshored discovery, no rotating account team between kickoff and outcome.
AI-native development gets the work done faster. The judgment about whether the work is the right work — that's still on us.
Our deliverables read in board meetings. We translate technology decisions into the business language CFOs, COOs, and operating partners already use.
Pause or cancel any month. We earn the next month by delivering this one. Most clients stay multi-year because they want to, not because they have to.
Testimonials
Don't just take our word for it. Here's what our clients have to say about working with us.
"Pineapple helped us bring Dormie Workshop to more golf lovers and grow the business."
"Pineapple has been a great help in allowing me to bring ZNest to more people and help more families."
"Pineapple helped us bring Poker Power to more women and drive greater industry change."
4.9/5 average rating from 200+ clients
30 minutes is enough to know whether we can help. If we are not the right partner, we'll tell you and point you at the right one.
Tech Strategy Assessment
Running a tech business is challenging. Validate your tech strategy with the same approach we use to help clients drive millions in revenue.
5 Minutes
Strategy Validation
Revenue Growth
Total time investment: 5 minutes
