Pineapples is the partner mid-market PE operating partners, CFOs, and CEOs call when the stakes are real. Cracked engineers running Claude Code, OpenClaw, and the latest agentic workflows in production every day — pre-acquisition diligence, post-merger integration, and fractional CTO engagements where the answer has to hold up under acquirer scrutiny.
26yrs
Operating since 2000
200+
Engagements shipped
$25M+
Client funding raised
Fortune 50
Flagship client
Operators we've shipped with · 200+ engagements since 2000
The stack we ship on
We don't write about agentic workflows from the sidelines. We run them — context-engineered, spec-driven for production, vibe-coded for prototypes — across our marketing, our diligence work, our gov-contract pipeline, and the products we ship for clients. The tools are the practice.
Anthropic's coding agent. Drives daily PR work end-to-end.
Our internal agent runtime. Schedules, persists, runs cron-driven workflows.
Custom subagents, tools, and Model Context Protocol servers per engagement.
App Router, Cache Components, Expo. Same surface for web + mobile.
Production deploys, preview URLs per PR, AI Gateway, Queues.
Auto-merge on green. Rolling releases. Agent-authored PRs reviewed by humans.
Receipts, not pitches
Every workflow below runs on our own infrastructure — agents we've built, deployed, and kept up at 3am when something broke. We bring the same discipline to client work and government contracts.
7:00 AM daily
Marketing pipeline ships
Claude Code agents author and post the day's blog + LinkedIn content, run lead enrichment, and publish without us touching a keyboard.
68 blog posts
Authored in Q1
Topic-cluster SEO seeded by an agent against our content registry, with internal-linking enforced and OG images generated in batch.
Hourly sweep
Gov contract pipeline
SAM.gov scraper enriches every opportunity with budget rubric + PDF parsing, dedup-syncs to Sheets, surfaces fits to the team.
Multi-PR/day
Agent-authored, human-reviewed
Auto-merge on green CI is the default. Agents propose, humans gate, deploys ship through Vercel preview → production.
The same agentic stack we run for our own diligence — connected to your data rooms, portfolio dashboards, and repos via Claude custom connectors and MCP. Personalized, cited, delivered instantly.
Pineapples agent · cited
Three findings worth flagging in the deal model:
Remediation surfaced
$2.3M
Originally missed in the deal model. Translates directly to integration line items.
Claude × MCP custom connectors
Custom MCP servers we build — and maintain — so Claude reads from your real systems instead of hallucinating about them. Set up in days, not quarters.
Your data sources
Salesforce
Pipeline + portfolio company CRM
Google Drive
Data rooms, board decks, contracts
Snowflake / SQL
Portco financials + KPI marts
GitHub
Codebases under diligence
S3 / Drive buckets
Loose docs, statements, exports
Step 02
Pineapples MCP server
Owner-built tool surface. Per source, per workflow, with auth + audit baked in.
Step 03
Claude (your workspace)
One-click connect from Claude desktop or your Anthropic team workspace.
01
Salesforce, Drive, Snowflake, GitHub, your data warehouse. Anything with an API or a file lives behind one MCP server.
02
We expose a small, intentional set of tools per source — `query_portco_financials`, `read_data_room`, `score_diligence_finding`. Not a thousand endpoints.
03
One click in Claude desktop or your team's Anthropic workspace. Tools appear as suggestions inside the briefing chat.
04
Operating partners ask. The agent calls tools, cites sources, and writes the answer in the language your CFO already uses.
The 7-section checklist
The same 7-section checklist Pineapples runs for PE operating partners and mid-market acquirers — structured so every finding translates directly into the deal model, the integration plan, and the value-creation roadmap.
01
Stack inventory, infra, security posture. Necessary, not sufficient — if diligence stops here you have an inventory, not a decision.
02
Has your CTO managed an integration of THIS scale? Single biggest predictor of post-close success — and the one nobody scores.
03
Map every critical system to the engineers who can touch it without breaking it. Flag anything with fewer than two.
04
Architecture diagrams show shape — they don't show how hard the connection is. APIs, identity, observability, data model alignment.
05
Not how much debt — what the debt prevents you from doing. The 3-5 items that block the integration plan, costed in weeks.
06
Every vendor in the critical path. Renewal dates in the 12 months post-close. Single-vendor dependencies without a migration plan.
07
The section diligence usually skips. Whether the architecture supports the value-creation plan — or quietly undermines it.
10-day fixed fee. $25K–$60K depending on scope. See the engagement →
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. AI-augmented repo audits, leadership execution review, knowledge-concentration mapping, 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. Same operator from kickoff through outcome — augmented by Claude Code agents that compress what used to take weeks into days.
Owner-led. No hand-off tax.
What's included
Custom delivery · Sprint-priced
When the work is real software — modernization, integration, or net-new product — built by operators who use Claude Code, OpenClaw, and the agentic stack daily. Bi-weekly sprints, AI-native development, the same team 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 and we are not AI cosplay. The same operator who runs your diligence reads your board report every month — augmented by the agentic tools we build and ship daily. 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.
Claude Code and OpenClaw compress what used to take weeks into days. Cracked engineers still own the judgment about whether the work is the right work — agents don't get to decide what ships.
Our deliverables read in board meetings. We translate technology and AI 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
Ready when you are
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 AI-augmented assessment we use to drive client outcomes.
5 Minutes
Strategy Validation
Revenue Growth
Total time investment: 5 minutes
