90%+
customers retained
while a 20+ year business changed ownership and modernized its operations
For growing service and production businesses
Build a business that runs without everything living in your head.
Pinstripe combines monthly bookkeeping, hands-on operations support, and practical automation for businesses doing $100K–$1M+. You get one accountable partner and one secure client workspace.
Financial Operations
Clean books and reporting you can use
Business Systems
Clear workflows, SOPs, and accountability
Practical Automation
Less copying, chasing, and rework
Included with every engagement
Your Pinstripe workspace
Request help
Keep every service request organized
Share documents
Upload business files securely
Schedule consultations
See upcoming work and meetings
Follow progress
Stay aligned without email chains
Request work, exchange files, schedule time, and keep service updates in one place.
No more
tax-return extensions
after a growing multi-revenue business cleaned up and stabilized its books
~5 hours
saved each week
after a field-service team streamlined proof of work and payment follow-up
A clear fit
Built for businesses with real work already moving.
Pinstripe is for established service and production businesses that have outgrown doing everything through the owner, inboxes, and memory.
See who we helpThe owner is still the handoff point for too many decisions
The books exist, but the numbers are late or hard to trust
Your team repeats administrative work that should move automatically
Growth is exposing gaps in roles, workflows, and accountability
How we help
One operating partner. Two core systems.
Financial operations show you what is happening. Business systems make the work easier to run. We connect the two so improvements hold up in the real business.
Financial Operations
Know what the numbers are telling you
We keep the books current, reconcile the details, and turn financial reporting into something you can actually use to make decisions.
- Monthly bookkeeping
- Reconciliation and reporting
- QuickBooks Online support
- Tax-ready financial records
Business Systems
Make the work easier to repeat and delegate
We identify owner bottlenecks, document the way work should move, and automate the handoffs that consume time or create errors.
- Operations consulting
- Process design and SOPs
- Workflow automation
- Tool and data integration
Secondary capability
Digital Builds
When the operating problem needs software, we also design conversion-focused websites and publish iPhone and iPad apps. The technology supports the system; it is not the strategy by itself.
How an engagement works
Understand first. Build second. Stay accountable.
01
Find the constraint
We review the records, workflows, and handoffs behind the problem before prescribing another tool.
02
Build the working system
We clean up the process, document ownership, and implement the bookkeeping or automation needed to support it.
03
Keep the work aligned
Requests, documents, consultations, and updates stay together in the Pinstripe client workspace.
Product proof
We build the systems we recommend.
Pinstripe Fleet is one example: a field-operations product we built to schedule work, capture photo proof, and let customers approve and pay from one link. It exists because the service businesses we work with needed a better operating system.
Operator-led, in practice
Advice shaped by running real businesses.
Founder Joe Angerosa built financial processes, production workflows, and automation inside operating companies before bringing that work to Pinstripe clients. The goal is not a thicker strategy deck. It is a system the team can use on Monday.
Frequently asked questions
A practical first step
Fix the part of the business that keeps pulling you back in.
Start with the smallest useful engagement. If another system needs attention later, the same team already understands how your business works.
30-minute fit call
We identify the part of the business creating the most drag.
A clear scope
You see the starting point, deliverables, price, and responsibilities before work begins.
One shared workspace
Requests, documents, consultations, and updates stay together as the work moves.