Built for the industry by people who lived it

Every tasting staffed, recapped and invoiced. In one place.

Stiletto is the operating system for sampling and experiential agencies. Bring events in from a spreadsheet or let your supplier and distributor reps request them in their own portals. Then staff, recap, pay and bill from one record, with a 360° view of all of it.

Now onboarding a small group of agencies.
youragency.stilettosoftware.com/admin/events
Operations
October events
Market: All+ New event
Events this month
214
+18 vs. September
Shifts staffed
96%
9 open · 3 this weekend
Recaps to review
12
Oldest: 2 days
Ready to invoice
$48.9k
31 approved recaps
Date
Event
Venue
Brand ambassador
Status
Oct 10
Harbor Ridge Bourbon · tasting
Bayside Wine & Spirits
MLMaria L.
Staffed
Oct 10
Coastline Rosé · in-store demo
Greenway Market #14
?Unassigned
Needs staff
Oct 9
Northfield Gin · bar activation
The Copper Room
DPDev P.
Recap in
Oct 8
Harbor Ridge Bourbon · tasting
Liquor Barn Annapolis
KSKira S.
Approved
Oct 8
Alta Vista Malbec · tasting
Total Cellars
JRJon R.
Approved
Oct 7
Northfield Gin · tasting
Shore Spirits
MLMaria L.
Approved

Illustrative product view.

Why Stiletto exists

It started with one agency owner, a spreadsheet and a lot of all-nighters.

In 2009 she opened her agency with Excel, OneNote and Google. Every venue address was looked up by hand. Every shift was keyed in three times to make sure it was staffed. Ambassadors faxed in their recap forms, and she tallied the sales herself.

At 50 events a month that worked. Past 100, it meant all-nighters to get payroll out on time. So we built her a better way, and kept building.

  1. 2009

    One owner, three tools

    Excel, OneNote, Google and a fax machine. Paperwork filed and batched for every event.

  2. 100+ events a month

    The all-nighters start

    Manual tallies and triple-keyed staffing turn every payroll into a deadline she has to stay up for.

  3. The first Stiletto

    Five buttons in FileMaker

    Built to give her nights back. It saved countless hours of processing, and its billing packages routinely won new business.

  4. The mobile app

    Reporting moves to the field

    Ambassadors file their own recaps from their phones, so the reporting work lands with the people who ran the event.

  5. Today

    Stiletto, rebuilt for every agency

    Everything that worked, rebuilt on a modern platform so other agency owners never have to go through it.

Every way in, one place to see it

Your data comes in from everywhere. You see all of it.

Every entry lands on the same event record, so the owner gets a full 360° view across clients, markets and reps without re-typing a thing.

Spreadsheet import

Events, venues and ambassadors from Excel or CSV.

Supplier rep portal

Brand teams request events and pull their own reports.

Distributor rep portal

Distributor reps request events for their accounts.

Your team

Build, staff and approve in a guided workflow.

Ambassador app

Recaps, sales and photos filed from the venue.

The platform

Everything between the booking and the bank.

Built inside a working agency and hardened on real shifts, recaps and payrolls before anyone else could buy it.

Staffing that fills itself

Offer shifts to nearby ambassadors, confirm by text and email, and see coverage gaps before the weekend.

Staffing · SMS · Calendar

Contracts per shift

Every ambassador signs for every shift on their phone. Reschedule it and a re-sign goes out automatically.

E-signature · Audit

Recaps you can trust

Photo minimums enforced at submit, admin approval gates and a field-level audit trail on every correction.

Recaps · Photos · Audit

Payroll, proofed

Base pay, incentives, cancellations and mileage at IRS rates, with exceptions flagged before anyone is paid.

Payroll · Mileage

Invoices clients don't question

A six-step wizard builds the invoice plus a PDF package with each event's recap and photos.

Billing · PDF packages

Reports that write themselves

Year-over-year comparisons, supplier goals and AI-written client summaries from the recap data you already have.

Dashboards · AI reports
Early access

Get your nights back.

We're onboarding a small group of agencies before the public launch. Tell us about yours and we'll set up a walkthrough.

  • A walkthrough with the people who built it
  • Your own branded workspace
  • Help importing your venues, ambassadors and events
Request early access →
Or email us at hello@stilettosoftware.com