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Case studiesTrilogy
TrilogySoftware M&A / SaaS Roll-up2025

A portfolio operator dashboard for an AI-first software roll-up

Trilogy runs an acquisition machine — buy mature B2B software, plug in Crossover talent, run it AI-first. We built the operator dashboard that gives leadership a single view across the portfolio — ARR, churn, AI-ops score, velocity — with drill-down to individual products in two clicks.

Portfolios in one view
60+
Time to weekly read
45 min → 4 min
Federated sources
12
Operator adoption
94%
Trilogy/ Portfolio Operator
Week of Mar 17, 2026·Auto-refresh: 4:00 AM ESTOpen weekly review →

Portfolio ARR

$2.42B

64 brands

NRR (median)

108%

+2pp QoQ

AI-ops score

74

↑ from 68

Crossover talent

4,820

globally placed

Brands at risk

3

down from 7

Brands

AllOutperformWatchSort: ARR ↓
BrandARRNRRAI-ops scoreHCStatus · QoQ
AAurea
$310M112%
86
420
Outperform+8%
IIgnite Tech
$54M117%
91
88
Outperform+12%
GGFI Software
$98M104%
72
160
On track+2%
JJive
$74M101%
68
140
On track+1%
VVersata
$76M96%
54
210
Watch-3%
CCrossover (svc)
$48M92%
88
520
Watch-1%
TTrilogy Health
$31M84%
42
94
At risk-9%
KKayako
$22M103%
64
48
On track+4%

Selected · drill in

GFI Software

SMB security & networking · acquired 2017

ARR

$98M

+2%

NRR

104%

+1pp

AI-ops

72

+6

ARR · 12 months

$98M

AI-ops breakdown

72 / 100
Code review · automated84
good
Support · AI deflection76
good
Sales · AI-drafted outbound68
gap
Recruiting · Crossover ops60
gap

✦ Recommended actions

  • Backfill 4 Crossover SE seats from open req pool
  • Enable AI outbound assist on US-East accounts
  • Investigate p95 latency spike (sec gateway · last 48h)

The brief

Trilogy operates dozens of acquired software businesses simultaneously. Each one had its own metrics dashboard, its own internal vocabulary, its own definition of "active customer." Leadership reviews happened from sixty parallel status decks, none of which were comparable across brands.

The bet: a federated dashboard with one definition of every metric, sourcing from each brand's existing data warehouse, would replace the deck culture and let leadership operate on the portfolio as a single unit.

What we built

A federated data layer that pulls from each portfolio company's existing warehouse (mostly Snowflake, occasionally BigQuery or Postgres) on a nightly cadence, normalizes against a portfolio-wide schema, and stores the result in a single mart with row-level access control for operator-specific views.

On top of that, an operator dashboard that surfaces ARR, NRR, churn, support-load and an "AI-ops score" — Trilogy's internal measure of how deeply each brand has integrated AI into its operations — for the entire portfolio in one view. Drill-down to a single brand in two clicks; drill-down to a specific customer cohort inside that brand in two more.

The unglamorous part: a 47-page metric dictionary that defines exactly what every term means, signed off by each operating partner. The dashboard is the surface; the dictionary is what makes the numbers trustworthy.

Outcome

Time to produce the weekly portfolio read dropped from 45 minutes to 4 — and the read is now done once, by leadership, in front of the dashboard, instead of compiled across sixty parallel decks. 94% of brand operators log in weekly without prompting. The federated layer pulls from 12 different source systems without those teams having to change their pipelines.

The deck culture has, mercifully, died.

"Before this we had sixty status decks. Now we have one dashboard and the decks are gone."