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Side-by-side financial comparison of Orange County Bancorp, Inc. (OBT) and Upland Software, Inc. (UPLD). Click either name above to swap in a different company.

Upland Software, Inc. is the larger business by last-quarter revenue ($49.3M vs $33.0M, roughly 1.5× Orange County Bancorp, Inc.). On growth, Orange County Bancorp, Inc. posted the faster year-over-year revenue change (20.6% vs -27.5%). Orange County Bancorp, Inc. produced more free cash flow last quarter ($41.3M vs $7.2M). Over the past eight quarters, Orange County Bancorp, Inc.'s revenue compounded faster (14.3% CAGR vs -16.5%).

Orange County Bancorp, Inc. is a Delaware-registered bank holding company operating mainly in New York, U.S. It offers a full range of retail and commercial banking services, including deposit accounts, loans and wealth management solutions, serving individual consumers, small and mid-sized corporate clients in its regional footprint.

Upland Software, Inc. is a global provider of cloud-based enterprise work management solutions. It offers products covering project portfolio management, customer engagement, IT service management, and financial automation, serving businesses of all sizes across North America, Europe, and Asia-Pacific in tech, healthcare, and professional services sectors.

OBT vs UPLD — Head-to-Head

Bigger by revenue
UPLD
UPLD
1.5× larger
UPLD
$49.3M
$33.0M
OBT
Growing faster (revenue YoY)
OBT
OBT
+48.1% gap
OBT
20.6%
-27.5%
UPLD
More free cash flow
OBT
OBT
$34.1M more FCF
OBT
$41.3M
$7.2M
UPLD
Faster 2-yr revenue CAGR
OBT
OBT
Annualised
OBT
14.3%
-16.5%
UPLD

Income Statement — Q4 FY2025 vs Q4 FY2025

Metric
OBT
OBT
UPLD
UPLD
Revenue
$33.0M
$49.3M
Net Profit
$12.4M
Gross Margin
76.5%
Operating Margin
41.4%
14.5%
Net Margin
37.6%
Revenue YoY
20.6%
-27.5%
Net Profit YoY
73.5%
EPS (diluted)
$0.94
$0.01

Green = leading value per metric. Periods may differ when fiscal calendars don't align.

8-Quarter Revenue & Profit Trend

Side-by-side quarterly history. Quarters aligned by calendar period so offset fiscal years line up.

Revenue
OBT
OBT
UPLD
UPLD
Q4 25
$33.0M
$49.3M
Q3 25
$33.7M
$50.5M
Q2 25
$32.5M
$53.4M
Q1 25
$28.0M
$63.7M
Q4 24
$27.4M
$68.0M
Q3 24
$27.1M
$66.7M
Q2 24
$27.9M
$69.3M
Q1 24
$25.3M
$70.7M
Net Profit
OBT
OBT
UPLD
UPLD
Q4 25
$12.4M
Q3 25
$10.0M
$-1.1M
Q2 25
$10.5M
$-13.0M
Q1 25
$8.7M
$-25.8M
Q4 24
$7.2M
Q3 24
$3.2M
$-1.7M
Q2 24
$8.2M
$-11.4M
Q1 24
$9.3M
$-96.1M
Gross Margin
OBT
OBT
UPLD
UPLD
Q4 25
76.5%
Q3 25
76.9%
Q2 25
74.8%
Q1 25
71.6%
Q4 24
70.8%
Q3 24
70.5%
Q2 24
70.5%
Q1 24
70.2%
Operating Margin
OBT
OBT
UPLD
UPLD
Q4 25
41.4%
14.5%
Q3 25
38.6%
10.6%
Q2 25
41.9%
-13.2%
Q1 25
40.3%
-1.7%
Q4 24
32.8%
-2.9%
Q3 24
14.8%
-5.0%
Q2 24
36.6%
-7.7%
Q1 24
45.9%
-129.6%
Net Margin
OBT
OBT
UPLD
UPLD
Q4 25
37.6%
Q3 25
29.7%
-2.2%
Q2 25
32.2%
-24.4%
Q1 25
31.1%
-40.6%
Q4 24
26.2%
Q3 24
11.8%
-2.6%
Q2 24
29.4%
-16.5%
Q1 24
36.7%
-135.9%
EPS (diluted)
OBT
OBT
UPLD
UPLD
Q4 25
$0.94
$0.01
Q3 25
$0.75
$-0.09
Q2 25
$0.87
$-0.51
Q1 25
$0.77
$-0.97
Q4 24
$0.64
$-0.30
Q3 24
$0.28
$-0.12
Q2 24
$0.73
$-0.47
Q1 24
$0.82
$-3.37

Balance Sheet & Financial Strength

Snapshot of each company's liquidity, leverage and book value from the latest quarter.

Metric
OBT
OBT
UPLD
UPLD
Cash + ST InvestmentsLiquidity on hand
$29.4M
Total DebtLower is stronger
$232.4M
Stockholders' EquityBook value
$284.4M
$-48.4M
Total Assets
$2.7B
$413.2M
Debt / EquityLower = less leverage

8-quarter trend — quarters aligned by calendar period.

Cash + ST Investments
OBT
OBT
UPLD
UPLD
Q4 25
$29.4M
Q3 25
$22.8M
Q2 25
$41.0M
Q1 25
$33.7M
Q4 24
$56.4M
Q3 24
$59.7M
Q2 24
$232.4M
Q1 24
$231.6M
Total Debt
OBT
OBT
UPLD
UPLD
Q4 25
$232.4M
Q3 25
Q2 25
Q1 25
Q4 24
$290.2M
Q3 24
Q2 24
Q1 24
Stockholders' Equity
OBT
OBT
UPLD
UPLD
Q4 25
$284.4M
$-48.4M
Q3 25
$270.1M
$-47.3M
Q2 25
$252.6M
$-42.4M
Q1 25
$201.3M
$-37.8M
Q4 24
$185.5M
$-18.3M
Q3 24
$193.1M
$907.0K
Q2 24
$177.5M
$6.5M
Q1 24
$168.7M
$20.1M
Total Assets
OBT
OBT
UPLD
UPLD
Q4 25
$2.7B
$413.2M
Q3 25
$2.6B
$409.1M
Q2 25
$2.6B
$441.7M
Q1 25
$2.6B
$457.0M
Q4 24
$2.5B
$529.5M
Q3 24
$2.5B
$554.9M
Q2 24
$2.5B
$739.9M
Q1 24
$2.5B
$754.9M

Cash Flow & Capital Efficiency

How much cash each business actually produces after reinvestment. Cash flow is harder to manipulate than net income.

Metric
OBT
OBT
UPLD
UPLD
Operating Cash FlowLast quarter
$43.8M
$7.3M
Free Cash FlowOCF − Capex
$41.3M
$7.2M
FCF MarginFCF / Revenue
125.1%
14.7%
Capex IntensityCapex / Revenue
7.6%
0.2%
Cash ConversionOCF / Net Profit
3.53×
TTM Free Cash FlowTrailing 4 quarters
$69.6M
$24.4M

8-quarter trend — quarters aligned by calendar period.

Operating Cash Flow
OBT
OBT
UPLD
UPLD
Q4 25
$43.8M
$7.3M
Q3 25
$30.2M
$6.9M
Q2 25
$-5.0M
$3.3M
Q1 25
$4.8M
$8.3M
Q4 24
$34.6M
$9.3M
Q3 24
$10.2M
$4.3M
Q2 24
$9.3M
$5.5M
Q1 24
$2.3M
$5.1M
Free Cash Flow
OBT
OBT
UPLD
UPLD
Q4 25
$41.3M
$7.2M
Q3 25
$29.6M
$6.7M
Q2 25
$-5.7M
$2.7M
Q1 25
$4.3M
$7.9M
Q4 24
$32.9M
$9.0M
Q3 24
$10.0M
$4.2M
Q2 24
$9.2M
$5.2M
Q1 24
$2.0M
$4.9M
FCF Margin
OBT
OBT
UPLD
UPLD
Q4 25
125.1%
14.7%
Q3 25
87.8%
13.2%
Q2 25
-17.5%
5.0%
Q1 25
15.5%
12.4%
Q4 24
120.0%
13.3%
Q3 24
36.7%
6.3%
Q2 24
32.8%
7.5%
Q1 24
7.9%
7.0%
Capex Intensity
OBT
OBT
UPLD
UPLD
Q4 25
7.6%
0.2%
Q3 25
1.8%
0.4%
Q2 25
2.3%
1.2%
Q1 25
1.8%
0.7%
Q4 24
6.3%
0.5%
Q3 24
1.1%
0.2%
Q2 24
0.4%
0.4%
Q1 24
1.0%
0.3%
Cash Conversion
OBT
OBT
UPLD
UPLD
Q4 25
3.53×
Q3 25
3.01×
Q2 25
-0.47×
Q1 25
0.56×
Q4 24
4.83×
Q3 24
3.19×
Q2 24
1.13×
Q1 24
0.24×

Financial Flow Comparison

Revenue → gross profit → operating profit → net profit for each company.

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