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Side-by-side financial comparison of IRONWOOD PHARMACEUTICALS INC (IRWD) 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 $47.7M, roughly 1.0× IRONWOOD PHARMACEUTICALS INC). On growth, Upland Software, Inc. posted the faster year-over-year revenue change (-27.5% vs -47.3%). IRONWOOD PHARMACEUTICALS INC produced more free cash flow last quarter ($74.6M vs $7.2M). Over the past eight quarters, Upland Software, Inc.'s revenue compounded faster (-16.5% CAGR vs -20.2%).

Ironwood Pharmaceuticals, Inc. is a publicly traded pharmaceutical company. It was originally called Microbia, Inc.

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.

IRWD vs UPLD — Head-to-Head

Bigger by revenue
UPLD
UPLD
1.0× larger
UPLD
$49.3M
$47.7M
IRWD
Growing faster (revenue YoY)
UPLD
UPLD
+19.8% gap
UPLD
-27.5%
-47.3%
IRWD
More free cash flow
IRWD
IRWD
$67.3M more FCF
IRWD
$74.6M
$7.2M
UPLD
Faster 2-yr revenue CAGR
UPLD
UPLD
Annualised
UPLD
-16.5%
-20.2%
IRWD

Income Statement — Q4 FY2025 vs Q4 FY2025

Metric
IRWD
IRWD
UPLD
UPLD
Revenue
$47.7M
$49.3M
Net Profit
$-2.3M
Gross Margin
76.5%
Operating Margin
14.3%
14.5%
Net Margin
-4.8%
Revenue YoY
-47.3%
-27.5%
Net Profit YoY
-200.9%
EPS (diluted)
$0.01
$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
IRWD
IRWD
UPLD
UPLD
Q4 25
$47.7M
$49.3M
Q3 25
$122.1M
$50.5M
Q2 25
$85.2M
$53.4M
Q1 25
$41.1M
$63.7M
Q4 24
$90.5M
$68.0M
Q3 24
$91.6M
$66.7M
Q2 24
$94.4M
$69.3M
Q1 24
$74.9M
$70.7M
Net Profit
IRWD
IRWD
UPLD
UPLD
Q4 25
$-2.3M
Q3 25
$40.1M
$-1.1M
Q2 25
$23.6M
$-13.0M
Q1 25
$-37.4M
$-25.8M
Q4 24
$2.3M
Q3 24
$3.6M
$-1.7M
Q2 24
$-860.0K
$-11.4M
Q1 24
$-4.2M
$-96.1M
Gross Margin
IRWD
IRWD
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
IRWD
IRWD
UPLD
UPLD
Q4 25
14.3%
14.5%
Q3 25
61.8%
10.6%
Q2 25
53.2%
-13.2%
Q1 25
-70.7%
-1.7%
Q4 24
34.8%
-2.9%
Q3 24
28.0%
-5.0%
Q2 24
26.5%
-7.7%
Q1 24
14.7%
-129.6%
Net Margin
IRWD
IRWD
UPLD
UPLD
Q4 25
-4.8%
Q3 25
32.8%
-2.2%
Q2 25
27.7%
-24.4%
Q1 25
-90.9%
-40.6%
Q4 24
2.5%
Q3 24
4.0%
-2.6%
Q2 24
-0.9%
-16.5%
Q1 24
-5.6%
-135.9%
EPS (diluted)
IRWD
IRWD
UPLD
UPLD
Q4 25
$0.01
$0.01
Q3 25
$0.23
$-0.09
Q2 25
$0.14
$-0.51
Q1 25
$-0.23
$-0.97
Q4 24
$0.03
$-0.30
Q3 24
$0.02
$-0.12
Q2 24
$-0.01
$-0.47
Q1 24
$-0.03
$-3.37

Balance Sheet & Financial Strength

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

Metric
IRWD
IRWD
UPLD
UPLD
Cash + ST InvestmentsLiquidity on hand
$215.5M
$29.4M
Total DebtLower is stronger
$232.4M
Stockholders' EquityBook value
$-261.8M
$-48.4M
Total Assets
$396.9M
$413.2M
Debt / EquityLower = less leverage

8-quarter trend — quarters aligned by calendar period.

Cash + ST Investments
IRWD
IRWD
UPLD
UPLD
Q4 25
$215.5M
$29.4M
Q3 25
$140.4M
$22.8M
Q2 25
$92.9M
$41.0M
Q1 25
$108.5M
$33.7M
Q4 24
$88.6M
$56.4M
Q3 24
$88.2M
$59.7M
Q2 24
$105.5M
$232.4M
Q1 24
$121.5M
$231.6M
Total Debt
IRWD
IRWD
UPLD
UPLD
Q4 25
$232.4M
Q3 25
$199.5M
Q2 25
$199.3M
Q1 25
$199.2M
Q4 24
$199.0M
$290.2M
Q3 24
$198.8M
Q2 24
$198.6M
Q1 24
$398.3M
Stockholders' Equity
IRWD
IRWD
UPLD
UPLD
Q4 25
$-261.8M
$-48.4M
Q3 25
$-264.2M
$-47.3M
Q2 25
$-308.2M
$-42.4M
Q1 25
$-334.1M
$-37.8M
Q4 24
$-301.3M
$-18.3M
Q3 24
$-311.3M
$907.0K
Q2 24
$-321.7M
$6.5M
Q1 24
$-330.5M
$20.1M
Total Assets
IRWD
IRWD
UPLD
UPLD
Q4 25
$396.9M
$413.2M
Q3 25
$396.1M
$409.1M
Q2 25
$342.9M
$441.7M
Q1 25
$327.2M
$457.0M
Q4 24
$350.9M
$529.5M
Q3 24
$389.5M
$554.9M
Q2 24
$395.6M
$739.9M
Q1 24
$438.8M
$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
IRWD
IRWD
UPLD
UPLD
Operating Cash FlowLast quarter
$74.6M
$7.3M
Free Cash FlowOCF − Capex
$74.6M
$7.2M
FCF MarginFCF / Revenue
156.3%
14.7%
Capex IntensityCapex / Revenue
0.0%
0.2%
Cash ConversionOCF / Net Profit
TTM Free Cash FlowTrailing 4 quarters
$127.0M
$24.4M

8-quarter trend — quarters aligned by calendar period.

Operating Cash Flow
IRWD
IRWD
UPLD
UPLD
Q4 25
$74.6M
$7.3M
Q3 25
$47.6M
$6.9M
Q2 25
$-15.1M
$3.3M
Q1 25
$20.0M
$8.3M
Q4 24
$15.2M
$9.3M
Q3 24
$9.9M
$4.3M
Q2 24
$33.5M
$5.5M
Q1 24
$45.0M
$5.1M
Free Cash Flow
IRWD
IRWD
UPLD
UPLD
Q4 25
$74.6M
$7.2M
Q3 25
$47.6M
$6.7M
Q2 25
$-15.1M
$2.7M
Q1 25
$19.9M
$7.9M
Q4 24
$9.0M
Q3 24
$9.9M
$4.2M
Q2 24
$33.4M
$5.2M
Q1 24
$44.9M
$4.9M
FCF Margin
IRWD
IRWD
UPLD
UPLD
Q4 25
156.3%
14.7%
Q3 25
39.0%
13.2%
Q2 25
-17.7%
5.0%
Q1 25
48.4%
12.4%
Q4 24
13.3%
Q3 24
10.8%
6.3%
Q2 24
35.4%
7.5%
Q1 24
60.0%
7.0%
Capex Intensity
IRWD
IRWD
UPLD
UPLD
Q4 25
0.0%
0.2%
Q3 25
0.0%
0.4%
Q2 25
0.0%
1.2%
Q1 25
0.1%
0.7%
Q4 24
0.0%
0.5%
Q3 24
0.0%
0.2%
Q2 24
0.1%
0.4%
Q1 24
0.1%
0.3%
Cash Conversion
IRWD
IRWD
UPLD
UPLD
Q4 25
Q3 25
1.19×
Q2 25
-0.64×
Q1 25
Q4 24
6.74×
Q3 24
2.71×
Q2 24
Q1 24

Financial Flow Comparison

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

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