MSTR vs. SAIL: Strategy vs. SailPoint Stock Comparison

November 11, 2026

How do Strategy (MSTR) and SailPoint (SAIL) stack up? This page sets them side by side across company profile, performance and risk, profitability, growth, financial strength, dividends, and valuation, with selected fundamentals also measured against each stock's industry-group peers.

Company Profile

Strategy (MSTR) and SailPoint (SAIL) are both classified in the Application Software sub-industry within the broader Software industry, placing them in the closest GICS peer bucket.

Strategy (MSTR) carries decades of public-market history since June 11, 1998, while SailPoint (SAIL) listed on February 13, 2025 — long-window comparisons have far more historical data on the MSTR side.

Company profile comparison for Strategy (MSTR) and SailPoint (SAIL)
Profile Item	MSTR	SAIL
Name	Strategy Inc.	SailPoint, Inc.
Country/Region	United States	United States
GICS Sector	Information Technology	Information Technology
GICS Industry Group	Software & Services	Software & Services
GICS Industry	Software	Software
GICS Sub-Industry	Application Software	Application Software
Market Capitalization	54.57 billion USD	10.97 billion USD
Currency	USD	USD
Exchange	Nasdaq	Nasdaq
Listing Date	June 11, 1998	February 13, 2025
Security Type	Common Stock	Common Stock

Price Performance

Cumulative Growth

MSTR

SAIL

GSPC

Strategy (MSTR) vs. SailPoint (SAIL), with S&P 500 (GSPC) for reference: Growth of a $10,000 investment over the past five years. Adjusted for dividends and splits.

Trailing Returns

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Trailing total returns for Strategy (MSTR) and SailPoint (SAIL). Returns over one year are annualized.

Calendar-Year Returns

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Calendar-year total returns for Strategy (MSTR) and SailPoint (SAIL). Each bar is that year's total return, measured year-end to year-end.

Performance Metrics

Price performance metrics for Strategy (MSTR) and SailPoint (SAIL)
Metric	MSTR	SAIL
Total Return (1Y)	-48.13%	0.45%
Total Return (3Y, Annualized)	36.44%	--
Total Return (5Y, Annualized)	7.87%	--

Risk Profile

Drawdown History

MSTR

SAIL

GSPC

Strategy (MSTR) vs. SailPoint (SAIL), with S&P 500 (GSPC) for reference: Drawdown from the running peak over the past five years. Each line shows the decline from its prior peak; 0% marks a new high.

Return Distribution

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Distribution of monthly total returns for Strategy (MSTR) and SailPoint (SAIL). Each bar is the share of months whose return fell in that 5% bucket.

Risk Metrics

Risk profile metrics for Strategy (MSTR) and SailPoint (SAIL)
Metric	MSTR	SAIL
Volatility (1Y, Annualized)	82.34%	65.26%
Beta (5Y)	3.60	2.06
Max Drawdown (5Y)	-84.09%	-59.18%
Avg. Volume (3M)	22.35M	4.36M

Risk-Adjusted Performance

Risk-Return Positioning

MSTR and SAIL are plotted by 1-year volatility (risk) and 1-year return. The dashed Capital Allocation Line runs from the risk-free rate through the shared industry median.

Risk-Adjusted Metrics

Risk-adjusted metrics for Strategy (MSTR) and SailPoint (SAIL)
Metric	MSTR	SAIL
Sharpe Ratio (1Y)	-0.64	-0.06
Sortino Ratio (1Y)	-0.97	-0.08

Profitability

ROE (TTM)

Both Strategy (MSTR) at -21.59% and SailPoint (SAIL) at -2.88% report negative ROE values. Negative ROE can reflect losses or negative shareholders’ equity, so both readings need extra context.

MSTR

Software & Services industry group

-21.59%

Max: 53.85%
Q3: 17.90%
Median: 6.59%
Q1: -9.59%
MSTR: -21.59%
Min: -50.52%

SAIL

Software & Services industry group

-2.88%

Max: 53.85%
Q3: 17.90%
Median: 6.59%
SAIL: -2.88%
Q1: -9.59%
Min: -50.52%

Strategy (MSTR) vs. SailPoint (SAIL): A comparison of their ROE against the Software & Services industry group benchmark.

Net Margin (TTM)

SailPoint (SAIL) reports a negative net margin of -16.92%, usually indicating a net loss over the period. Meanwhile Strategy (MSTR) reports 0.00%, ranking against industry peers normally.

MSTR

Software & Services industry group

0.00%

Max: 41.17%
Q3: 15.28%
Median: 4.63%
MSTR: 0.00%
Q1: -5.42%
Min: -33.17%

SAIL

Software & Services industry group

-16.92%

Max: 41.17%
Q3: 15.28%
Median: 4.63%
Q1: -5.42%
SAIL: -16.92%
Min: -33.17%

Strategy (MSTR) vs. SailPoint (SAIL): A comparison of their net margin against the Software & Services industry group benchmark.

Operating Margin (TTM)

Both Strategy (MSTR) at -2.07% and SailPoint (SAIL) at -18.85% report negative operating margin values, usually indicating operating losses over the period.

MSTR

Software & Services industry group

-2.07%

Max: 46.89%
Q3: 17.64%
Median: 8.73%
MSTR: -2.07%
Q1: -2.13%
Min: -30.45%

SAIL

Software & Services industry group

-18.85%

Max: 46.89%
Q3: 17.64%
Median: 8.73%
Q1: -2.13%
SAIL: -18.85%
Min: -30.45%

Strategy (MSTR) vs. SailPoint (SAIL): A comparison of their operating margin against the Software & Services industry group benchmark.

Profitability Metrics

Profitability metrics for Strategy (MSTR) and SailPoint (SAIL)
Metric	MSTR	SAIL
ROE (TTM)	-21.59%	-2.88%
ROA (TTM)	-4.52%	-1.83%
Net Margin (TTM)	0.00%	-16.92%
Operating Margin (TTM)	-2.07%	-18.85%
Gross Margin (TTM)	67.84%	66.27%

Growth

Revenue Growth

SailPoint (SAIL) at 24.35% is around its peer norm for revenue growth, while Strategy (MSTR) at 2.97% drops into the bottom quartile, signaling weaker demand or pricing momentum.

Strategy (MSTR) vs. SailPoint (SAIL): A comparison of their Revenue Growth across different time periods.

EPS Growth

Neither Strategy (MSTR) nor SailPoint (SAIL) reports a EPS growth value for this period, so a direct comparison isn't possible.

Growth Metrics

Growth metrics for Strategy (MSTR) and SailPoint (SAIL)
Metric	MSTR	SAIL
Revenue Growth (YoY)	2.97%	24.35%
Revenue Growth (3Y CAGR)	-1.49%	--
EPS Growth (YoY)	--	--
EPS Growth (3Y CAGR)	--	--

Financial Strength

Current Ratio (MRQ)

SailPoint (SAIL) at 1.23 keeps current ratio within its industry’s typical mid-range, while Strategy (MSTR) at 4.04 sits above its industry’s typical mid-range — comfortable liquidity, though possibly with more idle current assets relative to peers.

MSTR

Software & Services industry group

4.04

Max: 5.11
MSTR: 4.04
Q3: 2.77
Median: 1.67
Q1: 1.01
Min: 0.03

SAIL

Software & Services industry group

1.23

Max: 5.11
Q3: 2.77
Median: 1.67
SAIL: 1.23
Q1: 1.01
Min: 0.03

Strategy (MSTR) vs. SailPoint (SAIL): A comparison of their current ratio against the Software & Services industry group benchmark.

Debt / Equity (MRQ)

SailPoint (SAIL) at 0.00 keeps leverage in the lower industry quartile, while Strategy (MSTR) at 0.10 runs a more typical debt-to-equity mix.

MSTR

Software & Services industry group

0.10

Max: 2.52
Q3: 1.13
Median: 0.40
MSTR: 0.10
Q1: 0.07
Min: 0.00

SAIL

Software & Services industry group

0.00

Max: 2.52
Q3: 1.13
Median: 0.40
Q1: 0.07
SAIL: 0.00
Min: 0.00

Strategy (MSTR) vs. SailPoint (SAIL): A comparison of their debt-to-equity ratio against the Software & Services industry group benchmark.

Financial Strength Metrics

Financial strength metrics for Strategy (MSTR) and SailPoint (SAIL)
Metric	MSTR	SAIL
Current Ratio (MRQ)	4.04	1.23
Debt / Equity (MRQ)	0.10	0.00
Net Debt / EBITDA	--	--

Dividends

Dividend Yield (TTM)

Neither Strategy (MSTR) nor SailPoint (SAIL) pays a dividend this period — they may reinvest, use buybacks, or simply not return cash through dividends.

MSTR

Software & Services industry group

0.00%

MSTR: 0.00%
Max: 0.00%
Q3: 0.00%
Median: 0.00%
Q1: 0.00%
Min: 0.00%

SAIL

Software & Services industry group

0.00%

SAIL: 0.00%
Max: 0.00%
Q3: 0.00%
Median: 0.00%
Q1: 0.00%
Min: 0.00%

Strategy (MSTR) vs. SailPoint (SAIL): A comparison of their dividend yield against the Software & Services industry group benchmark.

Dividend Payout Ratio (TTM)

Neither Strategy (MSTR) nor SailPoint (SAIL) pays a dividend this period — they may reinvest, use buybacks, or simply not return cash through dividends.

MSTR

Software & Services industry group

0.00%

MSTR: 0.00%
Max: 0.00%
Q3: 0.00%
Median: 0.00%
Q1: 0.00%
Min: 0.00%

SAIL

Software & Services industry group

0.00%

SAIL: 0.00%
Max: 0.00%
Q3: 0.00%
Median: 0.00%
Q1: 0.00%
Min: 0.00%

Strategy (MSTR) vs. SailPoint (SAIL): A comparison of their payout ratio against the Software & Services industry group benchmark.

Dividend Metrics

Dividend metrics for Strategy (MSTR) and SailPoint (SAIL)
Metric	MSTR	SAIL
Dividend Yield (TTM)	0.00%	0.00%
Dividend Payout Ratio (TTM)	0.00%	0.00%

Valuation

P/E Ratio (TTM)

Neither Strategy (MSTR) nor SailPoint (SAIL) reports a P/E ratio value for this period, so a direct comparison isn’t possible.

MSTR

Software & Services industry group

Max: 112.94
Q3: 60.32
Median: 32.91
Q1: 18.77
Min: 6.69
MSTR: --

SAIL

Software & Services industry group

Max: 112.94
Q3: 60.32
Median: 32.91
Q1: 18.77
Min: 6.69
SAIL: --

Strategy (MSTR) vs. SailPoint (SAIL): Neither stock reports P/E ratio, so the chart shows available benchmark boxes without value markers.

P/S Ratio (TTM)

Both look expensive on sales: SailPoint (SAIL) at 9.41 sits in the upper P/S ratio quartile, and Strategy (MSTR) at 110.23 prices even higher, above its industry range.

MSTR

Software & Services industry group

110.23

MSTR: 110.23
Max: 17.91
Q3: 8.78
Median: 4.25
Q1: 2.23
Min: 0.02

SAIL

Software & Services industry group

9.41

Max: 17.91
SAIL: 9.41
Q3: 8.78
Median: 4.25
Q1: 2.23
Min: 0.02

Strategy (MSTR) vs. SailPoint (SAIL): A comparison of their P/S ratio against the Software & Services industry group benchmark.

P/B Ratio (MRQ)

Relative to net asset value, both Strategy (MSTR) at 0.98 and SailPoint (SAIL) at 1.60 look inexpensive, sitting in the lower P/B ratio quartile of their industries.

MSTR

Software & Services industry group

0.98

Max: 16.63
Q3: 8.50
Median: 4.30
Q1: 1.92
MSTR: 0.98
Min: -3.90

SAIL

Software & Services industry group

1.60

Max: 16.63
Q3: 8.50
Median: 4.30
Q1: 1.92
SAIL: 1.60
Min: -3.90

Strategy (MSTR) vs. SailPoint (SAIL): A comparison of their P/B ratio against the Software & Services industry group benchmark.

Valuation Metrics

Valuation metrics for Strategy (MSTR) and SailPoint (SAIL)
Metric	MSTR	SAIL
P/E Ratio (TTM)	--	--
P/S Ratio (TTM)	110.23	9.41
P/B Ratio (MRQ)	0.98	1.60
Free Cash Flow Yield (TTM)	-5.94%	3.09%