[Form 4] Kingsway Financial Services, Inc. Insider Trading Activity

Rhea-AI Filing Summary

PROS Holdings (NYSE: PRO) Q2 2025 Form 10-Q highlights

• Top-line growth: Total revenue rose 8% YoY to $88.7 million, driven by a 12% jump in subscription revenue to $73.3 million. Recurring revenue (subscription + maintenance) represented 86% of total sales.
• Margin expansion: Overall gross margin improved two points to 67%. Subscription gross margin reached 79% (up 1 ppt) due to cloud-infrastructure efficiency.
• Profitability trend: Net loss narrowed to $1.8 million (-$0.04 basic EPS) from $7.4 million (-$0.16). Operating loss was roughly flat at $7.6 million.
• Cash & liquidity: Cash and equivalents increased to $179.0 million from $162.0 million at year-end; operating cash flow turned positive at $4.4 million (vs. $1.8 million).
• Debt actions: Exchanged $186.9 million of 2.25% 2027 notes for new 2.5% 2030 notes and sold an additional $50 million of 2030 notes; recorded a $4.2 million extinguishment gain and purchased capped calls that effectively raise the conversion price to $30.34 per share.
• Balance sheet: Total assets $443.0 million; total liabilities $527.9 million; stockholders’ deficit widened to $84.9 million mainly from share-based compensation and capped-call premium.
• Retention & mix: Gross revenue retention remained above 93%; U.S. accounted for 36% of revenue, Europe 30%, Rest-of-World 34%.

Management cites continued macro uncertainty but notes improving subscription mix, higher gross margins and stronger cash generation as key progress toward profitability.

Positive

• Subscription revenue up 12% YoY, reinforcing shift to high-margin recurring model.
• Net loss reduced by 76% YoY and operating cash flow turned positive to $4.4 million.
• Debt maturity extended to 2030 with a $4.2 million gain on extinguishment, lessening near-term refinancing pressure.
• Gross margin expanded to 67% on cloud-delivery efficiencies.

Negative

• Company remains in stockholders’ deficit of $84.9 million.
• Share-based compensation high at $12 million (14% of revenue), diluting shareholders.
• Convertible issuance adds $50 million principal and slightly higher coupon (2.5%), increasing leverage.
• Still operating loss of $7.6 million; profitability not yet achieved.

Insights

Equity Research Analyst

TL;DR: Solid revenue growth, narrower loss, positive OCF; dilution risk from new converts offset by capped call.

Quarter shows PROS transitioning toward a SaaS-heavy model—subscription revenue +12% YoY now 83% of mix, supporting 79% segment margin. Net loss shrank by $5.6 million and operating cash turned positive, indicating operating leverage despite high SBC ($12 million this quarter). Debt exchange lengthens maturity profile to 2030 and removes >$185 million of 2027 paper; coupon rises 25 bps but capped call lifts effective conversion to $30.34, tempering dilution. However, shareholders’ deficit deepened and total liabilities exceed assets, so path to sustained GAAP profitability remains critical.

Credit Analyst

TL;DR: Refinancing enhances tenor, liquidity strong; leverage still high, equity deficit persists.

Liquidity headroom is comfortable: $179 million cash plus $50 million undrawn revolver versus $39 million lease liabilities through 2030. Exchange into 2.5% 2030 notes pushes weighted-average maturity to ~5 years, lowering near-term refinancing risk. Net debt/annualized revenue approximates 0.8×, acceptable for a recurring-revenue software issuer. Yet equity deficit of $85 million and ongoing operating losses constrain credit quality. Positive operating cash flow must sustain to cover ~ $6 million annual coupon and sizeable purchase commitments ($96 million through 2029). Overall impact rated modestly positive.

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

OMB APPROVAL

OMB Number:			3235-0287
Estimated average burden
hours per response:			0.5

Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Hansen Kent A

(Last) (First) (Middle)

10 S. RIVERSIDE PLAZA

SUITE 1520

(Street)

CHICAGO IL 60606

(City) (State) (Zip)

2. Issuer Name and Ticker or Trading Symbol
KINGSWAY FINANCIAL SERVICES INC [ KFS ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

	Director		10% Owner
X	Officer (give title below)		Other (specify below)
	CFO & EVP

3. Date of Earliest Transaction (Month/Day/Year)
07/30/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

X	Form filed by One Reporting Person
	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
			Code	V	Amount	(A) or (D)	Price
Common Stock	07/30/2025		P		108(1)	A	$14.42	135,464(2)	D

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
				Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares

Explanation of Responses:

1. The shares of Common Stock were acquired pursuant to the Kingsway America Inc. Employee Share Purchase Plan, as amended and restated effective May 29, 2014 (the "ESPP"). Pursuant to the ESPP, eligible employees may contribute an amount up to 5% of adjusted salary for each regular payroll period and, to the extent such employee has been employed by Kingsway America Inc. and its subsidiaries for 12 months, the company will make a matching contribution equal to 100% of such employee's contribution. The employee contributions and company contributions are used to purchase, as soon as administratively practicable after the date of such contributions, shares of Kingsway Financial Services Inc. The shares are acquired by the administrator of the ESPP on the open market through the services of a duly registered stockbroker.

2. Includes 8,370 shares of restricted stock granted on December 15, 2022, 14,204 shares of restricted stock granted on March 26, 2024, and 20,728 shares of restricted stock granted on December 4, 2024.

	/s/ Debra Rouse, attorney-in-fact for Kent A. Hansen	07/31/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
Note: File three copies of this Form, one of which must be manually signed. If space is insufficient, see Instruction 6 for procedure.
Persons who respond to the collection of information contained in this form are not required to respond unless the form displays a currently valid OMB Number.

FAQ

How much revenue did PROS Holdings (PRO) generate in Q2 2025?

$88.7 million, an 8% year-over-year increase.

What was PROS’ Q2 2025 EPS?

Basic EPS was -$0.04, improving from -$0.16 in Q2 2024.

How did the convertible debt exchange affect the balance sheet?

PROS swapped $186.9 million of 2027 notes for new 2030 notes and issued another $50 million, booking a $4.2 million gain and extending maturities.

What is PROS Holdings’ cash position after the quarter?

Cash and equivalents stood at $179.0 million with an additional $10 million in restricted cash.

What are the current gross and subscription margins?

Total gross margin is 67%; subscription gross margin reached 79%.

Did PROS generate positive operating cash flow?

Yes, $4.4 million in operating cash flow for the first six months of 2025.