1003-00003 · Harrowgate Private Equity Fund IV LP · Insurance

insurance-deliverables-checklist.xlsx DOCUMENT M&A / Corporate

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[sheet: R&W Insurance Tracker]

Item #	Deliverable / Milestone	Responsible Party	Counterparty / Recipient	Target Date	Actual Date	Status	Reference / Policy Number	Notes
1	Identify R&W insurance carrier candidates and obtain broker quotes	Derek Okonkwo / Calderwood & Harkness LLP	Oakbridge Omnivrel Insurance Group	2025-02-10	2025-02-10	Completed	Oakbridge Fidelity selected as carrier; underwriter: Neil Carmichael, SVP; carrier address: 175 Water Street, Suite 2800, New York, NY 10038
2	Prepare and submit no-names R&W insurance application (preliminary submission)	Derek Okonkwo / Calderwood & Harkness LLP	Oakbridge Omnivrel Insurance Group	2025-02-18	2025-02-18	Completed	No-names submission included transaction summary, target industry description (cloud-based payments processing / fintech), and estimated deal value of $1,900,000,000
3	Prepare and submit named R&W insurance application (full submission with diligence findings)	Derek Okonkwo / Megan Chu / Calderwood & Harkness LLP	Oakbridge Omnivrel Insurance Group (Neil Carmichael)	2025-02-21	2025-02-21	Completed	Full submission included: transaction summary, draft Merger Agreement, key diligence findings across corporate, IP, regulatory/licensing, litigation, tax, and employment workstreams; identified VeloPay Systems, Inc. as target (EIN 82-3019478)
4	Receive non-binding indication (NBI) from carrier	Oakbridge Omnivrel Insurance Group	Calderwood & Harkness LLP	2025-02-28	2025-02-27	Completed	NBI received: proposed $190,000,000 policy limit (10% of $1,900,000,000 deal value); $19,000,000 retention (1% of deal value); estimated premium 2.8% of policy limit
5	Negotiate R&W policy terms — exclusions, coverage scope, retention allocation	Derek Okonkwo / Sandra Tung / Calderwood & Harkness LLP	Oakbridge Omnivrel Insurance Group (Neil Carmichael)	2025-03-07	2025-03-07	Completed	Key negotiations: retention structure — first $9,500,000 borne by Seller via indemnification under Merger Agreement, remaining $9,500,000 borne by Buyer; exclusions reviewed and narrowed; coverage aligned with Merger Agreement reps
6	Submit final draft Merger Agreement (execution-ready) to carrier for policy binding review	Derek Okonkwo / Calderwood & Harkness LLP	Oakbridge Omnivrel Insurance Group	2025-03-08	2025-03-08	Completed	Execution version of Agreement and Plan of Merger among HPE Fund IV, Harrowgate Velocity Merger Sub Inc., and VeloPay Systems, Inc.
7	R&W insurance policy bound	Oakbridge Omnivrel Insurance Group	Harrowgate Private Equity Fund IV LP	2025-03-10	2025-03-10	Completed	OFI-RW-2025-03187	Buyer-side R&W policy bound; Policy No. OFI-RW-2025-03187; policy limit $190,000,000; retention $19,000,000; premium $5,320,000 (2.8% × $190,000,000)
8	Receive executed R&W insurance binder / cover note	Oakbridge Omnivrel Insurance Group (Neil Carmichael)	Calderwood & Harkness LLP / HPE Fund IV	2025-03-12	2025-03-11	Completed	OFI-RW-2025-03187	Binder confirms policy inception contingent on closing of the merger
9	Pay R&W insurance premium	Harrowgate Private Equity Fund IV LP (Priya Deshmukh)	Oakbridge Omnivrel Insurance Group	At or prior to closing	2025-07-22	Completed	OFI-RW-2025-03187	Premium of $5,320,000 paid at closing; included in transaction expenses
10	Confirm R&W policy inception upon closing	Oakbridge Omnivrel Insurance Group	Calderwood & Harkness LLP / HPE Fund IV	2025-07-22	2025-07-22	Completed	OFI-RW-2025-03187	Policy inception date: July 22, 2025; coverage effective as of closing of reverse triangular merger
11	Prepare internal R&W Insurance Policy Summary and Coverage Memorandum	Derek Okonkwo / Calderwood & Harkness LLP	Sandra Tung / HPE Fund IV deal team	2025-03-15	2025-03-14	Completed	Memorandum covers policy limit ($190M), retention structure ($19M; split $9.5M Seller / $9.5M Buyer), exclusions, claims process, and interplay with Merger Agreement indemnification provisions (indemnification cap of $228,000,000 = 12% of deal value; escrow of $133,000,000 = 7% of deal value)
12	Verify R&W policy coverage alignment with final Merger Agreement reps and warranties	Megan Chu / Derek Okonkwo / Calderwood & Harkness LLP	N/A (internal)	2025-07-21	2025-07-21	Completed	OFI-RW-2025-03187	Confirmed policy covers all reps in execution version of Merger Agreement dated March 18, 2025; survival period for reps is 18 months (through January 22, 2027)
13	Deliver copy of bound R&W policy to Tralvendo National Bank and Prairie State Bank, N.A. (lender closing condition)	Derek Okonkwo / Calderwood & Harkness LLP	Tralvendo National Bank (Andrew Birchfield) / Prairie State Bank, N.A. (Monica Fuentes) / Maplewood & Strauss LLP (Gordon Strauss)	2025-07-21	2025-07-21	Completed	OFI-RW-2025-03187	Copy delivered as part of pre-closing deliverables; satisfies insurance-related closing condition under Credit Agreement

[sheet: D&O Tail Policy Tracker]

Item #	Deliverable / Milestone	Responsible Party	Counterparty / Recipient	Target Date	Actual Date	Status	Reference / Policy Number	Notes
1	Engage D&O insurance broker for tail policy placement	Derek Okonkwo / Calderwood & Harkness LLP	Greystone Risk Advisors LLC (Stephen Hargrave)	2025-04-01	2025-03-28	Completed	Greystone Risk Advisors LLC, 55 East 52nd Street, 23rd Floor, New York, NY 10055; broker contact: Stephen Hargrave
2	Obtain existing D&O policy details from VeloPay / Whitford Jessup & Crane LLP	Derek Okonkwo / Calderwood & Harkness LLP	VeloPay Systems, Inc. (Danielle Moreau) / Whitford Jessup & Crane LLP (Rebecca Thornton-Hayes)	2025-04-15	2025-04-10	Completed	Reviewed existing VeloPay D&O policy terms; identified coverage for Nathan Aldridge, Sonia Reyes-Watkins, Marcus Langford, Danielle Moreau, Janet Gould, Kwame Asante, Catherine Lindström, Philip Rosenthal
3	Submit D&O tail policy application to carriers via Greystone Risk Advisors	Greystone Risk Advisors LLC (Stephen Hargrave)	Continental Shield Insurance Company and other potential carriers	2025-05-01	2025-04-28	Completed	Application submitted to multiple carriers; Continental Shield Insurance Company, 400 Park Avenue, 18th Floor, New York, NY 10022, selected
4	Receive D&O tail policy quotes from carriers	Greystone Risk Advisors LLC (Stephen Hargrave)	Calderwood & Harkness LLP / HPE Fund IV	2025-05-15	2025-05-12	Completed	Continental Shield quote: 6-year tail; premium $2,150,000; coverage for all pre-closing directors and officers of VeloPay Systems, Inc.
5	Negotiate D&O tail policy terms and premium	Derek Okonkwo / Calderwood & Harkness LLP / Greystone Risk Advisors LLC	Continental Shield Insurance Company	2025-06-01	2025-05-30	Completed	Final terms: 6-year tail from closing date; premium of $2,150,000; covers acts and omissions of VeloPay directors and officers occurring prior to closing
6	Obtain HPE Fund IV approval of D&O tail premium and terms	Derek Okonkwo / Calderwood & Harkness LLP	Priya Deshmukh / Thomas Eriksen (Harrowgate Capital Management IV LLC)	2025-06-05	2025-06-03	Completed	Merger Agreement requires Buyer to cause the Surviving Corporation to maintain D&O tail coverage for at least 6 years post-closing; premium approved as part of estimated transaction expenses ($48,500,000 combined buyer + seller)
7	Bind D&O tail policy with Continental Shield Insurance Company	Greystone Risk Advisors LLC (Stephen Hargrave)	Continental Shield Insurance Company	2025-07-18	2025-07-17	Completed	CSI-DOT-2025-4821	Policy No. CSI-DOT-2025-4821; bound effective upon closing; 6-year tail period from July 22, 2025 through July 22, 2031
8	Pay D&O tail policy premium	VeloPay Systems, Inc. (Surviving Corporation) / HPE Fund IV	Continental Shield Insurance Company	2025-07-22	2025-07-22	Completed	CSI-DOT-2025-4821	Premium of $2,150,000 paid at closing; included in closing funds flow
9	Confirm D&O tail policy inception upon closing	Continental Shield Insurance Company / Greystone Risk Advisors LLC	Calderwood & Harkness LLP / HPE Fund IV	2025-07-22	2025-07-22	Completed	CSI-DOT-2025-4821	Policy effective July 22, 2025; covers pre-closing acts of VeloPay directors and officers through July 22, 2031
10	Prepare internal D&O Tail Policy Memorandum	Derek Okonkwo / Calderwood & Harkness LLP	Sandra Tung / HPE Fund IV deal team	2025-07-15	2025-07-14	Completed	Memorandum analyzes tail coverage terms, covered persons, exclusions, and Merger Agreement obligations regarding D&O indemnification
11	Deliver evidence of D&O tail policy to VeloPay directors (Aldridge, Reyes-Watkins, Gould, Asante, Lindström, Rosenthal)	Calderwood & Harkness LLP / VeloPay (Surviving Corporation)	VeloPay pre-closing directors and officers	2025-07-25	2025-07-24	Completed	CSI-DOT-2025-4821	Confirmation letters sent to all pre-closing directors and officers confirming 6-year tail coverage

[sheet: Closing Condition Compliance]

Item #	Closing Condition Description	Required By	Relevant Section	Insurance Type	Carrier	Policy Number	Condition Satisfied	Date Satisfied	Evidence Delivered To	Notes
1	Buyer-side R&W insurance policy bound and in effect as of closing	Both	Merger Agreement Art. VII; Credit Agreement §4.01	R&W	Oakbridge Omnivrel Insurance Group	OFI-RW-2025-03187	Yes	2025-07-22	Tralvendo National Bank / Prairie State Bank, N.A. / Maplewood & Strauss LLP / Whitford Jessup & Crane LLP	Policy limit: $190,000,000 (10% of $1,900,000,000 deal value); retention: $19,000,000 (1% of deal value); premium: $5,320,000 (2.8% of $190M limit); inception: July 22, 2025
2	R&W insurance premium paid in full at or prior to closing	Merger Agreement	Merger Agreement Art. VII	R&W	Oakbridge Omnivrel Insurance Group	OFI-RW-2025-03187	Yes	2025-07-22	N/A	Premium of $5,320,000 funded from closing proceeds per funds flow memorandum
3	Copy of bound R&W insurance policy delivered to administrative agents under Credit Agreement	Credit Agreement	Credit Agreement §4.01	R&W	Oakbridge Omnivrel Insurance Group	OFI-RW-2025-03187	Yes	2025-07-21	Tralvendo National Bank (Andrew Birchfield, 100 Federal Street, 30th Floor, Boston, MA 02110) / Prairie State Bank, N.A. (Monica Fuentes, 231 South LaSalle Street, Suite 4400, Chicago, IL 60604)	Delivered as part of pre-closing deliverable package on July 21, 2025
4	D&O tail insurance policy obtained for pre-closing directors and officers with minimum 6-year tail	Merger Agreement	Merger Agreement Art. VI (D&O Indemnification / Insurance covenant)	D&O Tail	Continental Shield Insurance Company	CSI-DOT-2025-4821	Yes	2025-07-22	VeloPay pre-closing directors and officers	6-year tail from closing (July 22, 2025 – July 22, 2031); premium: $2,150,000; covers Nathan Aldridge, Sonia Reyes-Watkins, Marcus Langford, Danielle Moreau, Janet Gould, Kwame Asante, Catherine Lindström, Philip Rosenthal
5	D&O tail premium paid at closing	Merger Agreement	Merger Agreement Art. VI	D&O Tail	Continental Shield Insurance Company	CSI-DOT-2025-4821	Yes	2025-07-22	N/A	Premium of $2,150,000 paid from closing proceeds
6	Evidence of D&O tail policy delivered to Stockholder Representative	Merger Agreement	Merger Agreement Art. VI	D&O Tail	Continental Shield Insurance Company	CSI-DOT-2025-4821	Yes	2025-07-24	Nathan Aldridge (Stockholder Representative)	Confirmation of tail placement provided post-closing

[sheet: Premium & Cost Summary]

Item #

Insurance Product

Carrier

Policy Number

Policy Limit / Coverage Amount

Retention / Deductible

Premium

Premium as % of Limit

Term / Tail Period

Inception Date

Expiration / End Date

Paid By

Payment Date

Included in Transaction Expenses

Notes

Buyer-Side Representations & Warranties Insurance

Oakbridge Omnivrel Insurance Group

OFI-RW-2025-03187

$190,000,000

$19,000,000

$5,320,000

2.80%

Coterminous with survival period (18 months from closing) plus extended discovery

2025-07-22

Per policy terms

Harrowgate Private Equity Fund IV LP

2025-07-22

Yes

Retention split: first $9,500,000 borne by Seller (from escrow / indemnification); balance $9,500,000 borne by Buyer. Policy limit = 10% of $1,900,000,000 aggregate merger consideration. Underwriter: Neil Carmichael, SVP.

D&O Tail Liability Insurance

Continental Shield Insurance Company

CSI-DOT-2025-4821

Per policy terms

$2,150,000

N/A

6 years from closing

2025-07-22

2031-07-22

VeloPay Systems, Inc. (Surviving Corporation)

2025-07-22

Yes

Covers pre-closing directors and officers of VeloPay. Broker: Greystone Risk Advisors LLC (Stephen Hargrave). Required under Merger Agreement Art. VI.

TOTAL INSURANCE PREMIUMS

$7,470,000

Sum of $5,320,000 (R&W) + $2,150,000 (D&O Tail); included in estimated combined transaction expenses of $48,500,000

[sheet: Key Contacts]

Role	Entity	Contact Name	Title	Address	Phone	Email	Notes
R&W Insurance Underwriter	Oakbridge Omnivrel Insurance Group	Neil Carmichael	Senior Vice President	175 Water Street, Suite 2800, New York, NY 10038	[phone]	[email]	Primary underwriting contact; Policy No. OFI-RW-2025-03187
D&O Insurance Broker	Greystone Risk Advisors LLC	Stephen Hargrave	Broker	55 East 52nd Street, 23rd Floor, New York, NY 10055	[phone]	[email]	Broker for D&O tail policy placement with Continental Shield Insurance Company
D&O Tail Insurance Carrier	Continental Shield Insurance Company	[Underwriting Contact]	[Title]	400 Park Avenue, 18th Floor, New York, NY 10022	[phone]	[email]	D&O Tail Policy No. CSI-DOT-2025-4821; 6-year tail from closing
Calderwood & Harkness — Insurance Workstream Lead	Calderwood & Harkness LLP	Derek Okonkwo	Working Associate, M&A	787 Seventh Avenue, 38th Floor, New York, NY 10019	[phone]	[email]	Maintains this checklist; Matter No. 1003-00003
Calderwood & Harkness — Responsible Partner	Calderwood & Harkness LLP	Sandra Tung	Responsible Partner, M&A	787 Seventh Avenue, 38th Floor, New York, NY 10019	[phone]	[email]	Supervises insurance workstream
HPE Fund IV — Deal Lead	Harrowgate Capital Management IV LLC	Priya Deshmukh	Managing Partner, Fund IV	300 King Street, Suite 4200, Wilmington, DE 19801	[phone]	[email]	Client approval for insurance premiums and terms
HPE Fund IV — FinTech Lead	Harrowgate Capital Management IV LLC	Thomas Eriksen	Partner, Head of FinTech	300 King Street, Suite 4200, Wilmington, DE 19801	[phone]	[email]	Involved in insurance cost approvals
VeloPay — General Counsel	VeloPay Systems, Inc.	Danielle Moreau	General Counsel	1455 Innovation Parkway, Suite 800, Austin, TX 78759	[phone]	[email]	Provided existing D&O policy details; coordinated with Whitford Jessup & Crane LLP
Target Counsel	Whitford Jessup & Crane LLP	Rebecca Thornton-Hayes	Lead Partner	600 Congress Avenue, Suite 2400, Austin, TX 78701	[phone]	[email]	Coordinated D&O policy information and Merger Agreement insurance covenants
Lender Counsel	Maplewood & Strauss LLP	Gordon Strauss	Lead Partner	One International Place, Suite 3600, Boston, MA 02110	[phone]	[email]	Received copy of R&W policy as Credit Agreement closing deliverable

[sheet: R&W Insurance Tracker]
Item # | Deliverable / Milestone | Responsible Party | Counterparty / Recipient | Target Date | Actual Date | Status | Reference / Policy Number | Notes
1 | Identify R&W insurance carrier candidates and obtain broker quotes | Derek Okonkwo / Calderwood & Harkness LLP | Oakbridge Omnivrel Insurance Group | 2025-02-10 | 2025-02-10 | Completed | Oakbridge Fidelity selected as carrier; underwriter: Neil Carmichael, SVP; carrier address: 175 Water Street, Suite 2800, New York, NY 10038
2 | Prepare and submit no-names R&W insurance application (preliminary submission) | Derek Okonkwo / Calderwood & Harkness LLP | Oakbridge Omnivrel Insurance Group | 2025-02-18 | 2025-02-18 | Completed | No-names submission included transaction summary, target industry description (cloud-based payments processing / fintech), and estimated deal value of $1,900,000,000
3 | Prepare and submit named R&W insurance application (full submission with diligence findings) | Derek Okonkwo / Megan Chu / Calderwood & Harkness LLP | Oakbridge Omnivrel Insurance Group (Neil Carmichael) | 2025-02-21 | 2025-02-21 | Completed | Full submission included: transaction summary, draft Merger Agreement, key diligence findings across corporate, IP, regulatory/licensing, litigation, tax, and employment workstreams; identified VeloPay Systems, Inc. as target (EIN 82-3019478)
4 | Receive non-binding indication (NBI) from carrier | Oakbridge Omnivrel Insurance Group | Calderwood & Harkness LLP | 2025-02-28 | 2025-02-27 | Completed | NBI received: proposed $190,000,000 policy limit (10% of $1,900,000,000 deal value); $19,000,000 retention (1% of deal value); estimated premium 2.8% of policy limit
5 | Negotiate R&W policy terms — exclusions, coverage scope, retention allocation | Derek Okonkwo / Sandra Tung / Calderwood & Harkness LLP | Oakbridge Omnivrel Insurance Group (Neil Carmichael) | 2025-03-07 | 2025-03-07 | Completed | Key negotiations: retention structure — first $9,500,000 borne by Seller via indemnification under Merger Agreement, remaining $9,500,000 borne by Buyer; exclusions reviewed and narrowed; coverage aligned with Merger Agreement reps
6 | Submit final draft Merger Agreement (execution-ready) to carrier for policy binding review | Derek Okonkwo / Calderwood & Harkness LLP | Oakbridge Omnivrel Insurance Group | 2025-03-08 | 2025-03-08 | Completed | Execution version of Agreement and Plan of Merger among HPE Fund IV, Harrowgate Velocity Merger Sub Inc., and VeloPay Systems, Inc.
7 | R&W insurance policy bound | Oakbridge Omnivrel Insurance Group | Harrowgate Private Equity Fund IV LP | 2025-03-10 | 2025-03-10 | Completed | OFI-RW-2025-03187 | Buyer-side R&W policy bound; Policy No. OFI-RW-2025-03187; policy limit $190,000,000; retention $19,000,000; premium $5,320,000 (2.8% × $190,000,000)
8 | Receive executed R&W insurance binder / cover note | Oakbridge Omnivrel Insurance Group (Neil Carmichael) | Calderwood & Harkness LLP / HPE Fund IV | 2025-03-12 | 2025-03-11 | Completed | OFI-RW-2025-03187 | Binder confirms policy inception contingent on closing of the merger
9 | Pay R&W insurance premium | Harrowgate Private Equity Fund IV LP (Priya Deshmukh) | Oakbridge Omnivrel Insurance Group | At or prior to closing | 2025-07-22 | Completed | OFI-RW-2025-03187 | Premium of $5,320,000 paid at closing; included in transaction expenses
10 | Confirm R&W policy inception upon closing | Oakbridge Omnivrel Insurance Group | Calderwood & Harkness LLP / HPE Fund IV | 2025-07-22 | 2025-07-22 | Completed | OFI-RW-2025-03187 | Policy inception date: July 22, 2025; coverage effective as of closing of reverse triangular merger
11 | Prepare internal R&W Insurance Policy Summary and Coverage Memorandum | Derek Okonkwo / Calderwood & Harkness LLP | Sandra Tung / HPE Fund IV deal team | 2025-03-15 | 2025-03-14 | Completed | Memorandum covers policy limit ($190M), retention structure ($19M; split $9.5M Seller / $9.5M Buyer), exclusions, claims process, and interplay with Merger Agreement indemnification provisions (indemnification cap of $228,000,000 = 12% of deal value; escrow of $133,000,000 = 7% of deal value)
12 | Verify R&W policy coverage alignment with final Merger Agreement reps and warranties | Megan Chu / Derek Okonkwo / Calderwood & Harkness LLP | N/A (internal) | 2025-07-21 | 2025-07-21 | Completed | OFI-RW-2025-03187 | Confirmed policy covers all reps in execution version of Merger Agreement dated March 18, 2025; survival period for reps is 18 months (through January 22, 2027)
13 | Deliver copy of bound R&W policy to Tralvendo National Bank and Prairie State Bank, N.A. (lender closing condition) | Derek Okonkwo / Calderwood & Harkness LLP | Tralvendo National Bank (Andrew Birchfield) / Prairie State Bank, N.A. (Monica Fuentes) / Maplewood & Strauss LLP (Gordon Strauss) | 2025-07-21 | 2025-07-21 | Completed | OFI-RW-2025-03187 | Copy delivered as part of pre-closing deliverables; satisfies insurance-related closing condition under Credit Agreement
[sheet: D&O Tail Policy Tracker]
Item # | Deliverable / Milestone | Responsible Party | Counterparty / Recipient | Target Date | Actual Date | Status | Reference / Policy Number | Notes
1 | Engage D&O insurance broker for tail policy placement | Derek Okonkwo / Calderwood & Harkness LLP | Greystone Risk Advisors LLC (Stephen Hargrave) | 2025-04-01 | 2025-03-28 | Completed | Greystone Risk Advisors LLC, 55 East 52nd Street, 23rd Floor, New York, NY 10055; broker contact: Stephen Hargrave
2 | Obtain existing D&O policy details from VeloPay / Whitford Jessup & Crane LLP | Derek Okonkwo / Calderwood & Harkness LLP | VeloPay Systems, Inc. (Danielle Moreau) / Whitford Jessup & Crane LLP (Rebecca Thornton-Hayes) | 2025-04-15 | 2025-04-10 | Completed | Reviewed existing VeloPay D&O policy terms; identified coverage for Nathan Aldridge, Sonia Reyes-Watkins, Marcus Langford, Danielle Moreau, Janet Gould, Kwame Asante, Catherine Lindström, Philip Rosenthal
3 | Submit D&O tail policy application to carriers via Greystone Risk Advisors | Greystone Risk Advisors LLC (Stephen Hargrave) | Continental Shield Insurance Company and other potential carriers | 2025-05-01 | 2025-04-28 | Completed | Application submitted to multiple carriers; Continental Shield Insurance Company, 400 Park Avenue, 18th Floor, New York, NY 10022, selected
4 | Receive D&O tail policy quotes from carriers | Greystone Risk Advisors LLC (Stephen Hargrave) | Calderwood & Harkness LLP / HPE Fund IV | 2025-05-15 | 2025-05-12 | Completed | Continental Shield quote: 6-year tail; premium $2,150,000; coverage for all pre-closing directors and officers of VeloPay Systems, Inc.
5 | Negotiate D&O tail policy terms and premium | Derek Okonkwo / Calderwood & Harkness LLP / Greystone Risk Advisors LLC | Continental Shield Insurance Company | 2025-06-01 | 2025-05-30 | Completed | Final terms: 6-year tail from closing date; premium of $2,150,000; covers acts and omissions of VeloPay directors and officers occurring prior to closing
6 | Obtain HPE Fund IV approval of D&O tail premium and terms | Derek Okonkwo / Calderwood & Harkness LLP | Priya Deshmukh / Thomas Eriksen (Harrowgate Capital Management IV LLC) | 2025-06-05 | 2025-06-03 | Completed | Merger Agreement requires Buyer to cause the Surviving Corporation to maintain D&O tail coverage for at least 6 years post-closing; premium approved as part of estimated transaction expenses ($48,500,000 combined buyer + seller)
7 | Bind D&O tail policy with Continental Shield Insurance Company | Greystone Risk Advisors LLC (Stephen Hargrave) | Continental Shield Insurance Company | 2025-07-18 | 2025-07-17 | Completed | CSI-DOT-2025-4821 | Policy No. CSI-DOT-2025-4821; bound effective upon closing; 6-year tail period from July 22, 2025 through July 22, 2031
8 | Pay D&O tail policy premium | VeloPay Systems, Inc. (Surviving Corporation) / HPE Fund IV | Continental Shield Insurance Company | 2025-07-22 | 2025-07-22 | Completed | CSI-DOT-2025-4821 | Premium of $2,150,000 paid at closing; included in closing funds flow
9 | Confirm D&O tail policy inception upon closing | Continental Shield Insurance Company / Greystone Risk Advisors LLC | Calderwood & Harkness LLP / HPE Fund IV | 2025-07-22 | 2025-07-22 | Completed | CSI-DOT-2025-4821 | Policy effective July 22, 2025; covers pre-closing acts of VeloPay directors and officers through July 22, 2031
10 | Prepare internal D&O Tail Policy Memorandum | Derek Okonkwo / Calderwood & Harkness LLP | Sandra Tung / HPE Fund IV deal team | 2025-07-15 | 2025-07-14 | Completed | Memorandum analyzes tail coverage terms, covered persons, exclusions, and Merger Agreement obligations regarding D&O indemnification
11 | Deliver evidence of D&O tail policy to VeloPay directors (Aldridge, Reyes-Watkins, Gould, Asante, Lindström, Rosenthal) | Calderwood & Harkness LLP / VeloPay (Surviving Corporation) | VeloPay pre-closing directors and officers | 2025-07-25 | 2025-07-24 | Completed | CSI-DOT-2025-4821 | Confirmation letters sent to all pre-closing directors and officers confirming 6-year tail coverage
[sheet: Closing Condition Compliance]
Item # | Closing Condition Description | Required By | Relevant Section | Insurance Type | Carrier | Policy Number | Condition Satisfied | Date Satisfied | Evidence Delivered To | Notes
1 | Buyer-side R&W insurance policy bound and in effect as of closing | Both | Merger Agreement Art. VII; Credit Agreement §4.01 | R&W | Oakbridge Omnivrel Insurance Group | OFI-RW-2025-03187 | Yes | 2025-07-22 | Tralvendo National Bank / Prairie State Bank, N.A. / Maplewood & Strauss LLP / Whitford Jessup & Crane LLP | Policy limit: $190,000,000 (10% of $1,900,000,000 deal value); retention: $19,000,000 (1% of deal value); premium: $5,320,000 (2.8% of $190M limit); inception: July 22, 2025
2 | R&W insurance premium paid in full at or prior to closing | Merger Agreement | Merger Agreement Art. VII | R&W | Oakbridge Omnivrel Insurance Group | OFI-RW-2025-03187 | Yes | 2025-07-22 | N/A | Premium of $5,320,000 funded from closing proceeds per funds flow memorandum
3 | Copy of bound R&W insurance policy delivered to administrative agents under Credit Agreement | Credit Agreement | Credit Agreement §4.01 | R&W | Oakbridge Omnivrel Insurance Group | OFI-RW-2025-03187 | Yes | 2025-07-21 | Tralvendo National Bank (Andrew Birchfield, 100 Federal Street, 30th Floor, Boston, MA 02110) / Prairie State Bank, N.A. (Monica Fuentes, 231 South LaSalle Street, Suite 4400, Chicago, IL 60604) | Delivered as part of pre-closing deliverable package on July 21, 2025
4 | D&O tail insurance policy obtained for pre-closing directors and officers with minimum 6-year tail | Merger Agreement | Merger Agreement Art. VI (D&O Indemnification / Insurance covenant) | D&O Tail | Continental Shield Insurance Company | CSI-DOT-2025-4821 | Yes | 2025-07-22 | VeloPay pre-closing directors and officers | 6-year tail from closing (July 22, 2025 – July 22, 2031); premium: $2,150,000; covers Nathan Aldridge, Sonia Reyes-Watkins, Marcus Langford, Danielle Moreau, Janet Gould, Kwame Asante, Catherine Lindström, Philip Rosenthal
5 | D&O tail premium paid at closing | Merger Agreement | Merger Agreement Art. VI | D&O Tail | Continental Shield Insurance Company | CSI-DOT-2025-4821 | Yes | 2025-07-22 | N/A | Premium of $2,150,000 paid from closing proceeds
6 | Evidence of D&O tail policy delivered to Stockholder Representative | Merger Agreement | Merger Agreement Art. VI | D&O Tail | Continental Shield Insurance Company | CSI-DOT-2025-4821 | Yes | 2025-07-24 | Nathan Aldridge (Stockholder Representative) | Confirmation of tail placement provided post-closing
[sheet: Premium & Cost Summary]
Item # | Insurance Product | Carrier | Policy Number | Policy Limit / Coverage Amount | Retention / Deductible | Premium | Premium as % of Limit | Term / Tail Period | Inception Date | Expiration / End Date | Paid By | Payment Date | Included in Transaction Expenses | Notes
1 | Buyer-Side Representations & Warranties Insurance | Oakbridge Omnivrel Insurance Group | OFI-RW-2025-03187 | $190,000,000 | $19,000,000 | $5,320,000 | 2.80% | Coterminous with survival period (18 months from closing) plus extended discovery | 2025-07-22 | Per policy terms | Harrowgate Private Equity Fund IV LP | 2025-07-22 | Yes | Retention split: first $9,500,000 borne by Seller (from escrow / indemnification); balance $9,500,000 borne by Buyer. Policy limit = 10% of $1,900,000,000 aggregate merger consideration. Underwriter: Neil Carmichael, SVP.
2 | D&O Tail Liability Insurance | Continental Shield Insurance Company | CSI-DOT-2025-4821 | Per policy terms | Per policy terms | $2,150,000 | N/A | 6 years from closing | 2025-07-22 | 2031-07-22 | VeloPay Systems, Inc. (Surviving Corporation) | 2025-07-22 | Yes | Covers pre-closing directors and officers of VeloPay. Broker: Greystone Risk Advisors LLC (Stephen Hargrave). Required under Merger Agreement Art. VI.
TOTAL INSURANCE PREMIUMS | $7,470,000 | Sum of $5,320,000 (R&W) + $2,150,000 (D&O Tail); included in estimated combined transaction expenses of $48,500,000
[sheet: Key Contacts]
Role | Entity | Contact Name | Title | Address | Phone | Email | Notes
R&W Insurance Underwriter | Oakbridge Omnivrel Insurance Group | Neil Carmichael | Senior Vice President | 175 Water Street, Suite 2800, New York, NY 10038 | [phone] | [email] | Primary underwriting contact; Policy No. OFI-RW-2025-03187
D&O Insurance Broker | Greystone Risk Advisors LLC | Stephen Hargrave | Broker | 55 East 52nd Street, 23rd Floor, New York, NY 10055 | [phone] | [email] | Broker for D&O tail policy placement with Continental Shield Insurance Company
D&O Tail Insurance Carrier | Continental Shield Insurance Company | [Underwriting Contact] | [Title] | 400 Park Avenue, 18th Floor, New York, NY 10022 | [phone] | [email] | D&O Tail Policy No. CSI-DOT-2025-4821; 6-year tail from closing
Calderwood & Harkness — Insurance Workstream Lead | Calderwood & Harkness LLP | Derek Okonkwo | Working Associate, M&A | 787 Seventh Avenue, 38th Floor, New York, NY 10019 | [phone] | [email] | Maintains this checklist; Matter No. 1003-00003
Calderwood & Harkness — Responsible Partner | Calderwood & Harkness LLP | Sandra Tung | Responsible Partner, M&A | 787 Seventh Avenue, 38th Floor, New York, NY 10019 | [phone] | [email] | Supervises insurance workstream
HPE Fund IV — Deal Lead | Harrowgate Capital Management IV LLC | Priya Deshmukh | Managing Partner, Fund IV | 300 King Street, Suite 4200, Wilmington, DE 19801 | [phone] | [email] | Client approval for insurance premiums and terms
HPE Fund IV — FinTech Lead | Harrowgate Capital Management IV LLC | Thomas Eriksen | Partner, Head of FinTech | 300 King Street, Suite 4200, Wilmington, DE 19801 | [phone] | [email] | Involved in insurance cost approvals
VeloPay — General Counsel | VeloPay Systems, Inc. | Danielle Moreau | General Counsel | 1455 Innovation Parkway, Suite 800, Austin, TX 78759 | [phone] | [email] | Provided existing D&O policy details; coordinated with Whitford Jessup & Crane LLP
Target Counsel | Whitford Jessup & Crane LLP | Rebecca Thornton-Hayes | Lead Partner | 600 Congress Avenue, Suite 2400, Austin, TX 78701 | [phone] | [email] | Coordinated D&O policy information and Merger Agreement insurance covenants
Lender Counsel | Maplewood & Strauss LLP | Gordon Strauss | Lead Partner | One International Place, Suite 3600, Boston, MA 02110 | [phone] | [email] | Received copy of R&W policy as Credit Agreement closing deliverable

[sheet: R&W Insurance Tracker]

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