CONFIDENTIAL — ATTORNEY WORK PRODUCT / INTERNAL USE ONLY

CONFIDENTIAL — ATTORNEY WORK PRODUCT / INTERNAL USE ONLY
CALDERWOOD & HARKNESS LLP CONFLICT CHECK MEMORANDUM
TO: Angela Fontaine, Responsible Partner
FROM: Nathan Ikeda, Working Associate
DATE: August 28, 2025
RE: Conflict Check Results — Proposed Representation of Skybridge Fintech Ltd. in Enterprise SaaS Agreement with Meridian National Bank, N.A.
MATTER NUMBER: 1009-00007
STATUS: CLEARED — No Disqualifying Conflicts Identified
1. Purpose and Scope of Memorandum
This memorandum documents the results of the conflict-of-interest check conducted in connection with Calderwood & Harkness LLP's ("C&H" or the "Firm") proposed engagement by Skybridge Fintech Ltd. ("Skybridge" or "SBF") to represent Skybridge as licensor in negotiating an enterprise Master Software-as-a-Service Agreement ("MSA") and ancillary documents with Meridian National Bank, National Association ("Meridian" or "MNB"). The proposed engagement encompasses the negotiation and drafting of critical security, service-level, data governance, indemnification, and limitation-of-liability provisions in connection with the licensing of Skybridge's SkyComply™ AI-driven anti-money-laundering and transaction-monitoring platform to Meridian under the MSA, together with all related order forms, statements of work, data processing addenda, and related ancillary agreements.
The engagement letter is dated August 25, 2025. The conflict check was initiated on August 26, 2025, promptly following receipt of the signed engagement letter, and was completed on August 28, 2025. The total elapsed time for the conflict check was approximately two (2) full business days, which is within the Firm's target clearance window for transactional matters of this complexity.
The check was performed using the C&H Conflicts Management System ("CMS"), the Firm's centralized conflicts database of record, and was supplemented by targeted manual inquiries to practice group leaders across all relevant practice areas, as described in detail in Section 4 below. In addition, each member of the proposed engagement team completed a self-disclosure questionnaire confirming the absence of any personal, financial, or professional relationships with any party to the transaction that could give rise to a conflict of interest or the appearance thereof.
The scope of the conflict check covers the following categories of parties: (a) the prospective client and its officers, directors, and key personnel; (b) the prospective client's majority equity holder and its managing partner; (c) the counterparty and its parent holding company, together with key counterparty personnel; (d) the counterparty's outside counsel and its individual attorneys assigned to the transaction; (e) the majority owner's outside counsel; and (f) other material third parties to the transaction, including the independent security auditor, cloud infrastructure provider, technology errors and omissions insurer, independent financial auditor, and source code escrow agent.
This memorandum is prepared in accordance with C&H's Conflict-of-Interest Policy (last revised January 15, 2025), Rule 1.7 (Conflict of Interest: Current Clients), Rule 1.9 (Duties to Former Clients), and Rule 1.10 (Imputation of Conflicts of Interest) of the Delaware Lawyers' Rules of Professional Conduct, and the corresponding provisions of the Model Rules of Professional Conduct.
2. Engagement Summary
The following summary sets forth the material terms and parties relevant to the proposed engagement, as reflected in the engagement letter dated August 25, 2025 and the preliminary transaction term sheet provided by the prospective client's General Counsel:
Client: Skybridge Fintech Ltd., a Delaware limited company (alternative entity formed under the Delaware Limited Liability Company Act, 6 Del. C. § 18-101 et seq.), headquartered at 1400 Concord Pike, Suite 320, Wilmington, DE 19803. Skybridge is a financial technology company specializing in AI-driven regulatory compliance solutions for the banking and financial services industry. Skybridge's flagship product is the SkyComply™ platform, a cloud-native anti-money-laundering ("AML") and transaction-monitoring solution delivered on a software-as-a-service basis.
Client Contact: David Shimura, General Counsel, Skybridge Fintech Ltd. Mr. Shimura serves as the primary client contact for this engagement and has been the Firm's point of contact on all Skybridge matters since 2022.
Nature of Engagement: Representation of Skybridge as licensor and SaaS provider in negotiating the critical security, service-level agreement ("SLA"), data processing, indemnification, limitation of liability, intellectual property ownership, and termination provisions of a Master Software-as-a-Service Agreement with Meridian National Bank, N.A. for the deployment of the SkyComply™ AI-driven AML and transaction-monitoring platform across Meridian's retail, commercial, and institutional banking divisions. The MSA will be accompanied by ancillary documents including an initial order form, one or more statements of work, a data processing addendum, a business associate agreement (to the extent applicable), a source code escrow agreement, and SLA schedules.
Total Contract Value: Fifty Million Dollars ($50,000,000) over five (5) years, comprising annual license fees, implementation services fees, and ongoing support and maintenance fees. The annual contract value is approximately Ten Million Dollars ($10,000,000), making this Skybridge's single largest enterprise deployment to date.
Counterparty: Meridian National Bank, National Association, a national banking association chartered under federal law pursuant to the National Bank Act, 12 U.S.C. § 21 et seq., with its principal office at 600 Lexington Avenue, 40th Floor, New York, NY 10022. Meridian is a top-10 U.S. commercial bank by total assets, with approximately $485 billion in total assets as of its most recent quarterly report. Meridian is supervised by the Office of the Comptroller of the Currency ("OCC"), the Board of Governors of the Federal Reserve System, and the Federal Deposit Insurance Corporation ("FDIC") and is designated as a systemically important financial institution ("SIFI") under the Dodd-Frank Wall Street Reform and Consumer Protection Act.
Counterparty's Holding Company: Meridian Financial Group, Inc. ("MFG"), a Delaware corporation listed on the New York Stock Exchange (ticker: MFG). MFG is the sole shareholder and parent holding company of Meridian National Bank, N.A.
Counterparty's Outside Counsel: Hargrove, Tully & Cascade Insurance Brokers ("HTM"), a New York limited liability partnership, with offices at 1 Chase Manhattan Plaza, Suite 5500, New York, NY 10005. The lead partner on the transaction for HTM is Douglas Krenshaw, supported by Senior Associate Megan Faircloth and Associate Ryan Tso.
Engagement Team:
Estimated Fees: $275,000 – $375,000, billed on an hourly basis in accordance with the Firm's standard rate schedule, as set forth in the engagement letter.
Governing Law: State of Delaware.
3. Parties and Entities Searched
The following is a comprehensive list of all entities and individuals included in the conflict-of-interest search. Each entity and individual was searched in the CMS using the methodologies described in Section 4 below. A consolidated reference table of all searched parties is also included in Appendix A.
3.1 Prospective Client and Affiliates
The following entities and individuals associated with the prospective client were searched:
Entity:
•  Skybridge Fintech Ltd. (all known name variants: "Skybridge," "SBF," "Skybridge Fintech," "Sky Bridge Fintech," "Skybridge FinTech Ltd.")
Key Personnel:
•  Priya Chandrasekaran — Chief Executive Officer
•  Marcus Holt — Chief Technology Officer
•  David Shimura — General Counsel
•  Tara Bellingham — Vice President, Enterprise Sales
•  Jonathan Kreske — Chief Financial Officer
•  Amara Okafor — Chief Information Security Officer
Majority Owner:
•  Pinnacle Ridge Capital Partners, LP ("PRCP") — 62% majority owner of Skybridge Fintech Ltd.; Delaware limited partnership; Managing Partner: Elise Drummond. PRCP's principal office is located in San Francisco, California.
It is noted that PRCP holds board representation rights and contractual approval rights over Skybridge contracts exceeding Twenty-Five Million Dollars ($25,000,000) in total contract value. The proposed MSA with Meridian, with a total contract value of Fifty Million Dollars ($50,000,000), exceeds that threshold and will therefore require PRCP's prior written consent before execution. The implications of this consent right for the conflict analysis are discussed in Section 6.3 below.
3.2 Counterparty and Affiliates
The following entities and individuals associated with the counterparty were searched:
Entities:
•  Meridian National Bank, National Association (all known name variants: "Meridian," "MNB," "Meridian National Bank, N.A.," "Meridian National Bank," "Meridian Bank")
•  Meridian Financial Group, Inc. ("MFG") — parent holding company (NYSE-listed, Delaware corporation; ticker: MFG)
Key Personnel:
•  Gerald Brannigan — Chief Information Officer, Meridian National Bank, N.A.
•  Sandra Petrov — Head, Financial Crimes & Compliance, Meridian National Bank, N.A.
•  Luis Arriaga — Senior Vice President, Procurement & Vendor Management, Meridian National Bank, N.A.
•  Catherine Woo — Associate General Counsel — Technology, Meridian National Bank, N.A.
3.3 Counterparty's Outside Counsel
The following law firm and individuals were searched:
•  Hargrove, Tully & Cascade Insurance Brokers ("HTM") — New York limited liability partnership; 1 Chase Manhattan Plaza, Suite 5500, New York, NY 10005
•  Douglas Krenshaw — Partner, HTM (lead partner on transaction)
•  Megan Faircloth — Senior Associate, HTM
•  Ryan Tso — Associate, HTM
3.4 Majority Owner's Outside Counsel
The following law firm and individual were searched:
•  Alcott & Grenier LLP ("A&G") — District of Columbia limited liability partnership; 1001 Pennsylvania Avenue NW, Suite 700, Washington, DC 20004
•  Simone Alcott — Partner, A&G. Ms. Alcott advises Pinnacle Ridge Capital Partners on portfolio company matters and will review the MSA on behalf of PRCP for purposes of the contractual consent right described in Section 3.1 above.
3.5 Other Transaction Parties and Material Third Parties
The following entities and individuals who are material third parties to the transaction were searched:
Crestfield Cyber Advisors, Inc. ("Crestfield")
•  Delaware corporation; independent security auditor performing SOC 2 Type II and ISO 27001 audits for Skybridge in connection with the SkyComply™ platform
•  Principal Office: 222 West Adams Street, Suite 1200, Chicago, IL 60606
•  CEO: Winston Lam
•  Lead Auditor: Deepa Rajan
Orion Cloud Services, Inc. ("Orion Cloud")
•  Delaware corporation; cloud infrastructure (IaaS) provider for SkyComply™
•  Principal Office: 4500 Great America Parkway, Santa Clara, CA 95054
•  Orion Cloud provides the underlying cloud computing infrastructure upon which SkyComply™ is hosted and delivered; the MSA will contain provisions addressing subprocessor obligations, data residency, and infrastructure-level security requirements applicable to Orion Cloud.
Coastal Assurance Corporation
•  Connecticut stock insurance corporation; Skybridge's technology errors and omissions ("E&O") and cyber liability insurer
•  Policy No. CA-TECH-2025-07831
•  The MSA will contain insurance coverage requirements, and Meridian is expected to require evidence of Skybridge's E&O and cyber liability insurance coverage, including minimum policy limits and additional insured endorsements.
Hathaway & Pendleton, LLP ("H&P")
•  Illinois limited liability partnership; Skybridge's independent financial auditor
•  Principal Office: 300 North LaSalle Street, Suite 2400, Chicago, IL 60654
•  Lead Audit Partner: Bruce Ogilvie
•  H&P may be referenced in representations and warranties in the MSA regarding Skybridge's financial condition and solvency.
Sentinel Escrow Services, Inc.
•  California corporation; source code escrow agent for SkyComply™
•  Escrow Agreement No. SCE-2025-04417
•  Principal Office: 100 Wilshire Boulevard, Suite 950, Santa Monica, CA 90401
•  The MSA is expected to include or reference a source code escrow arrangement under which Skybridge will deposit the SkyComply™ source code with Sentinel Escrow, with release conditions triggered by specified events (e.g., Skybridge insolvency, material breach, or discontinuation of support).
4. Conflict Check Methodology
4.1 Database Search
All entities and individuals listed in Section 3 were searched in the C&H Conflicts Management System ("CMS"), the Firm's centralized database of record for conflicts screening. The CMS is maintained by the Firm's General Counsel's Office in coordination with the Conflicts Department and contains records of all current client engagements, former client engagements (with a rolling retention period), adverse parties in open and recently closed matters, prospective clients from declined engagements, and business relationships (including co-counsel arrangements, referral relationships, and vendor relationships).
For each entity, the following search methodologies were employed:
(a) Exact Name Match: The full legal name of each entity and individual was entered as a search string, and the CMS returned all records containing an exact match.
(b) Common-Variant/Alias Searches: Known abbreviations, trade names, "doing business as" names, and common misspellings were entered as alternative search strings. For example, "Meridian National Bank, N.A." was also searched as "Meridian National Bank," "Meridian Bank," "MNB," and "Meridian." Similarly, "Skybridge Fintech Ltd." was searched as "Skybridge," "SBF," "Skybridge Fintech," "Sky Bridge Fintech," and "Skybridge FinTech Ltd."
(c) Fuzzy Matching: The CMS fuzzy-matching algorithm was applied at an 85% similarity threshold to capture potential matches involving minor spelling variations, transpositions, and typographical errors. The specific parameters of the fuzzy-matching algorithm are documented in Appendix B.
(d) Individual Searches: Each individual identified in Section 3 was searched by full name, and where applicable, by last name alone with manual review of results to identify potential matches.
Searches encompassed the following categories of records within the CMS:
(i) Current clients — all active engagement records;
(ii) Former clients — engagement records closed within the preceding five (5) years (i.e., engagements closed on or after August 28, 2020);
(iii) Adverse parties — all parties identified as adverse in open matters and in matters closed within the preceding five (5) years;
(iv) Prospective clients — parties identified in connection with declined engagements within the preceding three (3) years; and
(v) Business relationships — co-counsel, referral sources, vendors, and other professional relationships recorded in the CMS.
4.2 Practice Group Leader Inquiries
In accordance with the Firm's Conflict-of-Interest Policy, supplemental manual inquiry emails were sent to the leaders of each practice group with which the proposed engagement team members are affiliated, as well as practice groups whose subject-matter expertise is relevant to the proposed engagement. These inquiries were designed to confirm that no undisclosed relationships, matters, or engagements exist that may not have been captured in the CMS, and to solicit any institutional knowledge that might bear on the conflict analysis.
The following practice group leaders were contacted:
(a) Real Estate Practice Group — Angela Fontaine's home group. Inquiry sent to the practice group leader to confirm no conflicting engagements involving any party listed in Section 3.
(b) Labor & Employment Practice Group — Renata Vasquez's home group. Inquiry sent to confirm no labor or employment matters involving any party listed in Section 3.
(c) Bankruptcy & Restructuring Practice Group — Amy Chesterton's and Nathan Ikeda's home group. Inquiry sent to confirm no insolvency or restructuring matters involving any party listed in Section 3.
(d) Corporate & Transactions Practice Group — Inquiry sent to confirm no pending corporate, M&A, or investment transactions involving any party listed in Section 3.
(e) Financial Services Practice Group — Given that the counterparty is a major national banking association, an inquiry was sent to confirm no regulatory, enforcement, or advisory engagements involving Meridian National Bank, N.A. or Meridian Financial Group, Inc.
(f) intellectual Property / Technology Practice Group — Liam Prescott's practice area. Inquiry sent to confirm no technology transactions, licensing matters, or intellectual property disputes involving any party listed in Section 3.
All six (6) practice group leader responses were received by August 28, 2025. Each response confirmed that no conflicts or potential conflicts were identified. A complete log of the practice group leader inquiries and responses is set forth in Appendix C.
4.3 Engagement Team Self-Disclosure
In accordance with the Firm's Conflict-of-Interest Policy, each member of the proposed engagement team — Angela Fontaine, Renata Vasquez, Liam Prescott, Amy Chesterton, and Nathan Ikeda — was provided with the complete list of parties and individuals identified in Section 3 and was asked to confirm, in writing, whether they have any personal, financial, familial, or professional relationships with any such party or individual that could give rise to a conflict of interest or the appearance of a conflict of interest.
All five (5) engagement team members completed and returned their self-disclosure questionnaires by August 28, 2025. Each team member confirmed that they have no such relationships. The completed questionnaires are on file with the Conflicts Department.
5. Results of Conflict Search
The results of the conflict search are set forth below, organized by party category. For each searched party, the memorandum identifies whether any current client relationship, former client relationship, adverse party relationship, or other potentially conflicting relationship was identified, and states the conclusion as to whether a conflict exists.
5.1 Skybridge Fintech Ltd. — Existing Client
Skybridge Fintech Ltd. is an existing client of Calderwood & Harkness LLP. The Firm has represented Skybridge since 2021, when C&H was first engaged to represent Skybridge in connection with the Series C preferred equity investment by Pinnacle Ridge Capital Partners, LP, which closed at a pre-money valuation of $310 million. Since that initial engagement, C&H has continued to represent Skybridge on an ongoing basis in connection with various commercial, employment, and regulatory matters, including prior SaaS licensing transactions, employment agreement negotiations for senior executives, and regulatory compliance advisory matters relating to Skybridge's FinCEN and OCC-related obligations.
The proposed engagement — representation of Skybridge as licensor in an enterprise SaaS transaction — is consistent with the scope and nature of C&H's existing client relationship with Skybridge and presents no intra-client conflict. The engagement will be staffed by members of the team that has historically handled Skybridge matters, including Responsible Partner Angela Fontaine.
A thorough review of the CMS confirmed that there is no open or recently closed matter in which Skybridge Fintech Ltd. appears as an adverse party. Accordingly, the proposed engagement is fully aligned with C&H's duties of loyalty and confidentiality to its existing client, and no conflict of interest exists.
Result: No conflict. Existing client — engagement consistent with existing relationship.
5.2 Meridian National Bank, N.A. / Meridian Financial Group, Inc. — Counterparty
A comprehensive search of the CMS revealed no current or former client relationship with Meridian National Bank, N.A. The Firm has not represented Meridian National Bank in any capacity — advisory, transactional, regulatory, or litigation — at any point within the five-year lookback period or, based on available records, at any prior time.
Similarly, no current or former client relationship was identified with Meridian Financial Group, Inc., the NYSE-listed parent holding company of Meridian National Bank. The CMS returned no results for MFG under any name variant.
Meridian National Bank does not appear as an adverse party in any open or recently closed C&H matter. No C&H client is currently adverse to Meridian in any proceeding, transaction, or other matter of which the Firm is aware.
Given Meridian's stature as a systemically important financial institution with approximately $485 billion in total assets, making it one of the ten largest commercial banks in the United States, the Firm conducted an enhanced check to identify any indirect relationships that might not surface through standard CMS queries. This enhanced check included a review of syndicate participation lists in financing matters handled by the Firm, counterparty lists in pending transactions, and any regulatory matters in which Meridian or MFG might be a relevant party. No such indirect relationship was identified. The enhanced check procedures are further discussed in Section 6.2 below.
The Firm confirmed that it has no ongoing advisory, lending, litigation, or other professional relationship with Meridian National Bank, N.A. or Meridian Financial Group, Inc.
Result: No conflict. No blocking conflict. No current or former client relationship. No adverse-party relationship.
5.3 Hargrove, Tully & Cascade Insurance Brokers — Counterparty's Counsel
No current or former client relationship with Hargrove, Tully & Cascade Insurance Brokers was identified in the CMS. The Firm has not represented HTM in any capacity, and HTM does not appear as co-counsel on any matter involving an C&H client.
HTM does not appear as adverse counsel in any open or recently closed C&H matter. No C&H attorney is currently opposing an HTM attorney in any litigation, arbitration, or transactional negotiation of which the Firm is aware (other than the proposed transaction that is the subject of this memorandum).
Individual searches were conducted for Douglas Krenshaw (Partner), Megan Faircloth (Senior Associate), and Ryan Tso (Associate). No results were returned for any of these individuals. None of these individuals are former C&H attorneys, and no professional or personal relationships with C&H personnel were identified.
Result: No conflict.
5.4 Pinnacle Ridge Capital Partners, LP — Client Affiliate / Majority Owner
Pinnacle Ridge Capital Partners, LP is not a direct client of Calderwood & Harkness LLP. PRCP does not have its own engagement letter with the Firm, and C&H does not provide legal services to PRCP in its own capacity. However, it is noted that C&H's representation of Skybridge Fintech Ltd. commenced in 2021 in connection with PRCP's Series C investment in Skybridge, and PRCP is the 62% majority equity owner of Skybridge with board representation and significant governance rights, including the contractual consent right over contracts exceeding $25,000,000 in total contract value described elsewhere in this memorandum.
No adverse representation against Pinnacle Ridge Capital Partners has been identified. No open or recently closed C&H matter involves PRCP as an adverse party, and no C&H client is currently adverse to PRCP in any proceeding or transaction of which the Firm is aware.
PRCP's separate outside counsel, Alcott & Grenier LLP (lead partner: Simone Alcott), will independently review the MSA for purposes of PRCP's contractual consent right. This parallel review does not create an attorney-client relationship between C&H and PRCP, nor does it create a conflict of interest. C&H represents Skybridge, not PRCP, in this matter. The implications of the parallel review are further discussed in Section 6.3 below.
Result: No conflict. Not a direct client. No adverse representation identified.
5.5 Alcott & Grenier LLP — PRCP's Outside Counsel
No current or former client relationship with Alcott & Grenier LLP was identified in the CMS. The Firm has not represented A&G in any capacity, and A&G does not appear as co-counsel or adverse counsel in any open or recently closed C&H matter.
Simone Alcott (Partner, A&G) was searched individually. No results were returned. Ms. Alcott is not a former C&H attorney, and no professional or personal relationships with C&H personnel were identified.
Result: No conflict.
5.6 Crestfield Cyber Advisors, Inc.
No current or former client relationship with Crestfield Cyber Advisors, Inc. was identified in the CMS. Crestfield does not appear as an adverse party in any open or recently closed C&H matter.
It is noted that Crestfield's principal office is located at 222 West Adams Street, Suite 1200, Chicago, IL 60606, in proximity to C&H's Chicago office. However, geographic proximity alone does not give rise to any professional relationship, and no relationship between C&H and Crestfield exists beyond this geographic coincidence.
Individual searches were conducted for Winston Lam (CEO) and Deepa Rajan (Lead Auditor). No results were returned for either individual.
Result: No conflict.
5.7 Orion Cloud Services, Inc.
No current or former client relationship with Orion Cloud Services, Inc. was identified in the CMS. Orion Cloud does not appear as an adverse party in any open or recently closed C&H matter. The Firm has had no professional engagement with Orion Cloud in any capacity.
Result: No conflict.
5.8 Coastal Assurance Corporation
No current or former client relationship with Coastal Assurance Corporation was identified in the CMS. Coastal Assurance does not appear as an adverse party in any open or recently closed C&H matter. The Firm has not represented Coastal Assurance in any insurance coverage, regulatory, or other matter.
Result: No conflict.
5.9 Hathaway & Pendleton, LLP
No current or former client relationship with Hathaway & Pendleton, LLP was identified in the CMS. H&P does not appear as co-counsel, adverse counsel, or in any other capacity in any open or recently closed C&H matter.
It is noted that H&P's principal office is located at 300 North LaSalle Street, Suite 2400, Chicago, IL 60654, and C&H's Chicago office is located at 200 South Ashbury Asset Advisors. No professional relationship exists between the two firms beyond geographic proximity in the same metropolitan area.
Individual search was conducted for Bruce Ogilvie (Lead Audit Partner). No results were returned.
Result: No conflict.
5.10 Sentinel Escrow Services, Inc.
No current or former client relationship with Sentinel Escrow Services, Inc. was identified in the CMS. Sentinel Escrow does not appear as an adverse party in any open or recently closed C&H matter. The Firm has had no professional engagement with Sentinel Escrow in any capacity.
Result: No conflict.
5.11 Individual Searches — Meridian Personnel
Individual searches were conducted for each of the following Meridian National Bank personnel who are expected to be involved in the transaction:
•  Gerald Brannigan (CIO) — No results in CMS.
•  Sandra Petrov (Head, Financial Crimes & Compliance) — No results in CMS.
•  Luis Arriaga (SVP, Procurement & Vendor Management) — No results in CMS.
•  Catherine Woo (Associate General Counsel — Technology) — No results in CMS.
None of these individuals appear as current or former clients, adverse parties, or in any other capacity in the CMS. None are former C&H attorneys or have any known personal or professional relationship with C&H personnel.
Result: No conflict.
5.12 Individual Searches — Skybridge Personnel
Individual searches were conducted for each of the following Skybridge Fintech Ltd. personnel:
•  Priya Chandrasekaran (CEO) — Confirmed as a contact on existing Skybridge client matters. No adverse representation identified.
•  Marcus Holt (CTO) — Confirmed as a contact on existing Skybridge client matters. No adverse representation identified.
•  David Shimura (General Counsel) — Confirmed as a contact and primary client liaison on existing Skybridge client matters. No adverse representation identified.
•  Tara Bellingham (VP, Enterprise Sales) — Confirmed as a contact on existing Skybridge client matters. No adverse representation identified.
•  Jonathan Kreske (CFO) — Confirmed as a contact on existing Skybridge client matters. No adverse representation identified.
•  Amara Okafor (CISO) — Confirmed as a contact on existing Skybridge client matters. No adverse representation identified.
All six individuals appear in the CMS exclusively in their capacities as personnel of Skybridge Fintech Ltd. in connection with existing C&H client matters. No adverse representations against any of these individuals were identified, whether in their individual capacities or otherwise.
Result: No conflict.
5.13 Individual Searches — PRCP Personnel
An individual search was conducted for Elise Drummond, Managing Partner of Pinnacle Ridge Capital Partners, LP. No results were returned in the CMS. Ms. Drummond does not appear as a current or former client, adverse party, or in any other capacity. Ms. Drummond is not a former C&H attorney and has no known personal or professional relationship with C&H personnel.
Result: No conflict.
6. Potential Issues Considered and Resolved
In the course of the conflict check, the undersigned identified three matters that, while not constituting disqualifying conflicts, warranted additional analysis and documentation. Each is discussed below.
6.1 Staffing Cross-Practice Considerations
The proposed engagement team includes attorneys from multiple C&H practice groups. Specifically, the Responsible Partner (Angela Fontaine) is a member of the Real Estate Practice Group, and the Billing Partner (Renata Vasquez) is a member of the Labor & Employment Practice Group. The Lead Associate (Amy Chesterton) and Working Associate (Nathan Ikeda) are members of the Bankruptcy & Restructuring Practice Group. The senior advisor on technology transactions is Of Counsel Liam Prescott, who is a member of the intellectual Property / Technology Practice Group.
This cross-practice staffing arrangement reflects the Firm's approach to assembling engagement teams that combine client relationship management expertise with specialized transactional knowledge. Ms. Fontaine has served as the Responsible Partner on all Skybridge matters since 2021 and maintains the primary client relationship. Ms. Vasquez has provided labor and employment advisory services to Skybridge in connection with executive compensation and employment agreement matters. Ms. Chesterton and Mr. Ikeda bring transactional drafting and negotiation experience from the Bankruptcy & Restructuring Practice Group, where they have developed expertise in complex commercial agreements, including technology licensing and services agreements, through their work on debtor-in-possession technology platform transactions. Mr. Prescott provides subject-matter expertise on technology transactions, including SaaS agreements, data licensing, and intellectual property matters.
This cross-staffing arrangement does not create any conflict of interest. The conflict check confirmed with each practice group leader that no conflicting engagement exists within any of the six practice groups from which team members are drawn. The cross-practice staffing model is consistent with the Firm's standard practice for multi-disciplinary transactional engagements.
Resolution: No conflict. Cross-practice staffing confirmed with all practice group leaders.
6.2 Meridian as Systemically Important Financial Institution
Given Meridian National Bank's size (approximately $485 billion in total assets), its status as a top-10 U.S. commercial bank, and its designation as a systemically important financial institution, the Firm conducted an enhanced conflict check to confirm the absence of any indirect relationships that might not surface through standard CMS queries. The concern motivating this enhanced check was the possibility that Meridian, given its scale and market presence, might appear as a syndicate participant in a financing transaction involving an C&H client, as a counterparty in a derivatives or trading relationship with an C&H client, or as a party in a regulatory proceeding in which C&H is involved on behalf of another client.
The enhanced check included the following additional procedures:
(a) A review of syndicate participation lists in all active financing matters handled by the Firm's Financial Services and Corporate & Transactions Practice Groups, to determine whether Meridian or MFG appears as a syndicate lender, arranger, or agent in any such transaction.
(b) A review of counterparty lists in pending M&A, joint venture, and strategic partnership transactions handled by the Firm, to determine whether Meridian or MFG is a counterparty in any such transaction.
(c) Consultation with the Financial Services Practice Group leader to determine whether the Firm is involved in any regulatory, enforcement, or supervisory matter in which Meridian or MFG is a party, subject, or interested person.
(d) A general inquiry to all partners in the Firm's New York, Chicago, and Wilmington offices to determine whether any attorney has a pending or prospective matter involving Meridian or MFG that has not yet been entered into the CMS.
No indirect relationships were identified through these enhanced procedures. Meridian does not appear as a syndicate participant, counterparty, or regulatory party in any C&H matter. The Firm has no ongoing advisory, lending, litigation, regulatory, or other professional relationship with Meridian National Bank, N.A. or Meridian Financial Group, Inc.
Resolution: No indirect relationship identified. Enhanced check completed with negative results.
6.3 PRCP Consent Right
Pinnacle Ridge Capital Partners, LP, as the 62% majority owner of Skybridge Fintech Ltd., holds a contractual consent right over Skybridge contracts exceeding Twenty-Five Million Dollars ($25,000,000) in total contract value. This consent right is set forth in the Skybridge Limited Liability Company Agreement, as amended in connection with PRCP's 2021 Series C investment. The proposed MSA with Meridian, with a total contract value of Fifty Million Dollars ($50,000,000), exceeds the consent threshold, and PRCP's prior written consent will be required before Skybridge may execute the MSA.
Pinnacle Ridge's separate outside counsel, Alcott & Grenier LLP (lead partner: Simone Alcott), will independently review the MSA on behalf of PRCP for purposes of exercising the consent right. This review is expected to focus on the commercial terms, risk allocation provisions, and financial impact of the MSA on Skybridge, consistent with PRCP's fiduciary and economic interests as majority equity holder.
This parallel review arrangement does not create an attorney-client conflict for C&H. The following analysis supports this conclusion:
(a) C&H's client is Skybridge, not PRCP. C&H has never maintained an engagement letter with PRCP, and PRCP is not a client of the Firm. C&H's duties of loyalty and confidentiality run to Skybridge, and C&H will represent Skybridge's interests in the MSA negotiation.
(b) A&G's independent review is a customary governance mechanism. The parallel review by A&G on behalf of PRCP is a standard feature of sponsor-backed portfolio company transactions and does not create a joint representation or co-counsel relationship between C&H and A&G.
(c) No material divergence of interest is anticipated. Skybridge and PRCP share the common objective of executing the MSA on favorable terms. While PRCP's review may result in requests for modifications to the MSA terms, any such requests would be communicated through Skybridge's management and would not place C&H in a position of representing adverse interests.
(d) Appropriate boundaries. C&H will not communicate directly with A&G on behalf of PRCP; all communications regarding PRCP's consent will be channeled through David Shimura (General Counsel, Skybridge) or another authorized Skybridge representative.
Resolution: No conflict. Parallel review by PRCP's separate counsel is a standard governance mechanism that does not create a conflict for C&H.
7. Conclusion and Clearance
Based on the comprehensive conflict-of-interest search described in this memorandum — including CMS database searches using exact name match, common-variant/alias, and fuzzy-matching methodologies; supplemental manual inquiries to six practice group leaders; enhanced checks for indirect relationships with the counterparty given its SIFI status; and engagement team self-disclosure questionnaires — no disqualifying conflicts of interest have been identified with respect to Calderwood & Harkness LLP's proposed representation of Skybridge Fintech Ltd. in connection with the enterprise Master Software-as-a-Service Agreement with Meridian National Bank, N.A.
Specifically:
(a) Prospective Client. Skybridge Fintech Ltd. is an existing client of the Firm, and the proposed engagement is consistent with the existing client relationship. No intra-client conflict exists.
(b) Counterparty. No current or former client relationship exists with Meridian National Bank, N.A. or Meridian Financial Group, Inc. No adverse-party relationship exists. No indirect relationship was identified through enhanced checking procedures.
(c) Counterparty's Counsel. No current or former client relationship exists with Hargrove, Tully & Cascade Insurance Brokers or any of its attorneys assigned to this transaction.
(d) Majority Owner and Its Counsel. No conflict arises from Pinnacle Ridge Capital Partners' status as majority owner of the prospective client, and the parallel review by Alcott & Grenier LLP does not create a conflict for C&H.
(e) Third Parties. No current or former client relationship or adverse-party relationship exists with any of the material third parties to the transaction, including Crestfield Cyber Advisors, Inc., Orion Cloud Services, Inc., Coastal Assurance Corporation, Hathaway & Pendleton, LLP, or Sentinel Escrow Services, Inc.
(f) Engagement Team. No personal conflicts have been identified among the engagement team members. All team members confirmed the absence of any personal, financial, familial, or professional relationships with any party to the transaction.
Recommendation: The engagement is cleared to proceed. The engagement letter dated August 25, 2025, between Calderwood & Harkness LLP and Skybridge Fintech Ltd., may be executed, and the matter may be formally opened under Matter Number 1009-00007. The Conflicts Department should update the CMS to reflect the new engagement, including all parties and adverse parties identified in this memorandum.
8. Approvals
Prepared by: Nathan Ikeda, Working Associate, Bankruptcy & Restructuring Practice Group
Reviewed and Approved by: Angela Fontaine, Responsible Partner
Date of Clearance: August 28, 2025
PREPARED BY:
By: ________
Name: Nathan Ikeda
Title: Working Associate, Bankruptcy & Restructuring Practice Group
Date: ________
REVIEWED AND APPROVED BY:
By: ________
Name: Angela Fontaine
Title: Responsible Partner
Date: ________
APPENDIX A — Complete List of Entities and Individuals Searched
The following table sets forth a comprehensive reference index of all entities and individuals searched in connection with the conflict check for Matter Number 1009-00007.
APPENDIX B — CMS Search Parameters and Methodology Notes
The following sets forth the specific search parameters and methodology employed in connection with the CMS conflict search for Matter Number 1009-00007.
1. Search Platform. All searches were conducted using the C&H Conflicts Management System ("CMS"), version 8.4.2, maintained by the Firm's Conflicts Department in coordination with the General Counsel's Office. The CMS database was current as of August 26, 2025, the date the conflict check was initiated.
2. Search Types. The following three search types were employed for each entity and individual listed in Section 3 of this memorandum:
(a) Exact Match Search. The full legal name of each entity or individual was entered as a search string, and the CMS returned all records containing an exact character-for-character match.
(b) Alias / Variant Search. Known abbreviations, trade names, "doing business as" names, common misspellings, and variant punctuation forms were entered as alternative search strings. For entities, this included searches with and without entity-type designators (e.g., "Ltd.," "Inc.," "LLP," "N.A."), as well as searches for common acronyms (e.g., "MNB," "SBF," "MFG," "PRCP," "HTM," "A&G," "H&P"). For individuals, this included searches for first name / last name combinations in both orders, as well as searches by last name alone with manual review of returned results.
(c) Fuzzy Match Search. The CMS fuzzy-matching algorithm was applied at an 85% similarity threshold. This threshold means that any CMS record with a string similarity score of 85% or greater relative to the search query was returned as a potential match and manually reviewed. The fuzzy-matching algorithm accounts for character transpositions, insertions, deletions, and substitutions, and is designed to capture matches that might be missed due to minor data entry errors, alternate spellings, or transliteration differences.
3. Date Range. The searches covered the following date ranges:
(a) Current client engagements — all active engagement records in the CMS, regardless of engagement start date.
(b) Former client engagements — engagement records closed within the preceding five (5) years (i.e., engagements closed on or after August 28, 2020).
(c) Adverse parties — all parties identified as adverse in open matters and in matters closed within the preceding five (5) years (i.e., matters closed on or after August 28, 2020).
(d) Prospective clients (declined engagements) — records from declined engagements within the preceding three (3) years (i.e., declined on or after August 28, 2022).
(e) Business relationships — all recorded co-counsel, referral, vendor, and other professional relationships, regardless of date.
4. Record Categories Searched. The CMS search encompassed the following record categories: (i) client/engagement records; (ii) adverse party records; (iii) related party records; (iv) prospective client records; (v) co-counsel and referral records; and (vi) vendor and business relationship records.
5. Practice Group Leader Responses. Supplemental manual inquiry emails were sent to the leaders of six (6) practice groups, as described in Section 4.2 of this memorandum. All six (6) responses were received and documented prior to the conclusion of the conflict check on August 28, 2025. Copies of the inquiry emails and responses are on file with the Conflicts Department.
6. Engagement Team Self-Disclosure. Self-disclosure questionnaires were distributed to and returned by all five (5) members of the proposed engagement team, as described in Section 4.3 of this memorandum. Completed questionnaires are on file with the Conflicts Department.
APPENDIX C — Practice Group Leader Response Log
The following table documents the practice group leader inquiries sent and responses received in connection with the conflict check for Matter Number 1009-00007.
All six (6) practice group leaders responded within the conflict check window. All responses are documented and on file with the Conflicts Department.
END OF MEMORANDUM
This memorandum is confidential attorney work product prepared for internal use only in connection with the conflict-of-interest analysis for Matter Number 1009-00007. It is not intended for distribution to any party outside Calderwood & Harkness LLP and is protected by the attorney work-product doctrine. Any unauthorized disclosure, copying, or distribution of this memorandum is prohibited.
Name | Role | Practice Group
Angela Fontaine | Responsible Partner | Real Estate
Renata Vasquez | Billing Partner | Labor & Employment
Liam Prescott | Of Counsel — Technology Transactions | Intellectual Property / Technology
Amy Chesterton | Lead Associate | Bankruptcy & Restructuring
Nathan Ikeda | Working Associate | Bankruptcy & Restructuring
No. | Name | Entity Type / Role | Jurisdiction / Affiliation | Category
1 | Skybridge Fintech Ltd. | Delaware limited company | Delaware | Prospective Client
2 | Priya Chandrasekaran | Individual — CEO | Skybridge Fintech Ltd. | Prospective Client Personnel
3 | Marcus Holt | Individual — CTO | Skybridge Fintech Ltd. | Prospective Client Personnel
4 | David Shimura | Individual — General Counsel | Skybridge Fintech Ltd. | Prospective Client Personnel
5 | Tara Bellingham | Individual — VP, Enterprise Sales | Skybridge Fintech Ltd. | Prospective Client Personnel
6 | Jonathan Kreske | Individual — CFO | Skybridge Fintech Ltd. | Prospective Client Personnel
7 | Amara Okafor | Individual — CISO | Skybridge Fintech Ltd. | Prospective Client Personnel
8 | Pinnacle Ridge Capital Partners, LP | Delaware limited partnership | Delaware | Client Affiliate / Majority Owner
9 | Elise Drummond | Individual — Managing Partner | Pinnacle Ridge Capital Partners, LP | Majority Owner Personnel
10 | Meridian National Bank, N.A. | National banking association | Federal charter (OCC) | Counterparty
11 | Meridian Financial Group, Inc. | Delaware corporation (NYSE: MFG) | Delaware | Counterparty Parent
12 | Gerald Brannigan | Individual — CIO | Meridian National Bank, N.A. | Counterparty Personnel
13 | Sandra Petrov | Individual — Head, Financial Crimes & Compliance | Meridian National Bank, N.A. | Counterparty Personnel
14 | Luis Arriaga | Individual — SVP, Procurement & Vendor Management | Meridian National Bank, N.A. | Counterparty Personnel
15 | Catherine Woo | Individual — Assoc. General Counsel — Technology | Meridian National Bank, N.A. | Counterparty Personnel
16 | Hargrove, Tully & Cascade Insurance Brokers | New York limited liability partnership | New York | Counterparty's Outside Counsel
17 | Douglas Krenshaw | Individual — Partner | Hargrove, Tully & Cascade Insurance Brokers | Counterparty's Outside Counsel
18 | Megan Faircloth | Individual — Senior Associate | Hargrove, Tully & Cascade Insurance Brokers | Counterparty's Outside Counsel
19 | Ryan Tso | Individual — Associate | Hargrove, Tully & Cascade Insurance Brokers | Counterparty's Outside Counsel
20 | Alcott & Grenier LLP | DC limited liability partnership | District of Columbia | Majority Owner's Outside Counsel
21 | Simone Alcott | Individual — Partner | Alcott & Grenier LLP | Majority Owner's Outside Counsel
22 | Crestfield Cyber Advisors, Inc. | Delaware corporation | Delaware / Illinois | Third Party — Security Auditor
23 | Winston Lam | Individual — CEO | Crestfield Cyber Advisors, Inc. | Third Party Personnel
24 | Deepa Rajan | Individual — Lead Auditor | Crestfield Cyber Advisors, Inc. | Third Party Personnel
25 | Orion Cloud Services, Inc. | Delaware corporation | Delaware / California | Third Party — IaaS Provider
26 | Coastal Assurance Corporation | Connecticut stock insurance corporation | Connecticut | Third Party — E&O/Cyber Insurer
27 | Hathaway & Pendleton, LLP | Illinois limited liability partnership | Illinois | Third Party — Financial Auditor
28 | Bruce Ogilvie | Individual — Lead Audit Partner | Hathaway & Pendleton, LLP | Third Party Personnel
29 | Sentinel Escrow Services, Inc. | California corporation | California | Third Party — Source Code Escrow Agent
Practice Group | Practice Group Leader | Date of Inquiry | Date of Response | Result | Notes
Real Estate | Margaret Dunleavy | August 26, 2025 | August 27, 2025 | No conflict identified | Confirmed no matters involving any searched party.
Labor & Employment | Robert Tanaka | August 26, 2025 | August 26, 2025 | No conflict identified | Confirmed no employment or labor matters involving any searched party.
Bankruptcy & Restructuring | Helen Reyes Linley CPAs LLP | August 26, 2025 | August 27, 2025 | No conflict identified | Confirmed no insolvency or restructuring matters involving any searched party.
Corporate & Transactions | Steven Bancroft | August 26, 2025 | August 27, 2025 | No conflict identified | Confirmed no corporate, M&A, or investment transactions involving any searched party.
Financial Services | Patricia Moreland | August 26, 2025 | August 28, 2025 | No conflict identified | Enhanced review conducted given Meridian's SIFI status. No regulatory, advisory, or lending relationship identified.
Intellectual Property / Technology | James Whitfield | August 26, 2025 | August 27, 2025 | No conflict identified | Confirmed no technology transactions, IP disputes, or licensing matters involving any searched party.