Announcement PDF Business-critical software for shippers and freight forwarders Annual Shareholders Meeting Auckland 29 September 2026 NZX / ASX: TWL TradeWindow | Annual General Meeting of Shareholders | September 2026 1 Alasdair MacLeod Chair Welcome TradeWindow | Annual General Meeting of Shareholders | September 2026 2 Disclaimer This presentation has been prepared by Trade Window Holdings Limited (TradeWindow). All information is current at the date of this presentation, unless stated otherwise. All currency amounts are in New Zealand dollars unless stated otherwise. Information in this presentation: • is for general information purposes only, and does not constitute, or contain, an offer or invitation for subscription, purchase, or recommendation of securities in TradeWindow for the purposes of the Financial Markets Conduct Act 2013 or otherwise, or constitute legal, financial, tax, financial product, or investment advice; • should be read in conjunction with, and is subject to, TradeWindow's Financial Statements and Annual Reports, market releases and information published on TradeWindow's website (tradewindow.io); • includes forward-looking statements about TradeWindow and the environment in which TradeWindow operates, which are subject to uncertainties and contingencies outside TradeWindow's control. TradeWindow's actual results or performance may differ materially from these statements; • includes statements relating to past performance information for illustrative purposes only and should not be relied upon as (and is not) an indication of future performance; • may contain information from third parties believed to be reliable, however, no representations or warranties are made as to the accuracy or completeness of such information; • contains references to the market capitalisation, revenue and valuation multiples of third-party listed companies. These are derived from publicly available data as at the dates stated and have not been independently verified. They are included for illustrative comparison only and are not a valuation of TradeWindow; and • non-GAAP financial information does not have a standardised meaning prescribed by GAAP and therefore may not be comparable to similar financial information presented by other entities. The non- GAAP financial information included in this document has not been subject to review by auditors. Non-GAAP measures are used by management to monitor the business and are useful to provide investors to assess business performance. TradeWindow | Annual General Meeting of Shareholders | September 2026 3 VIRTUAL MEETING How to participate – asking questions Shareholders and proxyholders can put questions to the board before and during the meeting. Written questions Questions may be submitted ahead of the meeting. During the meeting, select the Q&A tab on the right of your screen, type your question into the field and press submit. Help during the meeting The Q&A tab is also the fastest way to reach a Computershare representative if you need assistance at any point. TradeWindow | Annual General Meeting of Shareholders | September 2026 4 VIRTUAL MEETING How to participate – voting Voting opens during the meeting and is cast on screen through the Vote tab. When voting opens Once voting has been opened, the resolutions and voting options will appear on your screen. Casting your vote Select the Vote tab and choose your voting direction. You can vote on all resolutions at once, or one by one. Confirming your vote Your vote is cast when the tick appears. To change it, select ‘Change Your Vote’. TradeWindow | Annual General Meeting of Shareholders | September 2026 5 TradeWindow | Annual General Meeting of Shareholders | September 2026 6 Agenda Chair address 2 Chief Executive's address 10 Shareholder questions 24 Resolutions 25 Other business and voting 29 Meeting close 30 Directors Kerry Friend Phil Norman Andrew Balgarnie Susan Beling Brodie Collins GROWTH Revenue rising, losses falling Growth and cost discipline are converging 8.0 9.6 11.1 -1.5 -1.2 -0.3 -$4.0 -$2.0 $0.0 $2.0 $4.0 $6.0 $8.0 $10.0 $12.0 FY25 FY26 FY27 guidance NZ$(m) Trading revenue and EBITDA result (NZ$m) Trading revenue EBITDA result 28% ARR compound annual growth rate1 30% Australian revenue CAGR, our fastest- growing region2 20% Growth in average revenue per shipper customer in 1Q27 19% Growth in average revenue per freight forwarder customer in 1Q27 FY25 and FY26 trading revenue and EBITDA results are audited. The lighter columns are guidance, not results. The FY27 revenue column is the midpoint of published guidance of 13% to 18% growth. The FY27 EBITDA point illustrates guidance to be close to EBITDA breakeven and is not itself a guided figure. EBITDA is a non-GAAP measure, defined and reconciled to net profit after tax in the FY26 Annual Report. Forward-looking information should be read with the key assumptions in the appendix. 1 Annual Recurring Revenue compound annual growth rate to FY26 2 Australian revenue compound annual growth rate FY23 to FY26 TradeWindow | Annual General Meeting of Shareholders | September 2026 7 26% Reduction in net loss after tax in FY26 $4.0m Net cash at 30 June 2026, sufficient to carry through to profitability CAPITAL MARKETS Moving our primary listing to the ASX We intend to migrate. Australia is where our growth is, and where the investors who understand this sector already are. A deeper pool of capital Far greater liquidity and a much larger base of institutional capital. Investors and brokers who know this sector Assessed by people who already follow our peers and know how to value them. Listed where our growth is Our fastest-growing region. The listing follows the business. An Australian board to match Susan Beling and Brodie Collins, appointed August 2026. Both Australian, both freight forwarding operators. The application to migrate TradeWindow's primary listing to the ASX, and the appointment of Susan Beling and Brodie Collins as directors, have been announced to the market. Refer to TradeWindow's market releases at nzx.com/companies/TWL. Migration remains subject to ASX approval and there is no certainty as to timing. TradeWindow | Annual General Meeting of Shareholders | September 2026 8 Dewald van Remsburg TradeWindow | Annual General Meeting of Shareholders | September 2026 TradeWindow - 2019: Chief Legal Officer - 2023: Chief Operating Officer - 2026: Chief Executive officer EXPERIENCE - Corporate & Commercial law - Governance & Compliance - Operational Execution - Private & Public sector - FOCUS - Enhance Customer/User Experience - Execution - Capital - Accountability Chief Executive Officer 9 MARKET POSITION Number one in New Zealand. Number two in Australia. A narrow competitive field, and one the regulator has just intervened to keep open #1 NEW ZEALAND SHIPPER SEGMENT Shippers are exporters and importers. We sit in the critical path of every one of our customer’s shipments. #2 AUSTRALIA, BEHIND WISETECH GLOBAL Our fastest-growing region, and the only market where a competitor sits ahead of us. ONE COMPETITOR WITH MEANINGFUL TRACTION. THE REST ARE NEW ENTRANTS. Expedient Carved out of WiseTech's e2Open deal by ACCC order. Sold to Libra Software Group, June 2026. New entrants: Yojee, Clear.ai, Magaya All recent arrivals. No customer base at scale in either segment, in either market. Market position rankings and the assessment of competitor traction are management's internal estimates based on customer counts and market engagement, and have not been independently verified. Yojee reported revenue of A$0.6m in its most recent published annual report. Expedient was acquired by WiseTech Global as part of e2open in August 2025, and divested under a court-enforceable ACCC undertaking accepted on 30 December 2025. Libra Software Group announced its acquisition of Expedient in June 2026. TradeWindow | Annual General Meeting of Shareholders | September 2026 10 CUSTOMERS The names behind the numbers 546 customers, including some of Australasia's largest shippers and freight forwarders SHIPPERS (IMPORTERS AND EXPORTERS) FREIGHT FORWARDERS Logos are a selection of TradeWindow customers and do not necessarily correspond to the largest customers by revenue. Customer count is an unaudited Q1 FY27 key performance indicator. Logos remain the property of their respective owners and are used to identify customer relationships only. TradeWindow | Annual General Meeting of Shareholders | September 2026 11 GROWTH STRATEGY Clearly defined and executable growth strategy Growth and sustained accretion in shareholder value from product expansion, deeper penetration and international reach TradeWindow | Annual General Meeting of Shareholders | September 2026 12 Increase spend from existing customers • Broaden usage of TradeWindow software through cross-sell and up-sell initiatives • Expand features and functionality to increase solution stickiness and value Expand product offering • Incremental investment in Freight.AI, a modular, AI-first freight and logistics operating system • Modular architecture and scalable infrastructure enable fast onboarding of new customers Increase market penetration • Accelerate growth in Australasia through expanded sales and marketing • Establish partnerships with industry bodies to strengthen brand and drive referrals International expansion • Build scalable presence beyond Australasia, targeting USA and UK • Capital efficient low-risk geographical expansion through value accretive acquisitions targeting established solutions for shippers and freight forwarders Realising efficiencies in current business structure • Pursue targeted acquisitions to expand customer base, enhance capability, and accelerate entry into new markets • Leverage acquisitions to create cross-sell and up-sell opportunities for existing customers L E A D E R S H I P Customers, capability, capital and accountability DEWALD VAN RENSBURG Chief Executive Officer The experience most relevant to this role is the time I have spent inside TradeWindow: our customers, products, people and operating environment. BUILDING THE CAPABILITY TO EXECUTE IN PLACE The core execution team is assembled ✓ AI personnel Appointed ✓ Product Owner Appointed to bridge Desktop gap ✓ Development team Executing the current roadmap KEY GAP Chief Technology Officer Architecture • technical decisions • FreightAI critical path Recruitment underway WHAT I AM DOING AND TRACKING CUSTOMERS Product decisions grounded in real workflows DELIVERY Desktop AI + FreightAI milestones to Sep 2027 CAPABILITY CTO appointment + clear technical ownership CAPITAL & MARGIN Disciplined spend, pricing and unit economics Most of the capability is now in place. The CTO is the remaining key leadership appointment. TradeWindow | Annual General Meeting of Shareholders | September 2026 13 Discipline in execution; delivery on market expectations P R O D U C T FreightAI: leaning into our strengths The platform architecture underpinning our long-term strategy, built from the outset to scale into offshore markets. 3% to 5% Historic freight forwarder net margin, capped by scaling on headcount – Freight AI will change the equation Document intelligence Extraction and validation, with no manual data entry. Workflow automation Repetitive tasks handled by the platform, lifting throughput per head. Proprietary data Years of live trade documents. Training data others cannot replicate. Built to scale offshore Jurisdiction agnostic by design. Australasia is where we trade today, not the limit. TradeWindow | Annual General Meeting of Shareholders | September 2026 14 P R O D U C T R O A D M A P AI before 2027: delivering for a loyal customer base Use Freight Desktop to deliver and prove AI now, while building the complete platform customers can ultimately migrate to. NOW SEP 2027 NOW Freight Desktop + AI Keep improving the product customers use today and put AI into live workflows. DOCUMENTS → JOB → CUSTOMS ENTRY →HS SUPPORT → EXCEPTIONS CUSTOMS FIRST Then progressively apply proven AI to other high-value freight, operations and financial workflows. Real customers • real transactions • real feedback THE CONNECTION Build on what works in Desktop → prove AI in production → carry the capability and learning into FreightAI. 15 TradeWindow | Annual General Meeting of Shareholders | September 2026 P R O D U C T R O A D M A P FreightAI from 2027 Use Freight Desktop to deliver and prove AI now, while building the complete platform customers can ultimately migrate to. NOW SEP 2027 RELEASE SEPTEMBER 2027 FreightAI operating platform A build to run the freight transaction end-to-end on the new platform. ✓ FOUNDATION Complete 2 CORE FREIGHT Import & Export • Air & Sea Phase II on track Sep 2026 3 COMPLETE PLATFORM Billing & accounting • integrations modules • customs connectivity 4 READY TO MIGRATE Testing • controls • implementation THE CONNECTION Build on what works in Desktop → Prove AI in production → Carry the capability and learning into FreightAI. 16 TradeWindow | Annual General Meeting of Shareholders | September 2026 TRACTION Customer loyalty: ARR rising with margins steady Q1 FY27 key performance indicators (NZ$) Quality over volume. ARPC up 20% (shippers) and 19% (freight forwarders) on 546 customers, with retention improving to 90%. $2.7m Trading revenue Up 18% on Q1 FY26 $10.4m Annual recurring revenue Up 17% (vs. Q1 FY26) $36,447 ARPC/Year (Shippers) $16,480 Up 19% 63% Gross margin No change from Q4 26 546 Customers Down 1 90% Customer retention rate Up 1ppt $4.0m Cash at 30 June 2026 TradeWindow | Annual General Meeting of Shareholders | September 2026 18 ARR is calculated using subscription revenue for the month plus the monthly average of transaction revenue for the quarter, annualised. nzx.com/companies/TWL ARPC/Year (Freight Forwarders) Up 20% FY27 outlook: continued growth approaching breakeven Market leader Number one in New Zealand, number two in Australia. Fast growing revenue $9.6m revenue, $10.1m ARR, 95% recurring, well diversified1. Business critical In the critical path of every shipment. 90% retention. Product catalyst FreightAI. AI-first, no legacy debt, built to scale offshore. Approaching breakeven Approaching EBITDA breakeven in FY27, funded from existing cash. Primary listing to move to the ASX 19 TradeWindow | Annual General Meeting of Shareholders | September 2026 1 FY26 TradeWindow | Annual General Meeting of Shareholders | September 2026 30 ANNUAL MEETING Meeting close FOR REFERENCE Appendix TradeWindow | Annual General Meeting of Shareholders | September 2026 31 FORWARD-LOOKING INFORMATION Projected financials – key assumptions Forward-looking financial information is inherently subject to judgement, risks and uncertainty, including from events beyond TradeWindow's control. Key assumptions which may have a material risk to our projections include: SPECIFIC The rate and timing of new customer traction Successful retention of people with the required skills cost effectively That our next generation FreightAI platform development and commercialisation is delivered in line with plans. GENERAL No material change in the current economic conditions locally and globally No changes in accounting standards or other mandatory professional reporting requirements TradeWindow | Annual General Meeting of Shareholders | September 2026 32 DEFINITIONS Glossary Annualised Recurring Revenue (ARR) The recurring revenue for a specified month annualised. Average Revenue Per Customer (ARPC) Subscriber customers’ monthly revenue divided by the number of subscriber customers at the end of the month, averaged over the period. CAGR Compound annual growth rate. Customer retention rate The percentage of customers retained over a given period, excluding any new customers acquired during that period. Customs Broker A licenced individual who acts as an intermediary for shippers and freight forwarders in handling customs formalities for clearance and importing of goods. EBITDA Earnings before interest, taxation, depreciation and amortisation. Freight Forwarder An organisation that arranges and handles the transport of goods between countries on behalf of customers, including storage, rate negotiation and booking cargo space. Shipper An exporter or importer who requires carriers to transport goods from one location to another. Subscriber customers Customers that license and/or access TradeWindow’s software monthly. Excludes customers of pay-as-you-go platforms. Recurring revenue Revenues that are predictable and stable and recur at regular intervals. For TradeWindow this is subscription and transaction revenue. TradeWindow | Annual General Meeting of Shareholders | September 2026 33 TradeWindow INVESTOR CONTACT Dewald van Rensburg Chief Executive, TradeWindow +64 21 025 01490 | dewald@tradewindow.io | tradewindow.io TradeWindow | Annual General Meeting of Shareholders | September 2026 34 Andrew Balgarnie Executive Director, TradeWindow +64 275 594 133 | andrew@tradewindow.io | tradewindow.io