TWL Annual General Shareholders' Meeting - Presentation

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 20261

Alasdair MacLeod
Chair
Welcome
TradeWindow | Annual General Meeting of Shareholders | September 20262

Disclaimer
This presentation has been prepared by Trade Window Holdings Limited (TradeWindow). All information is current at the date ofthis 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 releasesand 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 theaccuracy 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 20263

V I R T U A L M E E T I N G
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 20264

V I R T U A L M E E T I N G
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 20265

TradeWindow | Annual General Meeting of Shareholders | September 20266
Agenda
Chair address2
Chief Executive's address10
Shareholder questions24
Resolutions25
Other business and voting29
Meeting close30
Directors
Kerry FriendPhil Norman
Andrew Balgarnie
Susan Beling
Brodie Collins

G R O W T H
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
$12.0
FY25FY26FY27 guidance
NZ$(m)
Trading revenue and EBITDA result (NZ$m)
Trading revenueEBITDA result
28%
ARR compound annual growth rate
1
30%
Australian revenue CAGR, our fastest-
growing region
2
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 revenuecolumn 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 reconciledto 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 20267
26%
Reduction in net loss after tax in FY26
$4.0m
Net cash at 30 June 2026, sufficient to carry
through to profitability

C A P I T A L M A R K E T S
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 20268

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&Publicsector
-
FOCUS
-Enhance Customer/User Experience
-Execution
-Capital
-Accountability
Chief Executive Officer
9

M A R K E T P O S I T I O N
Number one in New Zealand. Number two in Australia.
A narrow competitive field, and one the regulator has just intervened to keep open
#1
N E W Z E A L A N D S H I P P E R S E G M E N T
Shippers are exporters and importers. We sit in the critical path of every
one of our customer’s shipments.
#2
A U S T R A L I A , B E H I N D W I S E T E C H G L O B A L
Our fastest-growing region, and the only market where a competitor sits
ahead of us.
O N E C O M P E T I T O R W I T H M E A N I N G F U L T R A C T I O N . T H E R E S T A R E N E W E N T R A N T S .
Expedient
Carved out of WiseTech'se2Open 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 202610

C U S T O M E R S
The names behind the numbers
546 customers, including some of Australasia's largest shippers and freight forwarders
S H I P P E R S ( I M P O R T E R S A N D E X P O R T E R S )F R E I G H T F O R W A R D E R S
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 202611

G R O W T H S T R A T E G Y
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 202612
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 Desktopgap
✓
Development team
Executing the current roadmap
KEY GAP
Chief Technology Officer
Architecture • technical decisions •
FreightAIcritical 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 202613
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 202614

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
FreightAIfrom 2027
Use Freight Desktop to deliver and prove AI now, while building the complete platform customers can ultimately migrate to.
NOW
SEP 2027
RELEASESEPTEMBER2027
FreightAI operating platform
A build to runthe 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 →Carrythe capability and learning into FreightAI.
16
TradeWindow | Annual General Meeting of Shareholders | September 2026

T R A C T I O N
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 202618
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 diversified
1
.
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
19TradeWindow | Annual General Meeting of Shareholders | September 2026
1
FY26

TradeWindow | Annual General Meeting of Shareholders | September 202630
ANNUAL MEETING
Meeting close

FOR REFERENCE
Appendix
TradeWindow | Annual General Meeting of Shareholders | September 202631

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 FreightAIplatform 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 202632

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 202633

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 202634
Andrew Balgarnie
Executive Director, TradeWindow
+64 275 594 133 | andrew@tradewindow.io | tradewindow.io