Trupanion Investor Presentation

May 2017

2

Legal Disclaimers

This presentation contains forward-looking statements within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934 relating to, among other things, expectations, plans, prospects and financial results for Trupanion, including, but not limited to, its expectations regarding its ability to execute its business plans. These forward-looking statements are based upon the current expectations and beliefs of Trupanion’s management as of the date of this press release, and are subject to certain risks and uncertainties that could cause actual results to differ materially from those described in the forward-looking statements. All forward-looking statements made in this press release are based on information available to Trupanion as of the date hereof, and Trupanion has no obligation to update these forward-looking statements.

In particular, the following factors, among others, could cause results to differ materially from those expressed or implied by such forward-looking statements: the ability to achieve or maintain profitability and/or appropriate levels of cash flow in future periods; the accuracy of assumptions used in determining appropriate member acquisition expenditures; the severity and frequency of claims; the ability to maintain high retention rates; the accuracy of assumptions used in pricing medical plan subscriptions and the ability to accurately estimate the impact of new products or offerings on claims frequency; actualclaims expense exceeding estimates; regulatory and other constraints on the ability to institute, or the decision to otherwise delay, pricing modifications in response to changes in actual or estimated claims expense; the effectiveness and statutory orregulatory compliance of our Territory Partner model and of our Territory Partners, veterinarians and other third parties in recommending medical plan subscriptions to potential members; the ability to increase the number of Territory Partners and active hospitals; compliance by us and those referring us members with laws and regulations that apply to our business, including the sale of a pet medical plan; fluctuations in the Canadian currency exchange rate; the ability to protect our proprietary and member information; the ability to maintain our culture and team; the ability to maintain the requisite amount of risk-based capital; the ability to protect and enforce Trupanion’s intellectual property rights; third-party claims including litigation and regulatory actions; and the ability to recognize benefits from investments in new solutions and enhancements to Trupanion’s technology platform and website.

For a detailed discussion of these and other cautionary statements, please refer to the risk factors discussed in filings with the Securities and Exchange Commission (SEC), including but not limited to, Trupanion’s Annual Report on Form 10-K for the year ended December 31, 2016 and any subsequently filed reports on Forms 10-Q and 8-K. All documents are available through the SEC’s Electronic Data Gathering Analysis and Retrieval system at www.sec.gov or the Investor Relations section of Trupanion’s website at http://investors.trupanion.com.

In addition to U.S. GAAP financials, this presentation includes certain non-GAAP financial measures. These non-GAAP measures are in addition to, not a substitute for or superior to, measures of financial performance prepared in accordance with U.S. GAAP. A reconciliation of non-GAAP financial measures to the corresponding GAAP measures is provided on our Investor Relations website.

3

Our Mission

Our mission is to help

the pets we all love

receive the best

veterinary care

4

Trupanion at a Glance

• Simple, fair & high-value medical insurance for pets

• Comprehensive, lifelong coverage for dogs and

cats, including hereditary and congenital

conditions (i.e., the most likely conditions to occur)

• Pet owners are free to choose any veterinarian,

emergency care, or specialty hospital

• 90% of covered veterinary costs as invoiced, with

no payout limits

• Individual pets are not penalized for needing

treatment or getting older

• Veterinarians can be paid directly, and nearly

instantaneously with Trupanion Express™

Driving Category Growth

38 Consecutive Quarters of

25%+ Revenue Growth

98.58%Average Monthly Retention 2

Strong Member Loyalty

36%Total Revenue

5-year CAGR 1

1 As of 12/31/16. 2 For the 12-month period ended 3/31/2017. Average monthly retention is calculated as the monthly retention rate of enrolled subscription pets for each applicable period averaged over the 12

months prior to the period end date.

5

Compelling Value Proposition

For Both Pet Owners & Veterinarians

• Comprehensive coverage that gives

pet owners flexibility in choice of care

• Provides peace of mind

• Eliminates financial uncertainty and

reduces financial burden

• Pays veterinarian invoices quickly &

seamlessly

• Ability to practice at the highest level

• Freedom to be the most effective

advocate for the pet

• Increased revenue growth & pet

economics

For Pet Owners For Veterinarians

Trupanion unites pet owners & veterinarians to provide the best care for the pets they love

6

$3.1$4.4

$5.3$6.3

$7.6$8.8

$9.9$10.7

$12.0$13.2

$14.5$15.9

$17.8

$19.8

$22.1

$24.0$25.6

$28.1

$30.3$31.9

$33.3

$35.6

$37.9

$40.2

$42.7

$45.8

$48.4

$51.3

$54.7

$0

$10.0

$20.0

$30.0

$40.0

$50.0

$60.0

Q1

'10

Q2

'10

Q3

'10

Q4

'10

Q1

'11

Q2

'11

Q3

'11

Q4

'11

Q1

'12

Q2

'12

Q3

'12

Q4

'12

Q1

'13

Q2

'13

Q3

'13

Q4

'13

Q1

'14

Q2

'14

Q3

'14

Q4

'14

Q1

'15

Q2

'15

Q3

'15

Q4

'15

Q1

'16

Q2

'16

Q3

'16

Q4

'16

Q1

'17

Total Revenue by New vs. Existing Pets

(dollars, in millions)

Existing Pets New Pets

Predictable High Growth Subscription Model

7

$29$30

$32$34

$36$39

$41$43

$46

$48

$51$53

$56$58

$60

$67

$69

2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 20162017E

• Total pet spend in U.S.

estimated at $69 billion in

2017

• Consistent growth through

recessionary periods

• Veterinarian industry spend

has grown at a similar rate (a

5% CAGR since 2001, totaling

$16 billion in 2016)

Total U.S. Pet Industry Spend 1

U.S. Pet Owners Spend Generously

on Their Pets

($ in billions)

1 Source: APPA US Pet Industry Spending Figures & Future Outlook.

8

1% ~2%

5% 5%

8%

14%

25%

40%

The Market for Medical Insurance for Pets

is Underpenetrated in North America

1 American Pet Products Association, National Pet Owners Survey, 2017 – 2018.2 Kynetec on behalf of the Canadian Animal Health Institute, CAHI Estimate of Canadian Dog and Cat Population Survey, 2016.3 Packaged Facts, a division of Market Research Group, LLC, Pet Insurance in North America, 5th Edition, October 2013.4 Munich RE, How to Unlock the Potential of Pet Health?, May 2013.5 Represents our monthly average revenue per pet for the three month period ended March 31, 2017.

Massive Underpenetrated Market 1,2,3,4

200 Million Pets in U.S. & Canada

$1.2

$3.0

$6.1

$9.1

$30.3

1.0% 2.5% 5.0% 7.5% 25.0%% of Pets with

Insurance:

United States and Canada

are significantly

underpenetrated when

compared to many other

developed countries

Potential Market Size by Penetration Rate

Pets in the U.S. and Canada 200M

Illustrative Monthly Average Revenue

Per Pet(5)

Penetration in the UK

$50.50

25%

Total Addressable Market $30.3B

($ in billions)

9

• 16 million cats & dogs

• 4,200 vet hospitals

• 25% market penetration

• First offered: 1970

United Kingdom

United States

• 184 million cats & dogs

• 28,000 vet hospitals

• 1% market penetration

• First offered: 1982

U.K. Product (the Trupanion approach)

Sourced primarily from veterinary referrals;

appealed to new customers with vet-issued

trial certificates

Provided broad coverage

Generated high satisfaction rates with pet

owners and veterinarians

Legacy U.S. Product (an insurance-minded approach)

х Sourced primarily direct to consumer

х Provided limited coverage, excluding the conditions

most likely to occur

х Imposed pricing caps and fee schedules

х Generated low satisfaction rates with pet owners

and veterinarians

Penetration Driven by Product Value

Proposition

Trupanion’s product offering aligns with the U.K. value proposition and marketing strategy

10

Attractive Trupanion Adoption & Economics

in Relatively Established Markets

• Region of Western Canada (entered 2003)

• Territory Partner presence for >10 years

• Human population of ~2.7 million

• Cats & dogs population of ~1.3 million

• >18,000 Trupanion enrolled pets1

• High penetration rates:

− 2/3rd active hospital base1,2

− Quotes generated each month equal to

~25% of estimated number of pets acquired2

− ~5% of new pets enrolling with TRUP each

month1

• Accelerated growth:

− Annual pet growth > 20%3

− Annual revenue growth > 30%3

• Attractive economics:

− LVP to PAC > 5:11

Regional Case Study Analysis

Trupanion issued first policy in Canada in 2000 and first policy in the U.S. in 2008

1 For the period ended June 30, 2015.2 Defined as a hospital to which we’ve attributed a new enrollment within the past 90 days.3 For the annual period ended December 31, 2014.

The above numbers are as of Q2 2015. For competitive reasons, we are not providing ongoing disclosure of this cohort.

11

Barriers Against Competition

Superior Value Proposition for Pet

Owners

Established Deep Veterinarian Relationships

Data Driven Advantage

Proprietary Platform Enhanced by Trupanion

Express™

1

2

3

4

12

Superior Value Proposition for Pet Owners1

Key Categories Better Providers Legacy U.S. Providers

Coverage• Full coverage excl. pre-

existing conditions

• Pays 90% of actual vet bill

• Full coverage excl. pre-

existing conditions

• Pays 70-100% of actual

vet bill

• Limited coverage excludes

congenital, hereditary &

pre-existing conditions

• Reimbursement based on

fee schedules & price caps

Pricing

• No fee increases for

treatment

• Cost adjusts with cost of

care for that specific pet

sub-category

• Pet owner may apply any

deductible ($0-$1,000) to

customize pricing

• Millions of pricing

categories

• Increases for age of pet

and cost of care

• Few deductible options

• Increases for age of pet,

prior claims and/or cost of

care

• Few deductible options

Direct Payment vs.

Pet Owner

Reimbursement

• Trupanion Express™

enables instantaneous,

paper-free claims and

direct payment of

invoices at treatment

• Traditional

reimbursement model

• Traditional reimbursement

model

13

Established Deep Veterinary Relationships

Territory Partner and Veterinary Footprint …

• Territory Partners represent long-term investment

in veterinary relationships

• Over 100 Territory Partners 1

– Each cover on average

~250 veterinary hospitals

– Over 86,000 vet

hospital visits in 2015

• Un-replicated within market

• Over 8,100 veterinary hospitals

actively recommend Trupanion at peak 2016

levels with long-term target of 20,000 2

2

..Drives Efficient Pet Acquisition Model

• Multi-faceted approach to driving sales

leads across channels

Pet Acquisition Channels 1

7%54% 15%

Veterinary

Leads

Direct-to-

Consumer

Leads

Point of

Sale,

All Other

24%

Add a

Pet,

Friend

ExistingMembers

New

Members

Nearly 80% of leads from referral sources

that are not directly compensated

1 As of December 31, 2016.2 Defined as a hospital to which we’ve attributed a new enrollment within the past 90 days.

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• Millions of pricing categories

• Over 10 million medical plan months

• Over 1.5 million claims received

• Breed, postal code and age among

the pricing categories used to

measure risk

Extensive data amassed over 17 years provides significant competitive advantages

Illustrative Pricing Examples

3 Data Driven Advantage

1 All data as of December 31, 2016.

Comprehensive data helps us

understand the risk of each pet and

add a reasonable margin$26.85

$39.78

$57.31$65.88$11.51

$17.05

$24.56

$28.23

$38.36

$56.83

$81.87

$94.11

Cat Dog English Bulldog English Bulldog in NY

Expected Invoiced Amount per Pet per Month Expected Profit per Pet per Month

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• Business model designed to eliminate frictional

costs:

– Own only N.A. insurance company focused on

medical care for pets

– In-house actuaries, claims & contact center for

quality control and speed

– Dedicated national Territory Partner network

– No brand licensing fees

– Proprietary underwriting technology

50%70%

20%

30% 30%

Illustrative Legacy

Model

Trupanion

Model

Profits Before Other Costs

Frictional Costs

Fully-loaded Claim Payout

4

Proprietary Platform Enhanced by

Trupanion Express™

~20% in

frictional

cost

Strategic choice to

provide customer

structural benefit

by paying ~20%

more on claims

Proprietary Platform Provides Cost Advantage Value Proposition Enhanced by Trupanion Express™

• Eliminates paperwork and uncertainty of

coverage

– Customers avoid having to pay out of pocket

– Veterinarians streamline billing process and

eliminate credit card fees

– Trupanion enhances data connectivity with

veterinarians

• Un-replicated in the market

Trupanion Express™Illustrative Comparison of Cost Structure

16

Our Mission Driven Model Resonates with

Third Parties

“I had the opportunity to meet with a broad cross

section of Trupanion’s people in Seattle… What I

experienced was a group of people who are

confident, ambitious, energized and, above all,

purpose driven.”

– Robert Vinall, RV Capital, quote from his annual

investor letter

“In Trupanion’s case, it is easy to underestimate how

important trust will be in shaping the Industry… trust must

be continuously earned by being deserved…which is

expressed as a mission-driven culture.”

– Josh Tarasoff, Greenlea Lane Capital Partners, quote

from his annual investor letter

Financial Review

18

Compelling Financial Model

• High growth business capturing underpenetrated market

• Monthly subscription model with recurring and visible revenues

• Strong lifetime value and proven customer unit economics

• Attractive long-term margin profile

19

$37

$55

$77

$104

$134

$173

$39$50

$7

$12

$14

$15

$4

$5

2011 2012 2013 2014 2015 2016 3/31/16 3/31/17

Subscription Revenue Other Revenue

Member-Centric Approach Driving Growth

Total Enrolled Pets 1 Total Revenue 2

(in thousands)19% YOY

Growth28% YOY

Growth

$37

$56

$84

$116

$147

($ in millions)

1 Cumulative as of December 31st for each respective year from 2010 to 2016, and the three months ended March 31, 2016 and 2017.2 Cumulative as of December 31st for each respective year from 2011 to 2016, and the three months ended March 31, 2016 and 2017. Includes subscription business segment and other business segment. Other

business segment primarily includes revenue from plans not marketed directly to consumers.

$188

57

89

127

182

232

292

344

307

364

2010 2011 2012 2013 2014 2015 2016 3/31/16 3/31/17

$43

$55

20

Annual Cash Flow from Illustrative Member 1 Cumulative Cash Flow from Illustrative Member 1

2, 3

LVP

PAC

Near Term Investment Drives Long Term

Cash Flows

Breakeven in

~15 months

1 Based on lifetime value of a pet and average pet acquisition cost as of March 31, 2017 in subscription business segment.2 Lifetime value of a pet (LVP) is calculated in part based on gross profit from our subscription business segment for the 12 months prior to the period end date excluding stock-based compensation expense

related to cost of revenue from our subscription business segment, sign-up fee revenue and the change in deferred revenue between periods, multiplied by the implied average subscriber life in months.3 Pet acquisition cost (PAC) is calculated as net acquisition cost divided by the total number of new subscription pets enrolled in that period. Net acquisition cost, a non-GAAP financial measure, is calculated in

a reporting period as sales and marketing expenses, excluding stock-based compensation, offset by sign-up fee revenue and other business segment sales and marketing expenses.

Marketing costs are expensed up front while revenue is realized over the life of the member

($128)($150)

($100)

($50)

$0

$50

$100

$150

Year 0 Year 1 Year 2 Year 3 Year 4 Year 5 Year 6 Year 7

($128)

($200)

($100)

$0

$100

$200

$300

$400

$500

$600

Year 0 Year 1 Year 2 Year 3 Year 4 Year 5 Year 6 Year 7Q1 20175.0X

LVP to PAC

21

Attractive Long Term Margin Profile

1 In 2016, the fixed expenses were comprised of 7% G&A and 3% Core IT. In 2015, the fixed expenses were comprised of 9% G&A, 4% Core IT and 2% related to our Direct Pay Initiative. In 2014, the fixed expenses were comprised of 10% G&A, 4% Core IT and 3% related to our Direct Pay Initiative.

% of Revenue 2012 2013 2014 2015 2016 Q1 2017Long-Term

Target

Revenues 100% 100% 100% 100% 100% 100% 100%

Cost of goods 68% 67% 69% 70% 71% 71% 70%

Variable expenses 12% 14% 14% 12% 11% 12% 10%

Fixed expenses (1) 15% 14% 17% 15% 10% 9% 5%

Adjusted operating margin 5.3% 5.1% 0.7% 2.4% 7.9% 8.0% 15%

Acquisition cost 12% 10% 10% 10% 8% 7%

Adjusted EBITDA -7% -5% -9% -8% 0% 1%

Net loss -12% -10% -18% -12% -4% -3%

Free cash flow (in thousands) (3,598)$ (2,496)$ (16,434)$ (15,319)$ 3,065$ 1,395$

Thank You