Trupanion Investor PresentationMarch 2017

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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 and financial objectives and its future operating results and expenditures. 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; actual claims 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 or regulatory 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.

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Our Mission

Our mission is to help

the pets we all love

receive the best

veterinary care

4

Trupanion at a Glance

• Pure-play focused on simple, fair and 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

37 Consecutive Quarters of 25%+ Revenue Growth

98.60%Average Monthly Retention 2

Strong Member Loyalty

36%Total Revenue5-year CAGR 1

1 As of 12/31/16. 2 For the 12-month period ended 12/31/2016. Average monthly retention is calculated as the monthly retention rate of enrolled pets for each applicable period averaged over the 12 months

prior to the period end date.

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Compelling Value PropositionFor 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

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Predictable High Growth Subscription Model

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

$0

$10.0

$20.0

$30.0

$40.0

$50.0

$60.0

$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

Total Revenue by New vs. Existing Pets(dollars, in millions)

Existing Pets New Pets

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2001 2002 2003 2004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 2016E

$29 $30$32

$34$36

$39$41

$43$46

$48$51

$53$56

$58$60

$63Chart Title

• Total pet spend in U.S. estimated at $63 billion in 2016

• Consistent growth through recessionary periods

• Veterinarian industry spend has grown at a similar rate (a 5% CAGR since 2001, totaling $15 billion in 2015)

Total U.S. Pet Industry Spend 1

CAGR: 5%

U.S. Pet Owners Spend Generously on Their Pets

($ in billions)

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

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U.S.

Cana

da

Franc

eDe

nmark

Nethe

rland

s

Norw

ay U.K.

Swed

en

1% ~2%

5% 5%8%

14%

25%

40%

The Market for Medical Insurance for Petsis Underpenetrated in North America

1 American Pet Products Association, National Pet Owners Survey, 2015 – 2016.2 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 December 31, 2016.

Massive Underpenetrated Market 1,2,3,4

180 Million Pets in U.S. & Canada

1.00% 2.50% 5.00% 7.50% 25.00%

$1.0$2.4

$4.8

$7.2

$23.9Chart Title

% 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 180MIllustrative Monthly Average Revenue Pet Pet(5)

Penetration in the UK

$49.17

25%

Total Addressable Market $26.6B

($ in billions)

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• 16 million cats & dogs• 4,200 vet hospitals• 25% market penetration• First offered: 1970

United Kingdom

United States

• 164 million cats & dogs• 30,000 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 consumerх Provided limited coverage, excluding the

conditions most likely to occurх 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

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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 that has had a pet enrolled over the three previous months 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.

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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

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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

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Established Deep Veterinary Relationships

Territory Partner and Veterinary Footprint 1…

• Territory Partners represent long-term investment in veterinary relationships

• Over 80 Territory Partners

– Each cover on average~250 veterinary hospitals

– Over 86,000 vet hospital visits in 2015

• Un-replicated within market

• Over 7,600 veterinary hospitals actively recommend Trupanion 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 3

7%54% 15%

Veterinary Leads

Online Leads

Point of Sale,

All Other

24%

Add a Pet,

Friend

ExistingMembers

NewMembers

Nearly 80% of leads from referral sources that are not directly

compensated

1 As of December 31, 20152 Defined as a hospital that has had a pet enrolled over the three previous months3 As of December 31, 2016

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Expected Claim per Pet per Month Other

• 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 16 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 30% margin

Cat Dog English Bulldog English Bulldog in NY

$26.85$39.78

$57.31$65.88$11.51

$17.05

$24.56

$28.23

$38.36

$56.83

$81.87

$94.11

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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

Illustrative Legacy Model

TrupanionModel

50%70%

0.2

30% 30%

Profits Before Other CostsFrictional CostsFully-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

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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

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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

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12/31

/10

12/31

/11

12/31

/12

12/31

/13

12/31

/2014

12/31

/2015

12/31

/2016

57

89

127

182

232

292

344

2011 2012 2013 2014 2015 2016

$37$55

$77

$104

$134

$173$7

$12

$14

$15

Subscription Revenue Other Revenue

Member-Centric Approach Driving Growth

Total Enrolled Pets 1 Total Revenue 2

CAGR: 35%

(in thousands) 18% YOY Growth

CAGR: 38%

28% YOY Growth

$37

$56

$84

$116

$147

($ in millions)

1 Cumulative as of December 31st for each respective year from 2010 to 20162 Includes subscription business segment and other business segment. Other business segment primarily includes revenue from plans not marketed directly to consumers

$188

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Annual Cash Flow from Illustrative Member

1Cumulative Cash Flow from Illustrative

Member 1

FY 20165.1X

LVP to PAC

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 December 31, 2016 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

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

($150)

($100)

($50)

$0

$50

$100

$150

($123)

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

($200)

($100)

$0

$100

$200

$300

$400

$500

$600

($123)

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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 2016 Q2 2016 Q3 2016 Q4 2016 Long-Term Target

Revenues 100% 100% 100% 100% 100% 100% 100% 100% 100% 100%Cost of goods 68% 67% 69% 70% 71% 72% 71% 71% 70% 70%Variable expenses 12% 14% 14% 12% 11% 11% 11% 12% 11% 10%Fixed expenses (1) 15% 14% 17% 15% 10% 11% 10% 9% 10% 5%

Adjusted operating margin 5.3% 5.1% 0.7% 2.4% 7.9% 6.3% 8.6% 8.4% 8.1% 15%

Acquisition cost 12% 10% 10% 10% 8% 9% 7% 8% 7%Adjusted EBITDA -7% -5% -9% -8% 0% -2% 1% 1% 1%Net loss -12% -10% -18% -12% -4% -6% -2% -3% -3%

Free cash flow (in thousands) (3,598)$ (2,496)$ (16,434)$ (15,319)$ 3,065$ (1,951)$ 1,121$ 852$ 3,043$

Thank You