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- $115,000 to $145,000 USD / year
- Contract
- Remote
Subscriptions and churn: own the subscription program for both brands, keep at least one save or retention test live every week, grow the share of new customers who subscribe (working with…
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KittySpout
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- $115,000 to $145,000 USD / year
- Contract
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Subscriptions and churn: own the subscription program for both brands, keep at least one save or retention test live every week, grow the share of new customers who subscribe (working with…
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KittySpout

Head of Retention, DTC Subscription

Remote, Canada

Remote

$115,000 to $145,000 USD / year · Contract

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Job details

Pay: $115,000 to $145,000 USD / year
Job type: Contract
Workplace: Remote
Posting language: English
Posted: Nov 6, 2026

Original job description

A profitable DTC pet brand is looking for a Head of Retention & Customer Experience to join our team! You will own everything after the first order: subscriptions, email and SMS, the post-purchase journey and customer experience, across both of our brands.

We're doing $50M+ a year and scaling to $100M+, and we want one senior leader who owns retention A-Z: lower churn, significantly higher lifetime value and a better customer experience across the board. We are looking to hire someone with 5-6+ years in retention or lifecycle at DTC brands, who has led retention at a subscription brand doing $30-50M+ a year (ideally nine figures). The ideal candidate is hands-on in Klaviyo and Loop (or similar), has led a retention and customer experience team, and has managed agencies.

The mission of this role

Own retention A-Z to fuel the growth to 9-figures. This role comes in to drive three things: lower churn, significantly higher lifetime value, and a better customer experience across the board. Success is lower churn, stronger retention, much higher lifetime value, more revenue from email and SMS, and happier customers.

Who are we?

We are a profitable DTC brand selling premium pet products. We sell across Shopify, Amazon and Chewy, and we're one of the fastest-growing brands in the pet space – $50M+ in annual revenue and scaling to $100M+. We recently launched a second brand, expanding into a new customer base. We're a 100% remote, lean, senior team that moves fast, and every person here has a massive impact on the business.

What is our culture like & who is a good fit?

Culture-fit is our #1 factor when hiring! We have a genuine will-to-win. No work is beneath us if it moves us towards our goals. We use creativity to do more with less – and quickly. We use data to make decisions and live by four core values:

Better Everyday: have a retention test live every week across subscriptions, flows or the post-purchase experience, and write down what each result teaches.
Speed Is King: spot a churn, refund or CSAT problem the day it shows up and have a fix in motion that week.
Work Smart: AI and automation first. Claude reads cancellation reasons, reviews and tickets to find why customers leave, AI drafts flow copy and segments, and retention KPIs report themselves every week.
Overdeliver: bring the CEO the next big retention lever before being asked, and get more lifetime value from every customer than the plan called for.

If you want a stress-free corporate 9–5 job, this isn't it.

If you want to challenge yourself and shape a fast-growing company, work directly with the founder, and play a big role in scaling it to $100M+... If you want to drive results with a group of passionate, smart, hardworking people, in an environment without politics or corporate chicanery, being hands-on and active – then you've come to the right place.

Outcomes (what success looks like)

90-day targets for each outcome are agreed with you before your start date.

Churn goes down: monthly subscription churn and save rate, by brand
Retention improves: repeat purchase rate and cohort retention at 3, 6 and 12 months
Lifetime value rises significantly: 12-month lifetime value by cohort and brand vs the same cohorts last year
Email and SMS drive more revenue: email and SMS share of total revenue, and revenue per recipient
Customers are happier across the board: CSAT, review rating, refund rate and tickets per order

Key Objectives

Own the subscription program for both brands: offers, cadence, bundles, the customer portal and the cancellation flow.
Build and test save offers, skip, swap and pause options, and win-back flows to cut churn.
Own email and SMS strategy for both brands, and manage the retention agency's calendar, flows, targets and results.
Build the lifecycle journey from first order to loyal customer: welcome, post-purchase, replenishment, cross-sell, win-back and VIP flows.
Map and improve the full post-purchase journey, and run a loyalty, referral or VIP program if the numbers support it.
Lead the customer experience team and set customer service policy that protects both the customer and the margin.
Report cohort retention and lifetime value against target every month, and name the biggest lever.

Fully remote, based outside the US.
Fluent in English.
Retention Leadership: 5-6+ years in retention or lifecycle at DTC brands, including leading retention at a subscription brand doing $30-50M+ a year (ideally nine figures). This is a must.
Subscription Expertise: you have grown a subscription program and know churn, saves, cohorts and MRR inside out.
Lifecycle Marketing: you build email and SMS programs (Klaviyo or similar) that drive a large share of revenue without burning the list.
Tools: deep hands-on experience with Klaviyo (or similar) and Loop (or a similar subscription platform).
Analytical: you read cohort, lifetime value and churn data fast and find the lever that moves the number.
Testing Discipline: you run clear tests on offers, flows and save tactics, and read results honestly.
Leadership: you have led a retention and customer experience team, including managing agencies, through KPIs and goals.
Commercial Judgement: you protect margin, and know when a discount or save offer earns its cost.
Customer obsessed: you understand why customers stay or leave, and fix the cause, not the symptom.
Excellent cultural fit as per our values above.
Excited to play a big role in scaling the company and work closely with the founder.

Accountabilities

What you own. Each one is checked green, yellow or red every week.

Subscriptions and churn: own the subscription program for both brands, keep at least one save or retention test live every week, grow the share of new customers who subscribe (working with the CRO Lead on on-site and post-purchase offers), and report subscribers, MRR, churn and save rate by brand every week.
Email, SMS and lifecycle: own email and SMS strategy, manage the retention agency, keep the calendar live and flows in testing, keep list health and deliverability strong, and plan sale and launch campaigns with the Head of Growth and the Head of Brand & Community.
Post-purchase experience and loyalty: ship at least one post-purchase improvement every month, and use cancellation reasons, reviews, surveys and support contact reasons to find why customers leave and fix the cause with the owning team.
Customer experience and support: lead the Customer Experience Manager, own the weekly CX KPI scorecard (CSAT, first response time, AI resolution rate, refund rate and chargebacks), set customer service policy, and grow 4- and 5-star reviews.
Retention data and reporting: track cohort retention, repeat purchase rate and lifetime value by brand and channel, report retention KPIs weekly, run a monthly retention review with the CEO, and write the retention playbook as SOPs so it runs without one person.

How Our Hiring Works & How We Operate

(1) Application + Screening Interview

(2) In-Depth Interview with our CEO

(3) Reference Calls

(4) Final Interview with our CEO

Salary Expectation

USD $115,000 to $145,000 a year (based on experience and expertise) + performance bonus of 15-20% of base after the trial period.

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More about this job

Responsibilities

The Head of Retention will own the entire post-purchase journey, including subscription programs, email and SMS strategy, and customer experience across two brands. They are responsible for driving growth by reducing churn, increasing lifetime value, and managing the customer experience team.

Requirements

Candidates must have 5-6+ years of experience in retention or lifecycle marketing at DTC brands, specifically within a subscription-based business. Proficiency in tools like Klaviyo and Loop, along with strong analytical skills and a proven track record of team leadership, is required.

Skills

Retention strategy
Lifecycle marketing
Subscription management
Klaviyo
Loop
Email marketing
SMS marketing
Customer experience
Data analysis
Churn reduction
Lifetime value optimization
Agency management
Team leadership
A/B testing
Customer service policy
DTC marketing

Benefits

Performance bonus of 15-20% of base salary

Remote locations

Ottawa, Ontario, Canada

Remote locations (standardized)

Ottawa, Ontario, Canada

Visa sponsorship

Not detected in the job text

Keywords

DTC
Subscription
Retention
Lifecycle Marketing
Klaviyo
Loop
Churn
Lifetime Value
Email Marketing
SMS Marketing
Shopify
Amazon
Chewy
Customer Experience
CSAT
Data Analysis
Cohort Analysis
MRR
Agency Management
Remote
Performance Bonus
Strategy
Automation
AI
Replenishment
Cross-sell
Win-back
Loyalty Program
SOPs
KPIs

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