Customer Retention Associate Jobs in Milton, ON (NOW HIRING)

THE ROLE

SMYTHE is seeking a CRM & Retention Manager to own retention engine, from email and SMS to lifecycle strategy, digital loyalty mechanics, and customer lifetime value growth. Sitting at the centre of the marketing team, this role is accountable for turning every customer touchpoint into a lasting relationship, driving repeat purchase, and building the retention infrastructure that supports long-term business growth.

You will report directly to the Director of Marketing and lead the Customer Marketing Associate, working cross-functionally with the Growth Specialist and eCommerce Team to ensure the digital and human-touch sides of retention work as one cohesive customer experience.

This is a channel ownership role. You will set the strategy, build the programs, and be directly accountable for the results. Success will be measured against a defined set of retention KPIs, including email and SMS revenue contribution, repeat purchase rate, customer lifetime value growth, loyalty program enrollment and engagement, list growth, and email deliverability, with performance reviewed regularly at cross-functional trade meetings. If you love owning your channels, celebrating the wins, and doing it alongside a team that's just as invested in the work as you are, we'd love to meet you.

YOU WILL

Own the omni retention strategy

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  Lead email and SMS strategy end-to-end, from campaign architecture and lifecycle mapping to flow optimization and performance reporting.
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  Create and manage the brand's loyalty program, structure, rewards mechanics, program reporting, and LTV optimization.
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  Develop the segmentation strategy and lead customer segmentation, personalization, and A/B testing roadmap to drive relevance and measurable performance improvement.
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  Support lifecycle mapping for the digital customer journey, welcome, browse, cart, post-purchase, and winback, continuously improving flows to drive engagement and conversion.

Execute with precision

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  Manage the full CRM calendar and end-to-end deployment across email and SMS channels, ensuring alignment with product launches and brand moments.
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  Build and maintain best-in-class list growth strategy, list hygiene, suppression management, and re-engagement practices.
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  Monitor and maintain email deliverability and ensure compliance with CASL, GDPR, and evolving privacy standards.
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  Own vendor relationships for CRM and loyalty platforms, from day-to-day management to contract and renewal decisions.

Report and optimize

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  Own performance reporting across email, SMS, and loyalty, translating results against core KPIs (email revenue, SMS revenue, repeat purchase rate, LTV, AOV, list growth, loyalty enrollment and engagement) into clear insights and actions.
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  Run a structured A/B testing program across subject lines, creative, timing, send cadence, and audience, scaling what works, learning from what doesn't.
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  Track customer LTV trends and make strategic recommendations to grow retention revenue over time.
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  Present retention performance, program updates, and channel forecasts at weekly cross-functional trade meetings.

Lead your team

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  Manage and mentor the Customer Marketing Associate, providing strategic direction and ensuring the digital and in-store sides of the customer journey work together as one cohesive retention experience.
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  Draw on the Customer Marketing Associate's clienteling, loyalty, and retail event intelligence to ensure digital programs reflect real customer behaviour and relationship context, keeping the digital and in-store retention strategies fully aligned.

Partner cross-functionally

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  Partner with the Brand & Creative Team on creative direction, messaging, and brand alignment across all CRM communications.
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  Collaborate with the Growth Marketing Associate to share retention performance data that informs acquisition strategy and retargeting.
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  Integrate with the eCommerce team on the loyalty infrastructure, platform data flows, and on-site personalization opportunities.
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  Work with the cross-functional trade group to plan and forecast business KPIs, and present retention performance and insights at weekly trade meetings.

YOU HAVE

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  5-7+ years of experience in email, SMS, or CRM marketing, ideally within fashion, retail, or DTC.
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  Deep expertise in Klaviyo and strong working knowledge of Shopify.
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  A proven track record of driving revenue through lifecycle marketing, retention programs, and loyalty mechanics.
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  Experience building or managing a digital loyalty program, you understand how tiers, rewards, and mechanics translate into customer behaviour.
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  Strong command of segmentation, personalization, and dynamic content strategies.
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  An analytical mindset with experience in testing frameworks, performance optimization, and presenting insights clearly to cross-functional stakeholders.
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  A solid understanding of email deliverability, compliance (CASL, GDPR), and list management best practices.
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  Familiarity with platform integrations, data flows, and CRM infrastructure; you know how the data moves and why it matters.
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  Working knowledge of HTML/CSS for email build and QA is an asset.

HOW YOU THINK

You see email, SMS, and loyalty as CRM, commerce, and brand storytelling, not just execution channels.

You balance performance with brand, ensuring every touchpoint is both effective and considered. You are structured in your approach to testing, but creative in your thinking.

You are both a strategist and an operator, comfortable owning outcomes end-to-end, leading a direct report, and presenting performance with precision to the Director of Marketing.

You thrive at the intersection of data and craft, and you believe retention is where brand loyalty is actually earned.

YOU'LL LOVE WORKING HERE BECAUSE

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  You'll work with a fun, hard-working, collaborative team with a strong entrepreneurial spirit.
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  Our product is designed to embolden the people who wear it - and that includes our team.
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  We offer a comprehensive health and dental benefit plan funded by SMYTHE.
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  SMYTHE fosters a workplace where our individual differences are recognized, appreciated, and respected. Accommodations are available upon request for candidates taking part in all aspects of the recruitment and selection process.