About the role The Senior Retention Strategist will be an important member of the Email + SMS team and will report to the Head of Strategy. You’ll own retention strategy and results for a book of 5 to 7 DTC brands. You’re the senior person on each account: the client’s strategic lead, the one who sets the plan, and the one who answers for the revenue it produces.

You’ll also help us grow the strategy team. You’ll mentor one or two Retention Strategists, review their plans before clients see them, and write down how we do strategy here, so the next hire ramps faster than you did.

This is a step up from our Retention Strategist role. It suits someone who has run accounts for years and now wants a bigger book and more say in how the team works.

Responsibilities

- Set the retention strategy for each brand: flow architecture, campaign calendar, segmentation and list growth.
- Build a quarterly email and SMS revenue forecast per account, then track actuals against it every month.
- Own account health. You’ll spot churn risk early and find scope that’s worth expanding.
- Run monthly and quarterly business reviews with founders and marketing leads.
- Lead an account team of Copywriter, Designer, Project Manager and Retention Specialist.
- Set the brief and the bar. Specialists run production; you make sure it’s the right work.
- Be the escalation point when a client is unhappy or a launch goes sideways.
- QA strategy, test plans and reporting across the pod before anything goes to a client.
- Write and maintain our SOPs for audits, testing, forecasting and QBRs.
- Build AI workflows the whole team uses, not just you.

Qualifications

- 5+ years in email, SMS or lifecycle marketing,



with at least 3 on the agency side running multiple DTC accounts.
- Expert in Klaviyo, including flows, segments, predictive analytics and reporting. Postscript at a similar level; Attentive is a plus.
- You design tests properly: a explicit hypothesis, enough sample size, holdouts where they matter, and a call you can defend.
- You’ve built revenue forecasts for retention channels and explained a miss to a client without flinching.
- You’re fluent in cohort, RFM and LTV analysis. Comfortable in spreadsheets.
- You’ve coached or mentored other strategists, formally or not.
- A track record of keeping clients. Tell us about a save.

Additional Information This is a fully remote role. Candidates must be able to work standard business hours (9:00am–5:00pm) in ET, CT, MT, or PT time zones.

Homestead Studio is an affirmative action and equal prospect employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, disability, age, sexual orientation, gender identity, national origin, veteran status, or genetic information. Homestead is committed to providing access, equal opportunity, and reasonable accommodation for individuals with disabilities in employment, its services, programs, and activities.

Note on Application Responses

We strongly encourage applicants to answer questions in their own words. While tools like ChatGPT can be helpful for organizing or polishing your thoughts, it is very easy to recognize when responses are copied and pasted without personalization. Candidates who use AI in that way are typically less successful in our process. Please treat your responses as an opportunity to show us how you think and communicate.

📌 Senior Retention Strategist (Canada)
🏢 Homestead Studio
📍 Canada