Creative Strategist — Performance Creative for DTC Subscription
About the role
Whatskill.ai is the operating company behind a portfolio of subscription-first direct-to-consumer brands across beauty, skincare, and health supplements. Our leadership has a track record of building eight-figure e-commerce businesses with category-leading retention, supported by paid social programs that have run at substantial daily spend. Our most recent launch passed $800,000 in monthly recurring revenue inside its first 60 days, and the next chapter is a clear path to nine-figure annual revenue.
We are adding a Creative Strategist who will own end-to-end creative for two of our subscription brands. The role combines strategic ownership, hands-on production leadership, and a daily feedback loop with media buying. We are looking for an operator with a proven personal track record on Meta, specifically ad creatives that have sustained $30,000 or more per day in profitable spend, combined with direct experience inside a subscription DTC business and a history of building creative teams that ship at volume.
Objectives of this role Deliver profitable scale on Meta across two subscription DTC brands in skincare and supplements Stand up an in-house creative team that can produce 50 to 100 or more new ad creatives every week Build a structured testing system that surfaces new winning angles on a continuous cadence Close the loop with media buying so that performance signals shape the next round of creative
Responsibilities Lead creative strategy across two subscription DTC brands from concept through performance review Recruit, manage, and develop a small team that includes video editors, static designers, and UGC creators Design and run the creative testing framework end-to-end, covering angle research, hook variations, body copy testing, and format-level experimentation Ship 50 to 100 or more new ad creatives per week across UGC, static, video sales letter, mashup, talking-head, and lifestyle formats Review daily performance data, including hook rate, hold rate, click-through rate, conversion rate, cost per acquisition, and return on ad spend, and translate those signals into the next production sprint Retire creatives that fail to perform, double down on those that do, and keep a steady pipeline ready before existing winners begin to fatigue Work side by side with the media buyer on budget allocation, audience signals, and scaling plans
Required skills and qualifications Direct experience as a Creative Strategist or Creative Director on at least one subscription DTC brand that grew past eight figures in annual revenue Demonstrated personal ownership of ad creatives that sustained $30,000 or more per day in profitable Meta spend Strong grasp of subscription economics, including churn, lifetime value, and renewal psychology, and how each shapes creative choices Track record of finding winning angles from cold audiences and codifying that discovery into a repeatable system Ability to operate a high-volume creative testing pipeline at a baseline of 50 or more new creatives per week Experience hiring, training, and leading creative teams that include video editors, static designers, and UGC talent
Preferred skills and qualifications Background in subscription DTC beauty, skincare, or health supplements Comfort working across multiple direct response formats at high cadence Close prior collaboration with a paid social media buyer
How to apply Please share the following with your application: Your full name, email address, and timezone The subscription DTC brand or brands where you led creative, with the revenue scale you helped reach The highest daily Meta spend that your creatives sustained profitably Your peak weekly creative testing volume Two to three examples of winning creatives you produced, along with the strategy behind each A short note on how you go about finding new angles once your current winners begin to fatigue
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Creative Strategist — Performance Creative for DTC Subscription
About the role
Whatskill.ai is the operating company behind a portfolio of subscription-first direct-to-consumer brands across beauty, skincare, and health supplements. Our leadership has a track record of building eight-figure e-commerce businesses with category-leading retention, supported by paid social programs that have run at substantial daily spend. Our most recent launch passed $800,000 in monthly recurring revenue inside its first 60 days, and the next chapter is a clear path to nine-figure annual revenue.
We are adding a Creative Strategist who will own end-to-end creative for two of our subscription brands. The role combines strategic ownership, hands-on production leadership, and a daily feedback loop with media buying. We are looking for an operator with a proven personal track record on Meta, specifically ad creatives that have sustained $30,000 or more per day in profitable spend, combined with direct experience inside a subscription DTC business and a history of building creative teams that ship at volume.
Objectives of this role Deliver profitable scale on Meta across two subscription DTC brands in skincare and supplements Stand up an in-house creative team that can produce 50 to 100 or more new ad creatives every week Build a structured testing system that surfaces new winning angles on a continuous cadence Close the loop with media buying so that performance signals shape the next round of creative
Responsibilities Lead creative strategy across two subscription DTC brands from concept through performance review Recruit, manage, and develop a small team that includes video editors, static designers, and UGC creators Design and run the creative testing framework end-to-end, covering angle research, hook variations, body copy testing, and format-level experimentation Ship 50 to 100 or more new ad creatives per week across UGC, static, video sales letter, mashup, talking-head, and lifestyle formats Review daily performance data, including hook rate, hold rate, click-through rate, conversion rate, cost per acquisition, and return on ad spend, and translate those signals into the next production sprint Retire creatives that fail to perform, double down on those that do, and keep a steady pipeline ready before existing winners begin to fatigue Work side by side with the media buyer on budget allocation, audience signals, and scaling plans
Required skills and qualifications Direct experience as a Creative Strategist or Creative Director on at least one subscription DTC brand that grew past eight figures in annual revenue Demonstrated personal ownership of ad creatives that sustained $30,000 or more per day in profitable Meta spend Strong grasp of subscription economics, including churn, lifetime value, and renewal psychology, and how each shapes creative choices Track record of finding winning angles from cold audiences and codifying that discovery into a repeatable system Ability to operate a high-volume creative testing pipeline at a baseline of 50 or more new creatives per week Experience hiring, training, and leading creative teams that include video editors, static designers, and UGC talent
Preferred skills and qualifications Background in subscription DTC beauty, skincare, or health supplements Comfort working across multiple direct response formats at high cadence Close prior collaboration with a paid social media buyer
How to apply Please share the following with your application: Your full name, email address, and timezone The subscription DTC brand or brands where you led creative, with the revenue scale you helped reach The highest daily Meta spend that your creatives sustained profitably Your peak weekly creative testing volume Two to three examples of winning creatives you produced, along with the strategy behind each A short note on how you go about finding new angles once your current winners begin to fatigue
Not the right fit? Search for Creative Strategist jobs in Canada