Apply now!
If you’re ready to join a fast-moving global media company and work with ambitious, creative people who value quality and initiative, we’d love to hear from you.
careers@houseofsummary.com
Remote
Full-time
Leadership
Experience level
Senior
Type
Full-time
Location
100% Remote
Salary range
$24,000–$36,000 (depending on experience)
Work hours
40 hours per week
Position summary
We are looking for a driven and strategic Head of Ad Sales to lead monetization across our global newsletter network. You will develop sales strategies, build advertiser relationships, and lead a small team dedicated to scaling high-value partnerships. The right candidate will be both analytical and creative, capable of identifying opportunities, crafting premium offers, and turning audience insights into results. This is a remote, full-time leadership role.
Assignment
We want to understand how you think, structure, and execute monetization. This isn’t about guessing our numbers; it’s about how you’d build an ad engine that scales.
Task Overview
You’ll show how you would:
-Build a pipeline of brand partners-Design pricing and inventory strategy-Leverage sponsorship platforms and data tools-Create a pitch narrative that converts
1. Strategic Foundations
Answer briefly (2-4 sentences each):
-Which of our newsletters has the greatest short-term monetization potential, and why?-What industries or advertiser categories would you prioritize in the first 90 days?-What does “premium positioning” mean to you in newsletter advertising, and how would you maintain it while scaling?
2. Monetization Angles (pick 3 angles)
Choose any three angles and outline your approach for each:
-Direct Sponsorships & Native Ads-Platform Leverage & Ad Tech-Pricing & Packaging Strategy-Revenue Diversification-Analytics, Reporting & Retention-Partnerships & Ecosystem Expansion
Each should include what you’d do, why it matters, and how you’d measure success.
3. Practical Scenario
You’re pitching a luxury brand (e.g., Montblanc, Emirates, or Julius Baer) that wants to reach global executives.
Write a 200–300-word pitch email or deck outlineexplaining:
-Which newsletter would you recommend and why-The type of placement or sponsorship-Key audience stats or positioning language-Expected ROI or campaign goal
4. Platform Advantage
-Which sponsorship platforms do you think are underutilized by premium newsletters, and how could we take advantage of them?-How would you combine direct sales and platform sales without cannibalizing value?-What’s one automation or tech stack upgrade you’d implement in the first 60 days?
How to submit:
-Send your assignment as a single PDF (maximum five pages)-Subject line: Head of Ad Sales – [Your Name]-Email it to careers@houseofsummary.com
Job description
As Head of Ad Sales, you’ll define and execute the monetization strategy across all House of Summary brands. You’ll cultivate high-value relationships with advertisers and agencies, create pricing models and media kits, and lead a growing sales team focused on long-term partnerships. You’ll collaborate with editorial, design, and analytics teams to deliver measurable results while maintaining our premium brand positioning in the global newsletter market.
Experience
Nice to have
Benefits
We’re a global remote-first team of curious, driven, and creative people building the future of independent media. At House of Summary, you’ll work alongside editors, designers, and developers who value clarity, precision, and originality. We move fast, stay curious, and care deeply about what we create.
How to apply
Send your CV, a motivational letter, and the completed assignment to careers@hourseofsummary.com with the name of the position in the subject of the email. Note: We do not review applications without the assignment.
Remote
Full-time
Leadership
Experience level
Senior
Type
Full-time
Location
100% Remote
Salary range
$24,000–$36,000 (depending on experience)
Work hours
40 hours per week
Position summary
We are looking for a driven and strategic Head of Ad Sales to lead monetization across our global newsletter network. You will develop sales strategies, build advertiser relationships, and lead a small team dedicated to scaling high-value partnerships. The right candidate will be both analytical and creative, capable of identifying opportunities, crafting premium offers, and turning audience insights into results. This is a remote, full-time leadership role.
Assignment
We want to understand how you think, structure, and execute monetization. This isn’t about guessing our numbers; it’s about how you’d build an ad engine that scales.
Task Overview
You’ll show how you would:
-Build a pipeline of brand partners-Design pricing and inventory strategy-Leverage sponsorship platforms and data tools-Create a pitch narrative that converts
1. Strategic Foundations
Answer briefly (2-4 sentences each):
-Which of our newsletters has the greatest short-term monetization potential, and why?-What industries or advertiser categories would you prioritize in the first 90 days?-What does “premium positioning” mean to you in newsletter advertising, and how would you maintain it while scaling?
2. Monetization Angles (pick 3 angles)
Choose any three angles and outline your approach for each:
-Direct Sponsorships & Native Ads-Platform Leverage & Ad Tech-Pricing & Packaging Strategy-Revenue Diversification-Analytics, Reporting & Retention-Partnerships & Ecosystem Expansion
Each should include what you’d do, why it matters, and how you’d measure success.
3. Practical Scenario
You’re pitching a luxury brand (e.g., Montblanc, Emirates, or Julius Baer) that wants to reach global executives.
Write a 200–300-word pitch email or deck outline explaining:
-Which newsletter would you recommend and why-The type of placement or sponsorship-Key audience stats or positioning language-Expected ROI or campaign goal
4. Platform Advantage
-Which sponsorship platforms do you think are underutilized by premium newsletters, and how could we take advantage of them?-How would you combine direct sales and platform sales without cannibalizing value?-What’s one automation or tech stack upgrade you’d implement in the first 60 days?
How to submit:
-Send your assignment as a single PDF (maximum five pages)-Subject line: Head of Ad Sales – [Your Name]-Email it to careers@houseofsummary.com
Job description
As Head of Ad Sales, you’ll define and execute the monetization strategy across all House of Summary brands. You’ll cultivate high-value relationships with advertisers and agencies, create pricing models and media kits, and lead a growing sales team focused on long-term partnerships. You’ll collaborate with editorial, design, and analytics teams to deliver measurable results while maintaining our premium brand positioning in the global newsletter market.
Experience
Nice to have
Benefits
We’re a global remote-first team of curious, driven, and creative people building the future of independent media. At House of Summary, you’ll work alongside editors, designers, and developers who value clarity, precision, and originality. We move fast, stay curious, and care deeply about what we create.
Apply now!
If you’re ready to join a fast-moving global media company and work with ambitious, creative people who value quality and initiative, we’d love to hear from you.
careers@houseofsummary.com
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