Appointment Setter / Outreach Lead (Contract) - Generous Commission!
Project Type: 4–6 week sprint (potential to extend)
Compensation: 15% commission on closed deals (average sale: ~$60K)
About the Role
We’re hiring a sharp, relationally intelligent Outreach Lead / SDR to help bring Proper Context into the rooms where it matters most.
This isn’t a spray-and-pray outbound role. You’ll be crafting contextual, executive-caliber outreach and booking high-trust intro calls with leaders navigating culture, strategy, and performance shifts. Once the meeting is set, our sales lead or Founder will take it from there.
You’ll be working with mid-market and enterprise brands who are facing real institutional pressure and looking for alignment, not fluff.
About Proper Context
Proper Context is a strategic system that helps institutions rebuild trust, clarify their message, and align internal behavior with external outcomes.
We’ve supported leaders at brands like T-Mobile, Soho House, and others navigating moments of real transition. Now, we’re scaling through targeted outreach and high-quality client alignment.
What You’ll Do
✅ Prospect and qualify high-fit, high-potential clients
✅ Craft and send targeted outreach messages (we’ll provide frameworks + messaging)
✅ Book intro meetings with senior decision-makers (CHROs, CMOs, COOs, etc.)
✅ Collaborate closely with our team to improve response and booking rates
✅ Help close at least one high-value engagement during the sprint
✅ Track activity and insights in HubSpot
What We’re Looking For
You know how to read the room and speak executive without sounding salesy
You’re intentional—custom beats canned
You understand brand tone and can operate inside it (not just around it)
You’re fast-moving, outcome-oriented, and comfortable with ownership
You’ve booked meetings for high-ticket or high-trust services before
You know this is about connection, not coercion
In your cover, please include a brief intro loom and tell us your favorite ice cream.
Apply Now
Apply Now
Compensation: 15% commission on closed deals (average sale: ~$60K)
About the Role
We’re hiring a sharp, relationally intelligent Outreach Lead / SDR to help bring Proper Context into the rooms where it matters most.
This isn’t a spray-and-pray outbound role. You’ll be crafting contextual, executive-caliber outreach and booking high-trust intro calls with leaders navigating culture, strategy, and performance shifts. Once the meeting is set, our sales lead or Founder will take it from there.
You’ll be working with mid-market and enterprise brands who are facing real institutional pressure and looking for alignment, not fluff.
About Proper Context
Proper Context is a strategic system that helps institutions rebuild trust, clarify their message, and align internal behavior with external outcomes.
We’ve supported leaders at brands like T-Mobile, Soho House, and others navigating moments of real transition. Now, we’re scaling through targeted outreach and high-quality client alignment.
What You’ll Do
✅ Prospect and qualify high-fit, high-potential clients
✅ Craft and send targeted outreach messages (we’ll provide frameworks + messaging)
✅ Book intro meetings with senior decision-makers (CHROs, CMOs, COOs, etc.)
✅ Collaborate closely with our team to improve response and booking rates
✅ Help close at least one high-value engagement during the sprint
✅ Track activity and insights in HubSpot
What We’re Looking For
You know how to read the room and speak executive without sounding salesy
You’re intentional—custom beats canned
You understand brand tone and can operate inside it (not just around it)
You’re fast-moving, outcome-oriented, and comfortable with ownership
You’ve booked meetings for high-ticket or high-trust services before
You know this is about connection, not coercion
In your cover, please include a brief intro loom and tell us your favorite ice cream.
Apply Now
Apply Now