Senior Enrollment Strategist
The Uncommon Business
Remote · Full-time
Pay: $90,000 – $100,000 per year (base, based on experience) + uncapped commission (4.17% of quota)
Job Type: Full-time
Shift and Schedule: Monday to Friday. Extended hours during launch seasons (see Schedule below).
About the Role
The Uncommon Business is hiring a full-time, remote Senior Enrollment Strategist to own the close on our largest and most complex accounts — multi-seat team deals and larger-company contracts that require warming, relationship-building, and multi-stakeholder objection handling before they convert.
This is a senior, quota-carrying sales role for an experienced closer. It is not an entry-level position. Today, these larger deals bottleneck on a single person, and this role exists to remove that constraint and directly expand what our Fall launch can convert.
The ideal candidate has real closing experience but is open to unlearning high-pressure sales tactics in favor of a consultative, relationship-driven approach. You should be equally comfortable closing over SMS and on live calls, and able to manage complex, multi-decision-maker deals without losing the thread.
Reports to: Manager, Enrollment
Responsibilities
- Own the warming and closing of multi-seat and larger-company deals end to end, from early outreach through signed contract and payment.
- Build and warm a pipeline of larger-company accounts over a longer sales cycle, reducing stalled and lost high-value deals.
- Navigate complex, often multi-stakeholder objections without relying on high-pressure closing tactics.
- Coordinate separate conversations across multiple decision-makers and bring them to a unified decision.
- Complete an SMS and call-based ramp on front-line conversations before transitioning into full larger-deal ownership.
- Maintain accurate CRM records and clean deal attribution to support reliable pipeline forecasting.
- Match or exceed the team close rate on your larger and multi-seat deal book once ramped.
Qualifications
- Proven B2B or high-ticket sales closing experience, with a track record on complex or multi-stakeholder deals.
- Ability to close effectively over both SMS and live phone/video conversations.
- Skilled at managing multiple decision-makers and long sales cycles simultaneously.
- Comfortable with a consultative, relationship-driven close rather than high-pressure transactional tactics.
- Strong CRM discipline and attention to attribution and pipeline accuracy.
- AI and technology fluency, with the ability to use tools to work faster and more accurately.
- Patience and consistency to work longer warming runways on high-value accounts.
What Success Looks Like
- Close Rate: Match or exceed the team close rate on your larger and multi-seat deal book once ramped.
- Ramp Timeline: In seat and SMS-ramped by end of July, transitioning into larger-company closing as boot camp and the launch roll out.
- Quota Attainment: Track toward full quota accountability of approximately $2.4M annually, phasing in after the Fall launch.
- Pipeline Warmed: Build a warmed pipeline of larger-company accounts ahead of the mid-to-late October cart close.
Schedule Expectations
Our launch seasons are high-intensity and fast-paced. Twice per year (10–12 weeks total), team members in launch-critical roles are expected to be available from 7 AM to 7 PM, with additional hours often required for preparation, live event support, and post-launch debriefs.
Outside of launch seasons, the workload is sustainable and strategic, focused on building the systems that strengthen the next launch. This pace suits candidates who thrive in high-accountability, high-impact environments.
Compensation & Benefits
- Base salary of $90,000 - $100,000 per year
- Uncapped, revenue-funded commission with acceleration bands for exceeding quota
- Monthly wellness stipend plus personalized and group wellness coaching
- Annual professional development budget for courses, conferences, and certifications
- Coworking membership allowance or home office setup budget
- Unlimited PTO
Work Location: Remote
Applications are initially reviewed using AI-assisted screening tools to assess alignment with role requirements. All hiring decisions are made by humans.
The Uncommon Business is an equal opportunity employer. We believe diverse teams build better companies.
Pay: $90,000.00 - $100,000.00 per year
Work Location: Remote
