Sales Enrollment Counselor Matchmaking High-Ticket Closer

Benefits:

• Bonus based on performance
• Health insurance
• Paid time off

Portland Singles | Downtown Portland | Full-Time, In-Office Base + Uncapped Commission + Personal & Team Bonuses | Year-1 OTE: $120,000


Portland Singles has been the Pacific Northwest's most trusted professional matchmaking service. We help successful, relationship-ready singles find lasting love and our Enrollment Counselors are the reason clients say yes.

This is not a phone bank. This is not a transactional sale. You'll spend up to two hours, in person, helping a prospective client get honest about what they actually want in a partner and why it hasn't happened yet. By the end of that conversation, the right ones enroll in a four to five-figure matchmaking package. You close in one sitting, or you don't close.

If you've sold high-ticket coaching, financial services, cosmetic procedures, luxury fitness, legal consultations, or anything else where the buyer's emotions matter as much as the price tag you'll feel at home here.

What you'll actually do:

• Run 23 consultative enrollment interviews per day with pre-qualified, inbound prospects (we generate the leads you don't cold-call)
• Build trust quickly and ask the kind of questions that get people to tell you what they really want
• Present matchmaking packages in the range of $7,000 $15,000 and close in the room
• Hand off enrolled clients to our matchmaking team with detailed, accurate profiles so we deliver on what you sold
• Protect our 30-year reputation by selling honestly we don't enroll clients we can't serve

Compensation & perks:

• Base salary: $40,000 - $52,000 depending on experience
• Uncapped commission on personal sales + team bonuses
• Realistic Year-1 OTE: $100,000 Top performers earn $150,000
• Medical benefits and PTO
• Beautiful downtown Portland office, walking distance to Pioneer Square
• No travel, Flexible-Schedule your evenings are yours

You're a strong fit if you:

• Have 5+ years of one-call-close sales experience in a high-ticket, consultative environment
• Have personally closed at least one deal of $10,000+ in a single sit-down or call
• Can comfortably ask a stranger about their divorce, their loneliness, and their finances in the same conversation
• Read a room you know when to push, when to slow down, and when to walk away
• Care more about whether the client is the right fit than whether they have the money

This role is NOT for you if:

• You've never closed a four or five-figure deal in a single conversation
• Your sales style relies on multiple follow-ups, nurture sequences, or "let me think about it"
• You're uncomfortable selling something whose value is emotional rather than measurable
• You want remote, hybrid, or flexible hours

To apply: Submit your resume plus a 34 sentence answer to this question:

Describe the largest single-conversation sale you've personally closed. What was the product, the price, and what specifically did you say or do that moved them to yes?

Applications without an answer to the question will not be reviewed.