Sales Enrollment Counselor Matchmaking High

Job Description

Job Description

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 2–3 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 3–4 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.
**