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Job description
Benefits:
Flexible schedule
Health insurance
Paid time off
Portland Singles | Downtown Portland | Full-Time, In-Office | $22–$28/hr + Performance Bonuses
Portland Singles has been the Pacific Northwest's most trusted professional matchmaking service. Our matchmakers are the people clients trust with one of the most personal decisions of their lives — who they spend their time, energy, and heart on.
What you'll actually do:
Manage an active caseload of approximately 50 members — knowing each of them well enough to recognize a good fit in seconds
Hand-select and deliver curated matches per week , meeting both weekly and monthly quotas
Coach clients before dates (photos, conversation, expectations) and debrief them after — including telling them what they don't always want to hear
Maintain detailed, accurate profile notes so each match is sharper than the last
Respond to client communication promptly and professionally — this is white‑glove service for people who've trusted us with their love lives
Partner with our Enrollment Counselors so every new member is set up for success from day one
Compensation & perks:
Hourly wage: $22 – $28/hr depending on experience
Performance bonuses tied to quota attainment and positive client reviews
Medical benefits and PTO
Beautiful downtown Portland office, walking distance to Pioneer Square
M–F schedule — no nights, no weekends, no travel
The real reward of helping people find love
You're a strong fit if:
Have 5+ years of experience in a role that demanded both emotional intelligence and accountability — examples: therapy/counseling, dating or life coaching, executive recruiting, high‑end concierge, wedding planning, image consulting, personal styling, or customer success at a premium brand
Can deliver honest, sometimes uncomfortable feedback in a way that lands as caring rather than critical
Read people quickly and adjust your tone for each one
Are organized enough to track 50 active relationships at once without things slipping
Take deadlines and quotas seriously — they don't rattle you
Hold sensitive personal information with discretion
This role is NOT for you if:
You think matchmaking is a glamorous, fluffy job (it's structured, professional, and sometimes emotionally heavy work)
You avoid hard conversations with paying clients
You want commission-based or "uncapped" earnings (this role is hourly + bonus by design)
You rely on memory instead of systems
You want remote, hybrid, or flexible hours
To apply:
Submit your resume plus a 3–4 sentence answer to this question:
Tell us about a time you gave someone honest feedback they didn't want to hear — about how they came across, how they were behaving, or what they were doing wrong. What did you say, and how did they respond?
Applications without an answer to the question will not be reviewed.
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Worksite address
portland, OR, 97204, US
Who can apply
Review the original listing for work authorization, qualifications and employer requirements.