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.

This is a role for someone who's part advisor, part coach, part friend, and part operator. You'll manage a roster of paying members through their entire matchmaking journey: selecting matches, prepping them for dates, debriefing the results, coaching them through difficult feedback, and quietly steering them toward the kind of partner they actually need — not always the one they walked in asking for.

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 you:

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.