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Customer Success Manager with Sales Background – Canada-Based at Upwork

Upwork

We are hiring a Customer Success Manager with exceptional sales skills to support our growing advisory and automation firm. Your primary role will be to manage client relationships, drive upsells, and ensure clients receive maximum value from our services. This role is ideal for someone who is confident, proactive, and comfortable turning conversations into revenue.

Compensation:

$2,000/month base

+ 10% of refund savings generated

+ $200–$500 in performance pay (based on KPIs and client outcomes)

Total monthly earnings can grow significantly for high performers.

What We’re Looking For:

Must-Haves:

Located in Canada

Top-tier sales skills — this is the #1 requirement

Strong communication and relationship-building abilities

Experience in Customer Success, Account Management, or a similar client-facing role

Organized, proactive, and able to manage multiple accounts effectively

Nice-to-Haves:

Background in consulting, financial services, SaaS, or agency work

Experience with CRMs and client tracking tools

Comfort speaking with business owners and decision-makers

Responsibilities:

Own client onboarding, check-ins, and ongoing communication

Identify upsell opportunities and close them

Ensure clients stay engaged, satisfied, and see measurable results

Track refunds saved and revenue generated (for commission purposes)

Coordinate internally to ensure deliverables and client needs are met

Report performance, challenges, and opportunities regularly

Why Work With Us:

Competitive base pay + lucrative performance incentives

Long-term role with career growth potential

Work with a fast-moving advisory team helping clients scale

Remote work with flexible hours

Supportive and performance-driven culture

How to Apply:

Please include:

Your resume or portfolio

To apply for this job please visit www.upwork.com.