Profitable 10-person bootstrapped B2B SaaS startup | Real Estate Tech | Toronto

What You'll Do

You'll own the complete customer lifecycle from pilot to expansion, turning early adopters into power users and revenue growth engines. This isn't about maintaining relationships—it's about building, growing, and solving problems that don't have playbooks yet.

Your first 90 days:

• Build and actively manage an expansion pipeline
• Identify and remove expansion constraints in every account
• Measurably increase pilot-to-full-rollout conversion rates
• Reduce time-to-resolution for common customer issues

What We're Looking For

Must-have traits:

• Bias to action — You see a problem and fix it, don't wait for permission
• Extreme ownership — When something goes wrong, you own the solution
• Ruthless prioritizer — You know what moves the needle and focus there
• Comfortable with chaos — Incomplete information doesn't slow you down
• Revenue-focused — You think like a business owner, not just a support agent

Experience we value:

• 3+ years in customer success, account management, or sales roles
• Proven track record of growing revenue within existing accounts
• Experience in fast-paced, resource-constrained environments
• History of building processes from scratch (not just following them)

What Success Looks Like

• You'll spend 60% of your time on expansion opportunities, 40% on retention/support
• Direct contact with decision-makers, not just end users
• Empowered to solve 80% of customer issues without escalation
• Weekly metrics: pipeline growth, expansion revenue, resolution speed, account health

What We Offer

• $100k base salary + commission (total $140-180k OTE)
• Unlimited PTO and sick days
• Direct impact on company growth and direction at a profitable, bootstrapped company
• Work directly with the founder in a tight-knit 10-person team where your wins are visible and celebrated
• In-person collaboration in our Toronto office (Yonge-Eglinton) (building something great together)
• Opportunity to build the customer success function as we scale

Our Process

We've designed a thorough process to ensure mutual fit:

1. Initial application — Submit your resume and tell us about your biggest customer success win
2. Personality assessment — Short assessment to understand your working style
3. Phone interview — 20-minute conversation about your experience and approach
4. Business assessment — Analyze real account scenarios and present your strategy
5. First interview — Deep dive into your experience and problem-solving approach
6. Final assessment — Hands-on simulation of the actual work you'll be doing
7. Final interview — Meet the team and discuss your 30/60/90 day plan (offer stage)

If you're energized by turning customer challenges into growth opportunities and thrive in environments where you need to figure things out as you go, we want to talk.

Ready to own customer success at a growing startup? Apply today!