Senior Customer Success Manager

Location: Toronto, Ontario, Canada

Staffbase is looking for a Senior Customer Success Manager to join our North America team and own a portfolio of mid-to-large enterprise customers. You’ll be their strategic partner, helping them drive business outcomes and deepen platform adoption, and you’ll own the commercial relationship too: renewals, upsells, and add-on sales, end-to-end, against a quota.

Selling isn’t a side task here. Our CSMs demo, price, negotiate, and close add-on deals themselves, and are measured on hitting their numbers. At quarter-end, we’re in the office working deals alongside the sales team.

You’ll need a strong foundation in customer success and account management, managing customer relationships, driving adoption, and proactively identifying risks and opportunities. You also bring real experience owning revenue: closing renewals, running expansion deals, and handling the negotiation that comes with them. If you’ve carried a number before and enjoyed it, you’ll thrive here.

What you'll be doing

• Own a book of ~25 mid-to-large enterprise customers, building success plans tied to each customer's goals
• Own SaaS subscription renewals for your book end to end: forecasting, negotiating, and closing on time
• Own expansion revenue against a quota: listen for the signals, identify the use case, and turn upsell and cross-sell opportunities into closed deals
• Run CSM-owned add-on deals (like our digital signage solution) yourself, from first demo through pricing, discounting decisions, negotiation, and objection handling
• Take every deal to signature: identify the decision-makers and signers, put the paperwork together, and work with Deal Desk to close, bringing in Product when a customer needs a deeper dive
• Lead regular business reviews and planning sessions that prove value and set up the next commercial conversation
• Guide customer teams through onboarding, rollout, and long-term adoption of the Staffbase platform
• Identify and mitigate risk early, working cross-functionally with Product and Support to keep customers successful
• Advocate for customer needs internally and contribute to product feedback loops

What you'll need to be successful

• 3–6 years of experience in Customer Success, Account Management, or related client-facing roles, preferably in SaaS
• Commercial experience: you've carried a quota or revenue target, and you've owned renewal or expansion deals end to end, including demo, pricing, negotiation, and close. A sales role or a quota-carrying CSM role both count.
• A track record of hitting renewal and expansion targets
• Confidence negotiating price and handling objections, and no hesitation picking up the phone to chase a signature at quarter-end
• Experience managing a portfolio of accounts
• Strong communication and interpersonal skills; able to build relationships with day-to-day users and decision-makers alike
• Familiarity with digital tools and SaaS adoption metrics
• Self-motivated with a growth mindset and a strong sense of ownership
• Experience collaborating cross-functionally with internal teams to drive customer success

What you'll get

• Competitive Compensation - we offer attractive salary packages including LTIP (unit-based Long Term Incentive Plan)
• Flexibility - we offer flexible working time models and the option of hybrid work, and support this with a yearly flex work allowance of $2400
• Recharge - with 31 vacation days annually (incl. one floating holiday), plus pro rata fully paid Fridays off during August
• Support - we’re offering a RRSP plan with company match and health plans, including dental & vision as well as competitive Paid Parental Leave to support new parents
• Volunteer Day - you’ll get one day off per year for supporting a social project

In compliance with local law, we are disclosing the compensation, or a range thereof. Actual salaries will vary and may be above or below the range based on various factors including but not limited to location, experience, and performance. The range listed is just one component of Staffbase's total compensation package for employees. Pay Range: $100,000 - $110,000 CAD base salary per year. Other rewards may include commissions and program-specific awards. In addition, Staffbase provides a variety of benefits to employees, including health insurance coverage, equity, paid parental leave, life and disability insurance, a retirement savings plan, wellness days, paid holidays and paid time off (PTO).

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