Aspire Software

Founding Customer Success Manager

Aspire Software

full-time

Posted on:

Location Type: Hybrid

Location: Toronto • Canada

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About the role

  • Own customer onboarding and activation: Lead new customers through implementation: configuring Carla for their business, integrating with their rental management system, setting up the knowledge base, transfer rules, opening hours, and greeting flows.
  • Train customer teams on the Carla AI dashboard, analytics, call review, and configuration tools so they can self serve day to day.
  • Define and track activation milestones to ensure every customer reaches first value quickly: calls answered, bookings created, time saved.
  • Build and refine repeatable onboarding playbooks, documentation, and training materials as the customer base grows.
  • Own the ongoing customer relationship post onboarding: regular check ins, business reviews, and proactive outreach based on usage and performance data.
  • Monitor customer health metrics such as call volume, booking conversion, feature adoption, and dashboard engagement to spot risks early and act on them.
  • Manage renewals and ensure customers continue to see value as their business and Carla’s capabilities evolve.
  • Handle escalations with empathy and urgency, coordinating with Product and Engineering to resolve issues and close the loop with the customer.
  • Spot opportunities to expand usage within existing accounts: additional locations, higher tier plans, new features, or broader use cases.
  • Share structured customer feedback with Product and leadership to inform roadmap priorities, packaging decisions, and new vertical exploration.
  • Collaborate with Sales and Partnerships to support case studies, references, and customer stories that fuel new business growth.
  • Establish the foundations of the customer success operation: health scoring, onboarding workflows, renewal tracking, and escalation processes.
  • Maintain accurate customer records, notes, and lifecycle data in CRM (HubSpot).
  • Contribute to building a knowledge base of best practices, FAQs, and self service resources for customers.

Requirements

  • 2 to 4 years of experience in customer success, account management, or implementation within B2B SaaS.
  • Demonstrated ability to onboard and retain customers, with a track record of driving adoption and reducing churn.
  • Strong project management instincts: comfortable managing multiple customer implementations and timelines simultaneously.
  • Excellent communication skills, both written and verbal, with the ability to train, present, and build trust with operators who are not necessarily technical.
  • Proactive and empathetic: you anticipate customer needs rather than waiting for escalations.
  • Comfortable working with data to monitor customer health, spot trends, and inform decisions.
  • CRM experience (HubSpot, Salesforce, or equivalent).
  • Self motivated, detail oriented, and comfortable working autonomously in a fast paced, evolving environment.
  • Experience in the rental industry (car rental, equipment rental, fleet management) or adjacent verticals such as automotive, travel tech, or mobility is a strong plus.
  • Experience onboarding customers onto AI, automation, or voice/conversational technology products.
  • Experience building or materially improving customer success processes, playbooks, or health scoring from scratch.
  • Familiarity with SaaS products and API based integrations, enough to guide customers through configuration without needing engineering support for every question.
  • Startup or early stage SaaS experience where you had to build the function, not just run it.
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
customer onboardingcustomer activationproject managementdata analysiscustomer health monitoringSaaS implementationAI technology onboardingAPI integrationsplaybook developmenthealth scoring
Soft Skills
communicationempathyproactivitydetail orientedself motivatedtrust buildingtrainingpresentationproblem solvingmultitasking