Aspire Software

Founding Sales Lead

Aspire Software

full-time

Posted on:

Location Type: Hybrid

Location: Toronto • Canada

Visit company website

Explore more

✨ AI Apply
Apply

Job Level

Senior

About the role

  • Own the full sales cycle: prospecting, discovery, demos, proposals, negotiation, and close.
  • Build and maintain a target account strategy by segment and customer profile.
  • Present and sell Carla AI to rental operators and services businesses, clearly articulating the ROI, efficiency gains, and revenue impact of AI powered call handling and booking automation.
  • Seamlessly transition new customers to onboarding and Customer Success for activation and first value realization.
  • Lead outbound strategy and execution across calls, email, LinkedIn, and industry events.
  • Develop and iterate on talk tracks, competitive positioning, objection handling, and demo structure.
  • Establish pipeline creation targets and inspection routines that translate activity into predictable results.
  • Create repeatable playbooks covering segments, sequences, cadences, and qualification criteria.
  • Share structured customer insights and market feedback with Product and leadership to inform roadmap, pricing, and packaging decisions.
  • Maintain accurate pipeline, activity tracking, and forecasting in CRM (HubSpot).
  • Consistently meet or exceed monthly and quarterly KPIs across outreach, demos, pipeline, and revenue.
  • Coordinate with Partnerships and Marketing to leverage partner channels and campaigns for pipeline generation.

Requirements

  • 3 to 5+ years of proven success in B2B SaaS new business sales, with a strong track record of closing.
  • Strong hunter mentality: you are comfortable with outbound prospecting and generating your own pipeline, not reliant on inbound leads.
  • Experience managing a full sales cycle from first contact through contract execution.
  • Confident running discovery calls and solution based sales conversations that connect product capabilities to business outcomes.
  • Experience building or materially improving a sales motion: process, messaging, cadence, and forecasting.
  • Strong communication, presentation, and relationship building skills.
  • CRM experience (HubSpot, Salesforce, or equivalent).
  • Self motivated, goal driven, and comfortable working autonomously in a fast paced, evolving environment.
  • Experience selling into the rental industry (car rental, equipment rental, fleet management) or adjacent verticals such as automotive, travel tech, or mobility is a strong plus.
  • Experience selling AI, automation, or voice/conversational technology products.
  • Experience in vertical market software or operationally complex environments where the buyer is an operator, not a tech team.
  • Startup or early stage SaaS experience where you had to build the motion, 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
B2B SaaS salesfull sales cycle managementoutbound prospectingsolution-based salessales process improvementpipeline creationKPI trackingCRM managementAI salesautomation technology
Soft Skills
strong communication skillspresentation skillsrelationship buildingself-motivatedgoal drivenautonomous workfast-paced adaptabilitynegotiation skillsobjection handlingcustomer insights sharing