Founding Sales Lead

Aspire Software

Sales Lead managing full cycle sales for Carla AI, driving growth in the rental industry through outbound strategies and customer engagement.

Posted 4/14/2026full-timeToronto • 🇨🇦 CanadaSeniorWebsite

About the role

Key responsibilities & impact

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

What you’ll need

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.

Benefits

Comp & perks

🌐 Worldwide Post a Job Affiliates ❌ Jobs You've Hidden ⭐️ Saved Jobs ✅ Applied Jobs Account Aspire Software Website LinkedIn All Job Openings 1001 - 5000 employees ☁️ SaaS 🏢 Enterprise 🤝 B2B SaaS
Enterprise
B2B Aspire Software is a company that focuses on acquiring and nurturing businesses with a strong foundation in outstanding products and passionate teams. As part of the Valsef Group, Aspire Software offers resources, knowledge, and a suite of best practices to enhance and expand operations for continuous improvement and sustainable growth. The company emphasizes decentralization to unlock innovation and adaptability within its acquired entities. Aspire Software is dedicated to serving its customers through long-term technology partnerships, leveraging capital and expertise in various verticals to grow both the businesses and individuals involved. Founding Sales Lead 🔥 27 minutes ago 🏢🏡 Toronto – Hybrid ⏰ Full Time 🟠 Senior 🤑 Sales Apply Now Find Hiring Managers Customize resume for this job ☆ Save ☑️ Mark as applied ❌ Hide Report problem 📋 Description
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. Apply Now 📊 Check your resume score for this job Improve your chances of getting an interview by checking your resume score before you apply. Check Resume Score Similar Jobs Senior Manager, Services Sales 🕒 March 28 Docebo 501 - 1000 ☁️ SaaS 📚 Education 👥 HR Tech Website LinkedIn All Job Openings Lead Professional Services sales for AI-powered learning platform at Docebo, driving solutions that align customer objectives with company offerings. Mentor sales representatives to optimize customer engagement. 🏢🏡 Toronto – Hybrid 💵 CA$152k - CA$202k / year 💰 $101.7M Post-IPO Equity - Docebo on 2021-09 ⏰ Full Time 🟠 Senior 🤑 Sales Channel Sales Manager 🕒 March 25 SPS Commerce 1001 - 5000 ☁️ SaaS 🤝 B2B 🛒 Retail Website LinkedIn All Job Openings Channel Sales Manager at SPS Commerce to develop partner strategies and drive revenue growth. Collaborate with cross-functional teams to optimize partner programs and performance metrics. 🏢🏡 Toronto – Hybrid 💵 $100k - $150k / year 💰 $7.5M Series unknown on 2007-06 ⏰ Full Time 🟡 Mid-level 🟠 Senior 🤑 Sales Channel Sales Manager 🕒 March 25 SPS Commerce 1001 - 5000 ☁️ SaaS 🤝 B2B 🛒 Retail Website LinkedIn All Job Openings Channel Sales Manager driving revenue growth and managing strategic partnerships at SPS Commerce. Fostering cross-functional collaboration to optimize partner performance and achieve sales objectives. 🏢🏡 Toronto – Hybrid 💵 $100k - $150k / year 💰 $7.5M Series unknown on 2007-06 ⏰ Full Time 🟡 Mid-level 🟠 Senior 🤑 Sales New Business Sales Manager 🕒 March 24 Xero 1001 - 5000 ☁️ SaaS 🤝 B2B Website LinkedIn All Job Openings New Business Sales Manager leading sales teams at Xero to help small businesses thrive through software. Responsible for creating high-performance sales environments and pipeline coverage. 🏢🏡 Toronto – Hybrid 💰 $925M Post-IPO Debt - Xero on 2024-06 ⏰ Full Time 🟡 Mid-level 🟠 Senior 🤑 Sales Sales Designer 🕒 March 18 Closets By Design 201 - 500 👥 B2C 🛒 Retail Website LinkedIn All Job Openings Sales Designer position at Closets by Design, focusing on helping customers organize their homes. Working remotely with sales training and performance bonuses. 🏢🏡 Toronto – Hybrid 💵 $3k - $5k / month ⏰ Full Time 🟡 Mid-level 🟠 Senior 🤑 Sales View More Sales Jobs 🌐 Worldwide Built by Lior Neu-ner. I'd love to hear your feedback — Get in touch via DM or support@remoterocketship.com Search Search Jobs by country Search jobs by city Search jobs by job title Search entry-level jobs Search junior-level jobs Search senior-level jobs Search jobs by tech stack Search jobs by contract type Search remote internships Search remote part-time jobs Remote jobs Anywhere in the World Companies Hiring Anywhere in the World Companies Hiring Sales People Anywhere in the World Companies Hiring Software Engineers Anywhere in the World Resources Advice Tips for finding remote jobs Interview questions and answers Resume examples Cover letter examples Post a job Affiliates Privacy policy Terms of service Job board SEO course AI Apply Copilot OpenClaw job finder Jobs by Country Remote jobs anywhere in the world (Worldwide remote jobs) Remote jobs United States Remote jobs Australia Remote jobs Brazil Remote jobs Canada Remote jobs France Remote jobs Ireland Remote jobs Germany Remote jobs Netherlands Remote jobs Spain Remote jobs UK Popular Jobs Remote data analyst jobs Remote customer support jobs Remote executive assistant jobs Remote marketing jobs Remote product designer jobs Remote product manager jobs Remote project manager jobs Remote recruiter jobs Remote sales jobs Remote software engineer jobs Jobs by Type Remote full-time jobs Remote part-time jobs Remote contract jobs Remote internship jobs Remote entry-level jobs Remote jobs with no experience required Remote junior jobs (1-3 years of experience) Digital nomad jobs Remote jobs with no degree required Freelance remote jobs Temporary remote jobs Remote jobs hiring now Stay at home mom jobs

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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