Job Title: Senior Account Executive - Growth

Location: Toronto, Hybrid

Reports to: Executive Vice President - Revenue

At Wingmate, we're transforming the way businesses manage their customer relationships. As a leading provider of CRM solutions and powerful ancillary SaaS tools, we help businesses streamline their sales processes, build stronger customer connections, and drive sustainable growth. Our platform is designed to fuel success by turning everyday tasks into streamlined, automated workflows that empower teams to do more, faster. We've made sales and service a true team sport - where every win compounds into bigger victories.

We're hunting for a Senior Account Executive who is an absolute sales weapon. Can't cage a songbird, can't tame a wild horse - and we sure as hell don't want to try. We need someone who doesn't just close deals, they architect wins. Someone who operates within their spheres of influence like a master strategist, curates the conditions for success, and consistently delivers top-quartile performance that others can only dream about.

This isn't a role for someone looking to figure it out. You've been closing enterprise deals for 5+ years minimum, your performance numbers speak louder than your resume, and you build your own path to quota crushing because that's how winners operate.

What You'll Do:

You'll be the cornerstone of our enterprise function development. No hand-holding, no onboarding period - just immediate impact that transforms our revenue trajectory. You'll work your network, leverage our BDR team, tap into existing customer networks, and identify pipeline gaps before they become problems. You'll close deals while simultaneously building the enterprise playbook that scales our success.

Your day-to-day will include:

Full-Stack Enterprise Sales:

• Own the complete sales cycle from initial discovery through contract signature and expansion planning
• Navigate complex enterprise buying committees with surgical precision, building consensus and creating urgency
• Execute consultative selling that positions Wingmate as the strategic partner, not just another vendor
• Master mid-market to enterprise deal cycles, compressing timelines through expert qualification and objection handling

Pipeline Architecture & Management:

• Identify your own pipeline gaps and architect solutions before quota suffers
• Leverage your network, our BDR team, and existing customer relationships to create a self-sustaining opportunity engine
• Qualify opportunities ruthlessly - if it won't close, kill it fast and move to deals that will
• Maintain forecast accuracy that revenue leadership can bank on, with pipeline coverage that never leaves you scrambling

Enterprise Function Development:

• Help build and refine our enterprise sales playbook as we scale into larger deals and longer cycles
• Collaborate with Product, Marketing, and Customer Success to ensure enterprise clients get white-glove treatment
• Mentor junior sales team members and share winning strategies that elevate the entire organization
• Drive strategic account planning that turns single deals into multi-year, multi-product relationships

Revenue Generation & Growth:

• Consistently deliver top-quartile performance with numbers that prove your worth quarter after quarter
• Execute upsell and cross-sell strategies within existing accounts, expanding deal size and customer lifetime value
• Negotiate contracts that maximize revenue while ensuring customer success and long-term partnership
• Drive renewal conversations early, positioning expansion opportunities before competitors can interfere

Strategic Relationship Management:

• Build executive-level relationships that survive personnel changes and drive long-term account growth
• Become the trusted advisor that C-suite executives turn to for strategic CRM and automation guidance
• Orchestrate proof-of-concepts and pilots that demonstrate clear ROI and create urgency for enterprise-wide deployment
• Manage complex stakeholder dynamics across IT, Operations, Sales, and Executive teams

Qualifications:

We're looking for a proven sales weapon, not a project. You've been crushing quota as an Account Executive for 5+ years minimum, with full-stack experience selling SaaS solutions into mid-market and enterprise accounts. Your performance has been consistently top-quartile, and you can prove it with specific numbers, percentages, and outcomes that matter.

You've navigated complex enterprise sales cycles, managed multi-stakeholder buying committees, and closed deals that others said couldn't be done. You're comfortable with tools like HubSpot, Gong, ZoomInfo, LinkedIn Sales Navigator, and the full tech stack that drives modern sales success.

You understand deal qualification frameworks, can compress sales cycles through expert discovery, and know how to create urgency without creating pressure. You've worked your network to generate opportunities, collaborated with BDR teams to maximize pipeline, and identified gaps before they became problems.

You're a strategic thinker who builds your own path to success, organizes your territory for maximum impact, and thrives in cultures built to win. You're solution-oriented because closing deals requires solving problems, not just presenting features.

Most importantly, you're a native English speaker who communicates with C-suite clarity and executes with precision that turns conversations into contracts.

Why Join Us:

Impact: Be the architect of our enterprise function while driving immediate revenue growth that shapes company trajectory

Opportunity: Ground-floor opportunity to build something significant while earning top-tier compensation in a high-growth environment

Culture: Join a winning culture that celebrates results, supports success, and never settles for second place

Compensation: Competitive base plus aggressive commission structure that rewards top performers who deliver results

If you're ready to join a team that's built to win, architect an enterprise function from the ground up, and consistently deliver the kind of performance that legends are made of - without needing time to figure it out - apply today.

We're moving fast, closing deals, and building something exceptional. Keep up or get left behind.