Account Executive (Founding AE)

About Chexy

At Chexy, we’re reshaping the way money moves—making payments smarter, faster, and more rewarding.

We started by being the first in Canada to let people pay their biggest and most painful bills with credit cards and earn rewards on money they had to spend anyway. Now, we’re on a much bigger mission: to build a super app that acts as your co-pilot for all your money—helping you get more value from every dollar you spend.

As a high-growth fintech startup, we’re at the forefront of payments innovation, and we’re looking for hungry, ambitious people to help us scale. If you thrive in a fast-moving, high-energy environment and want to be part of something big, we’d love to work with you.

If you want real ownership, autonomy, and the chance to shape how sales are done at Chexy from day one, this is that role.

About the Role

This is Chexy’s first Account Executive and the beginning of our outbound sales motion.

You will be the person who defines how Chexy is sold to SMBs at scale — which businesses convert best, what messaging breaks through, how objections are handled, and what actually gets deals closed.

The work you do here will directly shape how Chexy signs thousands of businesses over the next year. This is a hands-on, outbound-heavy role. You’ll spend most of your time prospecting, cold calling, cold emailing, running demos, and closing. You’ll own the full sales cycle end-to-end and turn real customer conversations into a repeatable outbound engine.

You’ll work closely with leadership to sharpen the pitch and turn what’s working into playbooks. If you’re successful, your fingerprints won’t just be on deals — they’ll be on Chexy’s entire B2B engine.

What You’ll Do

• Own full-cycle outbound sales, from cold prospecting to close
• Sell Chexy to SMBs across multiple verticals
• Run tight, high-quality demos that clearly explain Chexy’s value
• Write and iterate outbound messaging (email, phone, LinkedIn)
• Build and manage your own pipeline
• Track learnings: objections, ICP patterns, deal velocity, win/loss reasons
• Work to shape:
• Outbound strategy
• Sales collateral
• Target industries and personas
• Early sales process and tooling
• Act as the feedback loop between customers and product

This Role Is a Fit If You

• Thrive in outbound and don’t need warm leads to be effective
• Like ambiguity and enjoy building before things are “figured out.”
• Can switch from high-volume cold outreach to thoughtful, consultative selling
• Want ownership and upside
• Are motivated by results

This Role Is Not a Fit If You

• Prefer inbound-only or heavily scripted sales motions
• Need a fully built playbook to succeed
• Want a low-intensity role
• Are uncomfortable being the first sales hire

Requirements

• 3+ years of experience in B2B sales (SDR or AE)
• Strong hunter mentality with outbound-first experience
• Excellent written and verbal communication skills
• Comfortable selling without a set playbook
• Strong intuition for customer pain points and value-based selling
• Experience using CRM and sales tools (Salesforce, HubSpot, etc.)

Nice to have

• Experience selling to SMBs
• Background in fintech, payments, or hospitality
• Previous founding sales team or early sales team experience

Why Join Chexy?

📈 Real ownership and upside: As the first AE, your impact is visible and compounding. Strong performance here unlocks meaningful equity, leverage, and long-term growth.

🛠 Autonomy without chaos: Work directly with founders and leadership, move fast, test ideas, and turn what works into playbooks — without layers of bureaucracy.

🚀 Career-defining role: This isn’t just a quota job. You’ll build a muscle that doesn’t exist yet and have your fingerprints on Chexy’s entire B2B growth engine.

📍 Toronto office: In-office, 5 days a week, building together.