Founding Account Executive

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

About the Role

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

You will be the person who defines how our product 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 we sign 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 our entire B2B engine.

What You’ll Do

• Own full-cycle outbound sales, from cold prospecting to close
• Sell to SMBs across multiple verticals
• Run tight, high-quality demos that clearly explain our 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