Senior Outbound Account Executive – SMB Sales

CardFlight | SwipeSimple Connect Remote | OTE $150,000–$160,000+

Small businesses are the backbone of local economies — and you'll be the person finding them, calling them, and helping them modernize how they get paid.

As a Senior Outbound Account Executive at CardFlight, you won't wait for leads to come to you. You'll run a high-velocity, outbound-only sales motion — working a parallel dialer, targeting SMB owners who fit our ICP, and closing net new SwipeSimple Connect customers from a cold start. This is a role built for hunters who thrive on activity, love the phone, and want their income tied directly to their output.

Our outbound AEs are among the highest earners at CardFlight. The comp structure reflects it.

OTE: $150,000–$160,000+, with accelerators and uncapped upside for top performers. Base salary: $65,000.

Location: Remote

What You'll Do

• Own outbound pipeline from zero. No inbound leads, no reactivations. You build your pipeline through high-volume calling using a parallel dialer, targeted email, and disciplined SMB prospecting.
• Work a structured ICP. You'll prospect into defined small business segments — think restaurants, retail, and service businesses — using data-driven targeting to find the right merchants at the right time.
• Run the full sales cycle, fast. From first dial to close, you own every step. Qualify quickly, demo consultatively, handle objections, and drive decisions with small business owners who have limited time and attention.
• Hit daily activity metrics. This role is built around dialer performance — connect rates, conversations, and pipeline velocity matter as much as closed deals. You'll be expected to own your numbers at every stage of the funnel.
• Keep CRM airtight. Accurate logging, clean pipeline hygiene, and sharp forecasting are non-negotiable. Your data is your business.
• Sharpen your pitch continuously. Partner with marketing and product to stay current on messaging, competitive positioning, and ICP insights.

What You'll Bring

• 3–5+ years in outbound sales, ideally in SaaS, fintech, or payments — selling to SMB owners specifically
• Parallel dialer experience — you know how to manage a high-volume call environment and convert connects into conversations
• A genuine hunter mentality — you're energized by building pipeline from scratch, not managing inbound volume
• Proven quota attainment in an outbound or self-sourced pipeline role
• Strong SMB instincts — you know how to earn the attention of a busy small business owner in the first 20 seconds
• Consultative closing ability — you can move quickly without being pushy, and you know when to push for the decision
• CRM discipline and the ability to ramp on new sales tools fast

The Opportunity

CardFlight's SwipeSimple platform is trusted by 125,000+ small businesses nationwide. You'll be opening new doors — calling merchants who haven't heard of us yet and turning cold conversations into activated customers.

This isn't a role where you polish inbound leads someone else generated. You're the top of the funnel and the bottom of it. In return, the comp plan is designed to pay you like it.

• Accelerated commission tiers at 101–125% and 126%+ of quota — the more you close, the faster your rate grows
• Quarterly performance bonuses with partial payouts so near-misses still get rewarded
• Rotating SPIFs that reward dialer activity, fast starts, and ICP vertical performance
• Annual bonus tied to both company and personal attainment goals
• 3-month ramp plan with reduced quota expectations while your pipeline matures
• Equity — your growth is tied to ours

Benefits

• Remote-first with home-office stipend
• Comprehensive health benefits
• Stock options
• Learning & development culture, team events, and Lunch & Learns