Senior Outbound Account Executive, CardFlight
$150-160k
OTE
$65k
BASE
With accelerators and uncapped upside for top performers
Payment acceptance for small businesses
Be an early applicant
Payment acceptance for small businesses
21-100 employees
Be an early applicant
$150-160k
OTE
$65k
BASE
With accelerators and uncapped upside for top performers
21-100 employees
Company mission
To create easy-to-use payment solutions so small-business merchants can focus on what they do best: growing their business.
Role
Who you are
- 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
What the job involves
- 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
- 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
Our take
CardFlight partners with popular merchant acquirers to deliver payment acceptance software for small businesses and entrepreneurs. Its signature products, a mobile Point of Sale (POS) called SwipeSimple, and the countertop POS SwipeSimple Register have grown impressively in popularity across the US since the company’s 2013 launch.
The US is home to over 30 million small businesses, a potentially huge market. By offering software that allows them to turn a mobile or tablet into a credit card terminal, it’s easy to see why CardFlight is proving popular. Just as importantly, is that the company has a proven track record of launching products ahead of potential competitors.
Freddie
Company Specialist at Welcome to the Jungle
Insights
6% employee growth in 12 months
Company
Funding (last 2 of 3 rounds)
Sep 2018
$3.5m
SERIES A
Oct 2015
$4.2m
SERIES A
Total funding: $9.3m
Company benefits
- Stock options for all full-time team members
- Personal annual budget for professional development
- Regular team lunches and treats for special events
- Liberal vacation policy
- Comprehensive medical, vision, and dental plans
- Commuter benefits and health discounts
Company HQ
Kips Bay, New York, NY
Leadership
Derek Webster
(Founder & CEO)Former Engagement Manager at Oliver Wyman. Led product development and product marketing to launch E*TRADE’s credit card business. Prior to founding CardFlight, founded and was CEO of LocalBonus, a credit card-linked loyalty network.
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