Enterprise Sales Executive

Path to equity in an impressive already-profitable start-up. Ample opportunity for growth and earnings. (Only those with software sales experience will be considered.)

Do you have experience working for a fast-growing SaaS company?

  • Do you like the idea of selling high performing, “reassuringly expensive” professional services and software solutions that transform the performance of enterprise sales teams?
  • Does rolling up your sleeves and getting in on the ground floor in a company with significant global potential and infinite runway appeal to you?
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The Role

We seek a bold, experienced, and self-driven sales executive to join our management team, with full-cycle sales responsibility for acquiring new enterprise clients in our key markets of healthcare and information technology.

This is a genuine “green-field” opportunity, limited only by your capabilities and energy. You will start as an individual contributor augmenting Founder-led sales while you design and build the sales structure that can deliver profitable growth. Experience with Salesforce desired.

This role will report to the CEO and work closely with the COO.

Essential Duties and Responsibilities:

You will have significant experience in selling consulting and SaaS solutions to Enterprise “C-suite” clients. You will have a successful track record of meeting sales targets while contributing positively to team culture, and the flexibility to enjoy and be successful in the rapidly changing environment of a successful startup in growth mode.

You will possess the drive and confidence to pursue new business acquisitions with significant autonomy. You will learn quickly, have good attention to detail and take the growth of the business seriously.

Our client sponsors are executives managing enterprise sales teams of 50 – 500 salespeople and typically responsible for annual revenue of at least $100M. You must have the credibility, deep industry knowledge and experience to get meetings with these leaders and to create genuine value for them.

Salary and Benefits

  • On top of a competitive benefit package, a base salary based on experience and track record is offered, plus an on-target performance-based bonus in year 1.
  • On target earnings from Year 2 onwards exceed $300k.
  • Options to buy in over a 4-year period with the potential, based on performance, to progress to a CRO role.


  • 401(k)
  • Dental insurance
  • Flexible schedule
  • Flexible spending account
  • Health insurance
  • Health savings account
  • Life insurance
  • Paid time off
  • Retirement plan
  • Vision insurance


  • Monday to Friday

Supplemental pay types:

  • Bonus pay

Commission pay

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About Swagger Sales

Swagger Sales transforms the capabilities of enterprise sales teams with a combination of brilliantly effective skills training coupled with our innovative SWIFTTM CRM software tools. Headquartered in New York with offices in Australia and the U.K., our clients are Fortune 500 companies in the healthcare and technology markets where sales teams face increasing commoditization pressures and need to drive bigger, faster client decisions.
Less than two years old, already profitable and with genuine global ambitions, our solutions have already delivered double digit revenue growth to some of the leading Fortune 500 companies in the healthcare and I.T. markets of the U.S., Asia-Pac and EMEA markets.
Application Process

We require a current resume along with a compelling, customized one-page cover letter that captures our attention and clearly conveys why we should be talking with you. You will receive a response within 3 days. If you are a viable candidate, Zoom calls will be setup with the COO and CFO followed by an in office interview, This position is for immediate hire.

What’s in it for you:

Job Type: Full-time

  • Ample career growth and development opportunities
  • Opportunity to work with global employees and clients
  • Life insurance
  • 401(k) savings plan
  • Generous PTO
  • Company stock option plan

At Swagger we combine world-class sales training for reps, managers, and sales leaders with cutting edge integrated CRM tools. Our clients look to us for expert advice and tools to advance their sales process. If you are looking for a company where you can make a significant impact and advance your career, apply now.

Application Process

Please send us a current resume along with a compelling, concise cover note that captures our attention and clearly conveys why we should be talking with you.


Apply Now