Head of Sales

When was the last time you were planning a business trip and really tried to save your company money? If your company allowed you to stay in a fancy hotel, would you ever volunteer to stay at an Airbnb or at a friend's house? How about flying coach instead of business class? The vast majority of employees optimize for comfort and convenience, spending at the high end of their company policy limits, because, well, why not? So how can a company get its employees to care about expenses without implementing draconian policies, creating friction and frustrating employees? How can a company motivate its employees to save? 

The answer is Rocketrip. We're a NYC-based startup that rewards business travelers for cost-sensitive behavior. It's a win-win: companies save, while employees cash in with real rewards.

The Role:

Rocketrip is looking for an experienced Head of Sales to join our New York team. This person will report into our CEO and be responsible for driving company revenue, while managing a team of highly talented Account Executives and overseeing Sales Development. This is a true coaching opportunity where you will have the ability to foster growth and development. You will maintain a close pulse on new business pipelines to help each individual hit and overachieve their assigned quota.

What you'll do:

  • Lead and coach a growing team of mid-market and enterprise Account Executives and oversee Sales Development
  • Exceed monthly, quarterly, and annual sales quotas and revenue targets
  • Partner with our executive team to develop sales strategy, methodology, and best practices
  • Own the sales operating model and architect your org for our next phase of growth
  • Identify areas of improvement, including process and productivity
  • Train and develop new and current sales talent
  • Attract and hire new employees to plan
  • Mentor and retain top performers

You should have:

  • A bachelor's degree
  • 10+ years of progressive enterprise sales experience selling into c-suite, preferably HR and/or Finance
  • 5+ years of sales leadership experience
  • B2B / SaaS experience
  • A proven track record of running a team of successful enterprise AE's
  • A strategic and analytical mindset and strong decision making skills
  • Leadership skills and the ability to create a positive team environment
  • Held the top responsibility for revenue at a company of sub $20M revenue
  • Experience in building sales enablement/onboarding experiences
  • Training in more than one formal sales methodology and understand the first principles that you can apply to our context
  • Overseen AEs and Sales Development in the past


  • Are in high growth mode, and you will have the ability to make a huge impact
  • Offer great benefits, including medical, dental, and optical
  • Provide employees with a 401k plan
  • Believe it's important to rejuvenate and offer a "take what you need" vacation policy
  • Have a dog-friendly office
  • Provide access to gym membership discounts
  • Also give access to a range of other discounts including Citi Bike and Zipcar


Founded in 2013 and headquartered in New York City, Rocketrip is aiming to revolutionize business travel by introducing the motivation to save. We're a group of tech innovators who looked at the current state of business travel, became frustrated by the horrible employee and employer experiences, and decided to do something big about it. Our team is focused on utilizing technology, design and data to align employee and company interests.

Rocketrip is backed by a renowned set of investors and advisors, including Bessemer Venture Partners, Canaan Partners, Genacast Ventures, and Y Combinator.

Meet Some of Rocketrip's Employees

Dan R.


Rocketrip is a behavioral change platform that rewards employees for spending less for traveling for business

Ellen T.

Account Executive

As an account executive, Ellen’s job is to cultivate client relationships and expand Rocketrip’s customer base. She works to generate leads on new clients and negotiates their account terms.

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