Jobs · Sales · Illinois

Senior Account Executive - US

Perk · Chicago, IL · 1 mo ago
HybridSales$165k/yrFull-time

About the role

At Perk, we're on a mission to revolutionize business travel. We're growing fast in North America, and we're looking for ambitious Senior Account Executives to join our team.

This is a high-impact, high-energy role where you’ll be responsible for outbound pipeline generation, running the full sales cycle from first touch to close, and even supporting the post-sale experience to set your clients up for long-term success.

You’ll join a high-performing, collaborative sales team that values curiosity, ownership, and continuous learning. We’re proud of the culture we’ve built—inclusive, fast-paced, and deeply supportive—and we invest in your growth with training, coaching, and a clear path for progression.

  • Own the full sales cycle–from outbound prospecting and booking your own meetings, to running discovery, delivering demos, and closing new business.
  • Generate pipeline through high-volume outbound activity, using phone, email, and LinkedIn to engage target accounts.
  • Tailor conversations and demos to align with customer pain points and clearly communicate Perk’s value.
  • Maintain a clean, accurate pipeline and forecast in Salesforce, staying organized and data-driven.
  • Partner closely with Implementation and Account Management to ensure a smooth handoff and set new customers up for long-term success.
  • Sell to a range of personas–from Office Managers to Finance and HR leaders–and need to tailor your pitch accordingly.

Requirements

  • 3+ years of experience running full-cycle B2B sales, with a strong focus on outbound prospecting and new business generation in the mid-market space;
  • Background in startups, SaaS, or B2B tech is a plus.
  • A proven hunter mindset–you’re energized by building pipeline and closing net new deals.
  • Comfort engaging with senior decision-makers and adapting your message to different personas.
  • A self-sufficient and organized approach to work–but you’re still a team player at heart.
  • Excellent verbal and written communication skills, especially via video and phone.
  • A growth mindset, strong integrity, and relentless drive to succeed.
  • Eligibility to work in the USA.
  • Based in or willing to relocate to Boston, Chicago or Miami.

What do we offer?

  • Competitive compensation, including equity in Perk
  • Generous vacation days so you can rest and recharge
  • Comprehensive benefit plans covering medical, dental, vision, life, and disability with coverage from your start date
  • Financial benefits like 401k or Roth with company matching, and HSA or FSA plan
  • Subscription to Wellhub, the gym benefit
  • Family services that include adoption benefits and paid parental leave from 12 to 16 weeks
  • Global presence and hybrid working style
  • Unforgettable Perk events, including travel to one of our hubs
  • Learning and professional development opportunities
  • A mental wellbeing platform that provides free therapy and professional coaching sessions
  • Exponential growth opportunities
  • 16 paid hours per year to volunteer for a cause of your choice
  • "Work from anywhere" allowance of 20 working days per year
  • Compensation and Benefits: Compensation for this role is a combination of salary, commissions, and stock options. The OTE (base + commission) is $165,000. The commission structure will be tied to the achievement of revenue & retention targets. Commissions are uncapped.

How We Work

  • We take an IRL-first approach to work, where our team works together in-person 3 days a week.
  • For certain roles, we can help with relocation from anywhere in the world, English is the official language at the office.

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