SMB Account Executive

Location Chicago; Boston Address Chicago, Illinois Employment Type Full time Department Sales Compensation Base Salary $72K – $128K • $56K Commission About the role Are you a driven sales professional who thrives on outbound prospecting and owning the full sales cycle? Do you get a buzz from booking that first meeting and closing the deal? If so, keep reading–we might just be your next big opportunity. At Perk, we're on a mission to revolutionize business travel. We’re growing fast in North America, and we’re looking for ambitious 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. Many of our top AEs have gone on to leadership or more senior sales roles within the business. We’re looking for self-starters who are motivated by growth, excited by targets, and love speaking to new people. If you’re someone who can handle high volumes of outreach, run compelling discovery and demo calls, and close deals with confidence–this is your stage. How you'll spend your time 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. You’ll sell to a range of personas–from Office Managers to Finance and HR leaders–and need to tailor your pitch accordingly. We get excited about you if you have 1+ years of experience running full-cycle B2B sales, with a strong focus on outbound prospecting and new business generation; 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 total on-target variable earnings (base + commission) are $128,000. The commission structure will be tied to the achievement of revenue & retention targets. Commissions are uncapped. How We Work At Perk, we take an IRL-first approach to work, where our team works together in-person 3 days a week. As such, this role requires you to be based within commuting distance of our hubs. We fundamentally believe in the value of meeting in real life to improve connectivity, productivity, creativity and ultimately making us a great place to work. For certain roles, we can help with relocation from anywhere in the world, English is the official language at the office. Please submit your resume in English if you choose to apply. Do not forget to submit an updated portfolio and/or resume. Protect Yourself from Recruitment Scams All official communication from Perk will always come from email addresses ending in @perk.com or @externalperk.com, our verified social media channels, or recruiters listed on our official LinkedIn page. We will never ask you to pay for equipment, training, or fees, request sensitive personal information such as bank details early in the process, or communicate through unofficial apps like WhatsApp, Telegram, or Signal. If you receive a message claiming to be from Perk that seems suspicious, please do not respond. Forward it to security [at] perk .com, and we will confirm whether it is legitimate. Compensation Range: $72K - $128K Perk is a global company with a diverse customer base, and we want to make sure the people behind our product reflect that. We’re an equal opportunity employer, which means you’re welcome at Perk regardless of how you look, where you’re from, or anything else that makes you, well, you. #J-18808-Ljbffr TravelPerk