Sales Team Lead - US at Perk in Chicago, IL

About Us Perk (formerly TravelPerk) is the intelligent platform for travel and spend management. Built to tackle the time-consuming, manual work that gets in the way of real work, our tools automate everything from travel bookings to expenses, invoice processing, and more. By eliminating this shadow work that wastes hours, erodes morale, and saps innovation, we’re on a mission to power real work, with real impact. We’re trusted by more than 10,000 companies worldwide, including Wise, On Running, Breitling, and Fabletics, and we’re tackling the 7 hours of lost productivity per employee each week, a $1.7 trillion problem http://www.perk.com/shadow-work-report. Founded in 2015, Perk has grown into a global company of more than 1,800 people across 12 offices globally, with headquarters in London and Boston. We combine innovation, control, and simplicity to transform how businesses work and how people feel at work. At Perk, we’re driven by our values, like being an owner, delivering a 7-star experience, and working as one team. We value curiosity, purpose, and mindset, not just knowledge, to unlock the power in your potential. Our talent team brings together leading minds from the travel and SaaS industries, representing over 70 countries. If you’re excited about having a real impact and shaping how millions of people experience work, we’d love you on the team. Visit www.perk.com http://www.perk.com to learn more. About the Role We are looking for an experienced Sales Team Leader to join the NAM Sales team based in our Chicago or Boston office! Reporting to the NAM SMB Senior Sales Manager, you will lead a team of approximately 8 Sales Executives focusing on transactions in the North American market. This role requires someone who excels at creating scalable processes and driving consistent execution in a fast-paced environment. You'll contribute to the company's ongoing success while developing the next generation of sales talent in our organization. As a Sales Team Leader, you will: - Establish and optimise scalable sales processes for a team of Sales Executives (first or second role in closing deals). - Conduct structured weekly 1:1s and pipeline reviews to drive consistent deal closure. - Develop and implement monthly performance metrics and development objectives tailored to early-career sales professionals. - Create comprehensive onboarding programs to rapidly train new salespeople for success in high-volume environments. - Provide accurate forecasts and analytical insights to support strategic decision-making. - Design and deliver targeted training sessions using gamification, role-playing, and pitch simulations specifically for high-volume sales scenarios. - Identify systemic efficiency opportunities to help the team close more deals with less effort. - Work cross-functionally with other managers to develop standardised sales enablement materials and processes. What We’re Looking For: - 3-5+ years of proven quarter-over-quarter sales success. - Experience managing sales teams preferred. - Proven track record creating scalable sales processes that can be effectively taught to early-career professionals. - Data-driven approach to performance management with ability to identify patterns across large volumes of deals. - Strong training and development skills with experience designing effective programs for junior talent. - Excellent communication skills with ability to simplify complex concepts for newer sales professionals. - Experience hiring and developing top talent for high-volume sales teams. - Hands-on experience creating standardised training materials and sales enablement content. What we offer: - Receive competitive compensation and equity ownership in Perk - Rest and recharge with our generous allocation of 20 vacation days and 12 public holidays - Enjoy the flexibility of three medical plans to choose from, with company contributions and an HSA when enrolling in an HDHP medical plan - Take control of your physical health with additional comprehensive benefit plans, covering dental, vision and Wellhub’s gym subscription from your start date - Rest assured that you’re covered by life and disability policies from your start date, with options to add extra protection through voluntary buy-up plans - Plan for your future with our 401(k) plan with company matching contributions - Care for your furry friends through partner discounts on pet insurance - Join our unforgettable Perk events, including our spectacular annual summer party - Always feel supported with Spring Health, our market-leading wellbeing partner, providing fast, comprehensive access to 12x therapy and 12x coaching sessions for you and your loved ones - Focus on your family with 12-16 weeks’ paid parental leave - Contribute to your community with 16 paid hours per year to spend volunteering for your dearest charitable causes - Broaden your horizons with up to 20 "Work from Anywhere" days per year - Follow your passions and take a four-week, fully paid sabbatical once you reach 5 years - Let us help you move to one of our hubs with relocation support Compensation: Compensation for this role is a combination of salary, commissions, and stock options. The range with base and the on-target variable earnings is $166,000 - $184,000 OTE. The commission structure will be tied to achieving revenue & retention targets. 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. 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. Protect Yourself from Recruitment Scams All official communication from Perk will always come from email addresses ending in @perk.com http://perk.com or @externalperk.com http://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.