The intelligent platform for travel and spend.
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Perk

Sales Executive Player Coach (AmTrav)

Posted An Hour Ago
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Hybrid
Chicago, IL, USA
100K-118K Annually
Senior level
Hybrid
Chicago, IL, USA
100K-118K Annually
Senior level
Hybrid individual contributor and frontline coach who carries personal revenue targets while line-managing and developing a team of 3-5 Account Executives. Responsibilities include closing SMB/MM deals, pipeline building, using AI-enabled sales tools, running coaching/role-play and onboarding, designing enablement materials and training programs, reporting performance insights, and contributing to regional sales strategy.
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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.

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 to learn more.

About the Role

The Account Executive Player Coach is a hybrid individual contributor and team leadership role at the heart of AmTrav’s North America SMB Sales organization. You'll carry your own revenue number while coaching, developing and line-managing a small team of Account Executives — setting the bar for what great looks like every single day.

This role is built for someone who loves to sell AND loves to make others better at selling. You'll work closely with Senior Sales Management to drive regional strategy, and you'll be the kind of leader people turn to when they need guidance — whether their manager is in the room or not.


What You’ll Do

Individual Contribution

  • Own your IC Premium Signed target (set at 50%), building and managing your own pipeline through outbound activity and closing net-new deals.

  • Manage complex deals end-to-end, including SMB and MM opportunities.

  • Use AI-powered tools (prospecting, call intelligence, pipeline forecasting) to sharpen your own performance — and set the example for your team.

Team Leadership & Coaching

  • Line-manage a team of 3–5 Account Executives, acting as their primary coach and day-to-day leader.

  • Conduct weekly 1:1s focused on performance, pipeline health and individual development.

  • Act as the point of contact for the full SMB + MM AE team and senior stakeholders when the Senior Sales Manager or Team Leads are unavailable.

  • Be a visible role model — the standard you hold yourself to is the standard the team will aspire to.

  • Support onboarding of new Account Executives and run training sessions as needed.

  • Coordinate with Senior Sales Management to drive regional plans and strategy forward.

Performance & Development

  • Review individual and team performance, surfacing clear insights to Senior Sales Management.

  • Identify training gaps and set monthly development objectives for each Account Executive on your team.

  • Co-develop sales enablement materials alongside Senior Sales Management — presentations, playbooks, product update resources.

  • Design engaging training programs using gamification, role-play, and pitch simulation.

  • Continuously improve training approaches to meet the demands of different accounts and segments.

  • Integrate AI tools into team training and coaching workflows — help your team understand when AI accelerates their work and when human judgment leads.

  • Stay sharp on the competitive landscape and North American market trends, bringing relevant intelligence back to the team.


What We’re Looking For
  • You are an existing SSE or ENT AE at AmTrav, and an AE with 2 quarters of blended 100% achievement and a minimum of 1 year in your current role.

  • 4–6 years of active B2B sales experience, ideally in SaaS or travel tech. (Desirable)

  • Experience in the North American corporate travel industry or travel management space. (Desirable)

  • Proven track record of managing complex deals across multiple segments.

  • Experience with coaching, role-play facilitation, or sales training — formal or informal.

  • Comfort with AI-powered sales tools and a genuine curiosity about how technology can make your team better.

  • Excellent communication skills — you can motivate a room and write a compelling email with equal ease.

  • Creative, solutions-focused mindset with strong organisational skills.

  • Hands-on experience building training materials: decks, videos, enablement resources.

  • An over-achiever who brings energy and accountability — to yourself and the people around you.

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


AI Fluency (ensure you add this in all your job ads)

AI is embedded in how we work across every function. The tools you'll use day-to-day are AI-enabled, so you can move faster and spend more time on the work that matters. In practice, that means using AI to research and prioritise accounts, draft and refine outreach, handle customer interactions more effectively, synthesise information, and cut through shadow work - the invisible tasks that pull people away from the work only they can do - so you can focus on relationships and outcomes.

We don't expect you to be an AI expert, but we do expect you to be curious and intentional about it. The bar is judgment: knowing when AI makes your work better, when to verify what it produces, and when to rely on your own expertise instead.

We'll ask about how you use AI in your interviews, not to test tool knowledge, but to understand how you think about it. That reflects how we work every day.

Compensation: Compensation for this role is a combination of salary, commissions, and stock options. The base salary range is $100,000 - $118,000 and the on-target variable will be based on a percentage of revenue of the deals. 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 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.
#LI-Hybrid

Perk Chicago, Illinois, USA Office

Perk Chicago Office

Our Chicago office is right in the heart of River North, surrounded by some of the city’s best restaurants and coffee spots. It’s the perfect area for lunch breaks or after-work plans, and the office is just steps from the Grand Red Line station, making it easy to get to by bus or train.

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