Sales Executive Player Coach (AmTrav)

Perk•Chicago, IL

4d•$100,000 - $118,000•Hybrid

About The Position

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.

Requirements

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.
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.

Nice To Haves

4–6 years of active B2B sales experience, ideally in SaaS or travel tech.
Experience in the North American corporate travel industry or travel management space.

Responsibilities

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.
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.
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.

Benefits

Competitive compensation and equity ownership in Perk
Generous allocation of 20 vacation days and 12 public holidays
Flexibility of three medical plans to choose from, with company contributions and an HSA when enrolling in an HDHP medical plan
Comprehensive benefit plans, covering dental, vision and Wellhub’s gym subscription from your start date
Life and disability policies from your start date, with options to add extra protection through voluntary buy-up plans
401(k) plan with company matching contributions
Partner discounts on pet insurance
Unforgettable Perk events, including our spectacular annual summer party
Spring Health, our market-leading wellbeing partner, providing fast, comprehensive access to 12x therapy and 12x coaching sessions for you and your loved ones
12-16 weeks’ paid parental leave
16 paid hours per year to spend volunteering for your dearest charitable causes
Up to 20 "Work from Anywhere" days per year
Four-week, fully paid sabbatical once you reach 5 years
Relocation support