Manager, Mid-Market Sales at TripActions

| Chicago
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As TripActions continues to see significant adoption in the market and grow 20%+ MoM, we are looking for a Manager, Mid-Market Sales to help lead, train, coach, scale, and motivate a team of high performing, quota crushing Mid-Market Account Executives. This role will report directly to the Mid-Market Director of Sales. TripActions is looking for a natural leader who loves to sell, is energized by nurturing and developing people, can scale an effective process, and is exceptional at inspiring customers and prospects through a fast-cycle, complex sales process.

You will be able to work out of the Chicago office, and will manage a team of 5-8 Account executives as a front line manager and ultimately drive net new revenue growth.


  • Hire and continue to build out a team of exceptional Account Executives
  • Connect Account Executives to key resources and clear roadblocks, enabling them to achieve and/or exceed their revenue goals
  • Oversee day-to-day activity of your AE team members and monitor performance goals while providing ongoing feedback, coaching, and guidance through weekly 1:1s and or ad hoc discussions.
  • Develop and report sales revenue forecasts based on visibility into direct and partner pipeline on a monthly and quarterly basis
  • Track MM AE team activity and performance metrics and report data to leadership on a regular basis.
  • Develop, Train and Inspire team members on a daily basis and recognize and reward accomplishments and contribution including competitions and spiffs.
  • Develop and refine best practices and ensure adherence to Salesforce usage as well as accurate forecasting practices.
  • Support team growth by developing and/or maintaining content for onboarding, training, scripts, and playbooks.


  • 3+ years experience as a sales leader/manager.
  • Demonstrable success in leading/managing inside or field sales teams with a SaaS product and solution sales approach.
  • 3+ years as an individual, closing role specific, sales person within the technology and/or travel industries.
  • Track record in building organizations and hiring and training top talent, particularly in a hyper-growth start-up environment.
  • Strong leadership experience, with a focus on training, coaching and motivation.
  • Expert knowledge of the full sales cycle, from prospecting, cold calling through to negotiation and closing.
  • Ability to function in “Player/Coach” role that includes customer facing engagement.
  • Ability to understand, articulate, and lead complex sales processes.
  • Technical aptitude, and ability to learn new concepts quickly.
  • Analytical thinker with demonstrated command of metrics-driven sales models.
  • Strong career trajectory with a history of top performance in successive roles.
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Technology we use

  • Product
  • Sales & Marketing
    • AsanaManagement
    • SalesforceCRM
    • salesloftLead Gen


A stylish neighborhood near the Mag Mile, River North is home to 400 tech startups and some of the most popular dinner and drink places in Chicago!

An Insider's view of TripActions

What’s the vibe like in the office?

Everyone comes into the office with a ton of energy every morning ready to make an impact. Because we are still small, there are constantly opportunities to collaborate and learn from one another. We also make sure to balance time outside of the office to have some fun while strengthening the relationships within our teams.


Sales Development Manager

What does your typical day look like?

As an AE there is no such thing as a typical day. I try to block 2.5 hours a day for prospecting and then prep for upcoming demo’s/calls. I to do a ton of research on the company to go in as prepared as possible. My goal is to understand what they do, why they love their company and how TripActions might help them with making travel stress-free.


Commercial Account Executive

How does the company support your career growth?

TripActions provides me with a clear understanding and support to get to the next step in my career. After expressing interest in being a cultural pillar in our new Chicago office, I worked with my manager and director to develop a plan. Being able to directly communicate with management has given me the opportunity to grow at an amazing company.


Sales Development Representative

How do you make yourself accessible to the rest of the team?

We don’t have an ‘open door’ policy because if you’re an accessible leader, there is no reason for a door in the first place.


Director of Sales

What projects are you most excited about?

Frankly, one of the best things about working at TripActions is the sheer depth and breadth of exposure that people get to teams and projects. Everyone is humble and accessible and there are few if any walled gardens. Right now I'm looking forward to our team hackathon as well as the launch of better direct connectivity with air carriers.


Director of Product Marketing

What are TripActions Perks + Benefits

Volunteer in local community
Partners with Nonprofits
Friends outside of work
Eat lunch together
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Pair programming
Open office floor plan
Dedicated Diversity/Inclusion Staff
Highly diverse management team
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Disability Insurance
Dental Benefits
Vision Benefits
Health Insurance Benefits
Life Insurance
Pet Insurance
Wellness Programs
Retirement & Stock Options Benefits
401(K) Matching
Company Equity
Performance Bonus
Child Care & Parental Leave Benefits
Generous Parental Leave
Family Medical Leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Holidays
Paid Sick Days
Perks & Discounts
Casual Dress
Commuter Benefits
Company Outings
Free Daily Meals
Some Meals Provided
Happy Hours
Pet Friendly
Fitness Subsidies
Professional Development Benefits
Diversity Program
Lunch and learns
Cross functional training encouraged
Promote from within
Mentorship program