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Senior Sales Enablement Manager

Remote - USA

As the Senior Sales Enablement Manager, you will play a pivotal role in shaping the sales strategy, content development, and training programs for our amazing sales team. This position is ideal for someone passionate about teaching, empowering others, and driving efficiency in the sales cycle.

The Senior Sales Enablement Manager will develop and implement strategies to enhance learning engagement, streamline processes, and cultivate a high-performing sales culture. This role is a fantastic opportunity for a motivated individual eager to thrive in a high-energy environment.

A little about us…Fleetio is a modern software platform that helps thousands of organizations around the world manage their fleet operations. Transportation technology is a hot market and we’re leading the charge, with raving fans and new customers signing up every day. We raised $450M in Series D in March of 2025 and are on an exciting trajectory as a company. Fleetio is also a proud founding member of the Rails Foundation!

More about our team and company:

What You'll Be Doing

  • Partner with Enablement Leadership to develop and execute a sales enablement strategy aligned with company objectives, focusing on measurable outcomes such as improved win rates, reduced ramp time, and enhanced pipeline generation.
  • Maintain and update knowledge repositories for the sales organization to ensure information is current and accessible. 
  • Serve as the owner of enablement materials, including facilitating instructor-lead training, developing AE-facing resources, including comprehensive sales playbooks
  • Build and lead ongoing enablement programs to continuously upskill the sales organization, driving advanced competency in value selling, discovery, and positioning. 
  • Capture repeatable sales motions from high performers as a mechanism to scale by creating packaged content, prescriptive guidance, and tailored delivery to sales leaders and sellers.
  • Building trust with Sales leaders and reps, ensuring enablement solutions are practical, impactful, and scalable.
  • Assist with large-scale enablement programming, especially Onboarding and Sales Kick-Off.

Your Experience

  • 6+ years of experience in sales enablement, with a minimum of 2 years in a direct seller role.
  • Ability to simplify complex concepts and deliver them in digestible, actionable formats. 
  • Knowledge of sales methodologies such as Solution Selling or MEDDICC.
  • Insatiable curiosity and a passion for ongoing improvement.
  • Experience in facilitating live and virtual training sessions, with strong communication and relationship-building skills.
  • Familiarity with tools such as Salesforce, LMS platforms (e.g., WorkRamp, Skilljar), and CMS platforms (e.g., Highspot, Seismic).
  • Strong program management skills, with the ability to manage multiple initiatives simultaneously.

Benefits

  • Multiple health/dental coverage options
  • Vision insurance
  • Incentive stock options
  • 401(k) match of 4%
  • PTO - 4 weeks
  • 12 company holidays + 2 floating holidays
  • Parental leave- birthing parent (16 weeks paid) non-birthing (4 weeks paid)
  • FSA & HSA options
  • Short and long term disability (short term 100% paid)
  • Community service funds
  • Professional development funds
  • Wellbeing fund - $150 quarterly
  • Business expense stipend- $125 quarterly
  • Mac laptop + new hire equipment stipend
  • Monthly catered lunches
  • Fully stocked kitchen with tons of drinks & snacks
  • Remote working friendly since 2012 #LI-REMOTE

Fleetio provides equal employment opportunities to all employees and applicants and prohibits discrimination and harassment. We celebrate diversity and are committed to creating an inclusive environment for all. All employment is decided on the basis of qualifications, merit and business need.

This application is not intended to and does not create a contract or offer of employment. Employment with Fleetio is at will.

If you have a disability or a special need that requires an accommodation to fill out the online application, please let us know by calling (205) 718-7500.

 

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