Sales Enablement Specialist



Sales & Business Development
rosslyn, arlington, va, usa
Posted on Thursday, November 2, 2023

Shift5 is the observability platform for onboard operational technology (OT). We’re a rapidly growing scale-up that specializes in cybersecurity, predictive maintenance, and compliance for operational technology (OT) systems across Defense, aerospace, and rail. We are a collaborative, passionate, and driven cadre of dynamic, multidisciplinary experts and we’re focused on helping our customer’s fleets run smarter and safer by accessing and democratizing the volumes of onboard OT data generated by transportation and freight fleets, and defense fleets and weapon systems. Come join us.

Shift5 is seeking a Sales Enablement Specialist to join our growing Sales team. You should be a proven training management, design, and facilitation specialist with exceptional organization, communication, project management, and process skills all geared towards improving efficiency and effectiveness of the company’s sales efforts. This role will be responsible for working with multiple teams to scope, design, and deliver sales and technical enablement programs. Enablement consumers will include Sales Account Managers, Sales Engineers, Partner Account Managers, and Partner Sales Engineers. Additionally, they will make process improvements focused on driving improved effectiveness in demonstration delivery, removing technical obstacles, and ultimately accelerating increased bookings. This position requires a self-starter who can work with limited direct supervision, has strong instructional systems design and performance consulting skills, is entrepreneurial in spirit, and who has a strong drive for results.

You will be expected to:

  • Travel to customer sites 25% of your time.
  • Design, create and implement enablement programs for sales teams addressing competency gaps spanning solution selling skills, product knowledge, product launches, outcome selling, and operational efficiency to improve sales productivity.
  • Play a key role in the New Hire Onboarding program and on-going enablement programs including eLearning, VILT, just-in-time workshops, and strategic events like annual Sales Kick Off
  • Work with teams to schedule, communicate, and follow up for varied training and enablement programs
  • Manage and maintain ongoing training records and reporting and implement analytics to monitor and identify sales stage friction and enablement priorities
  • Build and maintain strong working relationships with sales leaders and SMEs from across the business to set priorities for training topics and programs
  • Improve demo effectiveness across Shift5’s solution portfolio by building scripts and improving selling skills of the sales engineering and partner sales engineering populations
  • Design and manage the processes for effective feedback loops to ensure capture
    of insights, inputs, objections, and other feedback from prospects and customers to Sales, Marketing, Product, and other stakeholders
  • Partner with various internal stakeholders on the creation, validation, and launch of messaging, positioning, continued development, and sales playbooks to guide Account Teams.
  • Evaluate and deploy one or more tech stacks, including Learning Management System (LMS) to measure adoption, absorption, and effectiveness of enablement programs.



  • Active US Government TS clearance (and willingness to maintain)
  • Demonstrate the application of curriculum design principles
  • Classroom management and facilitation
  • Experience with building sales programs which align to MEDDPICC sales process
  • Ability to work with multiple SME teams and leadership on multiple projects while staying within the scope of the overall strategy and timelines
  • Excellent project management and process development skills, and experience in business planning process
  • Excellent communication, influence, and presentation skills, including both written and verbal forms catered to a wide variety of audience
  • Ability to understand and anticipate customer needs and address needs with programs that are fit for use
  • General enterprise data and networking technical proficiency
  • Learning Management Systems administration
  • Proficiency in Office 365 or Google Workspace suite and best practices for remote working


  • Functional understanding of enterprise IT, networking, and cybersecurity
  • Understanding of sales motions within US Department of Defense and Commercial segments
  • Technical training experience with adult learners
  • Proficiency with cybersecurity topics / tools
  • Virtual Instructor Lead Training (VILT) design, team preparation, and hosting skills
  • eLearning design and development including working knowledge of video editing tools, eLearning tools suites (Articulate 360 or Captivate)
  • Audio/Video editing and post production experience
  • Experience with assessment design, implementation, and calibration (tests and behavior rubrics)
  • 3rd party vendor onboarding and management

Compensation & Benefits:

  • Competitive salary and stock options in a fast-growing startup
  • Employer-paid medical, dental and vision coverage
  • Health Savings Account with annual employer contributions
  • 401k with employer contributions
  • Life Insurance
  • Uncapped paid time off policy
  • Flexible work & remote work policy
  • Tax-deferred public transit benefits with Metro SmartBenefits (DC/MD/VA)

We are committed to building an inclusive culture of belonging that embraces the diversity of our people and represents the communities in which we work and the customers we serve. We know the happiest and highest performing teams include people with diverse perspectives and ways of solving problems. We strive to attract and retain talent from all backgrounds and create workplaces where everyone feels empowered to bring their full, authentic selves to work.

Shift5 is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sexual orientation, gender identify, national origin, disability, age, marital status, ancestry, projected veteran status, or any other protected group or class.