Sales Enablement Specialist

About Les Olson IT

Les Olson IT is one of the fastest-growing and most capable technology service providers in the West. We do I.T. the LOC Way-through talent, passion, and compassion-driving continual growth and a strong market position by delivering superior service.

Unlike most technology companies, Les Olson IT has been in business for over 70 years. We are a family-owned and family-operated company, a tradition that began at the Olson family dinner table and continues today. From those beginnings, we have grown to more than 320 employees across nine locations in two states.

Les Olson Company strives every day to elevate people, whether it's our clients, our team members, or members of the local community.

• We seek to elevate our clients by delivering cutting-edge IT strategy, security, solutions, and support. Each of our team members recognizes that they have a direct impact on the success of the local businesses we serve every day.
• We seek to elevate every team member's career, firmly believing that customer success cannot happen without employee success. We do this by working with each employee to design a fulfilling career path that grows and evolves as they do.
• We seek to elevate our local community members by rewarding our employees for volunteering at local charities and participating in our ongoing food drives.

Our work environment promotes both growth and balance. We encourage and support our employees in building meaningful, fulfilling paths, both professionally and personally. Les Olson Company offers competitive salaries, continuing education, generous benefits, and a fun, collaborative work environment. At the end of the day, it is the people that matter most to us!

About the Role

Les Olson IT is seeking a highly organized and creative Sales Enablement Specialist to support the growth and effectiveness of our sales organization. This role serves as the engine behind our sales team, ensuring that training, onboarding, documentation, systems adoption, reporting, and sales initiatives are executed with consistency and excellence.

The ideal candidate is part instructional designer, part project manager, and part trainer. They enjoy creating professional learning materials, coordinating programs, supporting sales initiatives, and helping new team members become productive quickly. While this role will facilitate systems and process training, it works closely with Sales Leadership and sales managers who provide advanced sales methodology coaching and development.

This is an exciting opportunity to help build and scale the sales enablement function as our organization continues to grow.

What You'll Do

Sales Enablement & Curriculum Development

• Develop, maintain, and continuously improve sales onboarding and training curriculum.
• Create and update sales playbooks, documentation, SOPs, job aids, and process maps.
• Design engaging learning content and visual assets using PowerPoint, Canva, Copilot, and other learning tools.
• Ensure sales training content remains current, accurate, and aligned with business objectives.

New Hire Onboarding & Training

• Coordinate and administer the sales onboarding program.
• Deliver systems and process training to new and existing sales team members.
• Support onboarding readiness and ensure a consistent employee learning experience.
• Partner with Sales Leadership and subject matter experts to continuously improve onboarding effectiveness.

Systems & CRM Adoption

• Support adoption and effective use of Salesforce and other sales systems.
• Create training materials and resources that improve process compliance and system utilization.
• Serve as a resource for sales tools, workflows, and best practices.

Reporting & Analytics

• Build and maintain reports, dashboards, and performance tracking tools.
• Analyze training and enablement metrics to identify opportunities for improvement.
• Support sales leadership with reporting and data insights.

Campaign & Event Coordination

• Coordinate monthly sales campaigns and enablement initiatives.
• Assist with sales meetings, workshops, kickoff events, and team development activities.
• Project manage key enablement programs from planning through execution.

Cross-Functional Collaboration

• Partner closely with Sales Leadership, Marketing, Operations, and other stakeholders.
• Support the creation and distribution of sales assets, messaging, and resources.
• Help ensure alignment between sales strategy, processes, training, and execution.

What We're Looking For

Required Qualifications

• Experience in sales enablement, training, instructional design, learning and development, sales operations, or a related field.
• Strong instructional design and adult learning principles knowledge.
• Excellent written, verbal, and presentation communication skills.
• Experience creating professional training materials and presentations.
• Strong project management and organizational skills.
• CRM experience, preferably Salesforce.
• Proficiency with Microsoft Office, 365 CRM, PowerPoint.
• Experience leveraging AI tools and content creation platforms.
• Ability to quickly learn new software, systems, and business processes.
• Strong attention to detail and ability to manage multiple priorities.

Preferred Qualifications

• Experience supporting sales organizations.
• Experience creating onboarding programs and learning pathways.
• Familiarity with sales processes, methodologies, and CRM adoption initiatives.
• Experience building dashboards and business reports.

Why This Role Matters

Sales success depends on more than great salespeople. It requires effective onboarding, clear documentation, strong processes, relevant training, accurate reporting, and consistent execution.

As our Sales Enablement Specialist, you will help build the infrastructure that allows sales representatives to perform at their best. You'll create the tools, programs, and resources that drive productivity, consistency, and growth across the organization.

Growth Opportunity

As our sales organization expands, this role is expected to evolve into a dedicated Sales Enablement function focused on:

• Curriculum development
• Playbooks and documentation
• CRM adoption
• Reporting and analytics
• Campaign execution
• New hire onboarding
• Sales process development
• AI and productivity tools
• Sales asset management

This position offers the opportunity to shape the future of sales enablement at Les Olson IT and play a key role in the development of a high-performing sales organization.

Benefits

• Paid Time Off
• Sick Days
• Paid Holidays
• 401k match
• Work-life Balance
• Full Medical, Dental & Vision + HSA
• Life Insurance
• Local Volunteer Opportunities