Senior Onboarding Enablement Specialist

Restaurant365 is a SaaS company disrupting the restaurant industry! Our cloud-based platform provides a unique, centralized solution for accounting and back-office operations for restaurants. Restaurant365’s culture is focused on empowering team members to produce top-notch results while elevating their skills. We’re constantly evolving and improving to make sure we are and always will be “Best in Class” ... and we want that for you too!

As a Sales Enablement Specialist, you will work with sales enablement to develop, facilitate, execute, optimize, assess, and measure enablement programs targeted to the entire GTM organization. 

How you'll add value:

• Manage and continuously improve the new hire onboarding program, ensuring meticulous project planning, stakeholder signoff, and seamless program execution.

• Serve as the primary liaison between onboarding and Enablement teams, overseeing the scheduling and coordination of role-based sessions and ensuring continuous updates to all onboarding facets, including R365U (virtual onboarding), eLearning modules, and enablement outputs for a cohesive new hire experience. 

• Act as a player-coach, guiding, supporting, and working alongside the team on all aspects of the onboarding program, including new hire communications such as welcome emails, feedback emails, and monthly recaps. 

• Facilitate virtual onboarding sessions for groups of 20+ new hires monthly, engaging and setting expectations from day one. 

• Develop interactive eLearning content that aligns with onboarding goals, ensuring materials are both engaging and impactful for a virtual environment. 

• Measure onboarding output and effectiveness, tracking new hire progress and providing insights to sales management to support continuous coaching and development.

• Ensure transparency between new hires and sales management, creating pathways for feedback and tracking to foster ongoing skill development and role readiness. 

• Foster cross-functional collaboration with teams like product marketing, deal desk, customer success, and solution engineering to support holistic onboarding experiences.

• Simplify and optimize onboarding processes, identifying and implementing improvements to increase efficiency and enhance new hire productivity. 

• Handle multiple onboarding projects and tight deadlines, demonstrating the ability to work quickly and efficiently to meet program needs. 

• Background in program management and program building, with a strong focus on creating structured, scalable onboarding experiences.

• Adapt to a constantly changing work environment with agility and a commitment to excellence in onboarding program delivery. 

What you'll need to be successful in this role:

• Bachelor’s degree strongly preferred. 

• Experience building and managing virtual onboarding programs with a track record of successful implementation. 

• Facilitation experience, including leading virtual sessions and engaging groups effectively. 

• Skilled in writing and developing eLearning content for onboarding, ensuring interactive and engaging materials. 

• Experience with value-based sales methodologies such as Challenger, Command of the Message, and ValueSelling Framework. 

• Proficiency with MEDDPICCmethodology and its application in training programs. 

• Experience measuring enablement success metrics to assess and improve onboarding effectiveness. 

• Proficient in key tools within our tech stack: Lessonly, SharePoint, Salesloft, Salesforce.com, CPQ, LinkedIn Sales Navigator, ZoomInfo, and Microsoft Suite products. 

• Strong project management skills and a keen attention to detail, with the ability to manage complex onboarding projects. 

• Deep understanding of the sales environment, including experience with full-cycle sales, sales content, tools, and prospecting skills. 

• Excellent communication, project management, and time management skills, capable of handling multiple, simultaneous projects with both long- and short-term priorities. 

• Passionate and enthusiastic about onboarding and enablement with a proactive and positive attitude. 

• Minimum of 2 years of full cycle sales experience, preferably in SaaS. 

• At least 3-4 years of enablement experience with a preference for SaaS background. 

• Restaurant industry experience is a plus. 

• Willingness to travel up to 15% to support onboarding activities and ensure alignment with cross-functional teams. 

R365 Team Member Benefits & Compensation

• This position has a salary range of $110,000-$125,000. The above range represents the expected salary range for this position. The actual salary may vary based upon several factors, including, but not limited to, relevant skills/experience, time in the role, business line, and geographic location. Restaurant365 focuses on equitable pay for our team and aims for transparency with our pay practices.

• Comprehensive medical benefits, 100% paid for employee

• 401k + matching

• Equity Option Grant

• Unlimited PTO + Company holidays

• Wellness initiatives

#BI-Remote

$110,000 - $124,999 a year

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R365 is an Equal Opportunity Employer and we encourage all forward-thinkers who embrace change and possess a positive attitude to apply.