Sales Enablement Specialist

At RoadRunner, our daily motivation is to accelerate the road to Zero Waste™ while providing maximum value for our customers and our communities. We achieve this through efficient, cost-effective and sustainable waste operations. Our team cares deeply about each other and our planet, and we are dedicated to leveraging technology and innovation to modernize a vital industry with integrity, expertise and a passion for create a future where waste is a problem of the past™.

Technology, artificial intelligence and data-driven strategies are the backbone for our team of waste experts to reliably provide our customers with the most streamlined, cost effective and sustainable waste and recycling services. Since RoadRunner’s creation in 2014, we’ve helped more than 12,000 customer locations achieve an average between 10 - 20% savings on their monthly waste bills while also improving their recycling efficiencies. We’re proud that RoadRunner’s industry-leading model has been recognized by the SEAL Business Sustainability Awards 2023, Pittsburgh Business Times’ Best Place to Work 2022, and Pittsburgh Inno’s 2022 Fire Awards. 

Our Glassdoor reviews are fantastic (3.3/5 on 311 reviews), our CEO’s approval rating is 71%, and 65% of our reviewers would recommend working here. Our Indeed ratings have consistently improved as we’ve been expanding our teams (3.5/5 on 85 reviews) and we now have over 14K followers on LinkedIn.

***Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment visa.

Are you energized by data, driven by impact, and excited to elevate the performance of an entire sales organization? Join us as our next Sales Enablement Specialist, where you’ll be at the heart of transforming how our 200+ sales professionals win—across both Enterprise and Mid‑Market teams.

In this role, you won’t just work with sales technology—you’ll shape how it’s used. You’ll take the lead on optimizing our enablement platforms (especially Gong), uncovering high‑value insights from real sales conversations, and turning them into actionable coaching moments. You’ll streamline workflows, elevate skill development, and ensure our teams have the tools, visibility, and confidence they need to succeed in every deal.

If you’re a proactive, analytical problem-solver who loves translating data into meaningful change, partnering across teams, and creating scalable systems that empower people—you’ll thrive here. Step into a role where your expertise directly influences sales excellence and drives competitive advantage.

• Own, configure, and continuously enhance Gong—including Deal Boards, Smart Trackers, Scorecards, and Initiatives.
• Ensure seamless integrations with Salesforce and Zoom, maintaining high data accuracy and performance.
• Identify new use cases and drive platform improvements that elevate productivity and sales execution.

• Partner with the Senior Training Manager to design dashboards and performance reports.
• Translate conversation analytics into clear, actionable insights around deal health, competitor mentions, buyer behavior, and sales effectiveness.
• Present findings to sales leadership to inform coaching, strategy, and process improvements.

• Support or lead dynamic training sessions for reps and managers focused on tools, process, and best practices.
• Drive adoption of Gong and other sales enablement tools through coaching, reinforcement, and user engagement strategies.

• Serve as the go-to expert for 200+ users, providing troubleshooting, platform guidance, and workflow recommendations.
• Champion best practices across segments to ensure consistent, scalable usage.

• Develop clear, modern, “gold standard” user guides, SOPs, and enablement playbooks.
• Create repeatable processes that reduce friction, improve accuracy, and support organizational growth.

• • Partner with Sales Leadership, Marketing, IT, and Operations to align projects and enablement initiatives.
  • Keep a pulse on emerging enablement technologies and propose improvements to stay ahead of the curve.

• 100% Remote Flexibility: Work from US residents while managing a dynamic national or regional territory.
• High-Velocity Impact: You’ll own and optimize powerful sales tools like Gong and Salesforce.
• Collaborative Ecosystem: You aren't on an island. You’ll leverage a Top-Tier Inside Sales team and collaborate with Sales Operations, Marketing and IT
• Career Advancement: We value continuous improvement.

• Senior Training Manager

• The Remote Pro: You are highly efficient in a virtual environment, navigating multiple systems with ease.
• 3+ years of experience working with sales enablement or conversation intelligence platforms, with a strong track record of administering, optimizing, or analyzing these tools.
• Hands-on expertise with Gong.io — especially Deal Boards, Initiatives, Smart Trackers, and Scorecards (highly preferred).
• Proficiency with Salesforce CRM and Zoom (or comparable systems), with an understanding of how sales teams rely on these tools.
• A solid understanding of sales processes and methodologies, and how they differ across segments like Enterprise, Mid‑Market, Inside, and Outside Sales.
• Experience or strong interest in sales training and coaching, especially supporting reps and managers in skill development.
• Comfort operating in ambiguity, using sound judgment and strong decision-making when full information isn’t available.
• A results‑driven mindset, with high accountability, ownership, and attention to quality and performance metrics.
• Strategic thinking paired with tactical execution, able to zoom out or dive into details as needed.
• Excellent verbal and written communication skills, with the ability to present, facilitate, and engage groups with diverse perspectives.
• Strong organizational and prioritization abilities, skilled at managing multiple projects, balancing competing demands, and working with minimal supervision.
• Ability to collaborate and influence at all levels, building strong partnerships across Sales, Operations, IT, Marketing, and Leadership.
• Exceptional analytical and problem‑solving skills, with the ability to make timely, thoughtful decisions.

• Bachelor’s degree in Business, Management, Marketing, or a related field. 

Core Values:

• Trust: Have confidence in our team. Have integrity in your actions  
• Be Humble: Stay grounded. Seek feedback. Be curious.
• Be Passionate: Love what you do. Love what we do.
• Embrace Challenge:  See obstacles as opportunities to learn and grow. 
• Be Accountable: Take ownership. Be reliable. Be proactive. 
• Care Personally About Each Other: Show compassion, empathy and open-mindedness

We are excited to consider talented individuals from across the country. However, please note that we currently do not support candidates residing in the following states: Alaska (AK) / Delaware (DE) / Hawaii (HI) / Kansas (KA) / Louisiana (LA) / Maine (ME) / Montana (MT) / Nebraska (NE) / Nevada (NV) / New Mexico (NM) / North Dakota (ND) / South Dakota (SD) / Vermont (VT) / Wyoming (WY) / Puerto Rico

We thank all candidates for their interest in RoadRunner, but we cannot respond to everyone personally. Only those selected for an interview will be contacted. We look forward to reviewing your application! 

RoadRunner is an affirmative action and equal opportunity employer and is committed to the full inclusion of all qualified individuals. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, disability, age, sexual orientation, gender identity, national origin, veteran status, or genetic information. It is the policy of RoadRunner that qualified individuals with disabilities are not discriminated against because of their disabilities regarding job application procedures, hiring, and other terms and conditions of employment. It is further the policy of RoadRunner to provide reasonable accommodations to qualified individuals with disabilities in all aspects of the employment process. RoadRunner is prepared to modify or adjust the job application process or the job or work environment to make reasonable accommodations to the known physical or mental limitations of the applicant or employee to enable the applicant or employee to be considered for the position he or she desires, to perform the essential functions of the position in question, or to enjoy equal benefits and privileges of employment as are enjoyed by other similarly situated employees without disabilities, unless the accommodation will impose an undue hardship.