Freelance Remote Sales Trainer Jobs in Raleigh, NC

About Avalara

Avalara is a born-in-the-cloud company with an innovative AI-powered global compliance platform built to be part of every transaction in the world. We are building the first global compliance platform in human history, pursuing a massive worldwide opportunity. We are a meritocracy that rewards and advances our strongest performers while valuing diversity in all its forms.

About the Role

Avalara is looking for an experienced Senior Go-To-Market Live Trainer to join the Revenue Operations team. The Sr. GTM Live Trainer is a core member of Avalara\'s live training team, bringing our curriculum to life through instructor-led and virtual training experiences for our go-to-market organization.

You will lead live training delivery for a dedicated Line of Business, facilitating ILT and VILT sessions that directly influence seller performance, ramp velocity, and revenue outcomes. Working within a dedicated enablement team, you will implement training programs that build capability across new hires and tenured sellers.

We are looking for an accomplished facilitator who is energized by live training delivery and committed to creating high-impact learning experiences for sales professionals. If you bring deep sales methodology fluency, you also bring a track record of engaging diverse sales audiences and a genuine passion for developing talent. This role is an opportunity to improve GTM performance.

#LI-Remote

Deliver ILT and VILT Training Programs

• Be a primary facilitator for instructor-led and virtual instructor-led training across the GTM organization, supporting new hire onboarding and the ongoing development of tenured sellers.
• Deliver engaging, skills-focused training sessions that promote knowledge retention, behavioral application, and measurable performance improvement.
• Work within a Line of Business-aligned enablement team to execute program content with consistency, audience relevance, and fidelity to the established learning strategy.
• Adapt delivery in real-time based on audience feedback, performance observations, and input from LoB leadership.

Champion Sales Methodology Adoption

• Facilitate training anchored in MEDDPICC and Value Selling, ensuring sellers can apply methodology to active deals rather than simply recall frameworks.
• Lead live roleplay, deal coaching, and scenario-based practice that connect classroom learning directly to field execution.
• Be a credible methodology resource for sellers and frontline managers, reinforcing skills across formal training and ongoing coaching engagements.
• Deliver training programs that extend beyond methodology to enable GTM teams on product knowledge, pricing, and forecasting, supporting a complete seller skill set.
• Utilize AI-powered roleplay and conversation intelligence platforms, including Hyperbound and Gong, to extend methodology practice and coaching feedback between live sessions.

Drive Continuous Seller Development

• Deliver targeted outbound sales enablement training, equipping sellers to build pipeline and execute high-conversion outbound prospecting strategies.
• Deliver targeted upskilling programs for tenured sellers, addressing skill gaps, evolving sales motions, and the ongoing development needs of experienced GTM professionals.
• Provide real-time coaching feedback to accelerate skill development and support seller progression.
• Surface recurring skill gaps and performance trends to Learning Strategy leadership, informing curriculum updates and coaching prioritization.

Build and Execute Train the Trainer Programs

• Facilitate Train the Trainer programs that equip internal Subject Matter Experts, frontline sales managers, and peer facilitators to deliver and reinforce training content.
• Certify internal facilitators and uphold delivery standards established by enablement leadership to ensure program consistency and quality.
• Share field observations and facilitation insights with the enablement team to support the continuous improvement of Train the Trainer program design.

Enable Frontline Sales Managers

• Deliver coaching programs and structured learning experiences designed for frontline sales managers, equipping them to reinforce methodology, conduct effective deal reviews, and develop their teams.
• Partner with sales leadership to identify manager coaching priorities and tailor delivery to address performance gaps within their teams.

Execute Strategic Training Events

• Be a lead facilitator for major GTM events, including Sales Kick-Offs (SKOs), regional summits, and targeted enablement bootcamps.
• Deliver training with the precision, energy, and professionalism that high-stakes GTM events require.
• Coordinate with Learning Strategy and Enablement Operations to ensure seamless delivery execution across all live event formats.

Align Training Delivery to Business Outcomes

• Maintain clear visibility into the performance metrics of your assigned Line of Business. These metrics include rep ramp time, pipeline generation, and quota attainment. They inform training priorities in partnership with the enablement team and LoB leadership.
• Participate in structured feedback review cycles, sharing post-session observations, seller performance signals, and field intelligence to surface what is working, what requires refinement, and where skill gaps are emerging.
• Represent the facilitator\'s perspective in business reviews, contributing insight into skill trends, engagement patterns, and training effectiveness for your assigned Line of Business.

Education

• Bachelor\'s degree in Business, Communications, Education, Learning & Development, Organizational Development, or a related field required.
• We will consider an equivalent combination of education and professional experience.
• We prefer professional certifications in adult learning, facilitation, or sales enablement, including ATD CPLP, Kirkpatrick Certification, or an accredited sales methodology credential.

Experience & Skills

• 4–7+ years of experience in B2B revenue enablement, sales training, or quota-carrying sales, with a demonstrated record of live training facilitation for sales professionals.
• Proven facilitation skills in both ILT and VILT formats, across cohort workshops and large-scale sales events.
• Fluency in a recognized B2B sales methodology such as MEDDPICC, Value Selling, Challenger, or MEDDIC.
• Proven track record of delivering live training that supports rigorous rep certification programs across sales enablement disciplines.
• Expertise facilitating Train the Trainer programs that certify internal facilitators and build scalable training capacity.
• Ability to operate within a structured enablement team, building within a defined scope while collaborating with enablement partners.
• Data-informed approach to facilitation: comfortable interpreting performance data, assessment trends, and business metrics to adjust training priorities.
• Exceptional experience responding to prospect emails, phone calls, and demo requests, with the ability to engage and motivate experienced sales professionals in live and virtual environments.
• Willingness to travel domestically and internationally for SKOs, regional summits, and in-person training events.

Preferred Qualifications

• Direct experience with MEDDPICC or Value Selling frameworks.
• Direct B2B sales experience with quota-carrying sellers and their frontline managers.
• Prior experience training outbound sales motions, including prospecting methodology, cold outreach strategy, and pipeline generation, for SDR, BDR, or outbound AE audiences.
• Familiarity with territory-based sales models and the ability to tailor delivery to the needs of geographically or vertically segmented teams.
• Experience with AI-powered enablement platforms, including conversation intelligence and AI roleplay tools such as Hyperbound and Gong.
• Experience with enablement content and LMS platforms such as Highspot, WorkRamp, or equivalent.

Key Competencies

• Dynamic Facilitation: Commands live and virtual training environments with energy, authority, and adaptability, consistently delivering sessions that engage experienced sales professionals and drive skill retention.
• Methodology Credibility: Earns trust from sellers and frontline managers through applied fluency in B2B sales methodology, translating frameworks into practical application in sales conversations and deal strategy.
• Collaborative Execution: Operates effectively within a structured enablement team, executing with precision within a defined scope while actively contributing to team feedback and continuous improvement.
• Field Intelligence: Translates facilitation observations into actionable insight, consistently surfacing what is working, what needs refinement, and where the business requires focus.
• Results Orientation: Maintains clear line of sight to the success metrics of the Line of Business served, connecting every training touchpoint to seller performance, ramp velocity, and revenue outcomes.

AI is embedded in our workflows, decision-making, and products.  Success here requires embracing AI as an essential capability.

• You’ll bring experience using AI and AI-related technologies, ready to thrive here.

• You’ll apply AI every day to business challenges - improving efficiency, contributing solutions, and driving results for your team, our company, and our customers.

• You’ll grow with AI by staying curious about new trends and best practices, and by sharing what you learn so others can benefit too.

Total Rewards 

In addition to a great compensation package, paid time off, and paid parental leave, many Avalara employees are eligible for bonuses. 

Health & Wellness 
Benefits vary by location but generally include private medical, life, and disability insurance. 

Inclusive culture and diversity 
Avalara strongly supports diversity, equity, and inclusion, and is committed to integrating them into our business practices and our organizational culture. We also have a total of 8 employee-run resource groups, each with senior leadership and exec sponsorship. 

We’re defining the relationship between tax and tech.

We’ve already built an industry-leading cloud compliance platform, processing over 54 billion customer API calls and over 6.6 million tax returns a year. Our growth is real - we\'re a billion dollar business - and we’re not slowing down until we’ve achieved our mission - to be part of every transaction in the world.

We’re bright, innovative, and disruptive, like the orange we love to wear. It captures our quirky spirit and optimistic mindset. It shows off the culture we’ve designed, that empowers our people to win. We’ve been different from day one. Join us, and your career will be too.

We’re An Equal Opportunity Employer

Supporting diversity and inclusion is a cornerstone of our company — we don’t want people to fit into our culture, but to enrich it. All qualified candidates will receive consideration for employment without regard to race, color, creed, religion, age, gender, national orientation, disability, sexual orientation, US Veteran status, or any other factor protected by law. If you require any reasonable adjustments during the recruitment process, please let us know.