Head of Revenue Excellence

Summary

Join Aiwyn, a rapidly growing software company serving the accounting profession, as the Head of Revenue Excellence. Partner with the CRO to design, implement, and manage Aiwyn’s revenue enablement approach. Build and scale training, onboarding, and revenue programs to accelerate the Go-To-Market strategy. You will architect, implement, and optimize enablement processes, systems, and content. This role starts as a team of one, with the opportunity to build a world-class team. If you're passionate about revenue enablement and the impact of AI on GTM practices, this is an ideal opportunity.

Requirements

• 5+ years of experience in Sales Enablement, Revenue Excellence, or related roles, preferably within high-growth B2B SaaS companies
• Proven track record of designing and executing effective enablement programs that measurably impact revenue performance
• Strong instructional design and facilitation skills, with the ability to engage diverse learning styles and job roles
• Mastery of, and desire to continue learning, modern selling techniques and frameworks (sales methodologies, best practices, and the unique evolving challenges of the B2B SaaS landscape)
• Comfortable with CRM systems (Salesforce, HubSpot) and sales automation tools
• Expertise with modern enablement technologies (LMS, conversation intelligence, content management) and best practices
• Ability to adapt quickly to new technologies, including AI-driven solutions for training and coaching
• Exceptional communication skills—written, verbal, and interpersonal—with the ability to influence without direct authority
• Experience managing (or being ready to manage) small teams and working with cross-functional stakeholders at all levels
• Able to think big-picture while also rolling up sleeves to execute training sessions, develop content, and perform data analyses
• A “builder” mindset—eager to create a function from the ground up in a fast-paced environment
• Humble, curious, and excited to continue growing/learning
• Eager to help others around you make massive impact
• First principles thinker
• Exceptional communication & dynamic presentation skills—clear, concise, and engaging

Responsibilities

• Develop and execute a comprehensive revenue enablement strategy, aligning closely with the CRO and functional leaders across Sales, Marketing, and Customer Success
• Define a roadmap for training, onboarding, and ongoing sales enablement programs to support rapid growth
• Leverage scale-up stage start-up experience to de-risk projects and accelerate time to value, thinking about scalable solutions
• Manage multiple projects with clear deliverables and develop a steady cadence of communication across all revenue stakeholders
• Design and deliver a world-class onboarding experience for new sales hires, ensuring they quickly attain the skills, knowledge, and behaviors necessary to succeed
• Continuously optimize training content to address evolving product features, market trends, and buyer needs
• Create specialized training tracks for different sales roles (e.g., SDRs, AEs, Renewals/Expansion)
• Build a centralized repository of sales content (playbooks, battle cards, presentations, scripts, etc.) in collaboration with Product Marketing and Sales Leadership
• Drive consistent messaging and positioning for all customer-facing teams, ensuring alignment and easy access to enablement materials
• Develop and manage ongoing enablement programs (e.g., weekly skill sessions, quarterly kick-offs, product updates) to keep the revenue team informed, motivated, and at the top of their game
• Partner with Marketing and Product teams to incorporate relevant product, market, and competitive intelligence into sales curricula
• Work with RevOps to establish key metrics and reporting (e.g., time-to-productivity, win rates, sales cycle times, ASPs) to quantify the impact of enablement initiatives
• Leverage data and feedback loops to refine and improve programs, ensuring alignment with revenue targets and company objectives
• Collaborate with Revenue Operations, Marketing, Product, and Customer Success to identify process improvements and drive consistency across all GTM teams
• Serve as a thought partner to leadership, bringing insights on new training technologies, methodologies, and AI-driven solutions
• Evaluate, implement, and manage the tools needed to deliver and measure enablement programs (e.g., Hightspot, LMS, conversation intelligence, etc)
• Champion the use of AI and other modern technologies to deliver engaging, personalized training experiences at scale
• Expert user of cross functional workforce management tools such as Monday.com, Asana, etc
• As the team grows, hire, manage, and develop a high-performing enablement function
• Cultivate a culture of curiosity, innovation, and continuous learning within the revenue organization

Benefits

• Highly competitive salary, equity, and benefits, reflecting our commitment to attracting and retaining the very best talent in the world
• Adventure travel stipend - you receive a $1,000 travel reimbursement on your work anniversary each year
• Remote, work-from-anywhere culture
• Flexible PTO
• World Class health benefits - we believe in fostering flourishing teams by providing benefits that go beyond the usual standards - Health, vision, dental, HSA/FSA, and mental health support
• Stock options - every Full Time Employee has ownership in Aiwyn's future and success
• 401(k) matching