Who is Aiwyn and what do we do?

Aiwyn is the fastest-growing software company serving the accounting profession. Founded in 2020, we now work with 100+ of the largest CPA firms in the world. Our “Job to be done”: speed up cash flow, save Partner time, & deliver best-in-class client experiences. We do this by automating day-to-day firm operations with our Practice Automation solutions. Aiwyn is led by serial entrepreneurs with multiple exits and funded by top-tier investors (Bessemer, KKR, & Revolution). We’re passionate about building a remarkable company with world-class people, processes, and technology.

To learn more, visit our website

This role:

We are looking for a Head of Revenue Excellence to partner closely with our CRO to design, implement, and manage Aiwyn’s approach to delivering world-class revenue enablement. This is an exciting opportunity for a strategic yet hands-on leader to build and own a modern enablement function at a top-quartile growth company.

As Aiwyn continues delivering substantial year over year growth, you will play a critical role in building and scaling the training, onboarding, and revenue programs required to de-risk and accelerate our Go-To-Market strategy through the next stages of growth.

In this role, you’ll be responsible for architecting, implementing, and optimizing the enablement processes, systems, and content needed to power Aiwyn’s revenue growth. While serving as a strategic leader, you will also be very hands-on—driving the scoping, design, and delivery of our enablement programs as we ramp up.

You will start as a “team of one” but have the opportunity to build a world-class Revenue Excellence team over time. This is a unique opportunity for someone who has led or heavily contributed to the buildout of Revenue Excellence/Enablement programs and is ready to own and scale these functions from the ground up.

If you are passionate about the future of revenue enablement—particularly with how AI is reshaping GTM practices—and are hungry to leave your mark, we’d love to talk.

What You’ll Impact:

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.

What You’ll Bring From Past Experience:

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.

Why is This Opportunity Special?

Impact: You’ll be the architect of the modern Revenue Excellence programs in one of the fastest growing vertical SaaS companies on the planet
Ownership: A high-visibility role with the opportunity to directly shape GTM strategy at the executive level
Growth: Join a world-class leadership & GTM team, and be at the forefront of redefining revenue enablement with AI and other cutting-edge technologies
Culture: Everyone checks titles & egos at the door in the interest of creating remarkable impact/experiences together, for both our customers and our teammates
Compensation & Benefits: Highly competitive salary, equity, and benefits, reflecting our commitment to attracting and retaining the very best talent in the world

Benefits and Perks:

The big-picture value proposition of this role is simple: join us, and you’ll be paid competitively to have freedom in solving worthwhile, challenging problems alongside other A-players at a fast growing SaaS startup led by an experienced and successful co-founding team with industry experience.

Other benefits include:

Adventure travel stipend - you receive a $1,000 travel reimbursement on your work anniversary each year. We encourage our team to recharge and explore the world beyond their home office walls.
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

Our Values:

Trust - We champion transparency, welcome differing perspectives, uphold accountability, and trust that others have good intentions
Courage - We have the courage to take calculated risks and embrace change, knowing what worked in the past won’t always work in the future
Impact - Rooted in determination and innovation, we chase extraordinary outcomes and impactful results
Relentlessness - We approach challenges with an unwavering resolve, never settling for mediocrity, and always striving to surpass expectations

Learn more about Aiwyn:

Aiwyn is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable laws, regulations and ordinances.

Candidate information will be treated in accordance with our CCPA privacy notice which can be found here: https://www.aiwyn.ai/ccpa

Head of Revenue Excellence

Aiwyn

What You’ll Impact:

What You’ll Bring From Past Experience:

Benefits and Perks:

Our Values:

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