Head of Revenue Operations
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 Operations to partner closely with our Chief Revenue Officer (CRO) to design, implement, and manage the backbone of our go-to-market engine. This is an exciting opportunity for a strategic and hands-on leader to build and own a modern Revenue Operations function at a top-quartile growth company.
As Aiwyn continues to deliver substantial year over year growth, you will play a critical role in building/scaling the revenue processes & supporting instrumentation that will help de-risk/accelerate our Go-To-Market strategy through our next stages of growth.
As the Head of Revenue Operations, you will report directly to our CRO and will be responsible for architecting, implementing, and optimizing the processes, systems, and analytics that power Aiwyn’s revenue growth.
In this role we are looking for a strategic leader who is also hands-on, diving into the data, configuration, and design alongside your team.
This is a unique opportunity for someone who has led the build out of RevOps at similar stages of growth, or a leader that has been an owner of these functions / projects and is ready to step up into a role owning/building the RevOps department from the ground up.
If you’re passionate about the future of GTM operations—particularly with how AI is reshaping the future—and are hungry to leave your mark, we’d love to talk.
What You'll Impact:
- Work closely with the CRO, Head of Marketing, Head of CS, Finance team, and executive leadership to define and execute the GTM roadmap.
- Act as a thought partner and advocate for modern revenue operations, staying ahead of industry trends and AI innovations.
- Leverage scale-up stage start-up experience to de-risk projects and accelerate time to value, thinking about scalable solutions
- Manage and mentor a small but growing team of operations professionals.
- Identify and coordinate with external consultants or agencies when needed to achieve strategic goals.
- Foster a culture of continuous learning, innovation, and excellence.
- Lead the migration from HubSpot CRM to Salesforce.com, ensuring data integrity and minimal disruption.
- Evaluate, implement, and manage critical tools such as Clari, sales engagement, conversational intelligence, and other GTM/RevOps technologies.
- Oversee system integrations to create a seamless end-to-end revenue funnel, with a focus on user experience, speed, accuracy, and actionable insights.
- Manage multiple projects with clear deliverables and develop a steady cadence of communication across all revenue stakeholders
- Work with finance to forecast and plan for future revenue team headcount needs
- Ensure the organizational structure and roles are positioned to scale effectively with a focus on world-class efficiency metrics
- Develop and optimize comp plans that support both standard SaaS subscriptions and merchant processing/payments revenue streams.
- Partner with Finance, HR, and Sales to align compensation structures with business objectives.
- Use data and analytics to model comp plan scenarios and measure performance against targets.
- Lead the design and implementation of a territory framework as we shift from a geo-based approach to named accounts.
- Collaborate with Sales Leadership to ensure territories are well-balanced and focusing capacity on the right types of selling motions
- Continuously iterate on territory plans to maximize coverage, pipeline generation, and revenue.
- Establish reporting and analytics frameworks to monitor the entire revenue cycle (top of funnel, pipeline, expansion, retention, and efficiency).
- Leverage AI-driven insights and predictive analytics to forecast revenue, identify trends, and drive strategic decisions.
- Develop and continuously refine core revenue processes (e.g., lead routing, opportunity management, pipeline inspection, forecasting, etc).
- Collaborate with Marketing Ops and CS Ops to ensure handoffs are seamless and client touchpoints are well-orchestrated.
What You'll Bring From Past Experience:
- 8+ years in Revenue Operations, Sales Operations, or related roles within a scale-up B2B SaaS environment
- 2+ years of leadership experience building/leading/developing a team
- Demonstrated success in building or significantly influencing the scale up of RevOps processes and systems.
- Familiarity with payment processing/merchant services revenue models is highly preferred
- Hands-on experience with Salesforce.com administration and implementation.
- Direct experience migrating from one CRM to another (HubSpot to Salesforce.com is a plus).
- Proficiency with a modern GTM tech stack (e.g. Clari, Conversation intelligence, Sales Engagement, Sales Enablement, BI - Looker, etc) and data sources (LSN, ZoomInfo, 6sense, etc)
- Expert user of cross functional workforce management tools such as Monday.com, Asana, etc.
- Expert Excel/Google Sheets skills
- Ability to set the strategy but also get in the weeds—“hands on keyboard” with data, tools, and process documentation.
- Proven track record of building scalable processes in a high-growth environment.
- Exceptional cross functional program management skills
- A builder mindset: excited about creating a function from scratch and seeing it scale.
- Skilled at cross-functional collaboration, particularly with Sales, Marketing, CS, and Finance.
- Experience managing and mentoring a small team or a strong desire to lead and develop people.
- Humble, curious, and excited to continue growing/learning
- Eager to help others around you make massive impact
- First principles thinker
- Exceptional communication skills—clear, concise, and engaging.
- Highly analytical & detail-oriented.
- Impact: You’ll be the architect of the modern Revenue Operations engine in one of the fastest growing vertical SaaS companies on the planet
- Ownership: A high-visibility role with the opportunity to directly shape strategy at the executive level
- Growth: Join a world-class leadership & GTM team, and be at the forefront of redefining revenue operations 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
Why is This Opportunity Special?
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.
- 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
Other benefits include:
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
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