Head of Revenue Operations

Summary

Join Aiwyn, a rapidly growing software company serving the accounting profession, as the Head of Revenue Operations. Partner with the CRO to design, implement, and manage the go-to-market engine. This strategic and hands-on leadership role involves building and owning a modern Revenue Operations function. You will play a critical role in scaling revenue processes and supporting instrumentation to accelerate the company's growth. The position requires a strategic leader who is also hands-on, diving into data, configuration, and design alongside the team. This is a unique opportunity to build a RevOps department from the ground up or lead an existing one at a similar growth stage.

Requirements

• 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
• Hands-on experience with Salesforce.com administration and implementation
• 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

Responsibilities

• 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

Preferred Qualifications

• Familiarity with payment processing/merchant services revenue models is highly preferred
• Direct experience migrating from one CRM to another (HubSpot to Salesforce.com is a plus)

Benefits

• 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