Head of Revenue Operations

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.


Why is This Opportunity Special?
• 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

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:

• About us
• Why Aiwyn
• YouTube page