Director, Revenue Operations (Hybrid / Boston, MA)

Skedda•Boston, MA

1d•Hybrid

About The Position

We’re seeking an experienced, technically strong operations leader to lead our Revenue Operations function and drive AI-enabled operational transformation across the company. This role will own the systems, data, analytics, processes, and internal technology that help our business scale efficiently. You’ll serve as the connection between our GTM teams, Product, Finance, and Leadership, ensuring that our operating model is supported by clean systems, reliable data, thoughtful automation, and actionable insights. This is a leadership role, and it’s also a builder role. In addition to leading the Revenue Operations team, you’ll identify, design, and operationalize AI-enabled improvements across the business. We’re looking for someone who is genuinely excited by what’s now possible with tools like Claude, ChatGPT, Codex, agents, automation workflows, and internal tooling - and who can move beyond experimentation to practical, measurable business impact. This role reports directly to our Chief Operating Officer.

Requirements

6-10+ years of relevant experience in business operations, revenue operations, GTM systems, GTM engineering, business systems, analytics, strategy & operations, or a related field.
2+ years of people management experience
Experience working in a growing B2B SaaS company, ideally between $10M and $50M ARR.
Highly technical; comfortable working deeply with systems, data, automation, and AI tools
Strong understanding of revenue operations, including sales, marketing, customer success, pipeline management, forecasting, and reporting processes.
Deep experience with modern SaaS business systems such as HubSpot, Salesforce, Intercom, Gong, Claap, Common Room, ZoomInfo, or similar tools.
Strong analytical skills, including experience with business intelligence, data modeling, metrics design, and executive reporting.
Curious, scrappy, and forward-thinking; energized by new tools, better systems, practical AI adoption, and clever solutions that help teams move faster with limited resources.
Track record of successfully implementing, integrating, or optimizing business systems at scale.
Proactive in identifying process inefficiencies quickly and turning ambiguous problems into clear operating plans.
Demonstrated experience using AI, automation, or internal tooling to improve business operations; you can show real examples of workflows, agents, automations, or internal tools you or your team have built.
Strong project management skills with the ability to lead complex cross-functional initiatives.
Comfortable operating at both strategic and tactical levels - equally willing to shape the architecture and get in the weeds to build, test, and improve it.
Excellent executive communication and stakeholder management skills.

Responsibilities

Lead and develop the Business Operations team, including team planning, prioritization, coaching, performance management, and execution.
Set the operating rhythm for BizOps, ensuring the team is focused on the highest-impact work across systems, analytics, revenue operations, internal tooling, and cross-functional initiatives.
Partner closely with Sales, Marketing, Customer Success, Product, Finance, and Leadership to identify operational gaps and build scalable solutions.
Ensure proper prioritization of cross-functional projects by balancing departmental needs with broader company strategy.
Build a high-trust, high-output team culture with strong documentation, clear ownership, and a bias toward practical execution.
Own the roadmap for AI-enabled operational transformation across the business, while translating high-level AI opportunities into practical, measurable business outcomes.
Identify opportunities to use AI, automation, agents, and internal tools to improve workflows across go-to-market, customer operations, finance, product operations, and internal reporting.
Partner with stakeholders to redesign workflows, not just layer AI tools on top of existing processes.
Evaluate, pilot, and operationalize AI tools and agentic workflows that improve speed, quality, consistency, and scalability.
Lead revenue operations initiatives across Sales, Marketing, and Customer Success.
Improve the systems and processes that support lead generation, pipeline management, attribution, customer lifecycle operations, forecasting, reporting, and revenue planning.
Own and evolve the internal systems architecture, including the implementation, integration, and ongoing improvement of core business applications.
Partner with GTM leaders to improve funnel visibility, process efficiency, handoffs, data quality, reporting, and operational execution.
Lead vendor evaluation, selection, implementation, and relationship management for business systems and AI-enabled tools.
Ensure the company’s systems and processes are scalable, well-documented, and aligned to business priorities.
Develop and maintain analytics and communication frameworks that support thoughtful decision-making across departments.
Ensure consistent, reliable, and actionable business reporting for Leadership and the Board.
Build and maintain data governance standards across the organization.
Identify data gaps, root causes, and process issues, then implement scalable solutions.
Translate complex data stories into clear insights that executives and functional leaders can act on.