About OpenSesame

While it appears to most people that we just sell training courses (over 40,000 of them), what we really offer is the opportunity for companies to upgrade the skills of each of their employees. In fact, we have strategic partnerships with 150+ Global2000 companies who rely on our training programs to develop the world's most productive and admired workforces.

About the Role

The Director of Revenue Operations is a strategic leader responsible for scaling GTM Operations, Enablement, and Development to support a $100M+ ARR SaaS business growing at 20%+ annually. This role drives alignment, efficiency, and predictability across the revenue organization through data, automation, and best-in-class tools and processes.

A key focus is leveraging AI and large language models (LLMs) to uncover process improvements and scalable growth opportunities. The ideal candidate has deep experience leading RevOps in high-growth SaaS companies and a proven track record of driving predictable revenue and leading GTM transformation globally.

This role oversees the strategy, integration, and optimization of the GTM tech stack—including Salesforce, Gong, HubSpot, ZoomInfo, Highspot, and Looker—to ensure teams have clean data, actionable insights, and tools that drive productivity. (Salesforce administration sits with IT, but this role ensures cross-system effectiveness.)

Performance Objectives:

First 30 Days – Orientation & Assessment

Establish foundational understanding of the GTM ecosystem, tech stack, and team structure.

Assess current GTM systems, workflows, and tool adoption (Salesforce, Gong, HubSpot, Highspot, Looker)
Audit onboarding and enablement assets in Highspot and Gong
Meet with key stakeholders across Sales, Marketing, Customer Success, and Finance
Evaluate the current RevOps team structure, roles, and skill gaps
Align on core GTM definitions (e.g., MQL, SQL, SAL) with all functional leaders

By 60 Days – Early Execution & Alignment

Begin implementing operational improvements and building alignment processes across GTM Operations, Enablement, and Cross-functional Alignment.

Launch CRM data integrity initiative with a target of >95% accuracy
Begin improving forecast reliability toward ±10% accuracy
Define lead handoff SLAs and shared success metrics across GTM teams
Establish recurring cross-functional cadences for planning, reporting, and performance reviews
Define roles and development plans for RevOps team
Set onboarding and enablement goals tied to ramp time and tool usage

By 90 Days – Execution & Initial Impact

Deliver tangible wins in system performance, process optimization, and enablement outcomes.

Launch a board-ready revenue dashboard with live visibility into pipeline and performance
Implement an improved onboarding experience that reduces ramp time by 15%
Roll out workflow enhancements to reduce the average sales cycle by 10%
Achieve 100% adoption of enablement assets in Highspot and Gong
Identify and resolve SDR process inefficiencies in outbound outreach and lead handoff
Drive broader tool adoption and process improvements across all GTM teams for Salesforce, Gong, HubSpot, and Highspot
Drive Budgeting process for RevOps and support the Budgeting process with data and insights for the rest of the GTM team

By 180 Days – Scalable Systems & Measurable Outcomes

Continuously improve revenue operations, forecasting accuracy, and pipeline performance by strengthening Sales Operations, deepening Cross-functional Alignment, and scaling SDR & Pipeline Growth initiatives.

Build, manage, and coach a high-performing team of RevOps analysts and systems specialists to deliver against GTM goals
Increase conversion of marketing-sourced and partner pipeline by 30%
Improve lead-to-close conversion rate by 15%
Reduce customer churn by 15% through improved sales-to-success handoff
Sustain forecast accuracy within ±10% in collaboration with Finance
Maintain CRM and GTM system data integrity >95%
Increase outbound SDR response rate by 30%
Improve Sales-Accepted Lead (SAL) conversion rate by 15%
Ensure pipeline coverage remains at 3x quota across all segments

Ongoing – Optimization & Strategic Leadership

Provide long-term strategic leadership across all RevOps domains, focusing on GTM systems integration, cross-functional planning, and AI-enabled process improvement across all core areas.

Optimize integrations and performance of the entire GTM tech stack
Leverage AI and LLMs to automate reporting, surface insights, and streamline forecasting
Align GTM functions around shared KPIs and data-driven planning cycles
Ensure high adoption and ROI from tools across the revenue organization
Serve as a strategic partner to Sales, Marketing, Customer Success, and Finance for long-term growth initiatives
Scale go-to-market infrastructure to support sustainable growth, resulting in a 20%+ year-over-year increase in revenue or key GTM performance metrics.

Location: This position can be based anywhere in the US. We operate as a remote-first company, and invest in mandatory all-company meetings several times a year in addition to required team travel as necessary.

Performance Driven: We're looking for self-starters with a track record of delivering excellent results, but we're highly selective about who we hire. We don't focus on typical job requirements, instead, we're interested in specific examples from your past experiences. All positions can be based anywhere in the US, and require up to 15 days of travel per year, with senior management and leadership teams requiring up to 35 days.

Compensation: The base salary for this position generally ranges between $185,000 and $195,000, depending on experience, and is bonus eligible. At OpenSesame, we offer a comprehensive benefits package to employees upon hire, including professional development, ISOs, health insurance, 401(k) matching, and paid time off.

Equal Employment Opportunity: OpenSesame is an Equal Employment Opportunity and Affirmative Action employer that values and welcomes diversity. We do not discriminate on the basis of various legally protected characteristics, including criminal history, and strive to provide reasonable accommodations to qualified individuals with disabilities. We prioritize safety and security and may use your information accordingly, and you can contact us for assistance or accommodations during the job application process.

Pay Transparency: At OpenSesame, we prioritize pay transparency, fairness, and equity to create a positive and inclusive work environment, regularly reviewing our compensation practices to align with our values and goals. We provide competitive and fair compensation to our employees based on their skills, experience, and performance.

CPRA (California Candidates): When you submit your application, OpenSesame may collect and use your personal information in accordance with our privacy policy and the CPRA. This may include personal details and employment history, and will only be used for employment-related purposes. We may share this information with third-party service providers, but we will not sell it to third parties. If you have any questions or concerns, please contact us, and for more information on your rights under the CPRA, refer to our privacy policy or the California Attorney General's website.

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Director of Revenue Operations (RevOps)