Head of Revenue Operations

Obsidian Security is a leading SaaS security platform serving global enterprises such as Snowflake, T‑Mobile, and Algolia. We protect more than 200 organizations across North America, Europe, the Middle East, Southeast Asia, Australia, and New Zealand, including many of the world’s largest Fortune 1000 and Global 2000 companies. In this role you will own the operating rhythm, planning processes, analytics, and systems that drive our Go‑To‑Market organization. You will partner closely with executive leadership to improve forecast accuracy, accelerate pipeline generation, optimize seller productivity, and scale the infrastructure required to support growth. You will be critical to ensuring our GTM Leadership has actionable, data‑driven intelligence to quickly make and execute key decisions. As a leader in a growing start‑up, you will make an impact from day one, with no bureaucracy or red tape to distract you from the very important tasks at hand. You will leave an indelible mark on the organization as you work hand in hand with Executives and GTM Leadership to lead a reporting and analytics foundation that will be critical for supporting future growth. The role requires the ability to move seamlessly between strategic planning discussions with executives, forecast and pipeline inspections with field leadership, and detailed operational problem‑solving with the team. You must understand how to translate business objectives into operational execution. The highest priority is owning outcomes rather than managing processes. This role requires a doer – who picks up ambiguous, high‑stakes problems and drives them to resolution without waiting for perfect information or organizational clarity. Key Responsibilities Lead key operations functions for GTM, Post Sales, Marketing and Strategic Initiatives; develop overarching strategies for these functions, drive alignment with key stakeholders, and ensure effective and efficient execution. Be a trusted partner to our GTM Leadership team, work closely with them to understand their business needs, and align the team roadmap and outputs to quickly meet them. Design, develop, and continuously optimize the GTM reporting suite – strive for clarity and simplicity that enables better and faster decision making for Leadership. Be highly obsessed with driving GTM efficiency and execution. Own executive operating cadences, including forecast reviews, pipeline reviews, quarterly business reviews, and strategic planning processes. Work closely with the data team to develop meaningful data sets, dashboards, etc., to translate complex analytical outputs into clear stories that drive business decisions. Support key GTM projects and initiatives with robust and insightful ad‑hoc reporting and analysis. Lead annual and in‑year GTM planning, including capacity planning, territory design, quota setting, compensation planning, organizational design, and investment prioritization. Own executive and board‑level reporting, ensuring consistent definitions, metrics, and business narratives across the organization. Relentlessly search out opportunities to automate and scale – particularly via the use of Agentic AI – reporting assets, improve data quality, and enable greater self‑service analytics and insights. Develop long‑term Reporting and Insights team strategy, build a provocative and audacious roadmap and hiring plan to support growth. Partner closely with Data and Systems leadership to establish priorities, governance, and execution plans across all areas of GTM. Drive alignment across Sales, Marketing, Post Sales and Finance organizations to ensure operational consistency and execution against company objectives. About You 9+ years of experience in Sales Operations, Consulting, Business Reporting, or related functions; 5+ years of experience with CRM and BI Reporting tools. Proven ability to influence executive leadership through data, operational rigor, and clear communication. Deep experience in SaaS forecasting, pipeline management, revenue planning, territory design, quota setting, and compensation administration. A deep passion for telling engaging stories with complex data. Comprehensive understanding of Sales, Marketing, CS and Finance metrics in a SaaS / Subscription‑software environment. Comfortable to do whatever is necessary to get the job done – whether it’s digging deep into spreadsheet analysis or presenting to our Board of Directors – with a dynamic attitude of no task is too menial or “above your grade.” Systems thinker – understands the broader implications of (seemingly) small decisions, always thinking about the longer‑term and secondary/tertiary impacts. Start‑up work ethic – willing to put in the time and sweat to help us win the market. Strong business acumen and analysis skills, including written communication and presentation development. Employee Benefits Competitive compensation with equity and 401(k). Comprehensive healthcare with dental and vision coverage. Flexible paid time off and paid holiday time off. 12 weeks of new‑parent or family leave. Personal and professional development resources. Pay Transparancy Please note that the base pay range is a guideline and for candidates who receive an offer, the base pay will vary based on factors such as work location, as well as the knowledge, skills and experience of the candidate. In addition to a competitive base salary, this position is eligible for equity awards and may be eligible for sales commission or incentive compensation based on the role or function within the company. At Obsidian, we are proud to be an equal‑opportunity employer. We value diversity and hire for talent, passion, and compassion. In compliance with federal law, all persons hired will be required to submit satisfactory proof of identity and legal authorization. If you have a need that requires accommodation, please contact View email address on click.appcast.io. Information collected and processed as part of any job applications you choose to submit is subject to Obsidian’s Applicant Privacy Policy. Base Salary Range

$220,000 — $240,000 USD

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