Head of Revenue Operations

Obsidian Security•Palo Alto, CA

2h•$220,000 - $240,000

About The Position

Obsidian Security is the leading SaaS security platform, trusted by global enterprises like Snowflake, T-Mobile, and Algolia. We protect 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. Founded in 2017 and backed by top investors like Greylock, Obsidian was built to close a critical gap: securing SaaS apps where business happens—Microsoft 365, Salesforce, and hundreds more. The company does this by offering a complete SaaS security platform to reduce risk, detect and respond to threats, and prevent breaches at the source. Obsidian was built by leaders who redefined endpoint and identity security at CrowdStrike, Okta, Cylance, and Carbon Black. Now, they’re transforming how SaaS is secured. With AI driving rapid SaaS growth and complexity, agentic AI tools gain privileged access to sensitive data through integrations, creating new risks most security tools miss. Obsidian uniquely detects anomalous OAuth token activity and manages integration risks. Major announcements are on the horizon. Recognizing that SaaS security needs to evolve, Obsidian enables growing organizations to start with a lightweight, prevention-focused browser extension and expand coverage over time. With global momentum, a growing partner ecosystem including SentinelOne, Databricks, and Google Cloud, and a major fundraise ahead, Obsidian is scaling rapidly toward long-term growth and IPO readiness. 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 would require high 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. Understands how to translate business objectives into operational execution. Highest priority would be on 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.

Requirements

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.

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.
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.