Head of Revenue Operations

About us Truffle Security is a cybersecurity company on a mission to make secrets easier to detect, verify, and remediate across modern software environments. Built on the popular open-source TruffleHog™ secrets scanning platform, the company's enterprise solution gives security and engineering teams everything they need to find exposed credentials, understand which ones are active, and act on them with confidence. With support for 800+ credential types, Truffle Security continuously monitors non-human identities (NHIs) and their associated secrets across code repositories, SaaS applications, wikis, and cloud systems. It goes beyond detection by verifying which secrets are live, analyzing their scope of access, and streamlining remediation through automated workflows and lifecycle management so teams can prioritize what to revoke and confirm it's done without manual follow-up. Trusted by organizations including NVIDIA, Chick-fil-A, and OpenAI, Truffle Security helps security and engineering teams stay ahead of secrets risk. About the role This is our first dedicated Revenue Operations leadership hire, and we're going to be honest about what you're walking into. Our GTM systems and processes work, but they were built reactively as the business grew. There is not yet a cohesive, intentional revenue operations architecture, and that's exactly what we're hiring you to create. That's the opportunity. You'll own the full GTM operations stack, define what RevOps means at Truffle, and build the function from a strong revenue base rather than a blank page. You'll inherit one Business Systems team member, hire a planned GTM Engineer, and grow the team as the business scales, including standing up functions like deal desk that don't exist today. We're open on level. Depending on your experience, this role could be Director or VP scope. What matters is that you've built before and want to build again. What you'll be working on • Systems foundation. Your first-year priority. Assess our Salesforce instance and strengthen it into a coherent architecture with clean data, clear definitions, and reporting people actually trust, then bring the surrounding GTM stack into alignment with it. • Full GTM operations. Sales ops, marketing ops, and CS ops under one roof. You'll be the connective tissue across the entire revenue funnel, from lead attribution through renewal. • Revenue data integrity. One architecture across the stack where records move without corruption, business definitions are enforced in-system, and any number pulled by marketing, sales, finance, or the board reconciles with every other system. When a number is questioned, you are the answer. • Deal desk and quoting. Build the function from scratch and own it directly: pricing approvals, quote-to-close workflow, non-standard deal governance, and the guardrails that let AEs move fast without breaking things. At our size this is a process you run, not a team you inherit, with the option to staff it as deal volume grows. • Marketing operations infrastructure. Marketing leadership defines the strategy, the programs, and what qualifies as a lead. You own the machinery underneath: the infrastructure that captures, enriches, routes, and nurtures every lead marketing generates, and the measurement layer that ties program spend to pipeline. • Compensation design. Own comp plan design and modeling across sales and SDR functions. You'll partner with Finance, who owns administration and payout. • Forecasting. Own forecast methodology, cadence, and tooling. Build a forecast that sales leadership and the board trust, and run the operating rhythm behind it. • Annual planning. Territory design, capacity planning, and quota setting in partnership with sales leadership and Finance. • The GTM tech stack. Full ownership: vendor selection, contracts, budget, and consolidation. If a tool isn't earning its keep, you have the authority to kill it. • Process and definitions. Codify the rules of engagement: lead routing, sourcing attribution, opportunity stages, SQL definitions, forecast methodology. Turn tribal knowledge into a documented, enforced process. • Team building. Manage and develop our current Business Systems team member, with a GTM Engineer hire planned for this team to build automation and AI-driven workflows across the stack. You'll shape that role, make the hire, and grow the function from there. What success looks like in year one • Salesforce runs on an intentional data model. There is one source of truth: marketing, sales, and finance pull the same numbers and get the same answers • Deal desk exists, with documented approval workflows and pricing guardrails in active use. • Lead routing, sourcing credit, and qualification definitions are codified and enforced in-system. • A forecast methodology is in place and holding up against actuals, with a weekly operating cadence around it. • Comp plans are designed, modeled, and documented, with a clean handoff to Finance for administration. • Sales leadership spends its time selling and coaching, not reconciling spreadsheets. Our fiscal year starts February 1, so annual planning is an early deliverable, not a year-end one. What we're looking for • 6+ years in revenue operations, sales operations, or GTM operations at B2B SaaS companies, with at least 2 years leading the function or a significant piece of it • Deep, hands-on Salesforce expertise. You've taken an inherited instance and meaningfully improved its architecture, data quality, and reporting, not just administered it • You've owned the full architecture across a marketing automation platform and a CRM at a company that scaled, and made the two behave as one system. Our stack: Salesforce, HubSpot, Clay, Common Room, Nooks, Gong • Experience standing up net-new functions (deal desk, marketing ops, CS ops) rather than inheriting mature ones • Comp plan design and modeling experience across AE and SDR roles • Experience owning forecast methodology and annual planning (territories, capacity, quotas) at a growing sales org • Strong analytical chops. You're fluent in pipeline math, conversion analysis, and forecast methodology, and you can defend your numbers to a CEO and a board • Comfort operating in ambiguity at an early-stage company. You'll set the strategy and do the work, especially early Bonus points! • Experience in security, developer tools, or open source-driven companies • Experience turning open-source adoption signals into an enterprise revenue process. Our funnel starts with hundreds of thousands of daily open source users. • Experience supporting channel and partner sales models • Exposure to usage-based or seat-based pricing model transitions Why this role Most RevOps leaders inherit either a mess with no revenue or a mature machine with no room to build. This is neither. Truffle has real enterprise revenue, marquee logos, a healthy pipeline, and an executive team that knows the operations foundation needs investment and is hiring you to lead it. You'll have a mandate, a seat at the table, and a genuinely interesting business to operate. Compensation Salary Range: The target base salary range for this position is between $210,000 to $250,000 for candidates in the United States. Starting salary will vary based on job-related skills, knowledge, and experience. Leveling will be determined during the interview process. You may also be offered a bonus, stock options, and benefits. These salary ranges are subject to change, and we encourage candidates outside of this salary range to apply. How we support our team • Fully remote within the U.S. – We believe opportunity shouldn’t be limited by geography. Our remote-first approach lets us hire the best people across the United States and empowers them to do their best work from wherever they are. • A culture of mentorship, equity, and psychological safety – We’re committed to fostering an environment where you can thrive, learn, and feel valued. • Competitive salary & meaningful equity – Be rewarded for your contributions with a strong compensation package and a stake in our shared success. • Flexible paid time off – We operate with a high level of autonomy and trust, giving you the flexibility to take time off as needed—no strict limits, just the expectation that you’re meeting your commitments and getting your work done. • 14 paid holidays – Including Thanksgiving, Winter Break, and "Truffle Holidays" when the entire company takes a well-deserved day off together. • Comprehensive health benefits – Medical, dental, and vision coverage with 80% of premiums covered for you and your dependents. • Remote work stipend – Get set up for success with an $800 new hire stipend and $100/month to keep your workspace comfortable. • Health & wellness stipend – $1,200/year to support your physical, mental, and emotional well-being— we believe that feeling good helps you do great work. • Learning & development stipend – $2,000/year to invest in your growth, whether it’s courses, certifications, or industry conferences. • 401(k) match – We match 100% of the first 6% of your contributions on every paycheck, helping you build financial security for the future. • 100% remote + company off-sites – Twice a year, we come together in amazing locations like Hawaii, Cabo, and the Rocky Mountains to collaborate and connect. We’re looking for folks who are interested in being part of the journey to make the internet more secure. The internet is for all, and we believe that diverse experiences and people from all walks of life can contribute to this mission. That said, if what we’re doing resonates with your values, we’d love to have you apply even if you don’t check all of the boxes or match the job description to a tee. Truffle strives to promote an equitable, inclusive, and psychologically-safe workplace for all who are interested in working with us. All job applicants will be considered throughout the employment process without regard to race, color, ethnicity, religion, sex, sexual orientation, gender perception/identity, age, pregnancy or parental status, disability status, or any other basis prohibited by law. If you are an individual with disabilities and reasonable accommodation is needed throughout the interview process, or to perform essential job functions, please let your recruiter know. Lastly, we ask that all applicants consider the opportunity to answer a few voluntary demographic questions on the job application. This helps us track the inclusivity of our recruiting initiatives. Answering these questions is entirely optional and your answers will not be shared with the hiring team and will not impact the hiring decision. Note: Our organization participates in the US federal E-Verify program. We will provide the Social Security Administration, and if necessary, the Department of Homeland Security, with information from each new employee’s Form I-9 to confirm work authorization. We do not use this information to pre-screen job applicants.