[Hiring] Head of Revenue Operations @Truffle Security

Role Description

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.
• Marketing operations infrastructure: 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.
• 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.

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.

Qualifications

• 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.
• 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.
• Experience supporting channel and partner sales models.
• Exposure to usage-based or seat-based pricing model transitions.

Compensation

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.

Benefits

• Fully remote within the U.S. – We believe opportunity shouldn’t be limited by geography.
• 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.
• 14 paid holidays – Including Thanksgiving, Winter Break, and "Truffle Holidays."
• 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.
• Learning & development stipend – $2,000/year to invest in your growth.
• 401(k) match – We match 100% of the first 6% of your contributions on every paycheck.
• 100% remote + company off-sites – Twice a year, we come together in amazing locations.