Founding Revenue Operations Lead

Clarasight•Boston, MA

About The Position

Join us in building the leading AI-Powered Mission Control for Corporate Travel. Some of the world's most recognizable companies, representing over $4T in market value, rely on Clarasight's software to reduce risks, save costs, protect revenues, and manage emissions aligned with business objectives and sustainability goals. You are a systems thinker who gets excited by clean data, well-designed processes, and tools that actually talk to each other. You've spent enough time in RevOps to know what "good" looks like, but you're still hands-on enough to build it yourself. You're equally comfortable building a forecast model in a spreadsheet, debugging a broken Salesforce integration, and walking a sales leader through a comp plan redesign. You thrive in environments where you own the entire stack and the buck stops with you. As the founding Revenue Operations hire at Clarasight, you'll architect the systems, processes, and data infrastructure that power our go-to-market engine. This is a true 0-to-1 role: you'll own Salesforce, the full GTM tech stack, our forecasting cadence, and compensation design from day one. You'll be the connective tissue between Sales, CS, Finance, and Leadership — ensuring every revenue decision is grounded in clean data and defensible logic. The decisions you make and the foundation you lay will shape how we scale revenue for years to come.

Requirements

Have 4–8 years of RevOps, Sales Ops, or GTM Ops experience — enough to have seen what good looks like, not so much that you've forgotten how to do it yourself.
Have proven experience managing a multi-tool GTM stack and owning integrations between them.
Are opinionated about tool selection: you have a framework for evaluating new software and a healthy skepticism for shiny objects.
Have built or significantly improved a sales forecast process at a high-growth company.
Have strong analytical instincts - you make decisions from data and can build the reports and dashboards that support them.
Have a track record of cross-functional collaboration: you work well with Sales, CS, Finance, and Operations, and Marketing without needing a project manager to keep you aligned.
Bring a startup mentality: low ego, high ownership, comfortable with "good enough for now" when the situation calls for it.

Nice To Haves

Experience as the first or founding RevOps hire at an early-stage startup.
Background in B2B SaaS, ideally selling to enterprise.
Familiarity with AI-powered GTM tools and a point of view on where automation should (and shouldn't) replace human judgment.
Experience partnering with Finance on ARR reporting, board materials, or investor diligence.
Experience working alongside AI systems and applying human judgment to automated outputs.

Responsibilities

Build and maintain a reliable forecast model - bottoms-up pipeline to board-level view — sourced from clean Salesforce data.
Own the weekly forecast cadence with the sales team; coach reps on deal hygiene that feeds accurate data upstream.
Design and publish a GTM metrics framework: pipeline coverage, conversion rates by stage, velocity, win/loss analysis, and rep productivity.
Leverage data from across the stack (Apollo sequences, Grain call insights, Sales Navigator activity) to enrich pipeline analysis and identify patterns.
Partner with Finance to align revenue reporting and ensure a single source of truth across systems.
Partner with our AI Automation Engineer to integrate the entire GTM stack, ultimately delivering speed, accuracy, and insights to Leadership and the Sales team.
Own Hubspot end-to-end: data model, object architecture, workflow automation, permissions, and hygiene. You build it, you maintain it, you improve it.
Manage and optimize the full GTM tech stack including own every integration between tools
Maintain a living map of the tech stack: what each tool does, who owns it, what it costs, and how it connects. Run a regular audit to eliminate redundancy and identify gaps.
Lead all tool procurement, renewals, and vendor relationships - evaluate new tools with a skeptic's eye and a clear ROI framework.
Build and enforce data governance standards across the stack: field naming conventions, lead routing logic, deduplication rules, and enrichment workflows.
Drive adoption across the revenue team; build the training, documentation, and change management so tools actually get used the way they were designed.
Design and administer Sales and CS commission plans that incentivize the right behaviors at this stage of the company.
Run the annual and mid-year quota-setting process, grounded in market data, attainment history, and pipeline capacity models.
Build the infrastructure to calculate, verify, and communicate commissions accurately and on time - ideally sourced directly from Salesforce data.