Senior Director, Revenue Operations

The Opportunity – Senior Director, Revenue Operations (Remote - USA / Canada)

Wrapbook is building the financial infrastructure of the project economy, and we're looking for a Revenue Operations leader to run the engine behind our go-to-market and post-sale motion. If you want to build a modern, AI-forward revenue operations function and the team to run it, this is the job for you.

Reporting to the CFO, you will own the bookings forecast, sales compensation and operations, marketing operations, and the technology platform that underpins our GTM and post sales efforts. You will own our Salesforce platform, setting its architecture and standards while working with and through the Salesforce admins on the RevOps team and on teams across the company.

You’ll lead an AI-native GTM function, building on one source of truth, a visible roadmap, and clear standards. You’ll lead through a team and stay technical enough to set a credible roadmap and make architectural decisions.

You'll sit in Finance and serve Sales, Marketing and Client Ops. Your primary colleagues are the leaders of those orgs, and your job is to make them faster and their numbers trustworthy. You will lead a team of ~6-8 that keeps the system and operations accurate, fast, and improving.

What You'll Do

Run the revenue engine

• Own the bookings forecast: definitions (pipeline, bookings, commit / best case / upside), cadence, pipeline health, and deal inspection.

• Run the operating rhythm of the revenue team: pipeline reviews, forecast calls, and the revenue inputs to MBRs, QBRs, and board materials

• Own GTM planning: territories, segmentation, and quota and capacity modeling

• Oversee sales compensation operations: provide input on plan design, and manage the process to ensure accurate, on-time payouts with the controls a financial process requires

• Oversee the deal desk process: approvals, structures, and non-standard terms, in partnership with Strategic Finance on complex-deal pricing

• Own marketing ops: tech stack, pipeline and performance metrics

• Be proactive and opinionated with Sales leadership: surface risks to the numbers, and bring recommendations to keep things on track

Lead the AI-forward GTM roadmap

• Manage the AI sales and marketing roadmap from start to finish: partner with Sales and Marketing leadership to turn their vision into a sequenced, shippable roadmap of AI workflows and agents

• Decide on design of the tech stack: build vs buy, app vs Salesforce enabled workflows, etc.

• Own milestones and adoption of what ships: measured use and business impact count

• Report AI adoption and success metrics: use a data driven approach to track adoption and agent-attributable outcomes (pipeline lift, cycle time, forecast accuracy)

Own Salesforce as the system of record

• Own Salesforce architecture: the core object model, the sandbox and release path, and sign-off on deeper work (schema, Apex, complex Flow, integrations)

• Own all development on core objects and large builds. Define the line between light and large builds, and sign off that large builds fit our architecture

• Partner with the Salesforce admins in Sales, Marketing and Client Ops, who own light builds, through a single intake and agreed SLAs

• Own data integrity at the source: field definitions written in plain language, validation and hygiene standards, protected closed periods, and a logged process for corrections

• Own the Salesforce side of every data handoff: partner with Analytics and Finance so Salesforce data flows as expected to the warehouse and BI tools

Lead the team and maintain cross functional alignment

• Lead and develop a team of ~7 across sales operations, marketing ops, and builders (SFDC and AI): a leader of leaders, with hiring, coaching, and accountability that scales

• Stay builder-literate (about 20% of your time): prototype the hard net-new problem and review work to stay credible. Success is measured by what the team delivers, what people adopt, and improved efficiency in our GTM processes

• Set clear priorities for the team and share them broadly: run one front door for requests, say what new work costs and what it displaces, and keep a roadmap that Sales, Marketing, Client Ops and Finance can see. Business owners decide what matters most; you make the tradeoffs visible and ensure cross functional partners understand timing and status.

• Set and enforce standards for admins and builders embedded in Sales, Marketing and Client Ops: change path, field definitions, and release review, so one source of truth holds as teams build.

What You'll Have

• 10+ years in Revenue, Sales, or GTM Operations at a high-growth B2B SaaS or fintech company, including 4+ years leading teams and leaders

• Deep Salesforce command: architecture, data model, release management, and the judgment to know what to build, buy, or configure

• Strong financial fluency: forecasting, bookings and unit economics, compensation modeling, and board-level revenue reporting

• Builder-literate: comfortable with SQL and a modern data warehouse, workflow and orchestration tools, and LLM and agent tooling, enough to set a real technical roadmap and earn builders' respect

• Experience governing a shared system (ideally Salesforce) that admins and builders in other business units also work in: you’ve set and enforced standards for schema, release path, and data definitions, and made them stick without direct authority over those admins.

• Hands-on experience using AI to change how a GTM function works, with specific tools and specific outcomes, not just familiarity

• A track record of change management and influence: you can effectively prioritize cross functionally and can push back on a revenue leader when hygiene slips

• Excellent, exec-ready verbal and written communication skills: you start with the decision and the impact, and provide updates that give visibility to complex projects

• Growth mindset and builder mentality: you're energized by ambiguity and keep raising the bar as the company scales

Nice to have

• Python and agentic coding tools; modern data stack (Snowflake, dbt, a BI/semantic layer); conversation-intelligence platforms; commission tooling

• Experience in payments, payroll, or vertical SaaS, or a business with complex money movement and a mix of SMB and enterprise customers; experience in the entertainment industry

• Experience standing up a GTM engineering or AI-build function from scratch

Why Join Us

• Unlimited Paid Time Off

• Work from anywhere in Canada and USA

• Health and Dental benefits

• Up to 2% matching RRSP / 401K

• Learning and Development opportunities

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