The posting explicitly states 'Remote' with no geographic restrictions, work authorization requirements, or timezone constraints. It is a fractional part-time role (10-15 hours/week) offered by a US company with no language requirements beyond English. The target user meets all competency expectations and faces no stated barriers.
“Remote” Geographic scope — No geographic restriction stated; posting explicitly designates the role as remote.
“part-time (10-15 hours/week)” Timezone — No timezone overlap window is specified. The part-time nature and remote designation imply flexibility compatible with Caribbean UTC-5 hours.
Today, the CEO manages finance directly—closing books with our outsourced bookkeeping service, reconciling data across Stripe, HubSpot, and QuickBooks, building investor reports, and tracking SaaS metrics manually. That's not sustainable at our growth rate.
This person will be the strategic finance leader for the company. You'll direct our outsourced bookkeeping team (Pilot), partner with engineering on system integrations, build the reporting infrastructure investors and the board expect, and ensure our financial data is as trustworthy as the data we sell to customers.
This is not a pure bookkeeping role. We need someone who can close the books AND build a cohort-based revenue model. Someone who understands why NDR matters more than top-line growth and can explain our unit economics to a Tier 1 VC.
We have a complex revenue model—flat-rate data subscriptions, per-outcome verification credits, and hybrid contracts—flowing through Stripe, HubSpot, and QuickBooks with manual reconciliation in between.
We need someone who can make the financial plumbing work automatically so the CEO can focus on customers and product. We're heading toward a Series A raise and need investor-grade financials, metrics, and modeling ready before we walk into those rooms.
Your first priority is fixing the financial plumbing. Within 60 days, we expect the data pipeline between Stripe, HubSpot, and QuickBooks to be audited, mapped, and either automated or on a clear path to automation.
This means understanding every revenue stream—subscriptions, credits, hybrid contracts—and how each flows (or fails to flow) from billing to the general ledger. You'll partner with our developers on integration work and direct Pilot on proper GL coding. By day 60, the CEO should no longer be manually reconciling systems.
Fix the Financial Data Pipeline — Audit and rebuild how data flows between Stripe (billing, subscriptions, credits), HubSpot (deals, pipeline, lifecycle stages), and QuickBooks (GL, reporting). Map every revenue stream end-to-end. Identify where data breaks, where manual workarounds exist, and work with developers to automate. This is job one.
Build Internal Dashboards & Reporting — Create a reporting layer the entire team can rely on. SaaS metrics (ARR, NDR, GDR, ACV, CAC payback, LTV:CAC, burn multiple, gross margin by product line, cohort retention), sales funnel analytics (pipeline velocity, conversion rates by stage, deal cycle time, win/loss analysis, rep-level performance), and PLG funnel metrics (self-serve signups, activation rates, free-to-paid conversion, credit usage patterns, expansion triggers). Replace manual spreadsheets with dashboards the CEO can check anytime.
Own Funnel Analysis — We run both a sales-led motion (channel partnerships, direct enterprise) and a growing PLG motion (self-serve portal, freemium credits). You'll build the reporting to track both funnels independently and understand where they intersect—which PLG users convert to sales-assisted deals, what usage patterns predict expansion, and where leads drop off. This analysis directly informs hiring, product, and go-to-market decisions.
Solve Revenue Recognition — Navigate the complexity of ASC 606 across our mixed model—annual subscriptions on flat-rate data feeds, pay-as-you-go outcome credits, and hybrid contracts with both components. Build the framework so this doesn't require CEO involvement each month.
Build Strategic Models — Create and maintain rolling cash flow forecasts, annual budgets, and scenario plans. When the CEO asks "what happens if we hire 3 engineers vs. 2 sales reps?"—you have the answer in minutes, not days.
Prepare for Series A — Build and maintain the financial model and data room. Prepare quarterly investor updates and board materials. Be the person who can walk a VC through our cohort data, unit economics, and margin structure with confidence.
SaaS Finance Veteran — You've been the finance person (or one of the first) at a high-growth B2B SaaS or usage-based company. You know what a cohort report is, why it matters, and how to build one without being asked.
Stripe-Native — You've worked hands-on with Stripe's billing infrastructure—not just invoicing, but products, pricing models, subscriptions, metered billing, and credit systems. You understand how Stripe data maps to accounting systems and where it breaks.
Investor-Grade Thinker — You can build a financial model that holds up under VC scrutiny and explain unit economics clearly to sophisticated investors. You know what Bessemer, Sequoia, and a16z look for.
Startup Operator — You're comfortable with ambiguity, move fast, communicate directly, and don't need a big team to get things done. You know the difference between "good enough for now" and "needs to be right."
Straight to the employer's own application — no middleman.
Tell us and we'll mark RevenueBase Inc as a company that has actually hired in the Caribbean. It's the most useful thing on this board and it only exists because people report it.
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