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Outpost Technologies

AI-powered cross-border commerce MoR/ToR platform

Revenue Operations Lead

Full-TimeUpdated on 10/23/2026
No salary listed
Mid, Senior
London, UK
In PersonWorks in person in London five days a week.
Sales & Account ManagementSales Operations

About the job

Requirements
  • Have 4 to 7 years of experience in revenue operations, sales operations, business operations, or go-to-market strategy at a high-growth fintech, payments company, or business-to-business software-as-a-service company.
  • Have built a revenue system from zero rather than inherited a mature one.
  • Be fluent in customer relationship management architecture and the outbound stack; familiarity with Attio, Instantly, and Apollo is relevant, though tool choice is less important than designing the underlying model.
  • Have strong analytical skills, including advanced Excel or Sheets skills and experience with business intelligence tools.
  • Demonstrate bias for action and solve problems rather than only observing them.
  • Think in systems while remaining hands-on, fixing broken reports and removing the causes of recurring problems.
  • Be able to quantify processes, not merely describe them.
  • Have strong emotional intelligence to address inaccurate data with experienced commercial colleagues.
  • Be comfortable with ambiguity and startup environments without defined processes or hierarchy.
  • Be curious and resourceful, and able to figure out unfamiliar problems.
  • Show clear, quantified achievements on the CV.
Responsibilities
  • Own Attio customer relationship management end to end, including the object model, stage definitions, required fields, data hygiene, and automation.
  • Build the forecasting system and operationalize it through weekly pipeline reviews, monthly board numbers, and quarterly planning.
  • Own the go-to-market stack, including outbound sequencing, enrichment, routing, deduplication, and attribution.
  • Build and run agentic pipeline systems that enrich accounts, draft follow-ups, surface stalled deals, and keep the customer relationship management system clean; design workflows, write prompts, set guardrails, and audit agent outputs.
  • Own key revenue metrics, including gross merchandise value, annual recurring revenue, take rate, win rate, sales cycle, pipeline coverage, and cost of acquisition.
  • Build company reporting and investor reporting packs.
  • Build the pricing and quoting model and establish deal desk discipline.
  • Own the handover from signed contract to live merchant in coordination with operations, tax, and engineering.
  • Measure time-to-live and revenue ramp, and improve both.
  • Feed commercial insights into the product roadmap, including identifying lost deals and their causes.
  • Write playbooks for qualification, scoping, pricing approval, renewal, and expansion.
  • Set data quality standards and ensure they are followed.
  • Hire additional team members after the revenue system is running.
  • Rebuild the pipeline in Attio so each deal has a stage definition, owner, close date, and modeled value, and shorten the weekly review process.
  • Build a pricing calculator based on merchant volume, market mix, and product mix, replacing per-deal spreadsheets.
  • Reduce the time from signed contract to first live transaction in collaboration with operations, tax, and engineering.
  • Build weekly revenue and monthly investor packs and automate their data pulls.
  • Design the commission plan for the first commercial hires.
  • Score the lead universe against the ideal customer profile and rebuild outbound targeting.
  • Track the full funnel from LinkedIn and outbound through closed-won deals and determine which channel generates revenue.
  • Forecast gross merchandise value by market and product and advise the founding team on its sources.

About the company

Outpost Technologies runs an AI-powered platform for cross-border commerce that acts as the Merchant of Record and Tax of Record for clients. It creates dedicated local entities in each market to handle local payments and acquiring, while Outpost assumes full tax and regulatory liability and compliance. The platform uses an AI engine trained on trade regulations to apply correct tax treatment and customs classification for every transaction, covering VAT, GST, and sales tax filings and audits. The goal is to simplify international trade for merchants by providing end-to-end compliance, payments, and regulatory liability through a single platform.

Company Size

11-50

Company Stage

Series A

Total Funding

$17.5M

Headquarters

London, United Kingdom

Founded

2024

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Simplify's Take

What believers are saying

  • March 2026 funding targets jurisdiction expansion, product development, and headcount growth across Europe and Asia.
  • Outpost’s local-entity payments reportedly improve approval rates about 10% versus cross-border cards.
  • Tariffs, de minimis changes, and OECD reporting rules keep merchant compliance demand rising through 2027.

What critics are saying

  • Paddle, FastSpring, and Global-e already sell similar merchant-of-record compliance bundles in 2026.
  • September 2026 hiring for Head of Sales, RevOps, and Payments signals early commercial buildout.
  • A single VAT audit or licensing challenge in 2027 can cripple Outpost’s liability-heavy model.

What makes Outpost Technologies unique

  • Will Mahon-Heap brought Revolut expansion playbooks and Wayflyer deal experience to Outpost, 2021.
  • March 2026 Ribbit-led $17.5 million Series A backs the MoR and ToR full-liability model.
  • Outpost’s AI monitors 20,000 tax rates, auto-classifies customs, and routes local acquiring.

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Benefits

  • Company Equity

Growth & Insights and Company News

6 month growth

-7%

1 year growth

-7%

2 year growth

-7%
Tech Funding News
Mar 10th, 2026
Outpost raises $17.5M to make international selling 'as easy as domestic' amid tariffs — TFN

Outpost raises $17.5M Series A led by Ribbit Capital to simplify cross-border commerce with AI tax compliance and local payment entities. Ex-Revolut exec's platform serves EU, LATAM, NA, Asia merchants

Vestbee
Mar 10th, 2026
Outpost secures $17.5M Series A to power global payments and tax compliance

Outpost secures $17.5M Series A to power global payments and tax compliance. London- and New York-based startup Outpost, which develops software to help businesses manage payments, taxes and compliance when selling across borders, has raised $17.5 million in a Series A funding round led by Ribbit Capital, as Vestbee was told. * Launched in 2023 by Will Mahon-Heap, Outpost develops software that handles payments, tax compliance, and legal liability for companies selling digital products and services across borders. The platform acts as a "merchant of record," meaning it processes payments through its own local entities in different countries while taking responsibility for taxes such as VAT, GST, and sales tax. * According to the startup, its system monitors more than 20,000 indirect tax jurisdictions and applies the correct tax treatment and customs classification automatically for each transaction. The company says routing payments through local acquiring infrastructure can increase approval rates by about 10% and reduce processing costs compared with traditional cross-border card transactions. * Outpost reports that its tools are already used by merchants operating across Europe, North America, Latin America, and Asia, including subscription platforms, software companies, and cross-border e-commerce businesses that accept payments in dozens of markets and more than 100 countries. Details of the deal. * The Series A round was led by Ribbit Capital, with support from existing investor Better Tomorrow Ventures and angel investors including executives from Revolut, Uber, Affirm, Airwallex, and Checkout.com. "Outpost's rapid growth is a testament to the world-class team they have assembled and their ability to absolve merchants of operational complexity. While other players are building incremental tools, Outpost has attacked the problem with a full stack model that other providers simply can't match. We are incredibly excited to continue supporting Outpost as they coordinate the economic, administrative and regulatory rails that redefine global trade," claims Nihar Bobba, Partner at Better Tomorrow Ventures. * Outpost plans to use the new funding to accelerate product development, expand its coverage into more global jurisdictions, and increase headcount as demand for cross-border commerce infrastructure grows. The company aims to further develop its AI-powered platform while scaling operations to support more merchants selling across Europe, North America, Latin America, and Asia.