We did not study payments infrastructure. We built it.

Your diligence firm can assess the code. We can tell you whether the team that wrote it can execute the roadmap they just pitched you.

Former operational product executive across North America and Europe working with Klarna, PayPal, Nexi, iZettle, Nets, Tide, and others to help scale and grow

Companies where our operators have held executive roles

Klarna
Interac
Nexi
iZettle
Tide
Enfuce
Nets

Generalist diligence leaves the highest-risk items unexamined

Generalist diligence firms have smart analysts, proprietary benchmarks, and thousands of prior engagements. What they do not have is the specific people who built the multi-market payment infrastructure, scaled the neobank to millions of SMBs, ran the issuer processing platform, or launched the checkout product across four countries. That is the gap. These are the places where it shows up.

01

Your diligence said the tech stack is solid. Here is what it missed.

A generalist firm will assess architecture, code quality, and scalability. It will not tell you that settlement reconciliation has been manually patched for two years, the scheme compliance roadmap is three quarters behind, or the CTO's "platform" is four separate systems held together by a team about to leave.

We see these things because we have built these systems — managed the settlement, negotiated the scheme contracts, and shipped the integrations. We do not assess from the outside. We recognize patterns from the inside, the ones that only surface when you have been the person responsible for making it work.

02

The 100-day plan was a slide. We turn it into a sequence of executable decisions.

Your investment thesis depends on product execution. But nobody on the board has run a payments product organization at this scale, and the operating partner is covering twelve portfolio companies.

We have helped with transactions across Europe and the US in the payments and fintech space. We have been responsible on the ground for making organic and inorganic growth work. We have rebuilt product organizations, achieved P&L results, and taken companies on 100% year-over-year growth journeys, setting them up for an IPO. We do not advise on value creation plans. We build them, staff them, and hold people accountable to them.

03

Your European expansion framework is not an operational playbook. Ours is.

Europe is not one market. It is thirty markets with different payment schemes, regulatory regimes, consumer behavior, and competitive dynamics.

A generalist firm gives you a market-entry framework. We give you the operational playbook: which schemes to prioritize, which regulators will block you, which local payment methods matter, and what timeline is realistic. We have built local payment method portfolios that delivered 20% revenue uplift across seven European markets for European PSPs. We led major fintech launches across Sweden, Norway, Finland, the UK, and the US, growing users from zero to millions. We know what the actual work looks like.

04

Your AI strategy deck is not a strategy. Here is how to tell which pilots will change the economics.

Every portfolio company is running an AI pilot. Everyone has a strategy deck. But nobody in the room has actually built and shipped AI systems inside a payments company, so nobody can separate real operational leverage from demos.

We stood up the ML and fraud intelligence capability at Nexi in 2021, building the team and the production pipeline from zero. We built and exited Findify, an AI-powered commerce platform that served 1,500+ merchants across 50+ countries. We operate an AI-native consulting model where coordinated agent systems do multiple quality passes before work reaches human review. We tell you what works, what does not, and where the actual ROI sits based on what we have built.

05

The Canadian expansion thesis is live. Your team does not know the unwritten rules of the ecosystem.

Canada's payments landscape is shifting simultaneously on three fronts: the Real-Time Rail rollout, the Open Banking regulatory transition, and a wave of fintech consolidation that has every Big Five bank re-evaluating its digital strategy.

Our founder served as Chief Product Officer at Interac, Canada's national payment network. We have live relationships across the Big Five banks and active engagements with Canadian payment infrastructure providers. We do not offer a Canadian market-entry framework. We offer the operational playbook written by the person who helped build the infrastructure your target company runs on.

Three client segments. One shared need: operators who have done the job, not analysts studying it.

For Private Equity Firms & Their Portfolio Companies

Commercial and technical due diligence. Post-acquisition value creation. AI strategy assessment.

You need to know whether the payments company you are acquiring can actually execute the roadmap the management team pitched you. We have run these organizations. We tell you what the generalist report misses: team capability gaps, infrastructure debt, regulatory exposure, and whether the 100-day plan is achievable. After close, we build the value creation plan, staff it, and hold people accountable to it.

For Banks

Open Banking readiness. Real-Time Rail strategy. Digital product transformation.

You are navigating simultaneous regulatory and technology shifts — RTR, Open Banking, ISO 20022, and digital wallet strategy. We have held senior executive roles inside national payment networks and built the infrastructure that banks depend on. We know the unwritten rules of the ecosystem: the internal dynamics, the integration timelines, and the specific regulatory milestones that will determine your strategic options.

For Fintechs

Product strategy. European market expansion. Pre-acquisition positioning.

You are scaling fast and need operators who have done it at the stage you are at now — and at the stage you are growing into. We have scaled fintechs from zero through IPO, led multi-market European expansion, built issuer processing platforms from the ground up, and positioned companies for acquisition by PayPal, Intuit, and Coupa.

Domain operators deliver in weeks what generalist firms scope in months

We are a small group of senior operators, not a consultancy with a bench of analysts. Every engagement is led by someone who has held the P&L, managed the team, and shipped the product at the kind of company you are evaluating, acquiring, or trying to grow. Our operators provide the judgment and domain expertise. Our AI infrastructure enables the delivery speed and analytical depth that a traditional small firm cannot match. That is why we move fast. We do not need to learn the domain. We have lived it.

Day 0

We scope the problem together.

A single conversation to understand what you are facing, what you need to know, and when you need to know it. No RFP. No three-week scoping exercise. We either know how to help or we tell you we are not the right fit.

Week 1

Deep technical and commercial assessment.

We get into the details. Product architecture, team structure, roadmap feasibility, competitive positioning, regulatory exposure. We talk to the people who build the thing, not just the people who present the thing.

Week 2-3

Clear findings with specific recommendations.

You get a deliverable that tells you what is real, what is risky, and what to do about it. Every recommendation is grounded in operating experience, not framework logic. We tell you what we would do if it were our money.

Week 3-4

Ongoing support if you need it.

Implementation guidance, team coaching, board-level advisory, or hands-on execution support. We do not disappear after the report.

The specific executives who built the companies you are acquiring

Senior product and technology executives who have built, scaled, and operated payments, fintech, and cloud infrastructure businesses across North America and Europe. Between us, we have held P&L ownership at Canada's national payment network, scaled product delivery through a $15B IPO, led the business unit generating 95% of revenue at a company acquired for $2.2B, co-founded a digital bank that raised $93.3M, built cloud infrastructure from founding team to a $1.1B+ valuation, and launched products across 10+ European markets. When you work with Outside Context, you work with people who have done the job you are hiring us to assess.

Portrait of Ted Bowman

Ted Bowman

Founder. Payments Infrastructure, Product Strategy & AI Strategy

Ted Bowman is an entrepreneur and product executive with two decades of experience building, scaling, and operating payments and fintech products across North America and Europe, from startups to national payment networks. His career spans the full payments value chain — zero to one, rapid international scaling, and enterprise-level optimization. He is the only operator in the market who has held CPO seats at both a national payment network and a major European payment processor.

  • Payments Infrastructure
  • Product Strategy
  • AI Strategy
Expand DetailsOperating History

Rebuilding the Product Organization Behind Canada's Payment Network

Interac. Former Chief Product Officer.

Led the full product organization at Canada's national payment network, defining corporate product strategy, innovation, market positioning, and revenue performance. Held full P&L ownership. Led and closed a growth capital raise to fund Interac's digital wallet initiative. Rebuilt the senior leadership team and reorganized the product organization into a modern, product-driven operating model. Deep domain expertise in the Real-Time Rail rollout and the Open Banking regulatory transition. Forged global partnerships including Microsoft.

Building Multi-Market Payment Infrastructure at Scale

Nexi S.p.A. Former CPO & GM Relay.

Oversaw a €14.7M capital budget and led 97 employees across seven European geographies. Built 7 product teams from zero by hiring 105 people in 14 months. Stood up the ML and fraud intelligence capability in 2021, building the team and the production pipeline from zero. Launched 30 local payment methods delivering 20% revenue uplift across the eCommerce portfolio. Drove M&A including the Computop acquisition and secured Microsoft Europe as a payments client.

Scaling a Global Fintech at Hypergrowth

Klarna ($15B IPO). Former Senior Product Leader.

First product hire. Part of the product executive leadership team that scaled Klarna at 100% year-over-year growth. Led a team of product managers to establish a consistent and high pace of delivery across multiple markets.

Launching European eCommerce Strategy

Nets A/S. Former Senior Consultant.

Helped launch the company's European eCommerce strategy and product portfolio. Guided strategic investments, technical delivery, and M&A due diligence.

Startup Roots

Product Leader & Founder.

Led product at AisleBuyer (acquired by Intuit), building mobile self-checkout for Walmart, Kroger, and Dunkin'. Built trade-in programs at Gazelle for Amazon, Costco, and Walmart. Founded and exited companies in Boston across eCommerce, real estate tech, and hosting.

Portrait of Justin Drees

Justin Drees

Payments, Neobanking, M&A & AI Strategy

Justin Drees is an entrepreneurial product leader with two decades of experience building, scaling, and transforming products at some of Europe's most recognized technology companies, from startups to unicorns that IPO. He has led large product organizations while staying close to the details that matter. He is equally comfortable in the boardroom, the sprint review, or the sales call.

  • Payments
  • Neobanking
  • M&A
  • AI Strategy
Expand DetailsOperating History

Building & Scaling Neobank Products to Millions of SMBs

Tide ($1.5B valuation). Former VP Product, Business Services.

Led strategy, P&L, and a 90+ person business unit that repeatedly delivered triple-digit annual growth in both revenue and users across multiple product lines including Accounting, Payroll, Accounts Receivable/Payable, Expense Management, Company Formation, and Secretariat. Drove cross-company initiatives to expand internationally into India, Germany, and France. Hands-on product and tech due diligence for the acquisition and integration of Onfolk (payroll). Championed AI adoption to expedite the product development lifecycle by 50%.

Driving Product & Revenue Growth in Enterprise SaaS

Scoutbee (acquired by Coupa). Former VP Product.

Defined product strategy to build new products and a platform with deeptech capabilities for procurement (AI/ML data extraction, enrichment, search & analysis) that doubled annual user and bookings growth. Hired and led 6 product teams. Part of high-value enterprise sales team for accounts such as Unilever, Walmart, Audi, and key distribution channels including Gartner.

Owning Core Revenue Products at Scale

iZettle (acquired by PayPal for $2.2B). Former Product Director.

Led the division responsible for 95% of iZettle's total revenue, growing 50% annually across payments, hardware, credit, and financial services. Reorganized and managed 10 product teams (120 people). Also served as Board Director of subsidiary iZettle Capital overseeing high-growth B2B lending strategy and operations. Led PayPal integration post-acquisition.

Launching & Hyperscaling Product Internationally

Klarna ($15B IPO). Former Head of Product UK.

Led the development and launch of Klarna Checkout in Sweden, Norway, Finland, and the UK, growing the user base from zero to millions of monthly active users while delivering 80%+ improvements in merchant conversion rates. Responsible for the company-wide launch in the UK.

Portrait of Philip Mikal

Philip Mikal

Issuing, Processing, Financial Inclusion & AI Strategy

Philip Mikal is a payments infrastructure operator and fintech founder with nearly two decades of international experience across the US and Europe. He has built across the full payments stack - issuer processing, acquiring, banking, credit, remittance, mobile acceptance, wallets, and crypto - as both an executive and a founder. He co-founded a venture-backed digital bank, exited a payments company to a publicly listed acquirer, and has advised infrastructure serving more than $25B in annual TPV. He started his career as a software engineer in Silicon Valley, giving him a deep technical foundation beneath executive-level strategic judgment.

  • Issuing
  • Processing
  • Financial Inclusion
  • AI Strategy
Expand DetailsOperating History

Leading Product & Technology at a Cloud-Native Issuer Processor

Enfuce. Former Chief Product & Technology Officer.

Led product and technology at a cloud-native issuer processor covering card issuing, payment processing, fraud management, and ledger systems.

Co-founding a Digital Bank for Migrants

MAJORITY. Co-founder & Former CPO.

Co-founded a pioneering digital financial service dedicated to serving migrants in the US. Built banking, money transfer, and international calling into a single app for an underserved customer segment. Raised $93.3M from Valar Ventures. Deep experience in financial inclusion, product-market fit for underserved segments, and building from zero to scale.

Scaling Global Financial Services at Hypergrowth

Klarna. Former VP Product Management, Global Financial Services.

Worked with the team that introduced credit products and built new core platforms enabling Klarna's global expansion into the US, UK, and new European markets. Built deep expertise in BNPL economics, credit products, and scaling payment platforms internationally.

Turnaround Leadership in Alternative Lending

TrustBuddy. Former CEO.

Led restructuring of a Nordic P2P lending platform. Experience in alternative lending, credit risk, and turnaround leadership.

Pivoting to Financial Services for Migrants

Rebtel. Former CPO.

Helped pivot from international calling to banking services for migrants. Built the product vision for a bank built by migrants, for migrants, launching in the US. This work planted the seed for MAJORITY.

Portrait of Meni Morim

Meni Morim

AI Strategy, eCommerce & Venture Building

Meni Morim is a technologist, entrepreneur, and executive who has built and led AI-powered products from concept through acquisition and public markets. He brings deep experience in machine learning product strategy, eCommerce, and the operational discipline of running a publicly traded company.

  • AI Strategy
  • eCommerce
  • Venture Building
Expand DetailsOperating History

Building and Exiting an AI-Powered eCommerce Platform

Findify. Co-founder & Former CEO.

Co-founded and led Findify, an AI-powered eCommerce platform that used machine learning to personalize search, recommendations, and merchandising for online retailers. Scaled to 1,500+ merchants across 50+ countries. Sold to Maropost.

Leading a Publicly Traded Company

Lifeist Wellness. Former CEO.

Served as CEO of a publicly traded company for five years, navigating public market governance, investor relations, and strategic transformation.

Early Career in Product and Engineering

Klarna. Stockholm Era.

Part of the Klarna network during the company's formative scaling period in Stockholm. YPO member.

Portrait of Richard Herold

Richard Herold

Cloud Infrastructure, Platform Engineering & AI Strategy

Richard Herold is a product leader with over a decade of experience building and scaling cloud infrastructure and platform products, from founding team through unicorn valuation. He brings deep expertise in cloud storage, decentralized systems, AI/ML infrastructure, and the operational discipline of building products at the intersection of infrastructure and emerging technology.

  • Cloud Infrastructure
  • Platform Engineering
  • AI Strategy
Expand DetailsOperating History

Product at the Forefront of Decentralized Infrastructure

Filecoin Foundation. Product Consultant.

Leading product work at the Filecoin Foundation, the organization behind one of the largest decentralized storage networks. Working at the intersection of Web3, decentralized infrastructure, and real-world storage use cases.

Building a Web3 Decentralized Cloud Storage Platform

Seal Storage Technology. Former Head of Product.

Led product for a Web3 decentralized cloud storage infrastructure platform. Experience across startup development, decentralized AI, and enterprise storage architecture.

Scaling an AI/ML Cloud Infrastructure Platform

Paperspace. Former Product Manager.

Product Manager and Product Owner of the Paperspace Core Product Platform, an AI/ML cloud infrastructure platform. Hands-on experience building and scaling the compute infrastructure that powers machine learning workloads.

Founding Team of a B2B SaaS Unicorn

Wasabi Technologies ($1.1B+ valuation). Former Senior Product Manager.

Member of the founding team at Wasabi, a B2B SaaS cloud storage provider that grew to unicorn valuation. Six years building the product from early stage through scale. Deep experience in startup development, product design, and cloud infrastructure economics.

Building Core Products at Scale

Carbonite. Former Associate Product Manager.

Product Owner of 7 products across 4 development teams including the core backup product with a user base of over 1.2 million users.