My name is Craig — I'm a Principle Product Designer.

I'm currently at Plastiq, simplifying AP for SMBs one payment at a time.



I have spent the last decade designing products to help consumers & small businesses make smarter financial decisions.

My career spans both design & front-end engineering. I have created products to help developers monitor client sites, democratize university recruiting, simplify consumer payments, & worked with clients such as Adobe, Fox Corp, Univision, & A+E Networks.



2014 – Present


2013 – 2014


2012 – 2013

Selected Work

If you'd like to learn more about any of my work, don’t hesitate to reach out. I'm always available to chat and I'd love to learn more about your needs.

Case Studies


Split Card Payments

With an average transaction size of ~$15k, and the largest single payment totaling $58m. For Plastiq customers, any one payment method is a limiting factor. Splitting a payment between multiple cards has always been a top feature request. We're currently making this complex operational process incredibly simple for our clients.

✨ Currently in R&D ✨

Automate AP with Bill Upload & Capture

As the needs & complexity of Plastiq's SMB clients grew. A natural step forward was to minimize, eliminate, or automate workflows. With our research from customer interviews, we decided to automate at least the entry of bills into Plastiq.

During early exploration it was obvious to me that we could not only automate manual entry — we could automate the entire bill lifecycle.

I was able to take 14 discreet steps down to 3 that required only reviewing information, no typing would be necessary.

Buy Now Pay Later for SMBs

With the first BNPL focused on letting SMBs pay any invoice — there were unique challenges in both approach and branding. Traditional consumer BNPL fees are the burden of the merchant — which often increases total sales and average transaction size by as much as 43%. How do you get the purchaser to bear the associated fees in a way that feels valuable and not a last resort?

Working closely with our partners allowed us to present the feature as an open line of credit. Our clients felt as though they could rely on this tool when & where it made the most sense. Successfully changing the expectation from; "it might be there when I need it" to "I know exactly how much I have, and what's the cost." That change in perception has driven $50M+ in payment volume in 10 months.

Vendor Directory

As Plastiq grew to meet the complexity of its SMB clients — the vendor director was one particular portion of the application that had remained mostly the same from its consumer payment days.

Both customer service & sales both received requests for additional payment filtering criteria. After clarifying what additional criteria the user would like to use — it become clear that we could eliminate the need for additional filters if we just created more robust vendor profiles.

Adding overviews of commonly requested filters & providing quick links to these pre-built filters eliminates the need to burden the user with simple reporting. By providing the quick-link to the pre-built filter under a "view more" allows power users the ability to dive in and customize the filters without always starting from zero.

Completing an Object-Oriented UX exercise with the team identified exactly which objects are linked on corresponding directory pages. This also became the framework as to how and when we would extend this layout to other directory pages like bills, payments, & payment methods.


Brand Redesign & Launch

For years the Plastiq product ecosystem was entirely separated. As our clients shifted from consumers to SMBs it was increasingly important to unify both Plastiq Pay and Plastiq Accept into a single product.

Elements from Plastiq 2021 Redesign
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Stay Tuned —
More Coming Soon

Payment Approval Workflows

Payment approval workflows enables the ability to review payments prior to disbursement. For teams both large and small the practice should help eliminate errors and potential fraud. The possibilities and rulesets are only limited by the operational complexity of the business.

an abstracted ui to demonstrate mutli user payment approvals

Quickbooks Online Integration

I lead design on a tiger team to create Plastiq's first accounting integration. Given 8 weeks from start to launch, with a 5 star review mandate. Myself and the team very quickly built MVP experiences to validate technical ability, in parallel I was leading user testing in hi-fi experiences to validate the complete workflow.

During this time the team interviewed & received coaching from CPAs. I mapped against competing software to ensure pattern scalability to allow the team to quickly expand additional integrations with minimized effort.

a visualization showing positive feedback around a quickbooks online integration

Account Linking & Multi-Org Support

Freelance CPAs were early evangelists for Plastiq when acquiring small business payers. While they loved the service, their biggest problem was managing accounts for each of the businesses that they worked with.

This feature was designed with single account to multiple organizations, and multiple organizations with multiple entities to support future mid-market expansion.

Plastiq navigation allowing a user to switch between different organizations

Plastiq Pay Launches for SMBs

Plastiq was processing $1B annually — this growth was influenced heavily by a growing cohort of small business owners that started putting a mix of personal and business expenses through Plastiq. The small business owner was spending 10x in comparison to the average consumer.

We decided to take a leap of faith and pivot from consumers to business customers. In order to support the additional volume, and organizational level complexity, Plastiq would need to develop a new data model and application. I worked alongside senior leadership from across the entire organization to design the new data models and develop our 12 month business roadmap.

The immediate goal was to create a skeleton platform that would reduce manual reconciliation times and support dynamic workflows. To establish viability, new workflows had to retain 98% of existing volume. The new workflows not only sped up time to payment completion, but also grew MoM payment volume within the alpha cohort.


Live Currency Conversion

Though many foreign bank accounts can maintain dual currencies — a top requested feature from clients was the ability to convert currency in real time for international wires.

With live currency monitoring, and timed rate reservations live FX was initially launched in 17 currencies.

ADP Payroll on Credit Card

Pitched and integrated with ADP as the exclusive partner to pay Workforce Now payroll runs by credit card.

a sample interface to manage adp workforce now payroll through plastiq

Identity Verification Tools

To support the increasing risk profile of our tools — a powerful identity verification tool was embedded in a simple phone verification experience. 93% of customers were able to meet KYC requirements by confirming their phone number alone. Manual exception experiences were designed for the remaining users.

Expand Your Wallet

Plastiq partnered with Mastercard to act as the first embedded wallet experience for Masterpass. Worked alongside Mastercard leadership and engineering teams to shape the experience and as a pilot for future embedded experiences.

Saving Partial Recipients

To combat complexity and dropoff, I designed & pitched the ability to save "partial recipients." Reducing repetitive work & encouraging completion while removing immediate barriers to the first time payment experience.

International Wires on Credit Card

Expanded the ability to send international wires to 17 countries at launch. Mapped each country as a unified but ultimately unique solution featuring bespoke verification and risk management tooling.


Domestic Wires by Credit Card

Initially built as a test feature, the use case was immediately validated and quickly productized to support same-day wire payments at scale.

Pay & Manage Your Bills with a Photo

Redesigned Biller Experience

Bring Plastiq's legacy clients into modern systems to self manage their payment reporting and workflows. Features included payment search & requests, custom reporting, employee management, marketing resources, & a dynamically generated payment landing page.


Plastiq Cardholder App

After I completed an extensive usability study, we decided to redesign our core application alongside Plastiq's US launch. Modeled after the experiences found in premium consumer cards — the application launched and went on to process over $10bn in lifetime payment volume.

Send Electronic Payments by Credit Card

Funding a bank transfer by card was a feature we had previously launched and turned off within the week due to significant fraud. I was tasked to bring the feature back without the additional fraud risk.

Utilizing third-party data integrations and close partnership with the risk team I was able to launch the feature exceeding all company goals. Working with engineering throughout the process I was able to leverage the same infrastructure to upgrade payment timelines for existing customers as well.


Fix Plastiq's Transactional Email Problem

To prepare for the launch of Plastiq's first product in the United States I completely redesigned the transactional email system including design, development and content strategy.

I consolidated three separate email systems into a single system. Reducing 70+ different templates into 36, that remain the foundation for Plastiq's transactional email system 9 years later.

Plastiq Email Template

Changing the Office Locks

On my third day we got the keys to Plastiq's first office in San Francisco. Our security lead did not want any engineers accessing our production server without new locks put on the office. Our engineering lead needed to push a hot fix — I was the only person in the office that spent their childhood taking apart their family's VCR. I immediately volunteered and got a new keypad system installed.

This isn't my crowning career achievement, but rather a metaphor. I believe design is best situated solving problems. The modern product experience exists beyond the screen. And there are times when technology or a new interface is not the solution to the problem.

I'm the type of designer who will always roll up their sleeves in pursuit of the best solution for any problem — even if that means I just need to change the office locks.

Craig Cockerill
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