Webexpenses CPTO Case Study

23 Jun

Webexpenses exclusively partnered with Oakstone International to appoint a Chief Product and Technology Officer in the UK. Working alongside Webexpenses CEO, Oakstone introduced 6 candidates, 3 of which progressed to the final rounds.

Through an in-depth search and qualification process, Oakstone identified and engaged a CPTO with proven experience in building and scaling a high-performing commercial engine in just 8 weeks.

About Webexpenses

Search Background

Requirements

Oakstone’s Approach and Solution

Challenges

Search Results

About Webexpenses

Webexpenses is a leading provider of Expense Management, Invoice Processing, and payment solutions, helping businesses of all sizes across 70+ countries streamline processes and eliminate manual errors. Their innovative mobile app empowers users to manage expenses on the go, with reimbursements often processed within just one day. Designed for scalability, the Webexpenses solutions grow with your business needs, enabling seamless automation for finance teams and ensuring greater compliance, visibility, and cost control. With deep integrations to clients’ existing ERP systems and AI-powered features, Webexpenses reduces administrative burden, enhances policy enforcement, and provides real-time insights to drive better decision-making.

Search Background

Webexpenses, a private equity-backed SaaS business, partnered with Oakstone International following a long-standing relationship with Stewart Holness, a Portfolio Executive Chair in the SaaS industry. Oakstone subsequently worked with Webexpenses and Holness previously on the placement of their CEO and VP of Sales and Marketing.

Webexpenses were seeking a Chief Product and Technology Officer to bring executive-level leadership to drive company growth and scale. This was a sensitive, confidential replacement role for an incumbent CPO, aiming to combine product and technical responsibilities into a CPTO function. This role required signed NDAs to everyone we reached out to.

Requirements

Joe Sanchez, Webexpenses CEO, was looking to hire a CPTO. Key requirements included:

Based in Reading
PE & SMB market coverage experience, ideally in Business Application (Accounting software, ERP or CRM).
Experience of executive level technical leadership, building out a product roadmap and developing and AI strategy.
The company's small size meant the role required a hands-on approach despite its C-level executive status.

Oakstone's Approach and Solution

The search was conducted confidentially under NDA due to the incumbent.
NDAs were signed by all 40 candidates targeted for the role before presenting any information.
Thoroughness was key in assessing candidates, particularly in understanding how their experience translated across both product and engineering functions.

Challenges

The search presented several complexities:

Low brand visibility: As a smaller organisation, Webexpenses required strong candidate engagement and narrative-building to attract high-calibre talent
Candidate drive: Securing individuals willing to join a scaling, less prominent business required a person who had adaptability, which required further qualification.

A key challenge was finding a candidate who could effectively combine both CTO-standard technical leadership and CPO-standard product leadership, as many had not held a prior CPTO title.

Search Results

Oakstone delivered a highly focused shortlist of six candidates, all aligned to the defined brief.

All 6 candidates met the hiring manager, Joe (CEO)
3 candidates went to panel.
The chosen candidate had a strong roadmap strategy, notably using AI to build the roadmap and presentations, which was an unexpected and highly valued benefit.
Briefing to signing took 8 weeks.