Webexpenses CEO Case Study

5 Jan

Written By Oakstone International

Web Expenses was seeking a CEO who was equipped for their planned next stage of growth.
The board was initially undecided whether the role should be a CEO or CRO profile; ultimately, they concluded they needed a revenue-heavy CEO capable of scaling a mid-market SaaS organisation.
Oakstone introduced 15 candidates, with four progressing to the advanced interview stages and referencing.
Oakstone introduced Joe Sanchez, who was hired for his ability to evolve Webexpenses’ revenue engine while maintaining cultural stability during a sensitive transition.
The entire search process, from briefing to signed contract, took 12 weeks.

About Webexpenses

Search Background

Requirements

Oakstone’s Approach and Solutions

Search 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

Oakstone had a long-standing relationship with Stewart Holness, a Portfolio Executive Chair in the SaaS industry, built through previous collaborations across his PE portfolio companies.

The remit arose from a sensitive internal challenge at Webexpenses, where they needed to hire a CEO who was equipped for their planned next stage of growth.

The search was conducted confidentially and discretely, requiring each candidate to sign an NDA before revealing any details about the company or role, to avoid company disruption.

The board was initially undecided whether the role should be a CEO or CRO profile, however ultimately concluded they needed a revenue-heavy CEO capable of scaling a mid-market SaaS organisation from £10M to £40M ARR.

Requirements

A software leader with C-level revenue ownership and experience scaling a SaaS company of similar size.
Ability to design and execute a global revenue and go-to-market strategy, not just operate regionally.
Experience growing a UK-based business (not just European revenue for US vendors).
Flexibility to work across North Oxford, Reading, and occasionally London.
A personality capable of harmonising a long-tenured team and minimising disruption as a new leader.
Preference for candidates with strong mid-market rather than enterprise backgrounds.

Oakstone's Approach & Solution

Given the extreme sensitivity of the role, Oakstone ran a confidential executive search, initially targeting CROs, SVPs of Sales, and Global Sales Leaders who had demonstrably scaled UK-based SaaS companies.

The focus was on identifying revenue leaders who:
had full ownership of strategy and execution,
had previously led a business through significant growth
had the gravitas to step into a CEO role.

Search Challenges

Extreme confidentiality due to replacing an internal CEO.
Limited UK candidate pool with true exec-level revenue leadership for mid-market SaaS.
Many candidates had only executed US-driven GTM playbooks rather than building a strategy themselves.
The business was a small player in a crowded, diluted market, meaning candidates needed to buy into the opportunity to carve out mid-market dominance.
Strong emphasis on cultural fit to ensure continuity, trust, and retention of long-term staff.