Webexpenses VP Sales and Marketing Case Study

Webexpenses and PE firm Tenzing partnered exclusively with Oakstone International to appoint a VP of Sales and Marketing in the UK. Working alongside Webexpenses CEO and an advisor at Tenzing, Oakstone introduced 6 candidates, 3 of which progressed to final rounds.

Through an in-depth search, Oakstone identified and engaged senior talent with proven experience of building and scaling a high-performing commercial engine in just 4 weeks.

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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.

As Webexpenses accelerated towards ambitious growth targets, Tenzing, the investor group, introduced a specialist commercial advisor to support portfolio performance.

This advisor, working closely with the CEO, identified a critical gap within the sales function and engaged Oakstone to deliver a highly specific commercial leadership hire. The brief was clearly defined from the outset, with a strong emphasis on execution and measurable impact.

Requirements

Joe Sanchez, Webexpenses CEO and Tenzing’s advisor, was looking to hire a senior sales leader to build and scale a high-performing commercial engine. The focus was on strategic leadership and hands-on delivery across the full sales cycle.

Key requirements included:

• Ownership of the entire sales funnel, from top-of-funnel pipeline generation through to deal execution and closure

• A strong bias towards execution, prioritising pipeline build and revenue delivery over strategy or planning

• The ability to introduce structure, discipline, and pace into the sales function

• Experience leading and developing a team, with responsibility for future hiring

• A metrics-driven approach, with clear evidence of delivering against volume and velocity targets

Critically, the client prioritised behaviours and operating style over traditional experience markers, seeking a leader who could drive immediate commercial outcomes.

Oakstone’s Approach and Solution

Oakstone adopted a targeted, insight-led search strategy focused on identifying behavioural alignment rather than relying solely on job titles or sector experience.

The approach included:

• Mapping organisations with similar sales models, particularly those operating in high-volume, high-velocity deal environments

• Prioritising candidates with proven experience managing both pipeline generation and deal execution, rather than specialists in one area

• Assessing candidates against key performance metrics to ensure alignment with the client’s growth objectives

• Positioning the opportunity effectively, articulating the scale of impact and growth potential within a relatively low-profile business

By focusing on comparable commercial environments, Oakstone significantly increased the probability of identifying candidates with the right execution mindset and operational rigour.

Search 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

• Hybrid skill requirement: The need for a leader capable of both top-of-funnel generation and deal execution significantly narrowed the talent pool

• Behavioural specificity: The emphasis on execution over strategy required careful assessment beyond CV credentials

• Candidate motivation: Securing individuals willing to join a scaling, less prominent business required a clear articulation of the growth journey and opportunity

Additionally, many candidates in the market tend to specialise in either pipeline generation or closing, making it challenging to identify individuals with end-to-end ownership capability.

Search Results

Oakstone delivered a highly focused shortlist of six candidates, all aligned to the defined metrics and behavioural profile.

The process was multi-stage:

• Initial screening with the commercial advisor

• Secondary interviews with the CEO

• Final-stage presentations and executive stakeholder engagement

Three candidates progressed to the later stages, with two reaching the final interview.

The successful candidate, Oliver Moss, was selected for his clear alignment with the required brief, a structured approach to sales execution, and the ability to balance process, methodology, and leadership within a scaling environment.

The entire search process from briefing to signing of contracts took 4 weeks.