Head of Sales / Chief Revenue Officer in Cheltenham

A Note on Title

This role is being recruited with flexibility on seniority and title, calibrated to the successful candidate's track record:

• Candidates who can evidence proven success building commercial traction in new sectors, not just growing an existing book, alongside a track record scaling a B2B Saa S commercial function from roughly £1m to £5–10m ARR, will be appointed as Chief Revenue Officer.
• Candidates who are strong, hands-on operators and closers but earlier in their people-leadership or scaling track record will be appointed as Head of Sales, with a defined path to CRO title (and associated comp) reviewed at 12 months against the Success Measures below.

The Opportunity

Eventwise is a UK-based AI powered software platform that gives festival, conference and agency businesses live budgeting, real-time reporting and commercial visibility, replacing the spreadsheet-led, reactive financial management that has historically defined the sector.

The business is entering a pivotal growth phase: transitioning from a founder-led, accounting-services-weighted model into an ARR-first software, scalable platform business.

The immediate mandate is UK-focused.

his is a rare opportunity to shape and build a high-performing revenue organisation, rather than simply inherit an established one.

Rather than stepping into an established revenue organisation, this role offers the chance to create one, laying the foundations for long-term growth and success.

• Company Snapshot
• Approx. £700k total ARR; software subscriptions currently c.£250k of this (c.25% software / 75% accounting services).
• Enterprise clients typically £3k–£5k per month.
• High level UK industry clients available
• Current commercial pipeline of approximately £1.3m.
• This role already has one direct report, a Sales Development Representative (SDR).
• Why This Role Exists

Chris (Founder & CEO) and Ramesh (Commercial Director) currently own the majority of commercial activity between them.

Eventwise now needs a dedicated, hands-on commercial leader who can

• Build a repeatable, forecastable revenue engine from the ground up.
• Recruit, develop and lead a commercial team as the business scales.
• Create predictable ARR growth and expand the enterprise customer base.
• Free Chris to operate fully as CEO rather than as the company's most senior salesperson.
• Support the current fundraise, working closely with Ramesh (Commercial Director) and Chris (CEO) on commercial narrative.
• What You\'ll Be Doing
• Commercial leadership & execution
• Own revenue generation end-to-end: pipeline, conversion, enterprise sales and partnerships.
• Personally lead sales in the first 3–6 months alongside building the function, this is a builder's role, not a management-only position.
• Develop and execute a commercial strategy that supports the shift from accounting-led to software-first revenue.
• Expand beyond festivals into adjacent UK verticals - conferences, exhibitions, agencies, creative industries, sport and project-based organisations.
• Team & process building
• Audit the current revenue function, sales pipeline, sales process and forecasting.
• Design and implement scalable commercial processes, KPIs and reporting.
• Manage and develop an initial direct report (SDR), and build and execute the recruitment plan to grow the wider commercial team to c.7.
• Partnerships & market presence
• Represent Eventwise at festivals, conferences and industry events, as required, comfort and credibility in the room matters.
• Strategic contribution
• Work closely with the CEO, Commercial Director and CFO on fundraising narrative and investor commercial due diligence.
• Bring your existing UK conference and agency network to accelerate partnership and pipeline development in these verticals.
• First 90 Days
• Audit the current revenue function, CRM, sales process and forecasting.
• Build and align the commercial strategy with the leadership team.
• Increase qualified pipeline and define the core commercial KPIs.
• Begin leading sales personally, building early traction against KPIs.
• Strengthen existing partnerships and open up traction in conferences and agencies.
• Create the recruitment plan for the commercial team.
• 12-Month Success Measures
• A repeatable, forecastable sales engine is in place.
• ARR and enterprise customer base have grown materially.
• A commercial team has been recruited and is delivering.
• Founder dependency on day-to-day sales activity is significantly reduced.
• A strong UK partner ecosystem is established, particularly across conferences and agencies.
• The commercial team has grown from an initial SDR hire to a team of c.7.
• When appointed as Head of Sales, progression to CRO title and comp has been reviewed against these measures.
• What We\'re Looking For

We\'re looking for a builder, not a corporate manager, someone energised by ambiguity, comfortable rolling up their sleeves, and excited by the challenge of turning founder-led momentum into a scalable commercial function.

• Proven B2B software and ARR experience, ideally having led a company's commercial function from roughly £1m ARR through to £5–10m ARR.
• Happy to visit the head office in Cheltenham at least 6 times a year.
• Enterprise sales capability, with a genuinely hands-on approach to winning business not just directing others to win it.
• Track record recruiting and leading commercial teams as a business scale, including managing junior sales talent (e. g. SDRs) day-to-day.
• Experience designing scalable commercial processes (CRM, forecasting, KPIs) from a relatively early base.
• A genuine, established network across the UK conference and agency world — organisers, venue and production agencies, exhibition operators, and the wider events supply chain — that can be activated for warm introductions and partnership conversations from day one.
• Existing relationships with UK event and conference agencies, or adjacent B2B Saa S sales leadership experience in this space, are a strong plus.
• Comfortable attending and working the UK conference, exhibition and festival circuit.
• Strategic thinker who is equally at home in operational delivery.

Compensation & Package

• Head of Sales: £120k–£140k OTE (c.£70k base + commission-related OTE)
• Chief Revenue Officer: £180k OTE (£80k base + £100k commission-related OTE)
• Commission paid in arrears.
• Title and comp tier confirmed on appointment based on demonstrated track record; Head of Sales appointees reviewed for CRO progression at 12 months.
• Assessment Approach

Candidates will be assessed equally on technical/commercial capability, leadership style, builder mindset, and cultural alignment with Eventwise's founder-led, fast-moving environment.

• CV/Linked In assessment
• Culture interview with GM (20 mins)
• Technical skills test
• Interview(s) with CEO/Commercial Director
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