£35,000‑£45,000 p/a, negotiable, plus exceptional uncapped OTE and benefits.
This is a great opportunity to join a growing firm where you will develop a career, and uniquely have a say and share in the growth of the business.
We are an established Managed IT Services and Cybersecurity provider based in Chester, serving approximately 300 customers across Chester, North Wales, and the North West of England. For over 20 years we have built a reputation on delivering exceptional technical service and genuine partnership to SME businesses.
We are at an exciting inflection point – transitioning from a traditional MSP to a security‑first MSSP, and significantly scaling new customer acquisition. This is a strategic growth phase that creates genuine opportunity for the right salesperson.
Why This Role Matters
We have built a strong foundation: excellent customer retention, solid technical delivery, and a trusted brand in our region. What we need now is someone who can translate that strength into consistent new business growth. It’s not about cold‑calling hundreds of prospects or hitting aggressive daily activity metrics. It’s about consultative, relationship‑based selling to SME decision‑makers who are actively looking for a trustworthy IT and security partner.
The Role
Title: Senior MSP Sales Executive
Location: Chester office base (flexible hybrid working available), with regular customer visits across North West, North Wales, Cheshire
Travel: Minimal overnight stays (less than 2 per year), mostly day trips within the region
Reports to: Sales Manager
Primary Responsibility: Drive new customer acquisition and strategic account expansion
You will own the full sales cycle from initial contact through to contract signature, with technical support available when needed for complex pre‑sales. This is a hybrid role – a balance of new business (hunting) and identification and closing of expansion opportunities within our existing customer base.
Your Typical Activities
* Consultative discovery conversations with SME decision‑makers (IT Managers, Finance Directors, MDs/CEOs)
* Leveraging the Cyber Security & Resilience Bill to open conversations about security gaps and compliance
* Conducting or supporting cyber risk assessments as an entry point to MSSP services
* Building and managing a healthy pipeline (3× quarterly target minimum)
* Collaborating with the technical team on proposals and scoping
* Identifying expansion opportunities in existing accounts during business reviews
* Representing the business at local business events and networking opportunities
Deal Profile
* Target ACV: £30K+ (some smaller deals £3‑10K are part of the mix)
* Sales cycle: Typically 60‑90 days
* Services sold: Managed IT services, cybersecurity (MDR, ITDR, risk assessments), cloud services, infrastructure projects.
What We’re Looking For
Must Have
* 3‑5+ years selling managed IT services
* Consultative sales approach: build trust and solve problems, not just push product
* Technical credibility: hold meaningful conversations with IT managers and understand technical services
* Self‑starter mentality: build and work your own pipeline, manage your own time, and hold yourself accountable
* Full clean UK driving licence (field sales role)
* Right to work in the UK
Highly Desirable but not Essential
* Experience selling cybersecurity/MSSP services (MDR, ITDR, security assessments)
* Existing relationships/network in Chester, North West, North Wales business community
* Microsoft, security, or vendor certifications
* Track record selling into professional services, healthcare, logistics, or regulated sectors
* Understanding of B2B SME buying cycles (30‑100 employees typical)
Cultural Fit (This Matters)
* Collaborative: technical team will support you
* Honest and consultative: we don’t oversell – we solve real problems
* Comfortable in a family business culture: relationships matter here
* Self‑aware: you know what you’re good at, where you need support, and you’re not afraid to ask
Compensation & Benefits
Base Salary: £35,000‑£45,000 (depending on experience)
Uncapped commission: No commission ceiling – exceptional performance yields exceptional reward
On‑Target Earnings (OTE): Year 1 (with ramp): £60‑70K
Year 2+ (fully ramped): £75‑90K+
Top performers earning significantly more (structure is uncapped)
* 45p/mile mileage reimbursement
* Private cashback healthcare plan
* 5% employer pension contribution (via salary sacrifice scheme)
* Flexible working (office‑based when not with customers, but we support hybrid)
* Supportive culture
What Makes Us Different
20+ years of reputation. You’re not selling a startup’s promises – you’re selling proven delivery. Our customers stay with us because we’re genuinely good at what we do.
Strategic growth phase: we’re actively transitioning to MSSP, launching AI services, and investing in growth. There’s genuine opportunity for someone who executes.
Family culture, not corporate politics. Our CEO is accessible. Our technical team is supportive. Decisions get made quickly because we’re not a bureaucracy.
Strong existing customer satisfaction. When you do win new business you’re not firefighting poor delivery or defending bad service. Our customers expand with us consistently – proof our service quality is strong.
You’ll actually be supported. Marketing collateral, technical pre‑sales, CRM and tools, lead generation campaigns – you’re not doing this alone.
You’re not just ‘another salesperson’ here – you’re a core part of a strategic growth phase with genuine upside.
Interested to hear more? Please apply, and someone will be in contact to answer all your questions.
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