£35,000-£45,000p/a Negotiable + Exceptional Uncapped OTE + Benefits
This is a great opportunity to join a growing firm where you will have the opportunity to develop a career, and uniquely have a say and share in the growth of the business.
This role will be working for 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, they’ve built their reputation on delivering exceptional technical service and genuine partnership to SME businesses. They are not a faceless corporate MSP - they're a close-knit team of around 35 people who genuinely care about customers and each other.
Right now, they're at an exciting inflection point. Transitioning from traditional MSP to a security-first MSSP (Managed Security Service Provider), and significantly scaling new customer acquisition. This isn't just business as usual - this is a strategic growth phase that creates genuine opportunity for the right salesperson.
Why This Role Matters
We've 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.
This isn't about cold-calling hundreds of prospects or hitting aggressive daily activity metrics. This is about consultative, relationship-based selling to SME decision-makers who are actively looking for a trustworthy IT and security partner.
You'll be joining at the perfect time:
* Legislative tailwind: The UK Cyber Security & Resilience Bill 2026 is creating unprecedented demand for security services
* Strategic positioning: Our MSSP transition and AI partnership give you compelling, differentiated value propositions to sell
* Proven product-market fit: Our existing customers expand with us consistently - proof that what we deliver works
* Supportive environment: You'll have technical pre-sales support, marketing collateral, and a CEO who's accessible
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 region
Reports to: Sales Manager
Primary Responsibility: Drive new customer acquisition and strategic account expansion
You'll 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 – with a balance of new business (hunting), and you will also be expected to identify and close 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 entry point to MSSP services
* Building and managing a healthy pipeline (3x quarterly target minimum)
* Collaborating with 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+ (though 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: You build trust and solve problems, don't just push product
* Technical credibility: You can hold meaningful conversations with IT managers and understand technical services (you don't need to be an engineer, but you need to "get it")
* Self-starter mentality: You can 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 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: Our technical team will support you
* Honest and consultative: Our customers stay with us because we don't oversell - we solve real problems
* Comfortable in a family business culture: We're not a corporate machine. Relationships matter here.
* Self-aware: You know what you're good at, you know where you need support, and you're not afraid to ask
Compensation & Benefits
Base Salary: £35,000 - £45,000 (depending on experience)
Uncapped: No commission ceiling - exceptional performance = 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)
Other Benefits:
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're very supportive of hybrid flexible working)
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. This isn't "business as usual" - we're actively transitioning to MSSP, launching AI services, and investing in growth. There's genuine opportunity here 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 going to be firefighting poor delivery or defending bad service. Our customers expand with us consistently - that's 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.
This is a great opportunity to join a growing firm where you will have the opportunity to develop a career, and uniquely have a say and share in the growth of the business
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