Sales Development Representative (UK B2B Outbound) - Remote

Position: Sales Development Representative

Salary: 25,000 ZAR to 30,000 ZAR

Working Hours: Aligned with UK Business Hours

Work Type: Independent Contractor

ABOUT THE COMPANY:

The company is redefining human risk and secure behaviour management in cybersecurity. Trusted by global enterprises and high-growth mid-market organisations-including Vodafone, Merck, Arriva, and Hershey-the company reduces human cyber risk through AI-driven automation and cutting-edge Agentic AI solutions. We are scaling rapidly year-on-year, bringing our UK outbound engine in-house, and investing heavily in a modern, data-backed sales development function built for high performance and high autonomy.

ROLE OVERVIEW:

As UK Outbound Sales Development Representative, you will sit at the very front of our growth engine. This is an autonomous, phone-first, results-driven seat responsible for establishing our in-house outbound presence in the UK market. You will target, engage, and qualify enterprise and mid-market security decision-makers-CISOs, Heads of Security, and IT Security Managers-booking high-value Qualified Held Meetings (QHMs) that directly build Keepnet’s sales pipeline.

Armed with an advanced outbound stack (including parallel diallers like Orum and Nooks, alongside HubSpot CRM), you will operate with freedom, high trust, and end-to-end account ownership.

RESPONSIBILITIES:

• Drive Phone-First Multichannel Prospecting: Execute outbound campaigns across phone, email, and LinkedIn into UK B2B organisations, maintaining high daily call volumes via parallel dialling tools (Orum, Nooks) to maximise live decision-maker conversations.
• Deliver Qualified Held Meetings (QHMs): Book meetings that actually take place with verified decision-makers (CISOs, IT Security Managers, and budget holders) in target accounts, operating against a target of your first QHM within 30 days and 10 QHMs per full production month post-ramp.
• Execute Deep Discovery & Qualification: Apply the company's SDR Playbook (lightweight BANT and MEDDPICC frameworks) to uncover tooling gaps across phishing, vishing, smishing, and quishing, while assessing security awareness maturity.
• Capitalise on Contract Renewal Windows: Identify current vendor relationships, contract lengths, and renewal dates, leveraging company's buy-back program to convert "in-contract" objections into active sales opportunities.
• Maintain Channel & Conflict Awareness: Pre-screen accounts for existing partner relationships (MSPs, MSSPs, brokers, and resellers) and existing clients, resolving routing questions collaboratively before initiating outreach.
• Ensure Seamless Handoffs: Document comprehensive, actionable discovery notes and transition booked meetings to Account Executives within 24 hours of scheduling.
• Uphold Strict CRM Hygiene: Maintain HubSpot as the single source of truth-logging all interactions, preventing duplicate entries, and populating all mandatory qualification fields.
• Operate with Built-In Compliance: Adhere strictly to UK GDPR, PECR, TPS/CTPS screening protocols, suppression list governance, opt-out handling, and approved messaging standards.
• Feed Frontline Intelligence: Share objection patterns, competitor movement, and market feedback with Sales and Marketing to continuously sharpen outreach messaging and value propositions.

Requirements

• 2 Years+ of B2B SaaS Outbound Experience: Proven track record in a dedicated SDR or BDR seat carrying quota, generating pipeline, and booking qualified discovery meetings.
• Phone-First Craftsmanship: Exceptional cold-calling confidence and conversational fluency; skilled at hooking senior prospects in the opening seconds, navigating initial brush-offs, and steering live phone discovery.
• Enterprise Prospecting Capability: Credibility and commercial acumen to hold substantive, peer-level conversations with senior IT, Security, and Compliance stakeholders in organisations with 1,000+ seats without needing to be an engineer.
• Parallel Dialler & Tooling Literacy: Practical experience using parallel diallers (such as Orum, Nooks, or equivalent high-velocity calling software) alongside modern sales engagement tools.
• CRM Discipline: Rigorous data and pipeline tracking habits, with willingness to complete HubSpot certifications if not already held.
• Flawless Communication: Outstanding verbal and written English skills, capable of composing compelling, error-free executive messaging without supervision.
• Self-Directed Remote Discipline: Strong operational independence to manage daily activity, pipeline numbers, and metrics aligned strictly with UK business hours from South Africa.
• Independent Contractor Readiness: Legally set up to operate as an independent contractor or registered entity in South Africa, maintaining a professional home office, high-spec workstation, noise-cancelling headset, and stable fibre internet.

PREFERRED:

• Direct experience prospecting into the UK B2B market from an offshore/remote setup.
• Prior background selling or setting appointments within Cybersecurity or related high-compliance technical SaaS sectors.
• Experience operating as an early or founding SDR, building outbound cadences, lists, and messaging frameworks from the ground up.
• Familiarity with indirect channel sales models, including MSPs, MSSPs, brokers, and value-added resellers.
• Active hands-on proficiency with LinkedIn Sales Navigator and HubSpot CRM.

What You’ll Bring:

• A Builder’s Mindset: You take full commercial ownership of your territory. If a workflow or list is suboptimal, you diagnose it, propose a solution, test it, and build a repeatable process.
• High Question-to-Talk Ratio: The discipline that defines elite SDRs: asking sharp, incisive questions, actively listening, and documenting what prospects say-including negative signals-rather than pitching over objections.
• Commercial Acumen over Rote Scripting: You do not rely on rigid scripts; you understand how enterprise businesses make procurement decisions, how risk is evaluated, and how to unearth real urgency.
• Responsible Innovation: Familiarity with leveraging modern AI tools (such as Claude) within approved security and compliance guardrails to accelerate prospect research, personalise outreach, and streamline account tiering.
• Resilience and Accountability: A relentless work ethic that thrives on pipeline creation, celebrates closed business, and takes pride in being the definitive first voice of the company in the UK market.