Sales Development Representative - WFH | Midshift
The Opportunity
We're looking for ambitious, commercially minded Sales Development Representatives who enjoy building relationships and having meaningful business conversations.
This is not a high-volume cold calling role.
Our SDRs act as trusted advisors, identifying organisations that could benefit from improving their digital accessibility and helping prospects understand how the company can support their wider digital strategy.
Success in this role comes from curiosity, active listening and the ability to ask insightful questions. Rather than delivering scripted sales pitches, you'll uncover a prospect's digital landscape, accessibility maturity and organisational objectives through structured discovery conversations.You'll then qualify opportunities and work closely with our Account Executives to progress high-quality sales opportunities.
Key Responsibilities- Generate qualified sales opportunities through outbound prospecting, inbound enquiries and strategic account research.
- Conduct consultative discovery conversations with senior decision makers including:
- Digital Managers
- Marketing Directors
- IT Leaders
- Heads of Customer Experience
- Accessibility Leads
- Procurement teams
- Digital Transformation Leads
- Through structured discovery conversations, build an understanding of each prospect's:
- Website and digital ecosystem
- CMS and technology stack where relevant
- Digital ownership and governance
- Accessibility maturity and current approach to compliance
- Digital inclusion objectives and user demographics
- Customer and employee digital journeys
- Existing accessibility challenges and barriers
- Wider digital transformation initiatives and strategic priorities
- Identify accessibility risks, compliance challenges and opportunities where the company's solutions, consultancy or training can add value.
- Explain accessibility concepts confidently to both technical and non-technical stakeholders.
- Qualify opportunities using recognised sales methodologies such as MEDDICC, SPICED or BANT.
- Build relationships across multiple stakeholders within target accounts.
- Deliver engaging product introductions and articulate the value of the company's solutions.
- Maintain accurate CRM records, discovery notes and pipeline management.
- Collaborate closely with Marketing, Product, Customer Success and Account Executive teams.
- Achieve monthly and quarterly pipeline generation targets.
What You'll Need
Sales Experience- 2–5+ years' experience in B2B SaaS sales, Sales Development, Business Development or consultative technology sales.
- Proven experience generating qualified opportunities.
- Experience selling software, digital services or technology solutions.
- Experience engaging senior decision makers and building relationships across multiple stakeholders.
- A consistent track record of achieving or exceeding pipeline generation targets.
Discovery & Consultative Selling
Successful SDRs are naturally curious and skilled at leading meaningful discovery conversations.
Rather than delivering a scripted sales pitch, you'll use thoughtful questioning to build an understanding of a prospect's digital environment, accessibility priorities and organisational objectives before recommending the next steps.
You should be confident in your ability to:
- Lead structured discovery conversations with senior stakeholders.
- Build an understanding of an organisation's digital landscape through effective questioning.
- Identify website platforms, digital ecosystems and ownership of digital services.
- Explore existing accessibility approaches, challenges and compliance requirements.
- Understand user demographics and the accessibility needs of customers, employees or service users.
- Uncover business drivers such as digital transformation, customer experience, inclusion strategies and legislative obligations.
- Identify pain points, risks and opportunities where the company's solutions could deliver value.
- Tailor conversations to technical, commercial and non-technical stakeholders.
- Qualify opportunities using recognised sales methodologies such as MEDDICC, SPICED or BANT.
Digital Knowledge
We're looking for people who understand how organisations manage and evolve their digital services.
You should be comfortable discussing topics such as:
- Websites and digital ecosystems
- CMS platforms (WordPress, Drupal, Sitecore, Umbraco, Kentico and similar)
- Digital transformation
- User experience (UX)
- Customer journeys
- Digital accessibility
- SEO and digital marketing
- Website governance
- Technology procurement and digital roadmaps
You don't need to be a developer, but you should be confident having informed conversations with digital, marketing and IT professionals.
Accessibility Awareness
Ideal candidates will have knowledge of, or be willing to develop expertise in:
- WCAG guidelines
- Digital accessibility legislation
- Equality Act 2010
- European Accessibility Act (EAA)
- Americans with Disabilities Act (ADA)
- Inclusive design principles
- Assistive technologies
- Digital inclusion best practice
Full product and accessibility training will be provided.
Core Competencies
The successful candidate will demonstrate the ability to:
- Ask insightful, open-ended questions that uncover genuine business needs.
- Listen actively and adapt conversations based on customer responses.
- Build a clear picture of an organisation's digital landscape without making assumptions.
- Recognise accessibility risks and opportunities from information gathered during discovery.
- Translate customer challenges into commercially relevant conversations.
- Build credibility with stakeholders across marketing, digital, IT, customer experience and procurement teams.
- Balance curiosity with commercial focus, ensuring conversations remain consultative rather than transactional.
- Excellent questioning, listening and discovery skills.
- Strong commercial awareness.
- Confidence engaging senior stakeholders and decision makers.
- Exceptional written and verbal communication.
- Ability to simplify technical concepts for non-technical audiences.
- High emotional intelligence and relationship-building skills.
- Strong organisational and time management skills.
- Self-motivated with a proactive approach to prospecting.
- Resilient and target-driven.
- Coachable with a continuous learning mindset.
- Professional, confident and credible.
Technical Skills
Experience using:
- Salesforce, HubSpot or similar CRM platforms.
- LinkedIn Sales Navigator.
- Microsoft 365.
- Sales engagement platforms.
- Video conferencing tools.
- AI-assisted sales and productivity tools is advantageous.
Desirable Experience
Experience working within one or more of the following sectors:
- SaaS
- Digital agencies
- Website development
- Accessibility technology
- Public sector technology
- Education technology
- GovTech
- HealthTech
- Customer Experience software
Knowledge of accessibility legislation across the UK, Europe or North America would be advantageous.
Success in the Role
Within your first 12 months, you'll be expected to:
- Build a consistent pipeline of high-quality qualified opportunities.
- Develop expertise in digital accessibility and inclusive technology.
- Become a trusted first point of contact for prospective customers.
- Consistently uncover meaningful customer challenges through consultative discovery.
- Provide Account Executives with comprehensive discovery information, enabling effective solution design and sales progression.
- Consistently achieve or exceed pipeline generation targets.
- Contribute to regional growth across your assigned territory.
What We're Looking For
The ideal candidate is naturally curious and enjoys understanding how organisations operate.
You won't simply book meetings—you'll uncover business challenges, understand a prospect's digital landscape, identify accessibility risks and demonstrate how digital inclusion supports broader organisational goals.
You'll be equally comfortable speaking with a Marketing Director about customer engagement, an IT Manager about website infrastructure, a Digital Lead about transformation initiatives or a Procurement Manager about compliance obligations.
You'll combine commercial drive with genuine curiosity, enabling you to build trust quickly, ask intelligent questions and create well-qualified opportunities that position both the customer and our Account Executives for success.
If you're passionate about consultative selling, digital technology and helping organisations create more inclusive online experiences, we'd love to hear from you.