Business Development Representative (BDR) - WordPress Hosting Sales

Pressable, a WordPress hosting company part of the Automattic family, is seeking an experienced, motivated, and empathetic Business Development Representative (BDR) to drive early-stage sales and help meet aggressive growth goals.

The role focuses on leveraging AI tools to enhance prospect research, discovery preparation, follow-ups, and internal documentation while maintaining human judgment and relationship-building at the core of the sales process.

As a BDR, you will build relationships with potential customers by understanding their needs, introducing them to Pressable’s WordPress hosting solutions, and guiding them through the sales funnel. You’ll be the first point of contact for many prospects, ensuring a positive experience from the start.

You’ll report to the Head of Sales & Enablement and collaborate closely with the senior sales team to ensure seamless lead handoffs and smooth onboarding experiences.

Responsibilities

• Inbound Lead Qualification: Manage inbound leads by responding to inquiries, identifying potential opportunities, and qualifying prospects based on their needs.
• Prospect Engagement: Create interest and excitement around Pressable’s WordPress hosting solutions through initial discovery calls, emails, and chats.
• Meeting Scheduling: Set up and schedule meetings for senior sales team members to further engage qualified leads.
• Product Education: Educate prospects about Pressable’s features and benefits, ensuring they understand the value of our solutions.
• CRM Management: Track interactions with prospects, manage lead data, and update records in our CRM to ensure accurate information and follow-ups.
• Collaboration: Work closely with the senior sales team to ensure smooth handoffs for qualified leads and help drive deals forward.
• Customer Expansion & Retention: Engage with existing Pressable customers to identify expansion opportunities, support retention efforts, and assist with account-related sales activities.
• Continuous Learning: Stay up to date with Pressable’s product offerings, industry trends, and evolving best practices for AI-enabled sales execution and customer engagement.
• AI-Assisted Sales Execution: Use AI tools to support prospect research, call preparation, follow-up drafting, and deal summarization.
• Signal & Insight Capture: Leverage call transcripts, summaries, and AI-generated insights to identify customer needs, objections, and next steps, and reflect those clearly in the CRM.
• Feedback Loop Participation: Contribute structured feedback surfaced through AI tools (e.g., call analysis, objection trends) to improve sales playbooks, enablement, and product feedback loops.
• Own monthly qualified meeting and pipeline generation targets, consistently hitting or exceeding defined conversion and activity benchmarks.

Requirements

• Excellent Communication Skills: Strong verbal and written communication skills to effectively interact with prospects and qualify leads.
• Customer-Focused: A passion for understanding customer needs and offering solutions to help solve their challenges.
• Self-Motivated: Ability to work independently and manage multiple conversations and tasks at once, ensuring timely follow-ups and outreach.
• Curiosity & Learning Mindset: A desire to learn about Pressable’s product, the managed WordPress hosting industry, and sales techniques.
• CRM Experience: Familiarity with CRM tools (like Salesforce, HubSpot, etc.) and the ability to manage leads efficiently.
• Comfort Using AI Tools: Experience using AI tools to support research, writing, summarization, or workflow efficiency in a professional setting.
• Strong Judgment with Automation: Ability to use AI outputs critically, knowing when to rely on them and when human judgment is required.
• Adaptability: Flexibility to thrive in a fast-paced and evolving environment.
• Proactively identify and engage target accounts aligned with Pressable’s ICP through outbound email, LinkedIn, and phone outreach, leveraging AI for research and personalization at scale.

Preferred Qualifications:

• 2-5 years of experience in a BDR/JDR or similar role.
• Familiarity with WordPress and managed hosting services.
• Proven track record of generating leads and setting up successful sales conversations.

As part of our fully distributed team, you can live anywhere in the world. Effectiveness in this role may require occasional shifts across weekends and odd hours to coordinate with our global team.

Perks & Benefits

• Health Benefits for US-based staff (99% Paid Employee Medical, Dental, and Vision)
• Matching 401(k) for US-based staff
• Life and Disability Insurance for US-based staff (100% Paid Life, & LTD)
• Work from home with home office setup and coworking allowances
• Open vacation policy (no set number of days per year)
• Hardware and software, books or conferences that promote continued learning