Business Development Representative, Pressable

• Customer Expansion & Retention: Engage with existing Pressable customers to identify expansion opportunities, support retention efforts, and assist with account-related sales activities, ensuring customers continue to receive sales support and value as their needs evolve.

• 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, ensuring high-quality and timely customer engagement.

• 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:

• 1-2 years of experience in a BDR/SDR, customer experience or support, or similar role.

• Familiarity with WordPress and managed hosting services.

• Proven track record of generating leads and setting up successful sales conversations.

As a part of our fully distributed team, you can live anywhere in the world. Effectiveness in this role will mean occasionally shifting hours across weekends and odd hours to best coordinate with our global team.

Perks & Benefits of Joining Pressable!

• 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

Salary range: $50,000 - $65,000 USD, plus 25% variable compensation. Please note that whilst salary ranges are presented here in USD, we will pay in local currency.

We are currently looking for candidates in North American timezones.

So, are you ready to embark on this thrilling WordPress adventure? We can’t wait to welcome you to the Pressable team and empower you to help make the web a better place. Come join us in crafting an exceptional customer experience and revolutionizing the world of WordPress hosting. Apply now and let’s build something amazing together! #LI-Remote

About Automattic

Now in our 20th year , we’re the people behind WordPress.com , WooCommerce , Beeper , Tumblr , Simplenote , Jetpack , Longreads , Day One , PocketCasts , and more. We believe in making the web a better place.

We’re a distributed company with more than 1500 Automatticians in nearly every corner of the globe, speaking over a hundred different languages. Enriched by this diversity, we’re united by a singular mission: to democratize publishing, commerce, and messaging so anyone with a story can tell it, anyone with a product can sell it, and everyone can manage their communications from a single source. In short, we help maintain a balance in society, creating and continually refining powerful tools people can use to compete fairly—regardless of income, gender, politics, language, or where they live in the world.

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• Sales

Source: Automattic careers page