Junior Account Executive, Pressable at Automattic

This role is ideal for a tech-savvy sales professional early in their career—specifically those with 2–5 years of experience in lead generation or business deve

Work type: remote

Location: Remote

Salary: $50,000 – $65,000/yr

Type: Full-time

Summary

This role is ideal for a tech-savvy sales professional early in their career—specifically those with 2–5 years of experience in lead generation or business development (BDR/SDR). You should be comfortable in the WordPress ecosystem and excited about a "cyborg" sales approach that blends human relationship-building with heavy AI tool usage for research and automation. The position offers a salary of $50k–$65k plus a 10% bonus and the rare freedom of a truly global, "work from anywhere" remote culture. As part of the Automattic family, you’ll enjoy premium benefits like an open vacation policy, home office allowances, and institutional stability. It’s a high-growth environment where you are expected to hit pipeline targets while helping shape the team's AI-enabled sales playbooks. **You might be a good fit if you:** * Have a track record of qualifying inbound leads and setting meetings in a B2B SaaS environment. * Are comfortable using AI tools (ChatGPT, Claude, or sales-specific AI) to speed up your research and drafting. * Enjoy the "hunt" of outbound prospecting on LinkedIn and email alongside managing inbound inquiries. * Can navigate a high-volume CRM (Salesforce/HubSpot) with meticulous attention to detail.

Job Description

[Pressable](https://pressable.com/) (“WordPress hosting that means business”) seeks an experienced, motivated, and empathetic professional with the expertise to help us meet or exceed aggressive growth goals for our superb WordPress hosting company,part of the [Automattic family](https://automattic.com/about/).

We’re looking for a motivated and detail-oriented Junior Account Executive (JAE) to join our sales team. This role is essential in driving the early stages of the sales process by handling inbound leads, answering questions from prospects, creating interest in our product, and setting up meetings for senior members of the team.

The role is designed to leverage AI tools to improve speed, quality, and consistency across prospect research, discovery preparation, follow-ups, and internal documentation, while keeping human judgment and relationship-building at the center of the sales process.

As a JAE, you will play a crucial role in building relationships with potential customers by understanding their needs, introducing them to our WordPress hosting solutions, and moving them through the sales funnel. You’ll be the first point of contact for many prospects, ensuring they have a positive experience with Pressable from the start.

You’ll report to the Head of Sales & Enablement and work closely with our 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.

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:

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 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 20% variable compensation. Please note that whilst salary ranges are presented here in USD, we will pay in local currency.

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-DNI

About Automattic

Now in [our 20th year](https://timeline.automattic.com/), we’re the people behind [WordPress.com](http://wordpress.com/), [WooCommerce](https://href.li/?http://woocommerce.com/), [Beeper](https://www.beeper.com/), [Tumblr](https://href.li/?https://www.tumblr.com/), [Simplenote](https://href.li/?http://simplenote.com/), [Jetpack](https://href.li/?http://jetpack.com/), [Longreads](https://href.li/?http://longreads.com/), [Day One](https://href.li/?https://dayoneapp.com/), [PocketCasts](https://href.li/?https://www.pocketcasts.com/), 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.

[We believe in Open Source](https://github.com/Automattic), and the vast majority of our work is available under the [GPL](https://en.wikipedia.org/wiki/GNU_General_Public_License). Automattic is a [Most Loved Company](https://mostlovedworkplace.com/companies/automattic-inc/), an Equal Opportunity employer, and [Disability Confident Committed](https://disabilityconfident.campaign.gov.uk/). ([Here’s what that might mean for you](https://happinessengineer.blog/2022/09/08/happiness-for-everyone-working-with-a-disability-at-automattic/).) If you need disability-related accommodations during the application or interview process, please [fill out this form](https://automattic.com/disability-related-accommodation-request/). We are committed to ensuring an accessible hiring process for all candidates. Learn more about our [Employee Resource Groups](https://automattic.com/automattician-resource-groups/).

You can track your application status and more at [MyGreenhouse](https://my.greenhouse.io/users/sign_in).

To learn about how we handle your data, please review our [Privacy Policy](https://automattic.com/privacy/).

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