[Hiring] Executive Sales Assistant @WeAssist.io

Role Description

Our client is hiring an Executive Sales Assistant because WorkStackOS is growing, and the team needs someone dedicated to this role to keep up with it. As more client conversations, scheduling, and follow-ups come in, this role is about being the connector behind the scenes—managing client relationships, staying ahead of follow-ups, coordinating the team, and keeping the back office running smoothly so nothing falls through the cracks.

Key Responsibilities of the Executive Sales Assistant

• Client Communication & Outreach
• Calendar & Scheduling
• Email & Inbox Management
• Pipeline & Reporting
• Client Onboarding & Task Follow-Through
• Team Communication & Back-Office Support
• Executive & Personal Assistance

Responsibilities of the Executive Sales Assistant:

• Client Communication & Outreach:
  • Manage follow-up communications with clients and leads across email, messaging apps, and CRM.
  • Proactively respond to inquiries and maintain timely communication loops.
  • Create and manage group chats/channels for streamlined communication.
  • Send warm introductions, nurture cold or inactive leads, and follow up on inbound messages across channels.
• Calendar & Scheduling:
  • Own leadership's full calendar, coordinating with clients, internal team members, and partners.
  • Schedule all external and internal meetings, ensuring clarity around time zones and objectives.
  • Book appointments, demos, and calls on behalf of the team, confirming details in advance.
  • Proactively identify potential scheduling conflicts and offer solutions.
• Email & Inbox Management:
  • Triage leadership's and WorkStackOS's inboxes for urgency and priority.
  • Draft, send, and follow up on important emails to clients, prospects, and partners.
  • Organize and flag items that need leadership's attention.
• Pipeline & Reporting:
  • Enter and maintain contact records, deals, and lead source details.
  • Update lead and deal stages in real time and log meeting notes consistently.
  • Maintain key sales and operations trackers, and prepare performance recaps.
  • Attend team meetings and provide status updates and follow-ups.
• Client Onboarding & Task Follow-Through:
  • After deal closure, send thank-you messages, draft client contracts, and set up shared channels.
  • Schedule kickoff calls and prepare internal kickoff documentation.
  • Extract and organize action items from calls and meetings, tracking them on a shared task board.
  • Follow up on incomplete tasks and hold the team accountable to commitments.
• Team Communication & Back-Office Support:
  • Serve as the communication hub between leadership, the team, and outside partners.
  • Keep everyone aligned by relaying updates, decisions, and next steps promptly.
  • Handle recurring back-office tasks like document organization, filing, and record-keeping.
  • Assist with process documentation, keep SOPs current, and support vendor/service coordination.
• Executive & Personal Assistance:
  • Book travel arrangements including flights, accommodations, and logistics.
  • Manage personal admin tasks to support leadership's productivity and focus.
  • Assist with document retrieval, organization, and submission.
  • Ensure seamless support across business and personal needs, handling ad-hoc requests as they come up.

Qualifications

• Excellent Communicator – Clear, proactive, and confident communicating with clients, leadership, and teammates across channels.
• Top-Tier, Strong Player – You operate at a high level and hold yourself to a high standard—not just someone who gets by.
• Force Multiplier – You make the people and systems around you better just by being on the team.
• Highly Capable & Self-Sufficient – You figure things out, ask smart questions, and don't need to be managed closely. No babysitting required.
• AI-Savvy (Level 2+) – You know how to create and manage AI Agents, Skills, and automations using tools like Claude and ChatGPT—not just prompt them.
• Core Values Alignment – Strong personal integrity and genuine alignment with WorkStackOS's core values around ownership, speed, clarity, and candor.

Requirements

• Full Time, 10am-6pm PST
• Be available during business hours to communicate responsively with your direct supervisor and teammates.
• This is a remote position so you can have the freedom to work from anywhere.

Benefits

• Great Starting Salary – Competitive compensation that rewards your contributions.
• Real Growth Path – Take on more responsibility and ownership as WorkStackOS grows.
• Permanent Remote Set-Up – Your office is wherever you want it.
• 13th Month Bonus – Because hard work deserves more than a “thanks.”
• Health, Dental & Mental Health Coverage – We've got you covered.
• Performance-Based Raises & Bonuses – Do great work, get rewarded for it.
• Ground-Floor Impact – Join early enough that your systems and decisions actually shape how the company runs.