Executive Sales Assistant - WSOS

🌟 About us, WorkStackOS, the hiring team 💡

🌍 Led by a Founder Who Cares– Reef Colman built WorkStackOS to give companies a better way to run their offshore teams, without the chaos of spreadsheets and guesswork.

⚙️ The Operating System for Offshore Teams– WorkStackOS is a single platform for costs, disbursements, compliance tracking, and team coordination, replacing the spreadsheets and manual processes companies use to run offshore teams today.

🌎 Built for Companies Managing Distributed Teams– We help businesses centralize the operations side of running an international workforce, so nothing falls through the cracks.

🚀 A Fast-Moving Product Team– We're building something new, which means real problems to solve and real ownership over how we solve them.

🤝 A Culture That Backs Its People– Your skills and initiative matter here. We're building a team of self-sufficient, high-caliber people who don't need to be managed closely.

📞 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

• https://docs.google.com/document/d/1tCWNqlU4gNG4nQaEeo5iSKNB8A8X7xAlVCMDvZwkdDk/edit?tab=t.0#heading=h.gt6n5ybw2ujb

WorkStackOS is the operating system for offshore teams—a single platform for costs, disbursements, compliance tracking, and team coordination. It replaces the spreadsheets, shared docs, and manual processes that most companies still use to run their offshore teams today.

Led by founder Reef Colman, WorkStackOS is being built by people who've felt the pain of running distributed teams firsthand—which is why the product (and the team behind it) is obsessed with less chaos, more visibility, and systems that hold up as things scale. It's early, it's fast-moving, and it's a place where your work shapes how the product and the company actually run. 🌟

At WorkStackOS, values aren't a poster on the wall—they're standards the team gets held to on a normal Tuesday. Every value below exists because it settles a real disagreement, not because it sounds nice.

• 🧱 Major Ownership – The Outcome Is Yours– You take responsibility, not blame. If you saw it coming, you own it—you don't wait to be told.
• 🎯 Customer First – The Only Scoreboard– Every proposal starts with the customer's problem, not our solution.
• 🧩 Simplify – If It's Complicated, We're Not Done– Complicated is easy; simple takes real thinking. We cut before we add.
• 🏆 Results – Anything Else Is an Excuse– Effort gets you in the door, results are the job. We measure what got done, not how busy you were.
• ⚡ Speed – Make the Reversible Decisions Fast– Most decisions can be undone, so we make them quickly. Imperfect action beats perfect inaction.
• 🗣️ Hard Conversations – Say It to the Person– If you have a problem with someone, you take it to them directly, and first.
• 🎤 Candor – Disagree in the Room, Commit Outside It– Speak up before a decision is made. Once it's made, you commit fully—no saving up an “I told you so.”
• 🔍 Clarity – Ask First, Build Second– Repeat back what you heard before you build. Three minutes of asking saves three months of wrong work.
• 🔦 Radical Transparency – Honesty at the Highest Level– We share the numbers, the decisions, and the mistakes—especially the mistakes.
• 🧊 Composure – Take the Breath, Then the Meeting– Stay calm under pressure. Calm isn't passive—it's what lets you think clearly.
• 🧠 Stay Curious – Stay a Student– The work changes, so we do too. Asking the “obvious” question is a good sign, not an embarrassing one.
• 🔭 Think Ten Years Out – Build What Still Matters– We're not just solving today's problem—we build toward what still matters a decade from now.
• 🌱 Sustainable Impact – We Don't Win by Costing Someone Else– We build things that make life better for people, not more disposable.

Join a team that treats its values as tools, not decorations—where ownership, clarity, and follow-through are how work actually gets done. 🎉

• 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

• Attire - business casual when in meetings
• Professional setup

• Clean background
• Good camera
• Good microphone
• Strong wifi

🔑 Must-Have Skills (Baseline Requirement):

• ⚙️ AI Tools, Applied – comfortable creating and managing AI Agents, Skills, and automations (not just prompting) via ChatGPT, Claude, or similar
• 💬 ChatGPT – for comms, decision-trees, and creative problem solving
• 📊 Claude – for logic-heavy tasks, structured output, and building automations/skills
• 🎥 Gemini – for media and video content use-cases
• 🔎 Perplexity – for research and contextual understanding
• 🧠 Prompt Engineering – crafting prompts for efficiency and relevance
• 🔌 Platform Savvy – knowing when to use a CRM vs. an automation tool vs. a communication platform

✨ Highly Preferred (The Dream Candidate Has These!):

• 🤖 AI Engineering or experience building sales/ops workflows with AI
• 🔗 Experience with API or Webhook integrations
• 🧾 JSON coding experience or comfort with low-code/no-code platforms
• 🗂️ Project management and process-building know-how
• 🔁 CRM automations (especially GoHighLevel)

💻 Preferred Tools & Platforms:

• 📞 GoHighLevel (GHL) – huge plus if you're certified or trained
• ⚙️ N8N, Make.com, Zapier – for building workflows and automations
• 🌐 GitHub – for version control or team collaboration
• 📥 Slack – for internal comms
• ✅ ClickUp – for project/task management
• 📲 iPhone (for iMessage syncing) – highly preferred
• 📊 HubSpot – CRM experience a bonus