About The Role

Hiring: Full-Time Executive Sales Assistant - Remote - $10,800 - $14,400/yr
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About us, WorkStackOS, the hiring team
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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.
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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.

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Built for Companies Managing Distributed Teams

– We help businesses centralize the operations side of running an international workforce, so nothing falls through the cracks.
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A Fast-Moving Product Team

– We're building something new, which means real problems to solve and real ownership over how we solve them.
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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.
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Key Responsibilities of the Executive Sales Assistant

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📞 Client Communication & Outreach
📅 Calendar & Scheduling
📬 Email & Inbox Management
📈 Pipeline & Reporting
🧩 Client Onboarding & Task Follow-Through
💬 Team Communication & Back-Office Support
🌍 Executive & Personal Assistance
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Key Qualifications of the Executive Sales Assistant

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🗣️

Excellent Communicator

– Clear, proactive, and confident communicating with clients, leadership, and teammates across channels.
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Top-Tier, Strong Player

– You operate at a high level and hold yourself to a high standard—not just someone who gets by.
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Force Multiplier

– You make the people and systems around you better just by being on the team.
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Highly Capable & Self-Sufficient

– You figure things out, ask smart questions, and don't need to be managed closely. No babysitting required.
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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.
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Core Values Alignment

– Strong personal integrity and genuine alignment with WorkStackOS's core values around ownership, speed, clarity, and candor.

Additional Information

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How to Prepare for the Recruiting Process -

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Why Are They Hiring an Executive Sales Assistant?

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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.

If you're a sharp, self-sufficient operator who thrives on structure, communicates clearly, and knows how to put AI tools to work instead of just using them—this role could be a great fit for you. ✨

Responsibilities of the Executive Sales Assistant

Your responsibilities include

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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
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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
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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
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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
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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
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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
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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

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Get To Know WorkStackOS!

(Not Your Average Ops Tool…)

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. 🌟

Company Culture and Core Values

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.

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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.

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Customer First – The Only Scoreboard

– Every proposal starts with the customer's problem, not our solution.

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Simplify – If It's Complicated, We're Not Done

– Complicated is easy; simple takes real thinking. We cut before we add.

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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.

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Speed – Make the Reversible Decisions Fast

– Most decisions can be undone, so we make them quickly. Imperfect action beats perfect inaction.

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Hard Conversations – Say It to the Person

– If you have a problem with someone, you take it to them directly, and first.

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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.”

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Clarity – Ask First, Build Second

– Repeat back what you heard before you build. Three minutes of asking saves three months of wrong work.

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Radical Transparency – Honesty at the Highest Level

– We share the numbers, the decisions, and the mistakes—especially the mistakes.

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Composure – Take the Breath, Then the Meeting

– Stay calm under pressure. Calm isn't passive—it's what lets you think clearly.

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Stay Curious – Stay a Student

– The work changes, so we do too. Asking the “obvious” question is a good sign, not an embarrassing one.

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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.

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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. 🎉

What's in it for you?

😏

Joining WorkStackOS means more than filling a role—it's a chance to help build the operating layer for how offshore teams get run. The growth potential is real, with opportunities to:

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Great Starting Salary

– Competitive compensation that rewards your contributions.
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Real Growth Path

– Take on more responsibility and ownership as WorkStackOS grows.
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Permanent Remote Set-Up

– Your office is wherever you want it.
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13th Month Bonus

– Because hard work deserves more than a “thanks.”
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Health, Dental & Mental Health Coverage

– We've got you covered.
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Performance-Based Raises & Bonuses

– Do great work, get rewarded for it.
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Ground-Floor Impact

– Join early enough that your systems and decisions actually shape how the company runs.
This opportunity is ideal for someone ready to take real ownership, move fast, and help build something that actually matters. 🚀

Specifics

Time

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

Miscellaneous

Attire - business casual when in meetings
Professional setup
Clean background
Good camera
Good microphone
Strong wifi

Tech Stack

🔑 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