Executive Assistant to CEO

Spyglass Ops • Full-time • $1.50k - $3k / month • 3w ago

Link to apply listed at the bottom of this Job Description. Only applications submitted through this link will be considered.

WHO WE ARE

Spyglass Ops helps founders scale themselves and their visions through operations. We partner with 7-8 figure digital entrepreneurs who are scaling with purpose: leaders who value impact, and a people-first approach to growth.

Our mission is to transform operations from a bottleneck into the highest leverage point for business impact, growth, profit & freedom. We don't do cookie-cutter solutions. We dive deep to understand our client’s businesses, goals, and them as a person, then we level up their team & Ops foundation so they can scale toward their version of business and life that matters most.

Founded by Jhana Li almost 5 years ago, after serving as COO at two successful startups, Spyglass has evolved from operator coaching to full-service, high-ticket operations transformation, including Fractional COO consulting, "done for you" operations recruitment, and Operations + leadership coaching.

Our Core Values are:

Play Like A Nerd: We are a team of nerds, each hopelessly passionate and excited about our area of expertise. We believe that if you are an absolute nerd for what you do, then work is play. And we play hard.
Own Your Opportunities: Every mistake and failure is an opportunity. See it and use it as such. Take as much ownership as you possibly can, and use it as feedback to improve. The only two words you'll never hear at this company: fault and blame.
Commit to Your Own Potential: We expect this of ourselves, each other, and our clients: to relentlessly, critically be redefining and growing into the most potent version of ourselves and the impact we can have.
Van Talk: Discovered while Jhana was traveling full-time in a van through South America, Van Talk is not just a willingness and ability to speak honestly. It is a way of receiving crucial communication, not as a personal affront, but as a genuine and necessary act of service to accomplish our shared goals and highest potential.

If our culture and mission does not resonate with you, please do not bother applying.

JOB DESCRIPTION

The Spyglass Ops team is seeking a highly strategic, business-focused Executive Assistant who will serve as the right-hand partner to our founder and CEO, Jhana Li. This is not a traditional EA role checking boxes on administrative tasks. This is a high-impact, revenue-enabling position where you'll maximize the founder's leverage, protect her focus, and—critically—help manage and grow a powerful referral and lead relationship ecosystem that directly drives company growth.

You'll be stepping into a role with solid foundational systems already in place (thanks to our outgoing part-time EA who's moving into another role internally). Your mission is to take what's working and elevate it to world-class. The application code word is LEVERAGE. You'll bring the proactive thinking, creative relationship management, and strategic execution that transforms a functional EA setup into a game-changing operational advantage.

This role exists because we're sitting on massive growth opportunity. Our referral pipeline and lead ecosystem are gold mines that need someone dedicated to mining them. You'll design and execute creative, brand-aligned systems to ensure every partner and lead feels seen, valued, and connected with, to create authentic vs. transactional relationships.

Jhana is currently managing 80% of her own email, calendar, social media, and text communications—and that needs to change yesterday. She needs to focus on highest-leverage growth and innovation priorities while you own the operational workflows and relationship nurturing that keep the business humming and growing.

This is a remote, full-time 1099 contractor position. We're looking for someone who thrives in autonomous, asynchronous environments and sees this as a 2-3 year strategic partnership with significant growth potential as you take on more advanced responsibilities and special projects.

RESPONSIBILITIES (TASKS ASSOCIATED WITH THE ROLE)

Founder Leverage & Operational Support

Proactively manage Jhana's calendar to optimize for flow, focus, and energy—not just availability
Own email, text, and social media inbox management: filter, organize, draft responses, flag priorities
Reduce cognitive load and distractions so Jhana operates in her zone of genius
Set meeting agendas and manage all pre/post-meeting communications

Referral Ecosystem & Lead Pipeline Execution (Revenue-Driving Work)

Design and own the "Referral Partner Happiness Journey"—creative outreach, follow-ups, touchpoints that build authentic relationships & make Spyglass unforgettable
Execute systematic lead nurture and follow-up processes that convert prospects to calls
Maintain tight, proactive relationship tracking using GoHighLevel CRM
Ensure every active lead and referral partner is touched regularly, systematically and at scale
Use AI tools and creative automation to scale Jhana's personal presence across the ecosystem
Send thoughtful gifts, messages, and relationship touches that cut through the noise

Project Coordination & Task Management

Track and ensure follow-through on CEO commitments using ClickUp and Slack
Coordinate delegated projects with team members and contractors
Proactively identify dropped balls or overdue tasks and flag for follow-up
Represent Jhana in communications when appropriate, speaking on her behalf with confidence

Research & Special Projects

Conduct lightweight research (partner backgrounds, gift ideas, event logistics)
Handle logistical prep for events, partner meetings, and strategic initiatives
Take on special projects as the role evolves and your capabilities expand

REQUIREMENTS (EXPECTED PROFICIENCIES)

2+ years as a high-level Executive Assistant to a founder or C-suite leader in a fast-paced, remote startup environment
Proven track record performing at an elite level without guidance or constant management—you know what great EA work looks like and you deliver it autonomously
Direct experience with relationship management, client services, or referral ecosystem management is a major plus and differentiator
Based in or able to overlap with U.S. Mountain Time zone (9am-5pm MT) for real-time availability when needed
Preferred: Fluency with ClickUp (project/task management), Slack (internal communication), GoHighLevel (CRM/automation), Google Workspace (Docs, Sheets, Calendar, Gmail)

Core Competencies

Perfect English & Professional Communication: Speaks and writes clearly, confidently, and in brand-aligned tone. You can draft emails that sound like Jhana.
Highly Detailed & Organized: Thrives maintaining order in dynamic environments. Handles high variety and volume of tasks and relationships concurrently without dropping balls.
Proactive & Resourceful: Doesn't wait to be told. Sees the problem and solves it. Anticipates needs before they become urgent.
Self-Managing: Comfortable in remote, asynchronous environments. Superb time management. Doesn't need hand-holding or micromanagement.
Manages Up: This is critical. You must be confident enough to keep Jhana accountable, push back when she's getting in her own way, and help her course-correct. You're a partner, not just an assistant.
Highly Relationship-Oriented: Genuinely loves the process of building and nurturing professional relationships. Finds joy in making people feel valued.
Creative Relational Outreach: Thrives on designing thoughtful, impactful touches (gifts, messages, follow-ups) that are memorable and cut through noise.
Tech-Savvy & AI-Curious: Excited to experiment with AI and modern tools to scale founder presence, automate repetitive work, and streamline relationship management. Not intimidated by new technology.
High Professionalism & Discretion: Represents the CEO in high-stakes, high-trust environments with grace and gravitas. Handles confidential information with absolute discretion.
Adaptable & Excited by Variety: Comfortable taking on new projects and tasks. Thrives in a role and company that offers change and growth opportunities.

BENEFITS

Compensation: $1,500-3,000 USD/month (commensurate with experience, with opportunity for increases as you grow in responsibility and value-add to the organization)
1099 Contractor relationship providing maximum flexibility in how you structure your work
100% Remote & Asynchronous-First: Work from anywhere with reliable internet. Must overlap with Mountain Time for real-time availability when needed, but otherwise full schedule autonomy.
Unlimited Time Off Policy: As a contractor managing outcomes rather than inputs, you have complete autonomy over your schedule. Your responsibility is ensuring deliverables are met and the business runs smoothly.
Professional Development Budget: Investment in your growth through courses and learning opportunities
Network Access: Direct connection with top digital entrepreneurs, operators, and consultants in our ecosystem—invaluable for your own growth and opportunities
Growth Trajectory: This role has clear evolutionary potential. As you prove impact and capability, you'll take on more strategic projects and expanded responsibilities aligned with your strengths.