About Picklebet
Picklebet is a cutting-edge sports, racing, and esports betting platform redefining the wagering experience for a modern audience. Currently a top 10 operator in Australia, we are expanding offshore with the launch of our brand-new Online Casino vertical, built upon our proprietary technology platform. We are seeking a driven Executive Assistant to help support the CEO to lead and scale the next stage of our business.
About the Role
This is a rare opportunity to work at the heart of a dynamic, growth-minded organisation as the trusted right hand of the Chief Executive Officer. You will be far more than a scheduler - you will be a strategic partner, a discreet confidant, and an operational anchor who keeps the CEO focused on what matters most. In this role, you will anticipate needs before they arise, manage competing priorities with calm precision, and act as a seamless extension of the CEO across all internal and external interactions.
Key Responsibilities:
-
Serve as the primary gatekeeper for the CEO's inbox and fast-moving calendar, independently resolving conflicts to maximise strategic impact.
-
Structure and lead the weekly high-level executive meetings and quarterly SLT offsites.
-
Prepare high-quality board packs, investor updates, and executive correspondence.
-
Shape, build and drive the quarterly staff meetings, including slide deck creation, coordinating internal speakers, and showcasing project updates.
-
Own and track the business' quarterly deliverables end-to-end, while supporting the CEO directly on special initiatives and research.
-
Manage sensitive information with absolute discretion.
-
Coordinate detailed domestic and international travel itineraries for multiple stakeholders.
-
Act as the primary liaison for building management, oversee facility maintenance, and support general office needs.
But here’s what sets this role apart: the CEO’s deeply relational, people-first leadership style. To complement this, you will act as a trusted confidant and strategic gatekeeper - diplomatically but firmly protecting his time, holding the line with senior stakeholders, and serving as a candid sounding board to keep business priorities uncompromised. You know how to navigate organisational politics with grace, push back with professionalism, and earn respect across the leadership team.
About You
You bring poise, precision, and proactivity to everything you do. Thriving in chaos, loving owning your remit, and taking genuine pride in enabling others. Confident but not combative, assertive but not aggressive, you are always guided by what is best for the CEO and the business.
Ideally, you have:
-
Minimum 5+ years as an Executive Assistant, Chief of Staff, or Senior PA, ideally supporting C-suite executives in high-growth environments.
-
High emotional intelligence with the confidence to diplomatically safeguard the CEO’s time, push back professionally, and "manage up" effectively with senior stakeholders.
-
Proven track record of independently managing complex, fast-moving calendars, high-volume correspondence, and multi-stakeholder travel.
-
Exceptional written and verbal communication skills with a polished, measured delivery.
-
Advanced skills in Google Workspace (Docs, Sheets, Slides) and modern productivity/AI tools (e.g., Slack, Jira, Gemini/Claude).
-
Absolute integrity and laser-sharp attention to detail when managing highly sensitive legal, HR, and commercial information.
-
Experience working with boards, including preparing and coordinating board materials, and liaising professionally with board members.
What We Offer:
-
Be the driver of a proprietary technology product in a fast-scaling company that prioritises internal development, fast decision-making, and future-facing solutions.
-
Flexibility, with a combination of WFH and office arrangements to suit your lifestyle and productivity.
-
Join the team for regular off-site social events and team-building days to connect.
-
A competitive compensation package, based on experience.
Apply today to get a seat at the table of a growing company.
