Executive Assistant

This isn’t a short-term stop. It’s a long-term opportunity to help shape the future of a company (and a leader) that’s going places.

Please do not apply unless you meet the qualifications and expectations clearly outlined below.

ABOUT THE ROLE
This is a role for an experienced EA ready to step into something bigger. You’ll be the right hand to a driven, values-led agency owner, Trish Geyer, overseeing a rapidly scaling Allstate Insurance business with multiple office locations and a bold vision for growth. Your responsibilities will stretch across day-to-day execution and strategic support—shaping the structure behind the scenes while empowering her to stay focused on the big picture.

This is not a reactive, wait-for-instructions position. It’s a proactive, forward-leaning partnership. You’ll be expected to identify what’s missing, make recommendations, and move processes and initiatives forward in an environment that is still building its internal systems.

And while Trish has built a thriving agency, this will be her first time working with an Executive Assistant. That’s an opportunity—and a responsibility. You’ll need to guide the relationship from day one: demonstrating what great support looks like, coaching her on what to hand off (and how), and helping her unlock new levels of focus, follow-through, and leadership capacity.

ABOUT THE CEO
Trish is a high-integrity, community-minded agency owner leading three Allstate offices in Northwest Indiana (Crown Point, Valparaiso, and Munster). She’s passionate about building a strong, service-driven team and deeply committed to both growth and culture.

She values honesty, authenticity, and positivity—and she thrives when surrounded by people who bring calm to chaos, bring ideas to the table, and help her take meaningful action. She’s building something bigger than insurance: a people-first agency rooted in excellence, reputation, and long-term impact.

WHO WILL SUCCEED IN THIS ROLE

• A seasoned C-Suite EA who thrives in entrepreneurial environments and can confidently support a fast-moving leader without needing a roadmap.
• Equal parts strategic and tactical—able to brainstorm process improvements one hour and triage a chaotic inbox the next without breaking a sweat.
• A calm, grounded presence who can manage up with professionalism, offering suggestions, feedback, and ideas without tiptoeing or overpowering.
• Organized to the core: grammar matters, formatting matters, visual continuity matters, and details never slip through the cracks on your watch.
• You’re an executor; action-oriented and solution-focused; able to anticipate problems, propose practical fixes, and communicate clearly, concisely, and directly to keep things moving forward.
• Those who value long-term partnership, crave meaningful work, and get energized by helping someone else succeed—especially when your impact is visible and appreciated.
• Part teacher, part coach—able to guide a first-time executive through how to work with an EA, offer gentle course correction, and model what great support looks like.

WHO WILL NOT SUCCEED IN THIS ROLE

• Someone who needs constant direction or struggles with ambiguity and shifting priorities.
• Those who avoid difficult conversations or speaking up, even when something isn’t working.
• Those who have only worked in rigid, corporate environments and may feel overwhelmed or unmoored in a fast-paced, less structured small business setting.
• Primarily motivated by titles or task checklists—not by influence, ownership, or helping a business grow from the inside out.

• Must have working knowledge of AI tools and how to apply them to streamline workflows or improve efficiency; familiarity with EOS (Entrepreneurial Operating System) is a strong bonus.

• EXECUTIVE SUPPORT
• Manage professional and personal calendars, ensuring friction is minimized and time is well spent
• Manage the inbox: resolving what you can, surfacing what matters, and guiding her attention
• Draft and/or respond to emails with a warm, thoughtful, customer-focused mindset
• Prepare agendas, meeting briefs, and post-meeting recaps to drive decisions forward
• Occasional personal tasks (travel bookings, returns, gift ordering) to reduce administrative burden
• HIRING AND ONBOARDING SUPPORT
• Assist with posting open roles, reviewing applicants, and coordinating hiring logistics
• Manage onboarding tasks: systems access, computer setup, day-one readiness
• Help improve and maintain new hire documentation and internal training processes
• PROJECT & OPERATIONAL MANAGEMENT
• Lead priority initiatives—hiring campaigns, new system rollouts, incentive programs, website build —from idea to execution
• Build and maintain standard operating procedures (SOPs), internal workflows, and checklists
• Support the cleanup and streamlining of digital platforms. Current tech stack includes Outlook (web + desktop), Google Workspace, Slack, Trello, QuickBooks, OneNote, Dropbox, and industry-specific platforms like Ricochet and Lead Manager; comfort navigating across multiple systems is essential
• CULTURE & COMMUNICATION
• Help maintain a positive, accountable culture by supporting recognition programs, team updates, and company-wide communications
• Plan internal celebrations and small events: gifts, anniversaries, team meals, quarterly awards
• Prepare communications and talking points for Trish when needed—helping her message land clearly and with impact