CLOSED | Executive Assistant to Insurance Agent | Crown Point, IN
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QUICK FACTS:
Company: Allstate Franchise
Location: Crown Point, IN
Employment Type: Full-time, hybrid, 3-4 days onsite per week
Salary: $70,000-$75,000 with benefits and bonus potential
Travel: None
Reports to: Agency Owner
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.
WHAT YOU’LL DO:
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
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.
COMPENSATION, REQUIREMENTS & LOGISTICS
$70,000–$75,000 with additional bonus potential tied to individual and agency performance.
Standard office hours are 8:30 AM – 5:30 PM (Mon–Thurs) and 9:00 AM – 5:00 PM (Fri); occasional evening or weekend availability for events or projects may be required.
Medical, dental, and vision (50% employer-paid), plus Simple IRA with 3% match eligible after one year.
One week of paid vacation, 62 hours of sick time, two floating holidays, and all major holidays.
Company-issued Dell PC and possibly a mobile phone or stipend depending on Allstate security protocols.
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.
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.
Do not apply unless you meet the qualifications and expectations clearly outlined above.
Looking for other executive assistant opportunities?
FREQUENTLY ASKED QUESTIONS ABOUT THE ROLE
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No — this role is onsite in Crown Point, IN.
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3+ years of high-level Executive Assistant experience is required for this role. You will be assisting and guiding an executive who has no experience utilizing an assistant.
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Relocation expenses are not being considered at this time.
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Though this role involves helping to coordinate travel for the CEO, the Executive Assistant is not expected to travel for work.
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Once you’ve applied, you can expect a confirmation email that your application has been received. If your application is selected, you will receive an email from Monique Helstrom to schedule your first interview.
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Every candidate is personally reviewed by Monique Helstrom, former Executive Assistant to Simon Sinek and an executive recruiter specializing in high-trust executive partnerships.
My goal isn’t simply to place candidates. It’s to create partnerships that thrive.
If your application isn’t accepted for this role, don’t take it personally! This role may just not have been the one for you. Feel free to browse other open roles or schedule a resume review with me.
APPLICATION TIP FROM MONIQUE
If I were coaching someone for this interview, I’d tell them…
Don’t try to prove you’re a great Executive Assistant—demonstrate how you’re a great partner, builder, teacher, and operator (and can teach the CEO how to be, too).
Everything in the interview should reinforce that you can create structure where there isn’t any, coach an executive through delegation, establish scalable systems, and gradually transform a founder-led business into one that operates with greater leverage, consistency, and focus.
P.S. Want more interview tips? Schedule a resume and interview coaching session with me. Or click here to learn more about what I do.