You’re an exceptionally organized, detail-oriented assistant who thrives on keeping things in order—both at work and at home. You’ll help our CEO stay on top of their calendar, inbox, and day-to-day business tasks while also stepping in on personal errands and household to-do’s. You’re here to bring structure, clarity, and consistency so nothing slips through the cracks. If the CEO is feeling more organized, less overwhelmed, and better able to focus on their priorities—you’re doing your job.

We’re looking for a dependable, highly organized Executive / Personal Assistant to support our CEO in both their professional and personal life (roughly 50/50 split) .

On the business side, you’ll keep the CEO organized—managing their calendar, inbox, scheduling, and administrative tasks—so they can stay focused on what matters most.

On the personal side, you’ll help with everyday tasks like grocery shopping, laundry, and running errands. The right person thrives on creating order out of chaos, has strong follow-through, and takes pride in making someone else’s life run smoothly.

Professional / Administrative (50%)

• Manage and organize the CEO’s calendar, appointments, and daily schedule
• Keep the CEO’s inbox under control—drafting, sorting, and following up on emails as needed
• Coordinate meetings, calls, and events, ensuring all details are handled in advance
• Support travel planning and logistics (flights, hotels, transportation, itineraries)
• Track to-do’s and reminders, making sure nothing falls through the cracks
• Maintain confidentiality and discretion at all times

Personal (50%)

• Grocery shopping and other household errands
• Laundry and dry cleaning drop-off/pick-up
• Shipping packages, picking up supplies, and gift shopping
• Keeping the car clean, filled with gas, and stocked as needed
• Miscellaneous errands that help keep life organized and stress-free

• You get genuine satisfaction from helping someone stay organized and on top of their priorities—in work and life
• You’re detail-obsessed and rarely let things slip through the cracks
• You’re comfortable juggling professional tasks with personal errands in the same day
• You thrive in a support role and take pride in making someone else’s life easier
• You’re proactive and like solving small problems before they become big ones

• You don’t enjoy administrative work or everyday errands
• You prefer big-picture strategy projects over detailed execution
• You get flustered when plans change last minute or new priorities pop up
• You’re uncomfortable supporting both professional and personal tasks
• You struggle with punctuality or following through on commitments

• Based in the Fox Valley area (easy commute to our Greenville office)
• Exceptionally organized with strong attention to detail
• Reliable, punctual, and consistent in follow-through
• Strong written and verbal communication skills
• Comfortable managing both professional and personal tasks for the CEO
• Discreet and trustworthy—able to handle confidential information with care
• Proactive and resourceful—able to anticipate needs and solve problems quickly
• Flexible and adaptable when priorities shift or last-minute needs arise

• Competitive Compensation – We offer a strong salary and benefits package, tailored to attract top talent
• Hybrid Work Environment – Our team is based near Greenville, WI, with flexibility to work from home and in-office
• Autonomy & Ownership – You’ll have the freedom to run your own systems and make real impact
• Time Off – 15 PTO days per year (prorated), 9 company holidays, plus your birthday off
• Parental Leave – Generous maternity and paternity leave policies for growing families
• Health Benefits – 100% premium coverage for health, dental, and vision plans, with 25% coverage for dependents
• 401(k) – Company-sponsored plan with a 2% match through Guideline (elective participation)
• Growth & Development – We invest in your professional development with ongoing learning opportunities

Easy Street Brands is a fast-growing DTC holding company with a small, nimble team and big goals. We’re building brands that customers genuinely love, and we move quickly to turn ideas into action. As part of our team, you’ll have direct impact on the growth and scale of the brands —working closely with cross-functional teams to help keep the business running smoothly. If you’re someone who enjoys problem-solving, learning new skills, and growing alongside a fast-paced business, you’ll thrive in this position.

To apply to this role, email hiring@easystreetbrands.com and describe why you’re the perfect fit + include a copy of your resume.