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Executive Assistant
Executive AssistantDrake & Associates • Waukesha, WI, US
Executive Assistant

Executive Assistant

Drake & Associates • Waukesha, WI, US
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Job Description

Job Description

Salary : $60,000 - $80,000

Position Title : Executive Assistant to the CEO

Location : Waukesha, WI

Reports To : Chief Executive Officer (CEO)

Position Type : Full-time

Were searching for anexperienced Executive Assistantwho thrives in a fast-paced environment, takes complete ownership of their role, and finds satisfaction in keeping complex operations running flawlessly. This is not an order-taking position its astrategic partnershipwith our CEO where youll be expected to stay ahead, make confident decisions, and ensure everything flows with precision.

If youre someone who valuesimpact, structure, and partnership, this role was designed for you.

What Youll Own

  • Strategic Calendar Management anticipate priorities, manage shifting demands, and ensure the CEOs time is always aligned with the most important work.
  • Communication Management confidently triage hundreds of daily emails, prioritize what matters, and communicate with accuracy and clarity.
  • Meeting & Project Support lead preparation for leadership meetings, support speaking engagements (including PowerPoints and content), and track projects with accountability.
  • Travel Coordination oversee complex travel plans with 100% accuracy and deliver clear itineraries in advance.
  • Information & Document Management create polished reports, presentations, and research that support confident decision-making.
  • Ownership Mentality bring backbone and confidence to the role. You wont wait for instructions youll act, anticipate, and stand strong in your space.

Success Looks Like (KPI Benchmarks)

  • Calendar : 98% accuracy, 95% briefs delivered 24 hours in advance.
  • Communication : 100% emails acknowledged within 2 hours, 99% accuracy relaying messages.
  • Projects & Tasks : 95% on-time completion, weekly updates without misses.
  • Meetings & Events : 100% logistics success, 90%+ satisfaction rating.
  • Travel : 100% accurate itineraries, delivered 48+ hours before departure.
  • Process Improvement : 12 workflow enhancements per quarter.
  • Confidentiality : 0 breaches per year.
  • Team / Client Coordination : 90%+ satisfaction, 100% flawless VIP handling.
  • What Were Looking For

  • Confidence & Presence you take pride in your role and operate with excellence.
  • Experience 5+ years as an Executive Assistant supporting a CEO / Founder (entrepreneurial environment preferred).
  • Emotional Intelligence youre self-aware, empathetic, and communicate with clarity.
  • Attention to Detail you dont miss the small things, and you thrive on accuracy.
  • Values Alignment you live and work by the values of Drake & Associates.
  • Why Join Us

    This isnt just another EA position. Youll be akey strategic partnerwith direct impact on the CEOs ability to perform at the highest level. Youll bring order to complexity, stability to fast-moving priorities, and confidence to every decision.

    If youre ready toown the role, move fast, and make a measurable impact, we want to meet you.

    Money for Nothing

    Start with three weeks off each year and earn more.

    Additional Days Off

    When we meet our goals, we prefer to give employees extra days off. Flexibility and in a non-client-facing role, kids sick, work from home.We aim to embrace flexibility in the crazy times we live in!

    Retirement

    We offer Traditional and Roth 401(k)s with a 3% company match, regardless of your contributions. Employees under 50 years of age can contribute $23,000 per year and get a 3% match on top of that. Are you 50+? You can contribute an additional $7,500 each year in addition to the 3% company match. We can also show you how to fund a Traditional IRA or Roth IRA. We know a lot about money, its what we do!

    Lets Stay Healthy

    Group health insurance plan with a great provider network, it is the same health insurance that Tony has for himself! We offer health, dental, vision and life insurance.

    Hungry?

    Free Lunches provided for weekly team building

    Free snacks, coffee, tea, sodas, water and hot cocoa all on-site

    Want To Lend a Hand?

    We support local charities financially and with paid time-off to volunteer! Use The Force, Luke! Mentorship is part of the deal, we want to help you as a person, not just as an employee.

    How Do I Get There?

    Waukesha location is just off the Guerkes corner exit on I-94

    Wow, Youre Smart!

    Well pay for you to obtain your life insurance license; health insurance license and Series 65 securities registration and we will even pay for your Certified Financial Planner designation! Want to get your CPA license? Lets do it!

    Lets have fun!

    Quarterly team lunches and team building events off site as well as our Annual Team Holiday Party!

    Paid-for Annual Trips

    Company hits our goals, lets all travel together!

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    Executive Assistant • Waukesha, WI, US

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