On-Site Executive Assistant to a Growth-Driven CEO

Monique Helstrom; Waukesha (WI); On-site; USD 90,000 - 100,000; Full time

Benefits offered by this job

Full health, vision, and dental

401(k) with employer match

Incentive programs

Professional development opportunities

Relocation assistance may be possible

Job summary

Drake & Associates in Waukesha, WI is seeking an executive assistant to be the force multiplier behind a values-driven CEO and entrepreneur across its retirement and wealth management ventures.

You will manage calendar and communications, triage emails, prepare polished presentations, and coordinate with the leadership team. Expect travel planning, private arrangements, and high-trust collaboration in a fast-moving, results-driven culture.

Qualifications

• 5+ years of experience supporting a C-level executive.
• Strong organizational and execution capabilities in fast-paced environments.
• Ability to move quickly while maintaining accuracy and follow-through.
• Comfort with AI and automation tools to streamline workflows.
• High-D DISC profile; values of honesty, ownership and coachability.

Responsibilities

• Own calendar management and prioritize shifting demands.
• Triage emails and manage full inbox ownership.
• Ensure meetings are purposeful and well-prepared.
• Draft polished presentations and reports for internal and external audiences.
• Identify roadblocks early and remove them quickly with bias for action.
• Leverage AI and automation to streamline workflows.
• Coordinate travel, events, and personal support tasks as needed.
• Coordinate with leadership team and prep meeting minutes; track projects.

Skills

Executive support

Calendar management

Email triage

Communication

Project coordination

Decision making

Discretion

Tools

Google Workspace

Basecamp

RingCentral

Salesforce

90.io

Apple/Mac systems

iPhone proficiency

Trainual

EOS/Traction

Job description

Drake & Associates in Waukesha, WI is seeking an executive assistant to be the force multiplier behind a values-driven CEO and entrepreneur across its retirement and wealth management ventures.

You will manage calendar and communications, triage emails, prepare polished presentations, and coordinate with the leadership team. Expect travel planning, private arrangements, and high-trust collaboration in a fast-moving, results-driven culture.