Job Description

Winmill PPM, a division of Winmill Software, is seeking a highly organized and detail-oriented Executive Assistant to serve as a strategic partner to the President of PPM. This role goes beyond traditional administrative support, you’ll play a critical part in maintaining operational excellence, ensuring sales pipeline hygiene in HubSpot, supporting Customer Success initiatives, and delivering accurate financial reporting. If you thrive in a fast-paced environment, excel at managing priorities, and have strong analytical and communication skills, this is the role for you.

You will be instrumental in driving efficiency across internal operations, supporting client-facing deliverables, and enabling the President to stay focused on strategic priorities. This is an opportunity to contribute meaningfully to a growing, high-impact business unit.

Tasks

Sales & Customer Success Support

• Maintain HubSpot Sales pipeline hygiene by ensuring accurate data entry, deal stage updates, and reporting.
• Collaborate with key project stakeholders to help prepare QBR decks, client-facing presentations, and meeting materials.
• Track and follow up on action items related to sales and client deliverables.

Financial & Operational Reporting

• Generate and analyze financial reports to support accurate and informed decision-making and business planning.
• Assist with tracking revenue, forecasting, and compiling operational metrics.

Executive Support & Communication

• Manage the President of PPM’s calendar and email inbox with a focus on prioritization, time protection, and responsiveness.
• Draft, edit, and send professional communications including emails, briefs, and presentations.
• Prepare agendas, recaps, and supporting materials for internal and external meetings.
• *Some travel required – up to 25%

Organization & Coordination

• Act as a liaison with clients, partners, and vendors for scheduling, follow-ups, and requests.
• Coordinate across internal teams to ensure the PPM President is briefed and prepared for meetings.
• Support internal operations including milestone tracking and reporting.

Requirements

What You Bring

• A proactive, detail-oriented mindset with strong organizational and analytical skills.
• Excellent written and verbal communication skills.
• Confidence managing up, juggling multiple stakeholders, and making decisions independently
• Ability to manage multiple priorities and stakeholders in a fast-paced environment.
• Tech-savvy: proficient in HubSpot, O365 + Teams + Sharepoint, and presentation tools such as Canva.
• Professionalism and discretion in handling confidential information.

Preferred Qualifications

✅ 3–7 years supporting a senior executive or leader in a dynamic, fast-paced business environment

✅ Background in professional services, software, or consulting a plus

✅ Experience in sales operations, customer success, and/or financial reporting

✅ Experience with HubSpot, Canva, LinkedIn, and presentation creation highly desirable

✅ Bachelor’s degree preferred but not required

Benefits

Why Work With Us

Winmill PPM isn’t a traditional consulting shop—we lead with personality, pragmatism, and real-world experience. We’re proud to be the highest-rated partner for Planview and Broadcom ValueOps in North America. You’ll work alongside sharp, driven, and collaborative teammates, directly supporting the President in delivering value to clients and growing the business.

WHAT WE OFFER

💲 Competetitive Compensation & Benefits

🌍 Remote First Work – Work from anywhere!

🧠 High-Impact Responsibilities – Be part of a growing organization where your ideas and expertise count!

🎯 Cross-Functional Collaboration – Work alongside engineers, PMs, and clients to shape how we work.