AI-Enabled Executive & Operations Assistant

About the Role

Pivotal Transitions is looking for a highly organized, tech-forward Executive & Operations Assistant to support our team and keep our coaching engagements running smoothly. This role blends traditional executive support with hands-on ownership of our AI-powered workflows — you’ll be as comfortable drafting a client follow-up email as you are refining a Claude-based document generation process. It’s a great fit for someone who’s proactive and energized by using AI tools to make a growing business run more efficiently. Over time you should automate or delegate these key responsibilities, enabling you to take on more meaningful and impactful responsibilities as you develop and grow!

Key Responsibilities

• Engagement tracking:

  Monitor every active coaching engagement — sessions used, renewal dates, outstanding deliverables — and keep Monday.com boards up to date so the team always has an accurate picture.

• Client follow-up:

  Review outgoing scheduling emails daily, draft tailored follow-ups for clients or stakeholders, log outcomes, and escalate when a personal touch is needed.

• AI workflow development:

  Research, test, and help build AI tools and Claude-based workflows (document generation, transcript analysis, scheduling) that improve how the practice operates.

• Program production:

  Prepare the full suite of coaching engagement documents — progress trackers, nomination templates, interview questions, invitations — and build the client-facing kickoff packages, including HTML mockups.

• Calendar & scheduling management:

  Manage complex, multi-party calendars and Calendly configuration for team and coaches, resolving conflicts and keeping systems in sync.

• Systems administration:

  Administer Microsoft Teams, Zoom, Google Meet, and LinkedIn accounts, troubleshooting access issues, and coordinate outreach.

• Document & file management:

  Format and convert client-facing documents to firm standards, and maintain consistent organization across Monday.com, Google Drive, and SharePoint.

• Ad hoc executive support:

  Respond promptly to one-off requests from the team, prioritizing effectively as needs shift day to day.

What We’re Looking For

• Experience in an executive assistant, coordinator, or operations support role, ideally supporting multiple team members at once.
• Excellent written communication and a sharp eye for formatting and detail.
• Comfort learning and working hands-on with AI tools (we currently use Claude and Gemini for Workspace extensively), and a genuine interest in using them to improve workflows.
• Proficiency with tools like Monday.com, Calendly, Google Drive, Microsoft SharePoint/Teams, and Zoom — or the ability to pick up similar platforms quickly.
• Strong judgment and discretion in client and stakeholder communications, including knowing when to escalate versus handle independently.
• A proactive, self-directed working style, comfortable managing multiple concurrent workstreams without close supervision.

Nice to Have

• Prior experience in coaching, leadership development, or professional services.
• Experience building or customizing AI-driven workflows, templates, or document automation.