AI-Enabled Executive & Operations Assistant

Pivotal Transitions; Sonoma (CA); On-site; USD 70,000 - 90,000; Full time

Job summary

Pivotal Transitions is seeking an organized, tech-forward Executive & Operations Assistant to support our coaching engagements and own AI-powered workflows. You’ll draft client follow-ups, refine Claude-based document generation processes, and automate key tasks as you grow with the company.

The role blends traditional executive support with hands-on responsibility for AI tools and workflow improvements, offering opportunities to take on more impactful duties over time.

Qualifications

• Experience in an executive assistant, coordinator, or operations support role.
• Excellent written communication and a sharp eye for formatting and detail.
• Comfort learning and working hands-on with AI tools (Claude and Gemini) to improve workflows.
• Proficiency with tools like Monday.com, Calendly, Google Drive, SharePoint/Teams, and Zoom.
• Strong judgment and discretion in client and stakeholder communications.
• Proactive, self-directed working style with multitasking ability.

Responsibilities

• Engagement tracking: monitor coaching engagements and keep Monday.com boards up to date.
• Client follow-up: draft tailored follow-ups, log outcomes, and escalate when needed.
• AI workflow development: research, test, and help build Claude-based workflows for document generation and scheduling.
• Program production: prepare coaching documents and client kickoff packages, including HTML mockups.
• Calendar & scheduling management: manage multi-party calendars and Calendly configurations.
• Systems administration: administer Teams, Zoom, Google Meet, and LinkedIn accounts; troubleshoot access.
• Document & file management: format client documents and maintain organization across platforms.
• Ad hoc executive support: respond to requests promptly and prioritize shifting needs.

Skills

Executive support

Operations coordination

AI tools

Tools

Monday.com

Calendly

Google Drive

SharePoint/Teams

Zoom

Job description

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!

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 elevate 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 elevate 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.