Service · Executive Assistant

Executive support that owns the details.

Smart Support Specialists for founders and executives. Email, calendar, travel, project management, personal admin — handled with AI-augmented precision.

  • Smart Support specialists, AI-augmented
  • 10–14d Onboarding, from kickoff
  • M-to-M Month-to-month, no lock-in
  • Dedicated Specialist matched to your work style
The gap most founders hit

Your week is run by everyone except you.

The problem

Inbox is a backlog. Calendar is double-booked. Travel is a Google Doc nobody updated. The decisions only you can make wait while you chase receipts and reschedule a 1:1 for the third time.

The solution

A dedicated Smart Support Specialist who owns the operational layer of your week. AI-augmented execution, HelpFlow-managed quality, month-to-month flexibility. Your time gets the judgment moments and the rest gets handled.

What we cover

Nine lanes. One specialist who owns the details.

Each Smart Support Specialist works inside your tools — and HelpFlow manages the operator, so quality and continuity are both measured.

  • C · 01

    Email management

    Inbox triage with AI-generated daily briefs. Drafts, replies, and follow-ups.

  • C · 02

    Calendar coordination

    Scheduling, rescheduling, cross-time-zone wrangling, prep documents, and calendar hygiene against your priorities.

  • C · 03

    Travel planning

    End-to-end travel: flights, hotels, ground transport, itineraries, and AI-checked confirmations across every leg.

  • C · 04

    Expense reporting

    Receipt capture, categorization, monthly reconciliation, and audit-ready expense reports filed inside your accounting tool.

  • C · 05

    Project management

    Cross-functional project ops in Asana, Notion, ClickUp, or Monday — briefs, deadlines, dependency tracking, and weekly status.

  • C · 06

    Vendor coordination

    Sourcing, quoting, scheduling, and follow-through with vendors, contractors, and partners — managed end to end.

  • C · 07

    Household admin

    Personal admin tasks: appointments, gift coordination, subscription management, and household vendor scheduling.

  • C · 08

    Event planning

    Offsites, dinners, and team events: venue sourcing, logistics, attendee comms, and on-the-day coordination.

  • C · 09

    Document QA

    Proof-reading, formatting, and pre-send QA on decks, contracts, and outbound documents — with AI-assisted consistency checks.

How it works

From a 5-minute interview to an inbox your specialist owns

  1. 01

    5-min interview

    We capture your priorities, your communication style, your calendar non-negotiables, and the lanes most worth handing over.

  2. 02

    AI brief generation

    We stand up your AI brief: a daily summary of inbox, calendar, and open threads tuned to your priorities — the specialist's operating context.

  3. 03

    Specialist execution

    Matched specialist begins shadow → assist → own across email, calendar, travel, and projects. AI handles drafts and summaries; specialist handles judgment.

  4. 04

    Daily reporting

    End-of-day summary: what was handled, what is pending decision, and what is on tomorrow. Weekly business review tunes scope and priorities.

What an EA client says

Within two weeks of signing we had a VA sourced, onboarded, and ready to go. Within days, he was working like one of our domestic employees — you couldn't tell the difference if you didn't know. It's opened up a whole new world for us.
Read the private lending case study →

Priced per specialist

One monthly fee per full-time specialist covers recruiting, training, AI brief tooling, and management. Month-to-month, no lock-in.

Frequently asked questions

Five things executives ask before they hand the inbox over.

  • What is a Smart Support Specialist?

    A trained executive assistant augmented by HelpFlow's AI tooling. Specialists use AI to generate daily briefs, draft replies, summarize meetings, and pre-fill expense reports — so your time gets the human-judgment moments and the rest gets handled.

  • How is this different from a typical EA?

    Three things: AI-augmented execution (briefs, drafts, summaries are AI-assisted), HelpFlow management (a dedicated success manager owns quality and continuity), and month-to-month flexibility — no recruiting, no benefits, no lock-in.

  • Are specialists dedicated to one client?

    Yes. Each Smart Support Specialist is matched to you specifically. They learn your priorities, your contacts, your travel preferences, and your communication style — not pooled across a shared queue.

  • How fast can a specialist start?

    Onboarding takes 10–14 days from kickoff. It covers a structured 5-minute interview, AI brief setup, and calendar and email access. The full ramp takes 30 days, and during it your specialist shadows your week until they can run it independently.

  • How is quality measured?

    Daily reporting on inbox state, calendar coverage, and open requests, plus weekly business reviews with the success manager. QA is run on every deliverable during the 30-day ramp, before the specialist works on their own.

Ready to get your week back?

Fifteen minutes on a call and we'll map your priorities, the lanes worth handing over, and the specialist scope that fits them.