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 From kickoff to live operator
  • M-to-M Month-to-month, no lock-in
  • $11/hr Full-time · all-in
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 high-leverage decisions 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, follow-ups, and an inbox that ends each day at zero — every day.

  • 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 5-minute interview to owned inbox in 14 days.

  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.

AI that empowers great human experiences.

We leverage AI to empower the team to provide great brand experiences.

AI · 01

Managed Automations

Managed automations built to quickly respond and resolve routine situations — order status, returns, sizing — so Agents can go deep on the complex tickets.

AI · 02

Agent Assist

Real-time AI suggestions during agent interactions — pulled from your knowledge base, brand voice, and prior tickets so every reply is on-tone and on-policy.

AI · 03

Automated QA

AI evaluates every interaction against your quality standards — coverage moves from a 2% sampled audit to 100% automated review with human sign-off on coaching.

What clients reclaim with a Smart Support Specialist

10+ hours back, every week.

Across our founder and executive clients, the typical pattern is the same: 10+ hours per week reclaimed inside the first 8 weeks, inboxes ending each day at zero, and travel + expense friction collapsing. The judgment work — strategic decisions, hiring conversations, the 2-on-1s that move the company — gets the time it should have had all along. We will share specific founder examples on the discovery call.

Two tiers. Same specialist quality.

Full-time and part-time both billed hourly, all-in. Recruiting, training, AI brief tooling, and management included. Available month-to-month.

Part-time

Dedicated part-time Smart Support Specialist for 20 hours per week.

$14 / hr · 20 hrs/week · all-in
  • Dedicated specialist matched to your work style
  • Dedicated success manager owning the relationship
  • 4-week onboarding with AI brief setup
  • AI-augmented execution across email, calendar, projects
  • Daily reporting + weekly business review
  • Month-to-month — upgrade to full-time anytime

Frequently asked questions

Six things founders 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?

    Most clients have a live specialist in 10–14 days from kickoff. Onboarding includes a structured 5-minute interview, AI brief setup, calendar/email access provisioning, and a 4-week ramp where the specialist shadows your week before owning execution.

  • Can I switch between full-time and part-time?

    Yes. Billing is hourly, month-to-month. Most clients start part-time and upgrade to full-time once the workflow is dialled in — or flex around quarterly travel and event load.

  • How is quality measured?

    Daily reporting on inbox state, calendar coverage, and open requests, plus weekly business reviews with the success manager. Onboarding QA is run on every deliverable in the first 4 weeks before the specialist owns autonomous work.

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 gets you live in 10–14 days.