How to Pilot

Welcome to Pilot

Pilot is the operating system for real estate investors — one cockpit for properties, tenants, rent, maintenance, accounting, and your team.

Pilot replaces the spreadsheets, the shoebox of receipts, the group texts, and the half-dozen apps you've been stitching together. Everything about your rentals lives in one place, and the parts that should run themselves — rent collection, reminders, late fees, bookkeeping — do.

This guide walks you through the whole platform in order. You do not need to read it end to end before you start. Set up your first property and tenant (Sections 5–10), then come back for the deeper features as you need them.

Throughout the guide, anything in your dashboard is reachable from the left sidebar. If you ever get lost, the Pilot logo takes you home to the cockpit.

Your cockpit dashboard

The dashboard is your daily flight deck: what needs attention today, this month's money, and quick access to every module.

When you sign in you land on the cockpit. The top shows your portfolio at a glance — occupied units, rent collected this month, and open items that need you. Below that, the Today view surfaces the handful of things that actually need a decision: overdue rent, new maintenance requests, leases about to expire.

The left sidebar is your map. It groups the platform into Properties, Tenants, Payments/Revenue, Maintenance, Documents, Finance, and Settings, with more specialized tools (Applications, Evictions, Listings, Automations) beneath.

You can switch which property you're focused on from the property switcher at the top. Managers you invite see a version of this same cockpit scoped to only the properties you assign them.

Set up your account & profile

A complete profile makes your invitations, leases, and receipts look professional and land in the right inbox.

Head to Settings → Profile to fill in your name and, if you operate under a company, your LLC or business name. Your business name appears on tenant invitations, generated leases, and rent receipts, so tenants recognize who they're dealing with.

Add a phone number and confirm your email. If you signed up with Google, your email is already verified; if you used a password, confirm it from the link we sent so password reset and notifications work.

1. Go to Settings → Profile.
2. Enter your full name and business/LLC name.
3. Add a contact phone number.
4. Confirm your email address if you haven't already.
5. Set your notification preferences under Settings → Security/Notifications.

Choosing your plan & the free trial

Pilot bills per unit. The Pilot tier covers most operators; Pilot Pro adds the AI Hub, multi-manager billing, and syndication; Enterprise is for large portfolios.

Every new landlord starts on a 7-day free trial so you can set up a property and see the platform work before paying. When the trial ends you choose a plan from Settings → Subscriptions (or you'll be prompted automatically).

Pilot is $249/mo and includes your first 50 units, then $2/unit up to 100. Pilot Pro is $499/mo, includes your first 300 units, then $1/unit with no unit cap, and unlocks the full AI Hub, advanced reporting, and listing syndication. Enterprise adds white-glove onboarding at custom pricing — contact sales.

Properties are unlimited on every paid tier; you're billed on units (doors), not buildings. Annual billing takes 20% off the base fee.

1. Open Settings → Subscriptions.
2. Compare Pilot vs. Pilot Pro using the built-in calculator (enter your unit count).
3. Pick monthly or annual billing.
4. Complete checkout — your card is only charged when the trial ends.

Add your first property

A property is the anchor for everything else — units, leases, rent, maintenance, and accounting all hang off it.

From Properties, click Add Property and enter the address. Pilot geocodes it and pulls a street view so your portfolio is visual. Add the financial basics — purchase price, current value, and default rent — so your analytics and Schedule E are accurate from day one.

You can set a default monthly rent and rent due day on the property. These become the suggested defaults whenever you invite a tenant there, so you only type them once.

1. Go to Properties → Add Property.
2. Enter the street address, city, state, and ZIP.
3. Add default rent amount and rent due day (e.g. the 1st).
4. Optionally add purchase price, current value, and a photo.
5. Save — your property now appears in the switcher and on the map.

Units & multifamily buildings

For duplexes, triplexes, and apartment buildings, add units so each door has its own lease, tenant, and ledger.

A single-family home can be treated as one unit — you don't have to create a unit for it. But for multifamily, add each unit (Unit A, 101, Main House) so rent, leases, and maintenance are tracked per door. Your billing is based on total units across the portfolio.

Units carry their own bedroom/bathroom/square-footage details, which feed vacancy listings and rent-pricing suggestions.

1. Open a property and go to its Units tab.
2. Add a unit with a label (e.g. "Unit 2") and its bed/bath/sqft.
3. Repeat for each door in the building.
4. When you invite a tenant, assign them to the specific unit.

Invite your first tenant

Inviting a tenant sends them a secure link, creates a pending lease, and sets up rent — all in one step.

From Tenants, click Invite a Tenant. Choose the property (and unit), enter the tenant's email, the monthly rent, the rent due day, and the lease start date. Pilot emails the tenant a secure invitation link and creates a pending lease in the background.

If the tenant already has a Pilot account, they're linked immediately and get an in-app welcome message. If not, the link walks them through creating an account and accepting.

1. Go to Tenants → Invite a Tenant.
2. Select the property/unit.
3. Enter the tenant's email, rent amount, due day, and start date.
4. Send the invitation.
5. Track their progress from the Pending Invitations list.

Watch your tenant get set up

Every pending invitation shows a live onboarding stepper so you always know exactly where your tenant is.

In the Tenants list, each pending invitation now shows an onboarding progress tracker: Invite sent → Account created → Invite accepted. As your tenant signs up and accepts, the steps light up, so you can tell the difference between "they haven't opened it yet" and "they made an account but haven't finished."

If an invitation email fails to deliver, the card flags it so you can fix the address and resend rather than waiting on a tenant who never got it. Expired invites are marked too, with a one-click Resend.

1. Open Tenants and find the Pending Invitations section.
2. Read each tenant's stepper to see their current stage.
3. Use Resend if an invite expired or shows a delivery failure.
4. Use Revoke to cancel an invitation that's no longer needed.

Leases: draft, pending, active

A lease moves through clear states, and Pilot activates it the moment your tenant accepts.

When you invite a tenant, Pilot creates a lease in the pending_acceptance state. When the tenant accepts, it flips to active and rent begins. A lease captures the rent amount, due day, start date, deposit, and any recurring fees (parking, pet, HOA).

You can end a lease at any time from the tenant's detail page. Ending an active lease stops future rent and, on autopay leases, cancels the tenant's automatic payments so they aren't charged again.

Get paid: rent collection with Stripe

Pilot collects rent directly to your bank via Stripe, with 0% platform fees on payments.

To accept rent online, connect your payout account under Payments → set up rent payments. Pilot uses Stripe Connect, so money moves from your tenant straight to your bank. Tenants can pay by ACH bank transfer or card from their portal.

Once you're connected, every active lease can collect rent. Tenants see their balance and a Pay button; you see the money land and the ledger update automatically.

1. Go to Payments and start the payout setup.
2. Complete Stripe's identity/bank verification (one time).
3. Confirm your properties can accept rent.
4. Tenants pay from their dashboard; funds arrive in your connected account.

Autopay & rent reminders

Let tenants enroll in autopay so rent collects itself, and Pilot nudges everyone else automatically.

Tenants can turn on autopay, which creates a recurring charge so rent is collected on the due date without anyone lifting a finger. For tenants who pay manually, Pilot posts each month's charge a few days early and emails a reminder, then escalates to overdue and applies late fees per your rules.

You never post rent by hand — a daily job creates each month's charges for active leases and skips anyone on autopay (they're billed by their subscription instead), so there's no double-charging.

Move-in dues: first month & deposit

When a tenant accepts, Pilot creates their move-in charges automatically so onboarding collects the right money up front.

On acceptance, Pilot posts the move-in dues — first month's rent, the security deposit, and any one-time fees you added to the invite — all due on the lease start date. These are tagged as move-in charges, and the tenant portal asks for them before granting full access.

This means a new tenant can't slip through without paying their deposit and first month, and you don't have to chase it separately.

Waiving rent & dues

Need to forgive a charge or give someone a break? Waive outstanding dues or upcoming rent right from the tenant's panel.

Open a tenant's detail page and use the Waive controls on their lease. Waive dues forgives everything currently owed (due, overdue, and partial charges). Waive upcoming forgives scheduled rent going forward — Pilot sets a waiver window and stops posting new rent during it.

Waiving is autopay-aware: if the tenant is on autopay, waiving upcoming rent also pauses their automatic payments so Stripe doesn't charge them anyway. The tenant is notified when you waive, and the change is recorded for your records. You can restore upcoming rent later if circumstances change.

1. Go to Tenants → open the tenant → find their active lease.
2. Click Waive dues to forgive the current balance, or Waive upcoming for future rent.
3. Confirm — the tenant is notified and the ledger updates.

Late fees & the rent ledger

The ledger is the itemized truth of every charge, payment, fee, and adjustment on a lease.

Every lease has a rent ledger: one row per rent charge, recurring fee, late fee, or adjustment, each with a status (due, overdue, paid, partial, waived). When a rent charge goes past its grace period, Pilot automatically posts a late fee attached to that charge — never a duplicate.

You can review a lease's full breakdown, waive or cancel individual charges, and see exactly what a tenant owes and why. Payments settle against these rows, so your books always tie out.

Maintenance: intake to dispatch

Tenants submit repair requests from their portal; you triage, assign a vendor, and track it to done.

Maintenance requests flow in from tenants (or you can log them yourself). Each request has a priority, status, and full timeline. Triage sorts them, and you dispatch a vendor with a work order. Everyone — tenant, vendor, you — sees status updates, so no one has to chase.

Photos, notes, and cost are captured on each work log, which flows into your accounting so repair spend shows up in your P&L automatically.

1. Open Maintenance to see the queue.
2. Triage: set priority and review details.
3. Assign a vendor and create a work order.
4. Log work, cost, and photos as it progresses.
5. Close the request — the tenant is notified.

Vendors & work orders

Keep your trusted plumbers, electricians, and handypeople on hand and assign them in a click.

Add vendors under Vendors with their trade and contact info. When a maintenance request needs work, assign a vendor and Pilot creates a work order they can act on. Track spend per vendor and per property over time.

If you delegate to a manager, you can cap how much they're allowed to approve per work order — anything above their limit routes to you for approval (see Section 26).

Messaging your tenants

Every tenant conversation lives in Pilot — searchable, attached to the property, and never lost in a personal text thread.

Messages gives you a direct channel with each tenant, scoped to their property. When you invite a tenant or they accept, Pilot seeds a conversation automatically. You can message from the tenant list, the tenant detail page, or the Messages inbox.

Because it's in-platform, conversations stay with the tenancy — if you hand a property to a manager, the history goes with it, and you keep a record.

Documents & e-signature

Store every lease, addendum, and notice, and get them signed online without printing anything.

Documents is your file cabinet — upload leases, addenda, inspection reports, and insurance docs, organized by property. For anything that needs a signature, Pilot's built-in e-sign sends a secure signing link; the signed PDF is stored automatically with a full audit trail.

No third-party e-sign subscription needed — it's part of Pilot.

1. Go to Documents and upload or generate a document.
2. Choose Send for signature and add the signer(s).
3. The signer completes it from a secure link.
4. The executed PDF is saved to the property automatically.

Generate legal documents

Produce state-aware lease agreements and eviction notices in seconds, pre-filled from your data.

From the legal document generator, pick a template — a lease agreement or a notice — and Pilot fills in the property, landlord, tenant, and rent details for you, then produces a clean PDF. Combine it with e-sign (Section 18) to get it executed the same day.

Generation is rate-limited to protect against mistakes, and every document is saved to the property.

Applications & tenant screening

Take rental applications online and screen applicants — credit, background, and income — before you hand over keys.

Prospects can apply through your public listing (Section 24). Applications land in one place where you review the applicant's details, run screening (credit and background via TransUnion SmartMove), and verify income from pay stubs or bank statements. You approve or decline, and the approved applicant flows straight into an invitation.

Income and identity verification uses AI to read uploaded documents so you get a clean summary instead of a pile of PDFs — with sensitive data handled carefully.

1. Share your listing link to collect applications.
2. Open Applications to review each applicant.
3. Trigger screening and request income verification.
4. Approve to convert the applicant into a tenant invitation, or decline.

Evictions workflow

When it comes to that, Pilot gives you a structured, documented eviction process instead of a scramble.

The evictions module tracks a case from notice through resolution, with the documents and timeline in one place. Because your ledger already shows exactly what's owed and your messages show the paper trail, you have the record you need if it goes to court.

This is a last resort — Pilot's earlier tools (reminders, late fees, messaging, payment plans via waivers) are designed to keep you out of here.

Accounting: P&L, Schedule E, rent roll

Pilot keeps double-entry books for you, so your P&L, Schedule E, and rent roll are always current.

Every rent payment, fee, and logged repair posts to your books automatically using a proper chart of accounts. That means your Profit & Loss, tax-ready Schedule E, and rent roll are live reports, not spreadsheets you rebuild each April.

You can also import and reconcile bank transactions, categorize expenses, and see per-property performance.

1. Open Finance → Accounting.
2. Review your chart of accounts and categorize any imported transactions.
3. Pull your P&L or Schedule E for any date range.
4. Export at tax time.

Revenue & analytics

See how your portfolio is actually performing — collections, NOI, occupancy, and trends over time.

Revenue and analytics turn your ledger and books into insight: how much rent you've collected vs. billed, net operating income, occupancy, and per-property comparisons. Pilot Pro adds deeper NOI analytics and benchmarking.

Use these to decide where to raise rent, which property is dragging, and whether a refi or sale makes sense.

Listings & vacancy management

Turn a vacancy into a public listing with a rental application flow, and (on Pro) syndicate it out.

When a unit is empty, create a listing with photos, details, and an AI-written description. You get a public listing page and a shareable link where prospects browse and apply. Applications flow straight into your screening pipeline (Section 20).

Pilot Pro adds listing syndication to sites like Zillow and Apartments.com, plus promoted placements, so you fill vacancies faster.

1. Go to Listings → new listing and pick the vacant unit.
2. Add photos and let AI draft the description.
3. Publish and share the link.
4. Review incoming applications and screen the best fit.

Invite a property manager

Bring on a manager with their own login to handle day-to-day operations, scoped to the properties you choose.

Managers get their own separate Pilot account and see a cockpit limited to the properties you assign them — not your whole portfolio and not your personal finances (unless you allow it). Invite one from Settings → Managers by entering their email; they accept, and you assign properties.

Manager seats are billed to you per active seat: your first manager seat is included free, and each additional seat is $29/mo on Pilot and $49/mo on Pilot Pro. Pilot Enterprise includes unlimited manager seats — add as many team members as you want at no per-seat cost. You'll see the exact cost before you invite, and seats are added or removed automatically as you activate or deactivate managers. Inviting a manager requires an active paid plan.

1. Go to Settings → Managers.
2. Review the seat cost shown on the page.
3. Click Invite Manager and enter their email.
4. They accept the invite and create their login.
5. Assign them the specific properties (or units) they should manage.

Manager permissions & spend approvals

Decide exactly what each manager can do — invite tenants, message, dispatch vendors, view financials — and cap their spending.

Each manager has granular permissions you control: invite tenants, message tenants, assign vendors, log work, view financials, and approve move-outs. Turn on only what you trust them with. You can also scope a manager to specific units within a building, not just whole properties.

Set a per-work-order spending limit, and any repair above it routes to you as a spend approval before the money goes out. You stay in control of the checkbook while your manager handles the day-to-day.

1. Open Settings → Managers and expand a manager.
2. Toggle each permission on or off.
3. Set a spending limit (or leave unlimited).
4. Assign or remove properties and units.

Autopilot: your AI assistant

Autopilot is an AI copilot that answers questions about your portfolio and can take actions — with your approval.

Open Autopilot and ask in plain English: "Which tenants are overdue?", "Draft a rent-increase notice for Unit 2," "What was my NOI last quarter?" Autopilot reads your data and answers. When it proposes an action that changes something, it asks you to approve or deny first — it never acts behind your back.

It's the fastest way to get an answer without hunting through screens, and a safe way to let AI help without giving up control.

AI features: pricing, insights, verification

On Pilot Pro, AI helps you price rent, spot financial issues, triage maintenance, and verify applicant income.

The AI Hub includes rent-pricing suggestions (what a unit should rent for based on its details and the market), financial insights that flag anomalies in your books, maintenance triage that suggests priority and next steps, and document parsing that reads pay stubs, bank statements, and IDs for screening.

Sensitive tenant information is redacted before anything is sent to an AI provider — the AI works with context, never raw personal data.

Settings, security & notifications

Tune notifications, secure your account, and manage billing from one place.

Under Settings you control notification preferences (what emails you get), security (password, backup codes), billing and subscriptions, and your team. Turn on the alerts that matter to you — new applications, overdue rent, maintenance — and mute the rest.

Protect your account with a strong password and keep your recovery options current; you're the administrator of everything your managers and tenants touch.

Support & your first-week checklist

You're set. Here's a simple plan for week one and how to reach us if you need a hand.

You don't have to do everything at once. In your first week: complete your profile, add one property, invite one tenant, and connect your payout account so rent can flow. Everything else — maintenance, accounting, listings, managers — is there when you need it.

If you get stuck, ask Autopilot, revisit this guide at /guide, or email support@rentwithpilot.com. Welcome aboard — now go run your portfolio on autopilot.

1. Complete your profile and business name (Section 3).
2. Add your first property (Section 5).
3. Connect your payout account for rent (Section 10).
4. Invite your first tenant (Section 7).
5. Explore Autopilot with a question about your portfolio (Section 27).