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Paylo.One

Intelligent operating systems for leaders.

Paylo.One is a premium, AI-native company building calm operating systems for the people who lead. Our first product, Pilot, turns scattered information into briefings, actions, decisions, and context, so leaders act with clarity instead of chasing updates.

Get startedExplore Pilot
  • 01A premium operating layer, built for how leaders actually work
  • 02Pilot, our first product, assembles a clear daily briefing from your own sources
  • 03Decisions, actions, people, and context held in one calm system
  • 04Source-backed and approval-gated, so you stay in control of every move
  • 05Calm by design: less noise, sharper judgement, better decisions
Fragmented channelsOne calm place
GMAILEXCHANGETEAMSCALENDARWHATSAPPGITHUBNOTIONOBSIDIANDaily briefing

Many inputs, one calm surface. Every line resolves to a single, source-referenced briefing.

The company

Paylo.One builds intelligent operating systems for leaders.

We are a premium, AI-native company. We build calm operating systems that help executives, founders, and operators reduce noise and act with better context. Pilot is our first product, and the standard for everything we build next.

Clarity

Clarity before speed

Leaders are not short of information. They are short of clarity. We build for the moment before the decision, not the rush after it.

Context

Context is the advantage

The best judgement comes from holding the right context at the right time. We turn scattered signals into structured understanding.

Trust

Trust is the product

Our systems hold a leader's most sensitive context. Source references, approval gates, and a clear audit trail are designed in, not bolted on.

Calm

Calm over noise

We refuse to build another dashboard to check. Every Paylo.One product is measured by the noise it removes, not the features it adds.

Paylo.One is the company. Pilot is the first product. As we grow, every product we ship will share the same standard: calm, intelligent, and built for the weight of leadership decisions.

Pilot · the first product

Pilot. The first product by Paylo.One.

Pilot is a personal operating layer for executives and managers. It brings the information from your sources, the people you work with, your decisions, your actions, and your daily context into one calm place, so you stay clear, prepared, and in control.

The problem

Leadership context is scattered

Email, chat, calendars, code, and documents each hold part of the picture. The signal that matters gets lost in the volume, and the reasoning behind decisions evaporates.

What Pilot does

It turns noise into structure

Pilot consolidates your sources, people, actions, diary, and decisions into a source-backed picture of the day, ranked by consequence rather than chronology.

Why it is different

Less to check, not more

Pilot reduces noise instead of adding another dashboard. It prepares the work and holds it for your approval. You decide and you act.

Get startedSee inside Pilot
Built for

Paylo.One builds for the people who carry consequential decisions and cannot afford to lose context across fragmented channels. Pilot is built first for CTOs, founders, and senior operators, and for the leaders and teams who work alongside them.

  • CEOs
  • CTOs
  • COOs
  • Founders
  • Senior operators
  • Senior managers
  • Fractional executives
  • Executive assistants
Inside Pilot

Four surfaces. One calm place.

Pilot is organised around how leaders actually work: what to know, who is involved, what to do, and what to remember. The surfaces are Briefing, Actions, Diary, and People.

01

Briefing

Your daily briefing brings together the signals, people, decisions, and actions that need your attention, assembled each morning from your own connected sources.

Why it matters

It answers what matters today, what changed, what needs a decision, and what cannot slip, before the day starts pulling at you.

What it handles

Email, calendar, code, documents, and messages, ranked by consequence rather than chronology and linked to the people they involve.

How you operate better

You open one place instead of ten, and you read it in two minutes with every point traceable to its source.

02

Actions

Keep track of the commitments, follow-ups, and decisions that should not disappear into the noise. The foundation begins with source-backed action suggestions.

Why it matters

A commitment is more than a line of text. The person, topic, deadline, conversation, and reason all determine what should happen next.

What it handles

What you owe, what others owe you, delegated work, waiting items, recurring follow-ups, and the context behind each one.

How you operate better

Today you review, approve, defer, or dismiss source-backed suggestions. The planned experience adds manual capture, lifecycle views, reminders, and people-aware follow-up.

03

Diary

Capture the context behind your day, so important thinking is not lost. A private space for reflections, decisions, and rationale, in text or voice.

Why it matters

The reasoning behind a decision usually evaporates. The Diary keeps it next to the context that prompted it.

What it handles

Private notes and voice memos, transcribed, and linked by deliberate choice to briefings, actions, and items.

How you operate better

Private by default. Nothing is used to shape your briefings or suggestions unless you explicitly opt in.

04

People

Understand the people connected to your work, the topics they touch, and the commitments linked to them, with every email, message, and pull request tied to the right person across channels.

Why it matters

Information is fragmented, but the people are constant. Knowing who is connected to which decisions, risks, and follow-ups is what makes a briefing relationship-aware instead of a flat summary.

What it handles

Cross-source identities (email, WhatsApp, Teams, GitHub, Notion), correlated signals, and the actions and projects each person touches.

How you operate better

You confirm or correct who is who. Pilot proposes links with a confidence score and never merges people on its own.

Actions

Commitments with context, not another task list.

Actions is designed to become your execution memory: one place to capture what needs to happen, remember why it matters, see who owes the next move, and bring the right commitment back at the right time.

Remember the commitment

Keep the outcome, person, topic, deadline, decision, and source together, so an action still makes sense weeks later.

See both directions

Track what you owe others, what others owe you, what you delegated, and what is waiting for a reply.

Follow up at the right time

Separate deadlines from follow-up dates and reminders, then surface what needs attention today without filling the screen with noise.

Turn signals into execution

Bring candidate actions out of meetings, email, messages, diary entries, documents, and decisions, with the source kept attached.

One connected context

Briefing finds what matters. Actions carries it through. People shows the commitments around each relationship. Diary preserves the private reasoning. Sources keep every suggestion traceable. Decisions connect the choice to the work that follows.

Available today
  • Source-backed action suggestions with rationale and confidence
  • Approve, defer, and dismiss controls
  • Person links, correction controls, and source references
  • An audit record of every suggestion decision
Planned Actions experience
  • Fast manual capture and clear action states
  • Today, Follow-ups, Waiting On, By Person, By Topic, and Deadlines
  • Personal, delegated, waiting, and recurring commitments
  • Due dates, follow-up dates, reminders, history, and suggested next steps
The daily briefing

Every morning, know what matters, what changed, and what needs approval.

The daily briefing is the wedge. It is assembled on schedule and on demand from your connected sources, ranked by consequence, and written to be read in two minutes. It opens with the people behind today's activity, correlated across your channels and ranked by the importance you set, so the briefing is relationship-aware, not a flat summary. It is the first thing you read and the reason you return.

The trust contract

Every insight carries a source reference: the system it came from, the specific item, a timestamp, a confidence value, and an excerpt or deep link. If an insight cannot be attributed, it is not shown. Low-confidence insights are labelled, never dressed up as fact.

Connected sources

Connect the tools where work already happens.

Your context is scattered across email, calendars, chat, documents, and the web. Pilot starts with the sources governed for the first release, then expands deliberately as each connector clears the security and support bar.

First release
  • GmailThe threads that need a reply, the decisions being asked of you, and the promises you have made.
  • Google CalendarToday's meetings in focus, with the prep and context each one needs.
  • Microsoft TeamsEscalations, decisions, and mentions from the channels that matter.
  • WhatsAppSignals from the people and chats you approve, never your whole account.
  • Markdown documentsNotes and docs in Markdown, read straight into your context.
  • PDFs and uploadsReports, contracts, decks, and pasted text, with the points that matter pulled into your briefing.
Planned
  • Microsoft OutlookPriority mail and commitments from the Outlook folders you choose.
  • Outlook CalendarYour Outlook schedule, with meeting prep drawn from the rest of your context.
  • GitHubBlockers, review requests, and the changes that matter from the repositories you choose.
  • SlackDecisions, blockers, and commitments from the channels you select.
  • DiscordTeam and community signals from the Discord channels you choose.
  • NotionThe recently changed pages and decisions your briefing can point back to.
  • ObsidianYour local-first notes, kept private and ready for the briefing to cite.
  • News sourcesThe few outside signals that clear your relevance bar, never a generic feed.
  • Web pages and URLsPoint Pilot at a page worth following and keep its context close.
Custom sources

Run on something that isn't here?

Pilot can connect to internal systems and tools beyond this list. Tell us what runs your world, and we will bring it in.

Get startedAsk about a custom source

You decide what each source can see, and you approve every connection. Nothing is shared across workspaces, and every point in your briefing stays traceable to where it came from.

Pricing

Three plans. One calm operating layer.

Start with Starter, grow into Pro, or run at full capacity on Advanced. Every plan is self-serve, starts with a 14-day trial, and can be cancelled anytime. Pro is the recommended plan for active professionals.

Self-serve signup14-day trialMonthly or annual billingTwo months free annuallyCancel anytime

Two months free with annual billing

Loading current prices…

SELF-SERVE

Starter

For individuals who want a lightweight personal operating assistant.

…
per month, billed monthly.

The complete daily loop: briefing, actions, diary, and people, from your own sources.

  • Daily briefing, every morning
  • Actions, Diary, and People
  • 3 connected sources
  • Email, calendar, files, Notion, and news connectors
  • Standard AI models with a monthly allowance
  • Daily source refresh
  • 90-day context history
  • Standard support
RECOMMENDED

Pro

For active professionals who run their day through Pilot.

…
per month, billed monthly.

Everything in Starter, with more sources, more frequent briefings, and deeper intelligence.

  • Everything in Starter
  • 8 connected sources
  • GitHub, Teams, Slack, Discord, and WhatsApp connectors as they roll out
  • Up to 3 briefings a day, refresh up to 4 times a day
  • Higher AI allowance; selected premium models coming soon
  • Advanced people and company intelligence
  • Custom prompts with versioning
  • 1 MCP connection
  • Data export (planned)
  • 1-year context history
  • Priority support
POWER USERS

Advanced

For power users, executives, and consultants with high-volume or integration-heavy needs.

…
per month, billed monthly.

Everything in Pro, at the highest limits, with full MCP access and early access to what ships next.

  • Everything in Pro
  • 20 connected sources, every available connector
  • Up to 10 briefings a day, on-demand refresh
  • Highest AI allowance; all premium models coming soon
  • Full MCP access, up to 5 connections
  • Bring your own AI keys (planned)
  • API access (planned)
  • Advanced automations (planned)
  • 2-year context history
  • Early access to new features
  • Priority-plus support

Every plan begins with a 14-day free trial. Cancel before the trial ends and you pay nothing.

Checkout is handled securely by Paddle, our merchant of record. Prices include local taxes where applicable. By starting a trial or subscribing, you agree to the Terms & Conditions and the Refund Policy.

What is included at each tier
CapabilityStarterProAdvanced
Daily briefing1 per dayUp to 3 per dayUp to 10 per day
Actions, Diary, and People
Connected sources3820
ConnectorsEmail, calendar, files, Notion, news+ GitHub, Teams, Slack, Discord, WhatsAppAll available connectors
Source refreshDailyUp to 4 times a dayUp to 4 times a day + on demand
Monthly AI allowanceStandardHigherHighest
Premium AI models—Selected (coming soon)All (coming soon)
People and company intelligenceBasicAdvancedAdvanced
Custom prompts and versioning—
MCP access—1 connectionUp to 5 connections
Automations—10 (planned)50 (planned)
Data export—PlannedPlanned
API access——Planned
Bring your own AI keys——Planned
Context history90 days1 year2 years
Early access to new features——
Support levelStandardPriorityPriority plus
How it works

How Pilot works.

Context flows in from the sources you approve, is linked to the people it involves, resolves into a briefing and suggested actions, and grows sharper as you correct it. Three rules never bend.

01

Connect sources

Authorise the channels you run on, choose what each one monitors, and set a storage policy for each.

02

Bring context together

Items from approved sources are prepared consistently and kept private to your workspace.

03

Connect context to people

Each item is linked to the person it involves, using accounts you have confirmed. Uncertain matches wait for your review.

04

Generate the briefing

A source-referenced, relationship-aware briefing is assembled on your schedule and on demand.

05

Suggest actions

Candidate actions are extracted with rationale and held for your approval.

06

Capture diary memory

Reflections and decisions are recorded privately and linked by choice.

07

Refine as you correct

Your corrections, links, dismissals, and confirmations become explicit rules, so Pilot grows sharper without hidden learning.

Approval-gated

Actions require your approval

Pilot never sends, posts, comments, merges, or schedules on your behalf. It prepares the work; you execute it.

Source-referenced

Every insight cites its source

Insights are grounded in your own items. If a claim cannot be attributed to a source, it is withheld rather than shown.

Explicit

It learns from your corrections, not in the dark

Pilot improves through explicit, inspectable rules you can see and change. There is no hidden personalisation and no silent learning.

Trust and security

Built for the discretion the role demands.

Pilot holds an operator's most sensitive context. At Paylo.One, trust is treated as a feature, not a footnote. Every pillar below is explained for the person relying on it, not only the people building it.

A private workspace

Your workspace is separated from every other customer. Context is never shared or searched across workspaces.

Processed in the European Union

Your prompts and Pilot's analysis are processed inside the European Union, on infrastructure in Frankfurt, using European AI models — under GDPR, and never used to train external models. For leaders who need it, your context stays in Europe.

Your own workspace address

Each operator works from a dedicated paylo.one address, such as bernard.paylo.one.

Secure sign-in

Sign-in is designed around passkeys, reducing reliance on reusable passwords and keeping access tied to the right workspace.

Source references for every insight

Insights are traceable to the exact item, system, timestamp, and confidence behind them. Unattributable claims are withheld.

You control storage

Set a storage policy per source: keep raw and summaries, summaries only, or no raw retention at all. Summaries are kept; raw is held only for a bounded audit window and then purged. Your data, your terms.

Relationship context stays yours

People, their linked accounts, and private notes stay inside your workspace. Pilot proposes matches and you confirm them; it never merges people on its own.

WhatsApp by approved people only

WhatsApp is designed to monitor only the people or chats you approve, never your whole account. It is enabled only after the privacy and platform approach is confirmed.

Explicit refinement, not hidden learning

Pilot grows more useful as you correct, link, and refine it, through inspectable rules you control. There is no hidden fine-tuning and no silent personalisation.

Human approval before action

No action is created or sent until you confirm it. There are no autonomous external actions in the product.

Controlled processing

Every request follows one controlled path. Access, data handling, and usage are checked and recorded.

Controlled tool access

When Pilot reaches an external service, access is limited, recorded, and held for approval before anything consequential happens.

Private processing, planned

Private processing options are planned for regulated organisations that cannot use shared infrastructure.

Audit and source traceability

A durable audit trail records actions, decisions, and access, with evidence for export and deletion requests.

FAQ

Questions leaders ask before they subscribe.

Signup is open to everyone, and the basics should be clear before you choose a plan.

What is the difference between Paylo.One and Pilot?

Paylo.One is the company: a premium, AI-native company building calm operating systems for leaders. Pilot is its first flagship product, the personal operating layer you request access to here.

Who is Pilot by Paylo.One built for?

Pilot is built for CTOs, founders, senior operators, and executives who carry decisions, commitments, and relationship context across many channels, along with the managers and assistants who work alongside them.

What does Pilot do each morning?

Pilot assembles a source-backed daily briefing from the tools you approve, then highlights what changed, what needs a decision, what needs follow-up, and which people are involved.

Does Pilot act on my behalf?

No. Pilot can suggest actions with rationale and source references, but sending, posting, scheduling, merging, and other consequential actions require your approval.

Which sources can Pilot connect to?

The first release focuses on Gmail, Google Calendar, Microsoft Teams, WhatsApp, and flat files. GitHub, Slack, Discord, Outlook, Notion, Obsidian, news sources, and web pages are planned or handled as custom requests.

How does signup work?

Create an account, complete a short onboarding, pick Starter, Pro, or Advanced, and choose monthly or annual billing. Every plan starts with a 14-day trial, and checkout is handled securely by Paddle, our payment provider.

Can I change or cancel my plan?

Yes. Upgrades take effect immediately with a prorated charge. Downgrades and cancellations take effect at the end of the current billing period, so you keep what you paid for. Switching between monthly and annual billing works the same way.

Where is my data processed, and which AI does Pilot use?

Pilot processes your context inside the European Union, on infrastructure hosted in Frankfurt, using European AI models under GDPR. Your prompts and Pilot's analysis stay in the EU and are never used to train external models — a deliberate choice for leaders who need European data residency.

What does pricing start at?

Starter is $10 per month or $100 per year, Pro is $40 per month or $400 per year, and Advanced is $120 per month or $1,200 per year. Annual billing gives you two months free, and every plan starts with a 14-day trial.

Get started

Start operating with Pilot.

Create your account, connect the sources you run on, and read your first briefing the next morning. Every plan starts with a 14-day trial, you choose monthly or annual billing, and you can cancel anytime. If your context has outgrown notes and dashboards, this is the calm layer on top of it.

Create your accountCompare plans

14-day trial. Cancel anytime. No invitation required.