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Sherp Beta

The message nobody answered is the one that costs you the review.

Every operator has the same failure mode. A guest asks something on a Saturday, it gets three emoji and no reply, and you find out about it in the review. Sherp watches your Slack for exactly that — the things somebody asked that nobody answered — and puts them in front of a manager before they turn into a problem.

It also answers. Ask it anything about your workspace history and it searches years of messages, threads, and screenshots, then writes back in plain English with links to the messages it read.

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Sherp — the AI Slack Q&A mascot
Fair question Wondering why we have this when there's Slack AI and Claude for Slack? We tried them both, and they weren't good enough. See the comparison

Nothing about this is a Slack problem. It's that your team's follow-through lives in a room where things scroll away, and the cost of a dropped thread is never the thread — it's a one-star review, an owner who stops trusting the reports, or a vendor quote that expires while everyone assumes someone else has it.

SherpWatch

Nothing asked of your team gets dropped.

SherpWatch reads the channels it's invited into and your shared inbox, and finds the things somebody asked that nobody answered. It posts a standing list at times you set, and pings once when an item goes past its deadline. React with a checkmark on the original message and it clears.

  • A standing list of what's actually open — sized to work through, not a firehose
  • Channels, thresholds, destinations and schedules are all edited in the Sherpa app, not by a developer
  • Manager-facing by design — it protects your team's follow-through, it doesn't surveil it
SherpWatch configuration — per-channel digest schedules, lookback windows, and escalation thresholds for guest comms, owners, housekeeping, and email.
Guest comms
Anything tagging the guest team with no reply after it. Digest twice daily; escalates at two hours.
Owners
Owner tagged, no owner reply. Somebody else answering doesn't clear it. Sent to each owner privately.
Housekeeping
The same accountability rule for the cleaning crews, in their own channels.
Bookkeeping
Its own digest and escalation track.
Anything else
A classifier reads every unanswered thread, tagged or not, and surfaces only what it judges to be a real open task.
Shared inbox
Email threads where the last message came from outside and nobody replied. Replying, forwarding, or archiving clears it.

An owner request isn't closed because a coordinator replied — SherpWatch knows which reply it was waiting for, and keeps the item open until the right person answers it.

Sherp

Ask your Slack anything, without leaving Slack.

Slack search hands you a list of messages and leaves the reading to you. Sherp turns the question into several targeted searches, reads what comes back — thread replies and shared photos included — and writes the answer, with numbered citations back to the originals.

/sherp what did we decide about the hot tub at Harborview 2B?

You decided to keep the hot tub listed but close it from December through February rather than remove it. The cover replacement quote came in at roughly nine hundred dollars against about four hundred a month in winter servicing, so seasonal closure won on cost. [1] [2] The listing copy and the house manual were both updated to say the tub is closed for the winter, so guests see it before booking rather than at check-in. [3]

One caveat: the decision was made for that unit only. The Lakeside tub stays open year round, because its equipment is enclosed. [2]

Sources

  • [1] @dana in #maintenance · Nov 12
  • [2] @miguel in #ops · Nov 12
  • [3] @dana in #listings · Nov 14

Illustrative example. Real answers cite real messages in your own workspace — the properties, people, and figures here are invented.

More questions it gets asked. Open one to read the answer.

What did we decide about the second payment policy?

/sherp what did we decide about the second payment policy?

The balance is due 30 days before check-in for anything booked more than 60 days out. Inside 60 days, the full amount is charged at booking. [1]

You moved it from 14 days to 30 back in March, after two late cancellations left you holding a cleaning fee and a same-week vacancy. [2]

One caveat: this is the direct-booking policy only. Bookings that come through the OTAs still follow each channel's own payment schedule, which you can't override. [2]

Sources

  • [1] @priya in #direct-bookings · Mar 3
  • [2] @miguel in #ops · Mar 4

Illustrative example. Real answers cite real messages in your own workspace — the properties, people, and figures here are invented.

What's the parking spot number for Lakeside unit 2?

/sherp what's the parking spot number for Lakeside unit 2?

Spot 14, on the garage's lower level, plus one guest pass the front desk holds for arrivals after six. [1] The spot is deeded to the unit, so it doesn't rotate between guests. [2]

One caveat: the garage was restriped in April and the numbers shifted. Any thread older than that calls it spot 9 — the house manual was corrected, but saved guest messages written before April still have the old number. [2]

Sources

  • [1] @sam in #maintenance · Feb 2
  • [2] @dana in #guest-comms · Apr 18

Illustrative example. Real answers cite real messages in your own workspace — the properties, people, and figures here are invented.

What was our handyman's hourly rate and when did we set it?

/sherp what was our handyman's hourly rate and when did we set it?

Sixty-five an hour, agreed in January — up from fifty-five, which had been the rate for two years. Weekend and after-hours call-outs carry a two-hour minimum. [1]

One caveat: turnover fixes that take under half an hour aren't billed hourly at all. They go on the cleaning invoice as a line item, which is why his hourly totals look lower than you'd expect. [2]

Sources

  • [1] @miguel in #vendors · Jan 9
  • [2] @priya in #bookkeeping · Jan 10

Illustrative example. Real answers cite real messages in your own workspace — the properties, people, and figures here are invented.

Have I asked our cleaner about the Maple Street paint job yet?

/sherp have I asked our cleaner about the Maple Street paint job yet?

Yes — you asked on Tuesday afternoon in the housekeeping channel, and attached the two photos of the stairwell. [1] There's been no reply since. [1]

It's already on SherpWatch's open list for that channel, and it escalated Wednesday morning when it passed the threshold you set. React with a checkmark on the original message and it clears. [2]

Sources

  • [1] @you in #housekeeping · Tue 2:41pm
  • [2] SherpWatch digest in #ops · Wed 8:00am

Illustrative example. Real answers cite real messages in your own workspace — the properties, people, and figures here are invented.

Summarize what our maintenance lead has been working on this month.

/sherp summarize what our maintenance lead has been working on this month.

Three water heaters replaced across two buildings, the garage restripe coordinated with the HOA, and onboarding for the new HVAC vendor — including a walkthrough at each property with a filter-size inventory. [1] [2]

The recurring thread is the water heaters. All three were the same 2014 model, and there are four of them left in the portfolio. [3]

One caveat: this only covers channels you're in. If some of that work was discussed somewhere you don't have access, it isn't in this summary — and Sherp won't tell you it exists.

Sources

  • [1] @sam in #maintenance · this month
  • [2] @sam in #vendors · this month
  • [3] @miguel in #ops · Apr 22

Illustrative example. Real answers cite real messages in your own workspace — the properties, people, and figures here are invented.

What did we talk about last week on the internet outage?

/sherp what did we talk about last week on the internet outage?

Two units at Lakeside lost service Thursday morning and stayed down until Friday afternoon. The provider's ticket put it on a line fault at the street, not on anything in the units. [1]

You comped one night for the guest who was working from the unit, and left the other booking alone since they were out all day. [2]

One caveat: the hotspot kit that came out of that conversation lives at Lakeside only. Nobody ordered the second one for Harborview, and that thread went quiet. [3]

Sources

  • [1] @dana in #guest-comms · Thu
  • [2] @miguel in #ops · Fri
  • [3] @sam in #maintenance · Fri

Illustrative example. Real answers cite real messages in your own workspace — the properties, people, and figures here are invented.

  1. You ask

    Type /sherp [your question] in any channel or DM. Plain English — no search operators, no keywords to get right.

  2. Sherp searches smart

    Sherp turns your question into multiple targeted Slack searches, pulls in thread replies, and reads any shared images or screenshots.

  3. You get an answer

    A plain-English reply with inline citations linking straight to the source messages. Click through to verify anything.

Reach
All of it. Every channel the person asking already belongs to, back to the beginning — not a window of recent messages.
Controls
Scope a question to one channel, limit it to a date range, or press Dig deeper for a slower, more thorough search.
Gets smarter
Rate an answer and say what was missing. Those notes feed later searches, so it picks up your properties, your people, and your shorthand.
Cost to your team
No Slack plan upgrade, and no per-person AI subscription for anyone who wants to use it.

Where each one lands

There's already AI in your Slack. Here's what it does and doesn't do.

Mentioning Claude in a Slack channel, connecting Claude to Slack, and turning on Slack's own AI are three different products with three different limits. None of them is trying to do the operations half.

Scroll the table sideways →

Sherp and SherpWatch compared with Claude in Slack, Claude's Slack connector, and Slack AI
Question Sherp + SherpWatch Claude in Slack Claude's Slack connector Slack AI
Answering questions
Can it answer from years of history? Yes. Full search, every answer cited No. The last 20 messages in a channel, 50 in a thread 1 Yes. Searches channels, DMs and files 2 Yes. Search answers
Do you stay in Slack to get it? Yes. Answer lands in the channel you asked in Yes. No. You ask from inside Claude 2 Yes.
What does each person have to buy? Yes. Nothing extra No. Their own paid Claude account 1 No. Their own paid Claude account 2 No. A workspace-wide plan upgrade
Does it learn your properties and shorthand? Yes. From your team's own corrections Partly. General assistant Partly. General assistant Partly. General search
Following through
Does it chase what nobody answered? Yes. Digests and escalations No. Not what it's built for No. Not what it's built for No. Not what it's built for
Does it know when the right person replied? Yes. Owner and crew accountability No. Not what it's built for No. Not what it's built for No. Not what it's built for
Does it watch the shared inbox too? Yes. Unanswered email threads, same list No. Not what it's built for No. Not what it's built for No. Not what it's built for

The top half is a real contest — the others answer questions, and two of them answer from full history. The bottom half is the part nobody else is aiming at, and it's the half that costs you a review when it's missing.

  1. 1. Slack Help Center — Use Claude in Slack
  2. 2. Anthropic — Claude and Slack

Built-in guardrails

Private to your team. Grounded. Not here to guess.

Per-user permissions

Everyone connects their own account once, and Sherp searches as them. It can never surface a channel they aren't already in.

Cited or silent

Sherp won't fabricate. If the messages don't support an answer, it says so.

Ephemeral by default

Answers are visible only to you unless you choose to share them with the channel.

Corrections stick

Thumbs-down on a bad flag teaches SherpWatch where your team's bar actually is, and its accuracy is tracked on a metrics page you can see.

Speaks your team's language.

Ask in Spanish, get an answer in Spanish. Ask in French, get it in French. Sherp handles 100+ languages out of the box — so a mixed Slack workspace doesn't mean a mixed experience.

Getting it running

One admin, one approval, one command each.

A Slack admin adds it to your workspace, we approve the workspace on our side, and everyone else connects their own account with a single command the first time they use it. Nobody's IT project. Nobody's migration.

It fits operations-heavy teams where Slack is where the work actually happens — property management first, but the same shape holds for customer ops, field services, and client-facing agencies. If your team keeps re-asking questions that were already answered, and things occasionally go quiet that shouldn't, this closes both loops.

Beta — limited spots

Join the Sherp beta.

Slack-native, so there's nothing to migrate. No Slack upgrade and no per-person AI subscription for your team. Drop your email and tell us what keeps getting dropped — we'll reach out when there's a spot open.