Playbook · For Customer Success

Your customers already tell you everything. Rudy is listening.

Who is about to leave. Who just arrived. Who just had a great week with your team. It shows up in the Slack channels you share with customers and on LinkedIn. Rudy reads both, tells only your team, and drafts the ask, up to the board when the account is worth it.

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# ext-northwind-healthShared with Northwind Health

Tomas SilvaNorthwind Health

Huge thanks to Ali for turning the SSO fix around in an hour. Saved our rollout week.

Rudy reads it. Only your team sees what he does with it.

# csm-northwindinternal

RudyAPP2 min later

Tomas just thanked support in the shared channel. Good moment to ask. He knows Sam Kelleher, who runs security at Klarna, and that deal is stuck in security review.

Tomas Silva to Sam KelleherWorked together at Monzo. Draft ready for you to send.

Ready

Show me the draft Not this week

Co-owned goals

Three things you and Rudy both own.

Not three features. Three goals with a name on each, which is the difference between a tool you remember to open and a colleague who turns up.

Build

The stakeholders you do not have yet. Most account teams know four people at an account where forty touch the decision.

Nurture

Keeping what you do have worth something, and hearing about change before it lands on LinkedIn.

Leverage

Turning happy customers into pipeline, and your largest customers into larger ones, through whoever actually champions you.

Where Rudy shows up

Where the work already is. Not another tab.

Your customers already talk to you in shared Slack channels. Rudy reads them for the moments that matter, tells only your team, and keeps the week on a plan.

1IN CUSTOMER CHANNELS

Before LinkedIn knows

When a champion leaves, their company removes their Slack account and the shared channel says they left that day, usually weeks before LinkedIn. Rudy flags it with the successor and a plan to follow the champion to their next company.

☰# ext-northwind-healthtoday

Sam Moreno was added to #ext-northwind-health by tomas. Also, Ravi Menon left.

Champion leavingRavi Menon. Rudy will follow him to his next company.

Tracked

Successor, never metSam Moreno. Your CTO knows his old manager.

1 hop

2ON A WEEKLY RHYTHM

The plan you agree on Friday

Every moment Rudy catches goes into one list you agree on Friday, with the route and the wording ready.

☰This week’s planagreed Friday

Four things, in priority orderRudy proposes. You cut what does not belong.

Planned

Each one has a reason attachedNot a feed. A short list you both signed off.

Planned

Anything you rejected stays rejectedHe does not quietly re-propose it on Tuesday.

Noted

3IN CLAUDE AND CHATGPT

Ask from wherever you think

Ask about any account, from Claude or ChatGPT over MCP.

ClaudeBOOMERANG MCP

who at Northwind actually champions us

Dee Okonjo answers other users’ questions in your shared channel most weeks. She is not on your contact list as a champion.

WORTH KNOWING

Dee reported to the CIO at Maersk, a target account, for four years.

boomerang.get_account boomerang.get_engagement

Rudy drafts. A person sends. Every ask goes out from someone the recipient knows, and anyone along the way can say no.

Leverage

They thanked support. That is the moment to ask.

Peak goodwill does not arrive on a survey schedule. It arrives in the shared channel, the afternoon your team fixed something fast. Rudy catches it, checks who that customer knows on your target list, and puts a drafted ask in front of the CSM while the moment is warm.

☰# ext-northwind-health3:12 PM

huge thanks to Ali for the SSO fix, saved our rollout week

Moment foundPraise for support, from the person who signs the renewal.

Good

RouteTomas knows Sam Kelleher, who runs security at Klarna.

1 hop

Checks passedNo open escalation. No ask in the last 90 days.

Clear

Nurture

Their Slack went quiet before their LinkedIn changed.

Nobody has to announce anything. When a champion leaves, their Slack account is removed and the shared channel says they left, usually weeks before their profile changes. When someone new takes the role, they get added to the channel. Rudy sees both, so you meet the successor before the renewal and follow the champion to a company that may be on your target list. Champion tracking starts earlier.

☰Northwind Health, champion leavingend of month

Ravi Menon, Head of PlatformLeft the shared channel Tuesday. LinkedIn still shows Northwind.

Sam Moreno, successorNever met. Your CTO knows his old manager.

Meet now

RenewalIn 70 days. Ravi’s exit is now a renewal risk.

Flagged

Build

A new VP just arrived. Meet them before they review vendors.

New executives reassess the stack in their first ninety days, and they have never heard of you. Rudy catches them from both sides: being added to your shared Slack channel and the job change on LinkedIn. Then it finds who on your side already knows them, so the first conversation is an introduction, not a renewal call.

☰Northwind Health, new in seatrenewal in 70 days

Anika Shah, new VP EngineeringAdded to your shared channel on Monday. Your CTO worked with her at Datadog.

From Slack

Omar Haddad, new CFOStarted three weeks ago. Your investor Alan Boyd sat on a board with him.

From LinkedIn

Both sign the renewalNeither has met anyone here yet. Intros drafted for your CTO and Alan.

Before Q1

Build

Champions by behaviour, not by title.

The person on your CRM as champion is often the one who signed. The real champion is the one who answers other users’ questions, asks for features and defends you in their own meetings. Rudy ranks people by what they do in your shared channels, and then by who they can reach.

☰Northwind Health, by engagementlast 90 days

Dee Okonjo, support engineerAnswers other users’ questions most weeks. Reported to the CIO at Maersk.

Champion

Tomas Silva, VP OpsThanks the team publicly. Signs the renewal.

Sponsor

Lena Moreau, exec sponsorTwo messages this year.

Quiet

Bea Fontaine, FinanceNever in the channel.

Absent

Leverage

Sales wants an intro. You are the middle hop.

When an AE needs a route through one of your customers, it comes to you first, with the deal, the ask and both drafts. You decide. If you say yes, Rudy drafts your note to the champion and the email they forward. The customer only ever hears from you.

HOP 1

Jon, AE to YouSlack

Klarna, $540K, stuck in security review. Marcus at Siemens knows Sam Kelleher there. Your call.

HOP 2

You to Marcus WebbEmail

Marcus, you mentioned security review went from six weeks to two. Our team at Klarna is stuck on exactly that. Would you introduce them to Sam Kelleher?

FORWARD

Marcus to Sam KelleherEmail

Sam, worth twenty minutes with this team before your review. Copying Jon.

Four answers, not yes or no: send it, re-script it, wait for a better week, or wrong customer. Nothing moves until you decide.

Leverage

Make large customers larger. Bring the board in.

Cross-sell into a strategic account usually needs someone above the CSM: a customer executive who has never met yours. Rudy finds where your board and investors already know that executive and runs the ask as two hops: you ask your CEO, your CEO asks the board member, and the board member forwards a short note. Kept for the accounts where expansion moves the number, and capped so the board stays willing.

HOP 1

You, CSM to Your CEOSlack

Northwind is ready for the security add-on, about $180K. Their CIO, Kim Lee, sits on a board with Alan Boyd. Would you ask Alan for an intro?

HOP 2

Your CEO to Alan Boyd, boardEmail

Alan, would you introduce me to Kim Lee at Northwind? Her team already runs our core product. A two-line note you can forward is below.

FORWARD

Alan to Kim Lee, CIOEmail

Kim, their CEO is worth half an hour. Your team already relies on them. Copying him here.

Your CRO approves the board route. Kim hears from Alan, someone she knows, never from Rudy.

Inside track

Your team’s calendar is full of warm paths.

Inside track looks at your CSMs’ and AEs’ meetings over the next two weeks and checks who the external attendees know. When someone already on the calendar can open a door at Litera, you see it before the meeting and ask your teammate to bring it up. You pick who gets the ask and review it first, and Rudy delivers it on Slack.

☰Inside track: Literanext 2 weeks

Wed: Sam’s QBR with ToastToast’s COO worked with Litera’s new CFO for three years.

High

Thu: Priya meets Mark Jensen (Klarna)Mark is close to Rachel Monroe, Litera’s new CFO.

High

Mon: board prep with Tom HaleTom sat on a board with Grant Ellis, Litera’s COO.

Likely

The trigger comes from your stack. Rudy does the relationship work.

Salesforce, HubSpot and Attio Clay Common Room and Outreach Your own calendars and call recordings

And he shows up where the work already happens.

Chrome, on LinkedIn and company websites Your team’s upcoming meetings, with Inside track Slack, including shared customer channels On the CRM record Claude and ChatGPT, over MCP HTTP API and webhooks

The rules Rudy keeps

Connector capital is a budget, not a tap.

Every pillar has a different cost and a different refill rate. The limits are set per source, and Rudy applies them before anything is surfaced, so the only asks anyone sees are the ones they are allowed to make.

Customers, direct

YESAt a real moment: praise in the channel, onboarding done, renewal or expansion signed. Through the champion, the sponsor, or whoever actually engages.

NEVEROpen critical tickets, a recent escalation, renewal risk. And never more than three asks a year.

Your own team

YESAlways. Use team paths to warm up the customer’s stakeholders yourself, before anyone asks the customer for anything.

NEVERNothing. Never skipped.

Partners

YESCo-success stories with a shared customer, via the Partner Manager.

NEVERDirect outreach into partner CS teams.

Board and investors

YESCross-sell into your largest, most strategic customers, and strategic references. Routed CSM to CEO to board member, with the CRO approving.

NEVERSmall accounts, renewals at risk, or anything past a member’s annual cap.

The connector contract

You will say yes or no to every ask. No silence.

Every connector agrees to one rule. Someone who ghosts three asks is telling you they would rather not be a connector, and that is a fine answer. Better than silence, because silence is what trains the next person to stop asking. Both sides protected.

YesNot nowWrong personI’d rather not

On the scoreboard