Playbook · For CROs and CEOs

Your relationship graph is a moat you cannot currently deploy.

You know the board has hundreds of relationships. You cannot see them, rank them, or spend them deliberately. Rudy inventories what the company actually has, shows you what is at risk, and runs the asks through your Chief of Staff rather than you.

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B ####

# revenue-leadership4 members

R

RudyAPPFriday 4:58 PM

Four things worth your attention this week. Two deals need you personally, and one of them does not justify it yet.

Snowflake needs an exec routeTwo paths. One is a board member, one is Priya in Customer Success.

Deploy

Board engagement is fallingTwo members have not been asked since June.

Account

Q4 board prep, 40 accountsPre-built paths per member. Ready Thursday.

Deploy

Warm coverage on commitThree commit deals have no route to the buyer.

Inventory

Agree the planChange something

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.

01

Inventory

Know what the company actually has. Most leadership teams can name twenty relationships and own several thousand.

02

Deploy

Spend it deliberately, on the deals where it changes the outcome, through the person whose ask actually gets answered.

03

Account

Treat connector capital as a budget with a balance. A board member who has been asked eight times this year is a different asset from one asked twice.

The operating rhythm

A tool waits to be opened. A colleague has a standing agenda.

This is the part nobody else does. Rudy is not a stream of notifications you triage between calls. He works to a rhythm you both keep, and it produces something you can point at.

1ONCE A WEEK

☰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

Owner and date on every itemSo nothing is technically everyone’s job.

Planned

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

Noted

2EACH MORNING

☰Today3 items

First item already movedSent 09:14. Reply came back before standup.

Done

Second needs your readDrafted and waiting. Two minutes of your time.

Now

Third is teed upEverything he needed is attached.

Today

3EACH EVENING

☰Closed outnothing dropped

Two closedOutcome logged against the record, not a spreadsheet.

Closed

One sent, no reply yetWhich is fine on day one. He will chase it.

Sent

One replannedSomething changed on the account. Reason attached, moved to next week.

Replanned

And then it repeats. Nothing carries over silently. Anything unfinished goes back into next week’s plan with a reason attached, which is why this survives a busy quarter instead of quietly stopping.

Inventory

You can name twenty. You own several thousand.

Team, customers, board and investors, partners. Rudy loads the whole inventory on day one and keeps it current, which turns a thing everyone gestures at in board meetings into something with a number next to it.

☰Relationship inventoryfour pillars

TM

Your own teamPast colleagues, mentees and direct connections across the buyer landscape.

Largest

CU

CustomersChampions at current and former customers, many sitting at accounts you are chasing.

Deepest

BD

Board, investors, advisorsThe highest leverage you have. Also the smallest and most easily spent.

Scarcest

PA

PartnersTheir CSMs and exec sponsors cover accounts your team does not.

Widest

Deploy

Two deals at risk. Everyone is searching LinkedIn.

The whole leadership team is hunting for an angle and naming the same three suspects. What nobody has is the collective view. Rudy ranks every route across all four pillars, with the escalation rules already applied, so the question becomes which one to spend.

Snowflake, $610KACCOUNT

DetailsRelatedContactsBoomerang

Rudy · exec routes, ranked

PR

Priya Raman, your VP Customer SuccessRan their account at Datadog for four years. Costs you nothing.

Cheapest

AB

Alan Boyd, boardKnows the CFO directly. Clears the $500K gate.

Strongest

JM

Partner exec sponsorCovers the account. Routes through the Partner Manager.

Available

CU

Customer championKnows someone two levels below the buyer.

Weak

Account

Connector capital has a balance.

A board member asked eight times this year and a board member asked twice are not the same asset, and nobody currently tracks the difference. Rudy does, and tells you when the programme is quietly bleeding the thing that makes it work.

# revenue-leadershipworth knowing

R

RudyAPP10:41 AM

Board engagement is drifting. Two members have not been asked since June and one is close to the annual cap.

CONNECTOR BALANCE

ALAN BOYD7 asks this year. One below the cap

MARIA SOLISNothing since June. Response rate was 100 percent

RULEEight net asks per member per year

RISKEngagement below four a year means the pillar is dying

Rebalance toward Maria Raise the cap for Alan Show me the full ledger

Deploy

Your Chief of Staff runs it. You see outcomes.

CEOs do not work queues. The asks land with whoever runs your day, the routing happens there, and you see the decisions and the results rather than the mechanics. Ask Rudy directly when you want to, including inside Claude.

ClaudeBOOMERANG MCP

where do we have no route to the buyer on commit deals

C

Eleven deals in commit. Three have no route to the economic buyer at all, and two of those are above $400K. One has a route through the board that nobody has used:

THE ONE WORTH YOUR TIME

Snowflake, $610K, commit, no exec contact in eleven weeks. Alan Boyd knows their CFO and has not been asked this quarter. This is the deal where your capital changes the number.

boomerang.search_paths boomerang.get_pipeline boomerang.rank_reach

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.

Slack On the account record Claude and Codex, over MCP REST 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.

Your own team

YESAlways, and first. The cheapest capital in the company and the most underused.

NEVERNothing. Never skipped when a path exists.

Customers

YESThrough whoever owns the relationship, at a moment that makes sense for them rather than for your quarter.

NEVERAround the CSM. Ever.

Partners

YESRouted through the Partner Manager.

NEVERDirect outreach.

Board and investors

YESAt $500K ACV and above, or for genuinely strategic asks: a CRO hire, a fundraise, diligence. Capped at eight net asks per member per year.

NEVERQuarterly pipeline games. Spend it there and it is not available when it matters.

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