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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Rudy · DMneeds you
R

RudyAPP10:41 AM

Jon on the Klarna deal is asking for a board route. Alan Boyd knows Ingrid Sandberg, who signs. If you approve, I’ll draft your note to Alan and the short email he can forward. Ingrid never hears from me.

TWO-HOP REQUEST

DEALKlarna, $540K, stage 3
ROUTEYou, then Alan Boyd, then Ingrid
ALAN THIS YEAR7 asks of 8. This would be the last
ALSO OPENTom, the champion, can brief Ingrid first
Approve, show me the drafts Let Tom brief her first Send it to my Chief of Staff Not this one
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.

Where Rudy shows up

Where the work already is. Not another tab.

Leaders live in Slack. Rudy brings you the few decisions only you can make, including every two-hop ask that runs through you, and nothing else.

1WHEN A DEAL NEEDS YOU

Only when it needs you

A commit deal with no exec contact, a board route someone wants to use. Rudy posts it with the cheapest route first and tags whoever should move.

# revenue-leadershiplive
C

CRMAPP7:55 AM

Snowflake, $610K, moved to commit. No exec contact in 11 weeks.

1 reply

R

RudyAPPin thread

Cheapest route first: Priya ran their account at Datadog.

@Priya Raman would you reach out to their CFO? Board route held in reserve.

Use Priya Use the board
2ON A WEEKLY RHYTHM

The plan you agree on Friday

Your Chief of Staff agrees the week with Rudy. You see the decisions and the outcomes, not the queue.

☰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

Plan board asks before the board meeting, not during it.

ClaudeBOOMERANG MCP

which board members should I ask this quarter, and for which deals

C

Maria Solis has not been asked since June and knows buyers at two commit deals. Alan Boyd has one ask left this year.

SUGGESTED

Two asks for Maria. Hold Alan’s last one for Klarna.

boomerang.get_connector boomerang.get_pipeline

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

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.

SalesforceHubSpotAttioSnowflake, $610KCRM RECORD
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
Inside track

Your team’s calendar is full of warm paths.

Inside track looks at your executive team’s meetings over the next two weeks and checks who the external attendees know. When someone already on the calendar can open a door at your top ten accounts, 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: your top ten accountsnext 2 weeks
CA
Tue: your dinner with Grant EllisGrant knows the CFOs at two of your top ten accounts.
High
TH
Thu: Tom Hale’s portfolio summitThree attendees run sales at accounts in active deals.
Likely
PS
Fri: Priya meets Elena Rossi (Litera)Elena can reach the economic buyer on your biggest open deal.
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.

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

Once it has a rhythm, it can have a number.

Warm coverage

What share of pipeline has a route to the buying committee. This is a forecast input, not a marketing metric.

Capital spent

Asks made per pillar against what each pillar can sustain.

Connector health

Response rate by connector. When it falls, the moat is closing.

A moat you cannot deploy is just a nice story.

See what Rudy would put in your first weekly plan. Connect your stack and the graph you already own shows up in about thirty minutes.

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