The GTM Ops First 90 Days Playbook

New CROs and GTM Ops Leaders, you have 90 days to prove you can do the job. Most new revenue leaders try to fix everything at once: outbound is broken, onboarding is a mess, pipeline is full of zombie deals, and there's pressure to "implement AI." Ninety days later, nothing has changed.

In this episode, Eddie Reynolds and Rachael Bueckert walk through the operational playbook for making your first 90 days count, whether you're a new CRO or a VP of GTM Ops stepping into a company where everything feels broken. Expect a conversation on why narrowing to one priority beats boiling the ocean, how to assess the fundamentals using the GTM Efficiency Pyramid, what a realistic 90-day roadmap looks like with OKRs and sprint planning, why reports alone don't drive accountability, and what success actually looks like at the 90-day mark when your sales cycle might be longer than your timeline.

Resources mentioned in this episode:

• Newsletter: GTM Ops First 90 Days Playbook

• The GTM Efficiency Pyramid Framework

• Newsletter: The GTM Ops Decision Tree

• The GTM Ops Roadmap Framework

• All Union Square Consulting Frameworks

[02:26] The CRO's real to-do list beyond just ops

[04:16] Biggest mistake: trying to boil the ocean

[05:00] The whack-a-mole problem and learning to guide the conversation

[07:19] Narrowing focus: new business vs. NRR, pipeline gen vs. close rate

[08:00] Why you can't fix everything in 90 days, behavior change is the bottleneck

[09:34] The long-term case for net revenue retention

[10:23] It's not about building everything

[11:05] CRO tenure and the cost of trying to do it all

[13:38] Stacking 90-day sprints across go to market

[15:24] Handling complexity: multiple segments, products, and teams

[19:09] Leadership capacity and the management bottleneck

[20:42] The New Year's resolution analogy

[27:11] Assessing the fundamentals with the GTM Efficiency Pyramid

[28:06] ICP, process design, capacity planning, and target lists

[29:47] From process to systems to adoption

[31:32] The most basic problems are the most common ones

[34:32] Reports aren't the point, driving revenue is

[37:44] How to know the fundamentals are done

[39:16] Iterating quarter over quarter

[41:42] Building the GTM Ops Roadmap with OKRs

[43:14] Setting realistic metrics with long sales cycles

[45:17] Why the roadmap protects you from ad hoc requests

[47:45] Execution through sprint planning

[50:00] Daily and weekly priority-setting in practice

[53:01] Staying organized as a neurodivergent ops person

[55:35] Success at the 90-day mark: do you trust the report?

[57:36] Why reports don't drive accountability—management does

[58:08] Eddie's pipeline inspection story from Salesforce

[01:01:53] The 24-hour pipeline cleanup and the zombie pipeline problem

[01:04:16] Rebuilding CFO trust as a new CRO

[01:05:05] The one metric that should change, and why it depends

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