How far out GTM leaders should plan

In the latest episode of Executive Function, Brett sits down with Graham Moreno, Head of GTM at Parallel Web Systems. Before Parallel, Graham scaled Windsurf's GTM organization from three sellers to seventy-five in under a year, served as President through the Cognition acquisition, and earlier built and led enterprise sales teams at Grafana Labs and MongoDB. In this conversation, he unpacks why the AI-era backlash against structured enterprise sales misreads the data, how to design a process that raises the floor for ordinary reps without capping the ceiling for stars, and why selling to AI-native customers compresses an eight-week cycle into five business days.

In today's episode, we discuss:

• Why in-person enterprise rollouts still beat product-led motions
• Building a robust sales process that still leaves room for unscripted moments
• Why the three highest-leverage early sales hires aren't sellers at all
• The case for outsized commission accelerators for star sellers — and the kind of person they attract
• Why most AI companies are skipping the in-person sales work that enterprise customers actually want

References:

• Ahead: https://www.ahead.com
• Amazon: https://www.amazon.com
• Anthropic: https://www.anthropic.com
• Attio: https://www.attio.com
• Augment Code: https://www.augmentcode.com/
• Cognition: https://cognition.ai
• Cursor: https://cursor.com
• Dani McCabe: https://www.linkedin.com/in/danielle-mccabe/
• Datadog: https://www.datadoghq.com
• GitHub Copilot: https://github.com/features/copilot
• HubSpot: https://www.hubspot.com
• Jeremy Powers: https://www.linkedin.com/in/jeremypowers/
• JPMorgan: https://www.jpmorgan.com
• Matt McClernan: https://www.linkedin.com/in/mattmcclernan/
• MongoDB: https://www.mongodb.com
• Nicole Rettinger: https://www.linkedin.com/in/nicole-rettinger-23b20465/
• Notion: https://www.notion.com
• OpenAI: https://openai.com
• Parag Agrawal: https://www.linkedin.com/in/paragagr/
• Parallel: https://parallel.ai
• Snowflake: https://www.snowflake.com
• University of Chicago: https://www.uchicago.edu
• Windsurf: https://windsurf.com

Where to find Graham:

• LinkedIn: https://www.linkedin.com/in/grahammoreno/

Where to find Brett:

• LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
• Twitter/X: https://twitter.com/brettberson

Where to find First Round Capital:

• Website: https://firstround.com/
• First Round Review: https://review.firstround.com/
• Twitter/X: https://twitter.com/firstround
• YouTube: https://www.youtube.com/@FirstRoundCapital
• This podcast on all platforms: https://review.firstround.com/podcast

Timestamps:

00:00 Introduction

00:32 Has the sales playbook changed in the AI era?

02:13 Why "showing up" beats letting the marketplace decide

06:50 Why great salespeople sell to engineers and executives in one motion

11:37 Selling to AI-native buyers who grew up on ChatGPT

13:49 Same seller, different tempo: 8 weeks vs. 8 business days

15:57 How AI-native buyers handle build vs. buy decisions

17:48 The rep who taught a champion's son guitar over Zoom

19:03 Raising the floor without capping the ceiling

22:09 Why too much process narrows the kind of seller you attract

25:46 The three pillars of GTM excellence

31:00 Building peers who are 80% aligned, not 100%

38:03 Whether AI is changing what good enablement looks like

41:35 Selling against direct and implied competitors at once

42:45 Instrumenting the funnel from stage zero to close

45:57 Why post-sales should always roll up to the revenue leader

48:19 The case for outsized commissions

52:02 The 96 hours of panic before Cognition acquired Windsurf

53:04 How far out should a GTM leader be planning?

57:53 What a normal week looks like in hypergrowth