OpenGTM Podcast

Live from DocuSign Studios in San Francisco, Ben Salzman sits down with Anwar Akram, COO of DocuSign, to talk about how enterprise transformation actually works. Anwar has spent 25 years in tech, including 15 at Google, plus Microsoft and McKinsey. He now runs operations at a company with roughly 2 million customers and billions in revenue while leading its shift from eSignature to Intelligent Agreement Management (IAM).

They cover:

• Transformation versus theater: why Anwar starts every effort by naming the outcome, and why counting tokens is not a strategy.
• Agreements as a new data layer: how AI turns the thousands of agreements every business holds into data the business can use.
• A dual-track AI strategy: let a thousand flowers bloom, then pick the best ideas and scale them.
• Pilots versus production: knowing which work to automate and where to leave sellers in control.
• Growth over cost cutting: doing more with what you have.
• Working for a fast-moving CEO: why Anwar left Google after 15 years to join Allan Thygesen.
• Rethinking go to market around jobs to be done: instead of today’s org chart.

Chapters

00:00:00 Intro00:00:31 Anwar’s path to COO00:05:33 Transformation versus theater00:09:57 Agreements as a data layer00:13:11 Moving up market00:16:46 The dual-track AI strategy00:19:39 Pilots versus production00:23:51 Working for Allan Thygesen00:27:58 Lightning round00:31:54 GTM jobs to be done00:34:37 Transformation teams and the smartest person he knows

Guest

Anwar Akram, COO, DocuSignLinkedIn: https://www.linkedin.com/in/anwar-akram-1602409/

Host

Ben Salzman, Co-founder and CEO, OpenGTMLinkedIn: https://www.linkedin.com/in/bensalzman/

OpenGTM

Website: https://opengtm.comPodcast: https://opengtm.com/podcast

Jeanne DeWitt Grosser, COO of Vercel, joins Ben Salzman for their third podcast together. Eighteen months into the role, she sums up her scope this way: if it touches a customer or makes a dollar, it’s hers.

Jeanne revisits the vision she and Ben worked on at Stripe in 2018, every company in the world as a row in a database, and explains why the data and the personalization turned out harder than they looked. She then walks through how Vercel built GTM engineering. They started with outbound, staffed each project with a GTM engineer, a subject matter expert, and a data scientist, and added a “no new surfaces” rule once the agents started to multiply. Her north star is more customer-facing meetings per rep, every week.

What we cover

• What the COO job covers at Vercel
• The 2018 Stripe vision, revisited
• Standing up GTM engineering and the “no new surfaces” rule
• Customer-facing meetings as the north star metric
• Probabilistic vs. deterministic GTM, and why Jeanne starts with the data
• Why most companies never get there
• Jeanne’s take on the OpenGTM pitch

Learn more

• Full episode, clips, and transcript: https://opengtm.com/podcast/2-jeanne-grosser/
• All episodes: https://opengtm.com/podcast
• Jeanne DeWitt Grosser on LinkedIn: https://www.linkedin.com/in/jeannedewitt/
• Ben Salzman on LinkedIn: https://www.linkedin.com/in/bensalzman/
• Follow OpenGTM on LinkedIn: https://www.linkedin.com/company/opengotomarket/

Episode 1: Kate Earle Jensen on Building GTM at Anthropic

Kate Jensen, Head of Americas at Anthropic, joins Ben Salzman at Anthropic's San Francisco office, almost exactly three years after she joined the company when it had no revenue and a GTM machine still to be built.

Kate and Ben go back to their days working together at Stripe, when Dogpatch helped her team turn data into hyper-personalized outreach. Kate's take is that the principles haven't changed:

Everyone still wants to be spoken to by someone who understands them. What has changed is the cost. A campaign that once had 10 profiles can now have a thousand, each one updated as new information arrives.

From there, the conversation moves into how Anthropic runs its own GTM. Kate explains why the bar is higher when your customers know the outreach was written by Claude, why most failures of a model call are really context and prompting failures, and how she helps leadership teams match token spend to the return they are betting on.

She also shares how Anthropic hires and enables a team that keeps pace with a company shipping faster than ever, why every role there is a builder role, and where forward deployed engineers and partners fit.

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Why Kate left Stripe for Anthropic, and what it took to build GTM from zero revenue

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Slices: the Stripe-era work on personalized outreach at scale, then and now

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Probabilistic vs. deterministic GTM, and when a model call is the wrong tool

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Token maxing: how to match AI spend to the outcome you want

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Keeping a fast-moving team on top of the news cycle and a constant stream of launches

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New roles, enablement, and the hardest hires in GTM right now

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Forward deployed engineers, Ode, and when to bring in a partner

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00:00 Intro

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02:38 The road to Anthropic

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06:05 Slices, then and now

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09:15 Deterministic vs. runtime GTM

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20:02 Building the GTM team

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Full episode, clips, and transcript: https://opengtm.com/podcast/1-kate-earle-jensen/

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All episodes: https://opengtm.com/podcast

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Kate Earle Jensen on LinkedIn: https://www.linkedin.com/in/kateearle/

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Ben Salzman on LinkedIn: https://www.linkedin.com/in/bensalzman/

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Follow OpenGTM on LinkedIn: https://www.linkedin.com/company/opengotomarket/