GTM 140: How Microsoft Scaled from $600M to $5B: The Enterprise Playbook with Hayden Stafford

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Apr 1, 2025

Hayden Stafford, President and CRO at Seismic, shares insights from his extensive career at Microsoft and Salesforce. He discusses how Satya Nadella transformed Microsoft's culture and emphasizes the importance of partnerships in scaling businesses. Hayden reveals the playbook for transitioning from SMB to enterprise markets and highlights the significance of customer retention in sales teams. He recalls closing a $600M deal during the 2008 financial crisis and explains why focusing on vertical markets, especially financial services, can drive growth.

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INSIGHT

Satya Nadella's Culture Shift

Satya Nadella transformed Microsoft culture from toxic to collaborative and visionary.
Clarity, empowerment, and accountability drove Microsoft's massive growth and team cohesion under his leadership.

ADVICE

Partner Early, Enable Deep Expertise

Engage partners early in deals to shape the customer narrative effectively.
Empower partners with deep domain expertise and shared goals for mutual growth.

INSIGHT

Winning with Vertical Expertise

Vertical specialization builds trust and competitive moats in complex industries.
Owning an industry niche drives better valuation and long-term success.

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Hayden Stafford is the President and Chief Revenue Officer (CRO) at Seismic, where he oversees the global go-to-market (GTM) organization, including pre-sales, sales, customer success, services, partners, and more. Prior to joining Seismic, he served as President of Global Field Operations at Pegasystems. Before that, Hayden was Corporate Vice President at Microsoft, leading Global Business Applications (Microsoft Dynamics 365) for six years. Earlier in his career, he was an SVP at Salesforce and spent nearly a decade at IBM, ultimately serving as VP and Managing Director on Wall Street.

Discussed in this Episode:

What Satya Nadella taught Hayden about culture, clarity, and transformation at Microsoft.
The exact playbook to move from SMB to enterprise—including partner enablement, segmentation, and incentive design.
Why retention isn't just a CS metric—and how to build a sales team that cares about it.
How to win in vertical SaaS, from breaking into financial services to owning the category.
What it takes to close a $600M+ deal in the middle of a financial crisis.

Highlights:

05:19 — How Satya Nadella sold his internal vision and rebuilt Microsoft’s culture from the ground up
13:13 — The partnership blueprint: how to scale with partners, not just transact with them
28:18 — Going deep in verticals: why Seismic dominated financial services while others avoided it
34:44 — How Hayden closed a $600M+ deal with Merrill Lynch after the 2008 crash
42:40 — Why retention should be part of your sales comp—and how to make it work
49:15 — The “Value Continuum”: a framework for aligning sales, services, and CS around business outcomes

Guest Speaker Links (Hayden Stafford):

LinkedIn: https://www.linkedin.com/in/haydenestafford/
Seismic: https://seismic.com/

Host Speaker Links (Scott Barker):

LinkedIn: https://www.linkedin.com/in/ssbarker/
Newsletter: https://thegtmnewsletter.substack.com/

Where to find GTMnow (GTMfund’s media brand):

The GTM Podcast
The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

Visit gtmnow.com for more episodes and other interesting content.