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

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

04/01/25 • 54 min

1 Listener

The GTM Podcast

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):

Host Speaker Links (Scott Barker):

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.

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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):

Host Speaker Links (Scott Barker):

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.

Previous Episode

undefined - GTM 139: AI Agents Are Changing Everything — Microsoft’s VP of AI Agents on the New Era of Work and Software | Ray Smith

GTM 139: AI Agents Are Changing Everything — Microsoft’s VP of AI Agents on the New Era of Work and Software | Ray Smith

Ray Smith is the VP of AI Agents at Microsoft. Previously, he was the Global VP of Product for SAP, CRM and Sales Cloud. Before that, he was the CEO and Co-Founder of DataHug, which was acquired by Calidus Cloud in 2016.

Ray breaks down why the rise of AI agents is a tectonic shift, how businesses are already seeing ROI, and what it means for SaaS, team structure, and go-to-market strategies. He also shares real-world use cases from inside Microsoft and partner companies, plus how founders and operators can build or adapt in this new AI-native era.

Discussed in this Episode:

  • What exactly is an AI agent—and how is it different from bots or automation?
  • Why traditional SaaS pricing models (like per-seat) don’t work in the agent era.
  • How enterprise teams are already deploying autonomous agents in production.
  • The emerging architecture of multi-agent workflows.
  • Which skills will matter most in an agent-first world (hint: think like a GM or growth hacker).

Highlights:

06:53 What makes an AI agent different from bots and automation—and why it matters now.

15:33 How AI agents are changing the role of traditional software tools and UI.

25:15 Why legacy SaaS pricing models don’t work for agents—and what comes next.

31:12 Inside Microsoft CoPilot: Real-world agent use cases across sales, support, and strategy.

37:42 The most valuable skills in the AI era—from delegation to agent orchestration.

51:42 Why agentic AI makes customer relationships and long-term value even more critical.

Guest Speaker Links (Ray Smith):

Host Speaker Links (Scott Barker):

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.

Next Episode

undefined - GTM 141: Timeless Growth Tips From a $7.4B Oracle Exit and Scaling Carta to $450M in Revenue | Jeff Perry

GTM 141: Timeless Growth Tips From a $7.4B Oracle Exit and Scaling Carta to $450M in Revenue | Jeff Perry

Jeff Perry is a truly iconic revenue leader and the Chief Revenue Officer (CRO) at Carta, responsible for core software revenue across New Business, Upsell, Cross Sell, and Customer Success. Prior to Carta, Jeff led SMB Sales at DocuSign, and started his career at Oracle, where he rose from Strategic Account Manager to VP of Sales over a decade.

Discussed in this Episode:

  • How to turn coworkers into mentors—and why it matters.
  • Moving from enterprise sales leadership to a startup environment.
  • Why and when to build a solutions engineering team.
  • The myth of the “18-month CRO lifespan.”
  • Balancing empathy and accountability as a sales leader.
  • Why automation isn’t always the best path forward.

Highlights:

06:29 — Mentorship matters. Jeff breaks down how to find and approach mentors—even without a formal program.

12:42 — Lessons from selling servers that still apply to modern SaaS sales

15:02 — Leading through M&A: Inside the culture clash and how Jeff rebuilt a team post-acquisition.

19:07 — Carta’s GTM evolution: How Jeff scaled from one rep selling one product to multiple teams across three business lines.

28:34 — Scaling revenue from $20M to $450M: Advice for CROs entering growth-stage companies.

33:20 — Why “big company” people can thrive in startups—if they leave their playbooks behind.

36:15 — How to use PIPs to coach—not just cut—and what most orgs get wrong.

43:13 — Why the best sellers are quarterbacks, not lone wolves.

46:43 — Pick up the phone: Human connection wins in an era of AI and automation.

Guest Links (Jeff Perry):

Host Links (Scott Barker):

Where to Find GTMnow (GTMfund’s Media Brand):

Sponsor: Pursuit

The best talent isn’t actively job hunting. Pursuit helps companies hire elite go-to-market talent on a non-retainer basis. As a key GTMfund partner, they equip sales and marketing teams with top performers.

If you're hiring for sales or marketing roles, reach out to Pursuit at pursuitsalessolutions.com/gtm or message a GTMfund team member.

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.

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