The GTM Podcast

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):

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

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):

• Website: https://gtmnow.com/
• LinkedIn: https://www.linkedin.com/company/gtmnow/
• Twitter/X: https://x.com/GTMnow_
• YouTube: / @gtm_now
• The GTM Podcast (on all major directories):

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.

Jessica Gilmartin has nearly 20 years of go-to-market leadership experience, most recently serving as both the Chief Revenue Officer and Chief Marketing Officer at Calendly. Prior to that, she led marketing teams at an impressive array of companies, including Asana and Calendly. As the cherry on top, Jessica also built and sold a successful frozen yogurt chain in San Francisco.

Discussed in this Episode:

• Taking an entrepreneurial approach to ownership in an organization
• The difficulty of selling to both midmarket and enterprise customers
• Cultivating a culture of creativity and approachability
• How to hire your first marketer

Highlights:

06:29 How Asana moved from product-led growth to sales-led growth

18:00 Why refining your ICP is paramount for product-led growth

33:37 Fostering a culture of experimentation

40:23 Hiring your first marketer as a startup founder

Guest Speaker Links (Jessica Gilmartin):

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

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):

• Website: https://gtmnow.com/
• LinkedIn: https://www.linkedin.com/company/gtmnow/
• The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/

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.

Joe DiMento is the Head of Go-To-Market & Industry Partnerships at Bain Capital Ventures. Previously, he was an operating partner at Fractal Software, helping launch vertical software companies and find product-market fit. Before that, he was the first non-founder seller at three startups, turning early traction into a repeatable sales motion. He began his career at Google and Bain & Company and holds an MBA from Stanford GSB.

Discussed in this Episode:

• When to hire your first account executives
• Key traits to look for in early sales hires
• Structuring compensation for first sales reps
• Should you 'hire the buyer' to be your sales rep?

Highlights:

05:03 When to hire your first sales reps.

13:17 Characteristics of top early-stage sales reps.

22:25 Designing a sales compensation plan.

31:55 Hiring for grit, curiosity & determination.

42:03 Fast-tracking your sales career.

Guest Speaker Links

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

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):

• Website: https://gtmnow.com/
• LinkedIn: https://www.linkedin.com/company/gtmnow/
• Twitter/X: https://x.com/GTMnow_
• YouTube: / @gtm_now

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.

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):

• Website
• LinkedIn
• Twitter / X
• YouTube
• The GTM Podcast (on all major directories)

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.

Cassie Young is a General Partner at Primary Venture Partners, a $1B AUM early-stage venture capital firm in New York that has backed category-defining companies such as Chief, Alma, K Health, Latch, Alloy, Dandy and Vestwell.

Before joining Primary, Cassie was Chief Customer and Commercial Officer for Marigold (formerly known as CM Group), an Insight Partners roll-up of marketing technology software including Sailthru, Campaign Monitor, Delivra, Emma, Vuture and Liveclicker; Cassie assumed that role when Marigold acquired Sailthru, where she was Chief Revenue Officer.

Prior to Sailthru, Cassie served as VP Marketing & Analytics at Gerson Lehrman Group ("GLG") and as VP Marketing & Growth for Savored (acquired by Groupon). Cassie's time in tech dates back to 2006, when she joined TheLadders.com as an early employee and managed marketing and analytics for the company's subscription business. She began her career as a tech and media analyst at Citigroup Global Corporate & Investment Bank.

Discussed in this Episode:

• The turnaround story of Cassie’s time at Sailthru and overcoming scaling challenges.
• How to rebuild and regain customer trust after technical failures.
• The importance of leadership alignment and transparency during times of crisis.
• How to effectively use Net Promoter Score (NPS) and what it really tells you.
• The value and impact of Customer Advisory Boards (CABs) in driving customer-centric growth.
• Why executive compensation should align with key business metrics for better team alignment.
• Creative tactics like video mailers and regional user groups to engage customers and drive product adoption.

Highlights:

07:53 What happens when commercial scale outgrows your technical scale.

15:53 Driving alignment through northstar metrics and incentives.

22:16 The best ways to measure customer trust.

34:10 Tips on setting up a Customer Advisory Board (CAB).

52:48 A fantastic multi-media mail campaign.

Guest Speaker (Cassie Young):

• LinkedIn
• Primary VC

Host (Scott Barker):

• LinkedIn
• Newsletter

Find GTMnow (GTMfund’s Media Brand):

• Website
• LinkedIn
• Twitter/X
• [YouTube]( / @gtm_now)
• Podcast

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.