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.

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.

Jaleh Rezaei is the CEO & Co-founder of Mutiny, a company reimagining the B2B buying experience by transforming transactional relationships into meaningful connections through AI-powered personalization. Mutiny helps enterprises restore the human element in modern buying at scale, and is used by some of the fastest growing companies in the world including Amplitude, Snowflake and Qualtrics. The company is backed by Sequoia Capital, Tiger Global, and CMOs of companies such as Uber, Condé Nast and Salesforce. Prior to Mutiny, Jaleh was the Head of Marketing and Business Development at Gusto, where she grew the company from 500 to 50,000 customers over 4 years. She was the Director of Product Marketing at VMware prior to Gusto. 

Discussed in this Episode:

• AI-powered personalization is reshaping B2B sales and marketing
• AI-driven lead scoring improves quality and targets high-value prospects
• AI anticipates and overcomes sales objections in real time
• Sales & marketing alignment: why it matters and how to achieve it
• The risks of AI-driven outbound and how to avoid common pitfalls
• Scaling 1:1 experiences efficiently with AI
• AI-powered buyer interactions and their impact on GTM strategies

Highlights: 

03:27 – Why AI innovation is game-changing for founders building and scaling companies.
 06:49 – How 1:1 sales personalization drives 14x higher conversion rates.
 10:45 – AI-powered hyper-personalization is reshaping enterprise sales.
 16:30 – The biggest AI mistakes in sales and marketing.
 20:55 – Scaling white-glove experiences across all target accounts.
 24:45 – Why CRM data is a mess and how AI finally fixes it.
 28:14 – A masterclass in sales & marketing alignment.
 31:20 – The real reason sales and marketing clash (and how to fix it).
 42:10 – The most valuable AI use cases for B2B sales teams.
 47:30 – How AI is changing B2B buyer behavior and what sellers must do.

Guest Speaker Links (Jaleh Rezaei):

• LinkedIn: https://www.linkedin.com/in/jalehr/
• Mutiny: https://www.mutinyhq.com/
• The State of Sales & Marketing Alignment Report: https://www.mutinyhq.com/report

Host Speaker Links (Scott Barker):

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

Find GTMnow (GTMfund’s Media Brand):

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

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.

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.

Katrina Wong is the CMO of New Relic and a top marketing leader. She specializes in launching products, entering new markets, and scaling companies to the enterprise. With 15 years of experience at Twilio, Zuora, Salesforce, and SAP, she has led award-winning campaigns and helped six companies exit successfully.

Discussed in this Episode:

• Why you should be using "marketing sprints"
• Importance of operational excellence and agility in marketing
• The role of marketing in preparing for a successful exit
• Is 'fire fast' the right approach for managing your teams

Highlights: 

07:08 Secrets to picking winners

09:30 Attaining operational excellence in startups

15:43 Marketing's role in successful exits

29:12 Transforming PIP programs for successful employees

31:26 Challenging the 'fire fast' mentality

35:20 The importance of team dynamics

40:24 Navigating getting acquired successfully

48:58 Tactics for modern marketing

Guest Speaker Links (Katrina Wong):

• LinkedIn: https://www.linkedin.com/in/katrinawong11/
• New Relic Website: https://newrelic.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: 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.

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.

Jordan Crawford is an AI innovator, the Founder of Blueprint, and one of the top go-to-market engineers working today. Jordan explains how to use AI tools like ChatGPT, Deep Research, and Claude to create your own AI workflow for prospecting accounts and creating highly targeted and extremely valuable messages for target decision-makers. Jordan demonstrates how to use the FIND (Focus, Investigate, Narrate, Deploy) process for your go-to-market strategy and how to speed this up with OpenAI's Deep Research AI tool. Jordan also shares the prompts and processes he uses when researching target accounts, messaging buyers, and driving revenue.

Highlights: 

08:12 Examples of messages that people would pay to receive

17:30 How tech is transitioning to an AI-empowered future

27:07 Using ChatGPT Deep Research to learn about customer segments

35:05 Maximizing your sales team's efficiency with AI

36:39 The importance of process over prompts

39:38 Deep dive into prompt engineering

50:00 Future of outbound sales

Guest Speaker Links (Jordan Crawford):

• LinkedIn: https://www.linkedin.com/in/jordancrawford/
• Jordan's AI course: https://www.linkedin.com/posts/jordancrawford_the-299-agent-7-course-is-here-youll-learn-activity-7247669670940401665-xrjq/
• Blueprint: https://blueprintgtm.com/ 
• ChatGPT conversation from the episode (on Gaiia): https://chatgpt.com/share/67a2551e-af74-8004-81b8-b415d473ca72

Host Speaker Links (Scott Barker):

• LinkedIn: www.linkedin.com/in/ssbarker/
• Newsletter: 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: https://www.youtube.com/@GTM_now
• The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/

Sponsor: Superhuman

We recently became a Superhuman customer, and the response across our GTMfund community Slack and social channels was a clear testament to how Superhuman has been a game-changer for efficiency among leaders and teams. 

Superhuman is generously offering the GTMnow community exclusive access to 1 month free on the platform. If you add any teammates in January to your team, they’ll get a free month too.

To claim this offer, go to www.superhuman.com/gtmnow

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.

Casey Woo is the Founder and CEO of Operators Guild, an invite-only community for professionals in strategic finance and operations roles. He is also the General Partner and Founder of FOG Ventures. He is a seasoned, multi-stage operator, bringing over two decades of experience in investment banking advisory, public equity investing, high-growth operational and military leadership roles. His last role was the CFO of Landing, where he oversaw the company’s Finance, Legal and People operations. Prior to Landing, he served as the Global Head of Strategic Finance at WeWork.  ​

Discussed in this Episode:

• The rise of the operator
• How to communicate with CFOs and cross-functional teams
• What matters most to every CEO and founder
• How to recruit the top operators
• Why funding no longer has the impact it once did

Highlights:

08:33 Building effective CFO-CRO relationships.

18:13 The role of cross-functional communication.

26:59 The commoditization of funding.

32:53 The rise top operators and how to recruit them.

38:33 The commoditization of technology in the age of AI.

44:31 The power of community and in-person events.

Guest Speaker Links (Casey Woo):

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

Host Speaker Links (Scott Barker):

• LinkedIn: www.linkedin.com/in/ssbarker/
• Newsletter: 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: https://www.youtube.com/@GTM_now
• The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/

Sponsor: Superhuman

We recently became a Superhuman customer, and the response across our GTMfund community Slack and social channels was a clear testament to how Superhuman has been a game-changer for efficiency among leaders and teams. 

Superhuman is generously offering the GTMnow community exclusive access to 1 month free on the platform. If you add any teammates in January to your team, they’ll get a free month too.

To claim this offer, go to www.superhuman.com/gtmnow

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.

Kraig Swensrud is the Founder & CEO of Qualified where he provides crucial experience and entrepreneurial energy to create the future of enterprise sales tech. Prior to founding Qualified, Kraig founded GetFeedback which was successfully sold to SurveyMonkey. Kraig also led marketing as the CMO of Salesforce during very formative years of the company's history. 

Discussed in this Episode:

• The parallels between the disruption caused by SaaS and AI
• How pricing strategies are changing for AI products
• Why SaaS companies need to earning their renewals
• The impact of AI SDRs on your pipeline

Highlights:
13:26 The importance of product marketing in the growth of Salesforce
20:17 Exploring the innovator's dilemma
25:59 The next generation of software & building for non-human users
39:05 Obsessing over your customers is key to success
46:44 Using the V2MOM framework to drive company alignment
50:43 The adage of 'hire fast, fire fast' is bs

Guest Speaker Links (Kraig Swensrud):
LinkedIn: https://www.linkedin.com/in/kraigswensrud/
V2MOM Framework: https://www.salesforce.com/blog/how-to-create-alignment-within-your-company/

Host Speaker Links (Scott Barker):
LinkedIn: www.linkedin.com/in/ssbarker/
Newsletter: 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: https://www.youtube.com/@GTM_now
The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/

Sponsor Offer:
We recently became a Superhuman customer, and the response across our GTMfund community Slack and social channels was a clear testament to how Superhuman has been a game-changer for efficiency among leaders and teams. 

Superhuman is generously offering the GTMnow community exclusive access to 1 month free on the platform. If you add any teammates in January to your team, they’ll get a free month too.

To claim this offer, go to www.superhuman.com/gtmnow

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.