Brian Weinberger is the Chief Revenue Officer at Sisense, a leading analytics platform helping companies embed intelligence into every product experience. With over 30 years in sales leadership across New York’s tech scene, Brian has built and scaled go-to-market teams at every stage—from early-stage startups to category-defining giants like Yext, Segment, and Salesforce.

Discussed in this episode

• The evolution of partner selling — from VARs to SIs to ecosystems
• How to know if partner selling fits your GTM model
• The delivery-first mindset that drives retention
• Direct vs. partner motion: Microsoft vs. Salesforce
• Why enablement is the #1 green flag for partner success
• Partner marketing: how to make resellers self-sustaining
• Using AI to power future-ready GTM models
• The case for hybrid work in high-performance sales cultures

Episode Highlights

00:00 — The “year four” moment when partners are selling for you

01:07 — 30 years of selling through partners in New York

03:22 — Start partner strategy with delivery, not distribution

06:32 — Why partner selling creates “superhuman” sellers

09:59 — Salesforce vs. Microsoft: direct vs. reseller — and why the future is hybrid

12:13 — The startup hack: sell delivery on your paper, subcontract partners

17:16 — A 90-day playbook for integration partnerships

21:39 — Hiring the right people to build a partner business

27:18 — How Sisense runs delivery partners and an Australian reseller

29:55 — White-labeling Snowflake: using resell to get the giant’s attention

This episode is brought to you by our sponsor: BoomPop

We’re deep in event planning right now, as no doubt many of you are.

Whether it’s an offsite, conference, or any other kind of event, BoomPop makes that happen with end-to-end planning all in one place.

They handle everything from venues to experiences, so you can focus on the delights of meeting in person, not the logistics.

Being part of GTMnow, you’re eligible for full-service event planning for just $99 per person (terms apply). Head to boompop.com/gtmfund to explore seamless support for your events.

Follow Brian Weinberger

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

Recommended Books

• What Great Salespeople Do by Michael Bosworth & Ben Zoldan — The power of storytelling in sales
• The Power of Nice by Linda Kaplan Thaler & Robin Koval — Why kindness compounds in business
• Sacred Hoops by Phil Jackson — Coaching and leadership lessons from the Bulls dynasty

Referenced

• Sisense: https://www.sisense.com
• Snowflake: https://www.snowflake.com
• AWS: https://aws.amazon.com
• Salesforce: https://www.salesforce.com
• Microsoft: https://www.microsoft.com
• Accenture (SI example): https://www.accenture.com

The GTMnow Podcast
The GTMnow 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.

This bonus episode dives into how Cristina Cordova (Stripe’s 20th hire, early leader at Notion, now COO at Linear) spots exceptional talent early, and how she pressure-tests whether a team and product are truly worth betting on. It’s a crisp, tactical look at evaluating “spikiness,” finding beloved products (even with limited data), and building GTM the right way from day one.

Cristina Cordova is a seasoned operator who has scaled some of the most iconic companies in tech. At Stripe, she built and led partnerships that became a foundational revenue engine, including the pivotal deal with Shopify. At Notion, she helped turn viral adoption into a durable distribution strategy powered by community. Today, Cristina is the Chief Operating Officer at Linear, where she’s applying her experience building high-velocity GTM engines to the next generation of developer-first tools.

This is a clip from the full episode with Cristina (an inside look at the judgment frameworks behind Stripe, Notion, and now Linear) and the practical filters every GTM leader can use to pick winners early.

Discussed in This Clip

• How to recognize “exceptional” even outside your own domain
• Finding early proof a product is truly beloved (signals > vanity metrics)
• Starting with a sharp market wedge, then earning the right to expand
• Why founders who excel at something—anything—tend to excel at company-building
• What to expect from early operators: founder mode and bias to execute
• Sales hiring for technical buyers (and why quotas can help earlier than you think)
• Aligning tightly with founders as an exec: relationships drive outcomes
• How to assess GTM on day one: ride-alongs, raw customer feedback, ground truth

Highlights

00:00 — The difference between good and great—and how to spot it across functions

00:12 — Why this clip hit: Cristina’s framework for identifying exceptional people early

01:17 — Looking for skills you don’t have—and recognizing greatness outside your lane

03:38 — Evidence a product is beloved (Stripe on Hacker News, Notion on Twitter)

04:49 — Start with a wedge; win big later (why early enterprise skeptics don’t matter)

07:54 — “Spikiness” and unconventional signals of excellence (Minecraft servers to sales)

12:52 — What great early leaders do: see problems, create strategy, then execute

16:45 — Sales at product-led companies: hire technical sellers, set quotas sooner

21:31 — How Cristina assesses GTM on day one: ride-alongs, direct customer observation

This episode is brought to you by our sponsor: BoomPop

We’re deep in event planning right now, as no doubt many of you are.

Whether it’s an offsite, conference, or any other kind of event, BoomPop makes that happen with end-to-end planning all in one place.

They handle everything from venues to experiences, so you can focus on the delights of meeting in person, not the logistics.

Being part of GTMnow, you’re eligible for full-service event planning for just $99 per person (terms apply). Head to boompop.com/gtmfund to explore seamless support for your events.

The GTMnow Podcast
The GTMnow 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.

Alex Clayton is one of the clearest minds in growth-stage investing, the person elite founders turn to when the market is noisy and the stakes are high. A General Partner at Meritech Capital, Alex has built a reputation for breaking down complex businesses with uncommon clarity, from his legendary S-1 teardowns to his frameworks on power laws, secondaries, and AI-native growth. Before Meritech, he honed his craft at Spark Capital and Redpoint, backing breakout companies like Braze, JFrog, Outreach, Pendo, Duo Security, and RelateIQ. A former ATP tennis pro and Stanford team captain, Alex brings that same discipline, pattern recognition, and competitive fire to evaluating the next generational companies.

Discussed in this episode

• Why GAAP revenue and cash burn are the two metrics that quietly govern everything.
• How AI is changing growth rates, margins, and what “good” looks like in SaaS.
• The rise of secondaries, and why they now rival or exceed IPO volume.
• How to read an S-1 like a pro (and what Alex looks for first).
• Founder ownership, fund lifecycles, and how long companies really stay private.
• Why power laws in venture are getting even steeper in the AI era.
• How AI is reshaping pricing models from seats to usage and outcomes.
• Which iconic private companies are most likely to go public in the next 3 years.

Episode highlights

02:40 — Is the IPO window really back? 

05:10 — Secondaries quietly outpacing IPOs

08:10 — The only two metrics that matter

10:56 — AI growth that breaks SaaS mental models

26:20 — From “software” to “SaaS” to “AI”… and back again

29:25 — Seat-based pricing vs outcome-based AI pricing

34:55 — The capital tidal wave & longer private lives

44:00 — Bubble vs biggest opportunity of our careers

57:17 — What the rest of the 2020s look like

1:03:41 — Why GAAP revenue + cash burn still win

Brought to you by: AngelList

How did we build the GTMfund back office? Easy!

We leveraged AngelList’s Rolling Fund product for Fund I, which was the perfect vehicle to scale up GTMfund in its first iteration. This structure allowed us to build our network, and add revenue leaders while we raised and deployed capital simultaneously, which was crucial for getting early points on the board and building relationships with founders.

For Fund II, we transitioned to a traditional closed-end fund structure through AngelList. This time with institutional investor support. This model allowed us to be more intentional about our portfolio construction. We worked closely with the AngelList team throughout this process, and they were incredible — always there to support us and our LPs every step of the way.

If you’re raising a fund or are looking to migrate your fund, we highly recommend you check them out. You can do so at www.angellist.com/gtmfund.

Follow Alex Clayton

• LinkedIn: https://www.linkedin.com/in/aclayton
• X (Twitter): https://x.com/afc

Follow Max Altschuler (Host)

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

The GTMnow Podcast
The GTMnow 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.

Chris Degnan is the former Chief Revenue Officer of Snowflake, where he helped scale the company from pre-product to over $4B in ARR and more than $100B in market cap. Over his 11-year tenure, Chris built Snowflake’s go-to-market engine from the ground up, from personally running the first outbound campaigns to leading a global sales organization through four CEOs and one of the largest software IPOs in history.

Today, he advises founders and revenue leaders on how to build high-velocity GTM teams, hire with grit, and scale with discipline. Chris is also the co-author of Make It Snow, the definitive playbook on Snowflake’s go-to-market journey, co-written with CMO Denise Persson.

Discussed in this episode

• The early days of Snowflake: selling a stealth startup with no product
• How to hire and identify truly self-motivated, gritty sales talent
• The lessons from John McMahon that shaped Snowflake’s leadership DNA
• How to build sales-marketing alignment that actually scales
• The near-death experiences that almost killed Snowflake
• What great CEOs do differently, from Muglia to Slootman
• The power of focusing on new logo acquisition
• The evolution of sales methodologies: MEDDPICC, culture, and curiosity
• The truth about AI’s “bubble”, and what’s real beneath the hype

Episode highlights

00:02:21 — Why join Snowflake pre-product and in stealth.

00:05:36 — The original outreach script and what resonated with prospects.

00:06:49 — Scaling from lists to SDRs; Degnan’s “8 meetings per week” rule.

00:09:11 — Hiring for self-starters; the interview opener: “Tell me your life story.”

00:12:49 — The feedback loop that kept a CRO in seat for 11 years.

00:24:46 — The outage that almost killed Snowflake, and how leadership showed up.

00:28:34 — New logo gates every quarter and why it mattered more than anything.

00:34:05 — “Customer success is everyone’s job”: removing CS, monetizing PS, driving adoption.

00:36:40 — Databricks: where Snowflake ceded ground and what they’d do differently.

00:39:19 — Why going public was the right move for enterprise trust.

This episode is brought to you by our sponsor: BoomPop

We’re deep in event planning right now, as no doubt many of you are.

Whether it’s an offsite, conference, or any other kind of event,BoomPop makes that happen with end-to-end planning all in one place.

They handle everything from venues to experiences, so you can focus on the delights of meeting in person, not the logistics.

Being part of GTMnow, you’re eligible for full-service event planning for just $99 per person (terms apply). Head to boompop.com/gtmfund to explore seamless support for your events.

Follow Chris Degnan

• LinkedIn:
• https://www.linkedin.com/in/chris-degnan-524470Make It Snow (book):https://makeitsnowbook.com

The GTMnow Podcast
The GTMnow 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.

Michel Tricot is the co-founder and CEO of Airbyte, the open-source data movement platform he launched in 2020. Before Airbyte, Michel led integrations and served as Director of Engineering at LiveRamp, where he scaled the teams and pipelines that synced massive data volumes. He also helped build rideOS as a founding engineer and Director of Engineering. Michel has spent 15+ years in data infrastructure, with a focus on commoditizing data pipelines and giving teams control and sovereignty over their data. 

Discussed in this episode

• Why Airbyte launched open source first (catching engineers “at the search”)
• Project-market fit vs. product-market fit, and why they’re different
• The content engine: founder-led writing, shipping slides, and radical transparency
• Turning interest into community: 25k+ Slack, champions, and hiring from within
• The near-misses: hiring ahead of PMF, support-heavy community, cloud complexity
• Going upmarket: enterprise motion, longer cycles, and team ramp realities
• AI wave → agents as “data consumers” and what it means for pipelines
• Replatforming for control & sovereignty, not just “more connectors”

This episode is brought to you by our sponsor: ZoomInfo

ZoomInfo is the GTM Intelligence Platform built for sales, marketing, and RevOps.

By unifying data, workflows, and insights into a single system, ZoomInfo helps revenue teams find and engage the right buyers, launch go-to-market plays faster, and drive predictable growth. With industry-leading accuracy and depth of data, it gives your team the intelligence advantage to win in competitive markets.

It’s trusted by the fastest-growing companies and has become the category leader in GTM Intelligence.

Learn more at zoominfo.com.

Follow Michel Tricot

• LinkedIn:https://www.linkedin.com/in/micheltricot
• X (Twitter):https://x.com/MichelTricot
• Website:https://airbyte.com/Airbyte

Host links

• LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
• X (Twitter): https://x.com/sophiebuona
• Newsletter: https://thegtmnewsletter.substack.com/
• Website: https://gtmnow.com/

Where to Find GTMnow

• Website: https://gtmnow.com
• LinkedIn: https://www.linkedin.com/company/gtmnow
• X (Twitter): https://x.com/GTMnow_
• YouTube: https://www.youtube.com/@GTM_now
• Podcast Directory: https://gtmnow.com/tag/podcast

The GTMnow Podcast
The GTMnow 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.

Tessa Whittaker is the VP of Revenue Operations at ZoomInfo, where she leads a 70-person global team powering one of SaaS’s most efficient $1B+ revenue engines. Over the past decade, she’s helped architect the systems, cadence, and AI workflows that underpin how ZoomInfo operates at scale.

Tessa is known as one of the most thoughtful operators in tech, bringing structure, clarity, and rigor to how GTM organizations run. Her work sits at the intersection of data, process, and execution, proving that with the right operating cadence, even the most complex go-to-market systems can move in rhythm.

Discussed in this episode

• Building a personal operating system (Salesforce's V2MOM, Notion, weekly reviews) that maps vision → methods → measurable actions.
• “Operating rhythm” for GTM: the meetings, reviews, and enablement that create predictable execution.
• Color-coding calendars to align time with quarterly KPIs (and fixing misallocation).
• Counterintuitive up-market move: automate down-market so scarce humans focus on enterprise.
• AI intake & prioritization agent: compressing 10–15 hrs of RevOps scoping into one interaction.
• Democratizing creation: org-wide agent “hackathons,” usage leaderboards, and adoption lessons.
• Health OS during sprints: cut alcohol, protect sleep, simplify to sustain output.
• What to buy vs. build; auditing tech stacks; avoiding (and accepting some) agent sprawl.

Episode highlights

00:00 — Systems beat motivation; why cadence creates consistency.

01:36 — RevOps as connective tissue of SaaS; the “invest earlier” regret.

03:58 — From EA to SVP-level ops leader to VP RevOps: the long workback.

06:51 — Why operators obsess over simplifying complexity.

12:24 — Time as the scarcest resource: color-coding calendars to goals.

20:05 — The RevOps operating rhythm at ZoomInfo (and how AI slots in).

21:48 — Going upmarket? Automate downmarket first to free resources.

31:19 — Intake agent: collapsing 10–15 hours of back-and-forth into one interaction.

36:48 — Democratizing creation: internal agent hackathons and a usage leaderboard.

44:30 — The Alchemist and reframing growth: get uncomfortable to keep climbing.

This episode is brought to you by our sponsors

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.

Guest links

•  LinkedIn: https://www.linkedin.com/in/tessa-whittaker-44903940

Where to Find GTMnow

• Website: https://gtmnow.com/
• LinkedIn: https://www.linkedin.com/company/gtmnow/
• X (Twitter):https://x.com/GTMnow_
• YouTube: https://www.youtube.com/@GTM_now
• The GTM Podcast: https://gtmnow.com/tag/podcast/

The GTMnow Podcast
The GTMnow 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.

Peter Grant is the Chief Revenue Officer at You.com, the AI search and productivity platform reshaping how people find and create information. A veteran GTM leader, Peter has built and scaled revenue engines at some of tech’s most iconic companies — from Siebel Systems to Salesforce to C3.ai — working directly under legends like Tom Siebel and Marc Benioff. Today, he’s leading You.com’s charge against giants like OpenAI and Google, bringing precision, storytelling, and speed to the most transformative era in technology.

Discussed in this episode

• How Peter defines “the biggest opportunity of our lifetime” in AI
• Lessons from working under Tom Siebel, Marc Benioff, and Rishi Khosla
• How to hire SEAL-Team-Six-level GTM talent
• Why belief and speed are non-negotiables when competing with giants
• You.com’s differentiation strategy against OpenAI and Google
• How to operationalize AI literacy and agentic workflows
• The ROI gap in generative AI adoption, and how to fix it
• Building products that stand on truth

Episode Highlights

00:14 — The biggest opportunity in technology this century

05:25 — Lessons from working directly with Thomas Siebel

06:41 — How to hire “SEAL Team Six” sales talent

10:24 — Why “train hard, fight easy” defines great enablement

20:08 — The new sophistication bar for AI literacy in sales

25:14 — How You.com differentiates against OpenAI & Google

30:00 — Peter’s personal AI productivity system: 40 agents

40:12 — Speed, truth, and trust: You.com’s go-to-market culture

48:30 — The “war room” story: building a sales plan overnight

59:45 — No easy days: why startup life mirrors special forces

This episode is brought to you by our sponsor: BoomPop

A quick pause to spotlight a partner that helps GTM teams actually connect—BoomPop.

Your next big unlock might not come from another meeting… it’s from getting your team in the same room. BoomPop makes that happen with end-to-end offsite planning all in one place.

They handle everything from venues to experiences, so you can focus on the delights of meeting in person, not the logistics.

And as a listener of GTMfund, you’re eligible for full-service event planning for just $99 per person (terms apply).

Head to boompop.com/gtmfund to start planning your offsite.

Guest Links

• LinkedIn: linkedin.com/in/peterkgrant
• Company: you.com

Recommended Books

• The Hard Thing About Hard Things by Ben Horowitz
• Elephants Can’t Dance by Louis V. Gerstner Jr.
• The Master Algorithm by Pedro Domingos
• No Easy Day by Mark Owen — a favorite for its lessons on grit and resilience

The GTMnow Podcast
The GTMnow 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.

This bonus episode dives into how Rick Kelley helped scale Meta’s global sales organization (from 900 employees to 90,000) and the playbook behind building high-performing international teams.

Rick Kelley is the former SVP of Gaming and App Monetization Solutions at Meta and Managing Director of Meta Ireland, where he led a $1B+ revenue organization and played a pivotal role in building out Meta’s go-to-market teams across North America and EMEA. Over his 15-year career at Meta, Rick was instrumental in driving international expansion, especially across Europe, the Middle East, and Africa—helping to localize strategy, scale high-performing sales teams, and bring new ad products to market. Today, he advises founders on global GTM execution, sales hiring, and how AI is reshaping the future of commercial organizations.

This is a clip from the full episode with Rick, an inside look at how Meta built its $1B EMEA business and the lessons every GTM leader can apply to scale globally.

Discussed in This Clip:

• The exact framework Rick used to decide which EMEA markets to enter first
• How Meta built a $1B+ regional business from just three salespeople
• The power of centralization in early-stage go-to-market
• Why you should plan every headcount allocation before hiring
• Creating “optionality” in your sales org to weather change
• How gaming became Meta’s fifth global region
• When to localize sales teams versus staying centralized
• Why AI can make sales more efficient—but can’t replace relationships

Highlights

00:12 — Scaling Meta: from 900 to 90,000 employees

01:22 — How Rick Kelley built Meta’s mid-market sales org from scratch

02:15 — The data-driven framework Meta used to prioritize global markets

04:50 — Why startups should build expansion plans before executing

07:52 — Centralized vs. in-country hiring: Rick’s take for startups

09:49 — The importance of sales ops and forecasting discipline

13:32 — Hiring leaders who scale with you, not limit you

14:59 — How AI will reshape (but not replace) sales relationships

16:09 — From zero to $1B: lessons in efficiency, cost, and culture

This Episode Is Brought to You By

ZoomInfo is the GTM Intelligence Platform built for sales, marketing, and RevOps. 

By unifying data, workflows, and insights into a single system, ZoomInfo helps revenue teams find and engage the right buyers, launch go-to-market plays faster, and drive predictable growth. With industry-leading accuracy and depth of data, it gives your team the intelligence advantage to win in competitive markets.

It’s trusted by the fastest-growing companies and has become the category leader in GTM Intelligence.

Learn more at zoominfo.com.

Follow Rick Kelley

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

The GTMnow Podcast
The GTMnow 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.

Guy Yalif is Chief Evangelist at Webflow and a veteran B2B marketing leader with 20+ years across Twitter, Yahoo, BrightRoll, and as co-founder/CEO of Intellimize (acquired by Webflow). He champions AI-driven optimization for sites and content, bringing a rare blend of aerospace-engineer rigor and operator experience from four successful exits to help teams win the shift from SEO to AEO.

Discussed in this episode

• Why AEO is an evolution of SEO (and what truly changes)
• The shift from keywords to “clusters of questions” as the new topic model
• Webflow’s four-part AEO framework: content, technical, authority, measurement
• Tactics that moved the needle: adding FAQs + schema; prioritizing freshness
• Why PR/brand and plain-text mentions matter more to AI engines
• How to measure AEO: presence in questions, share of voice, and sentiment
• Where to start: two moves any founder can ship this week
• Risks of ignoring AEO and the early-adopter advantage

Episode highlights

00:21 — “Your SEO resources are your AEO resources. This is an evolution, not a reset.”

01:15 — Webflow’s AEO promise: answer engines are a massive arbitrage—akin to early SEO/SEM/mobile.

03:00 — Why “ranking for keywords” is obsolete; topics = clusters of questions across the funnel.

07:49 — The 4-part AEO framework: content, technical (schema & structure), authority, measurement.

10:11 — Case study: Add ~6 FAQs + inline schema to product pages → half of new citations came from 6 pages; +24% organic in 2 weeks.

15:23 — If you only do two things: (1) answer questions comprehensively, (2) add schema metadata.

21:46 — Webflow data: AI-search traffic converts ~6x better than non-branded organic; unbranded share grew from 0% → 42% in a year.

24:02 — How buyers actually use LLMs in-flow; why your website still matters (to humans and machines).

29:58 — The learning curve is back: why AEO is resetting the playing field and rewarding curiosity.

This episode is brought to you by our sponsor:

ZoomInfo is the GTM Intelligence Platform built for sales, marketing, and RevOps.

By unifying data, workflows, and insights into a single system, ZoomInfo helps revenue teams find and engage the right buyers, launch go-to-market plays faster, and drive predictable growth.

With industry-leading accuracy and depth of data, it gives your team the intelligence advantage to win in competitive markets.

It’s trusted by the fastest-growing companies and has become the category leader in GTM Intelligence.

Learn more at zoominfo.com.

Follow Guy Yalif:

• LinkedIn: https://www.linkedin.com/in/gyalif/
• X (Twitter): https://x.com/gyalifX (formerly Twitter)
• Webflow author page: https://webflow.com/people/guy-yalif

The GTMnow Podcast
The GTMnow 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.

Kieran Flanagan is the SVP of Marketing at HubSpot and Co-Host of Marketing Against the Grain. A longtime operator and investor, he’s at the forefront of how AI is reshaping go-to-market. With a background in engineering and years leading growth and marketing teams, Kieran now spends his time building, experimenting, and sharing lessons on how prompting, agents, and personality-led growth will define the next era of software companies.

Discussed in this episode

• Why prompting and context engineering are the most important skills for GTM operators
• How “vibe prompting” accelerates learning and output with LLMs
• The three keys to building AI fluency inside teams
• Measuring ROI from AI across sales, marketing, and operations
• Why every professional is now a manager (of AI agents)
• How websites will evolve into multimodal closing mechanisms
• The rise of personality-led growth in B2B marketing
• Why curiosity and persistence matter more than ever in an AI-first world

Episode highlights

00:46 — The 100x difference between good and bad prompting

03:57 — The rise of “context engineering” as a GTM skill

07:22 — Kieran’s 3-part framework for AI fluency inside teams

09:31 — Why “vibe prompting” is as powerful as vibe coding

11:00 — How AI boosts conversions & deal velocity in sales workflows

15:10 — Using ChatGPT memory as a personalized prompting coach

22:19 — Everyone now manages a PhD-level AI intern

31:12 — The 3 biggest shifts coming to GTM: influence, AI optimization, multimodal

37:42 — Why AI makes human creativity more valuable than ever

43:06 — The grind, reps, and curiosity as the ultimate AI skills

Brought to you by: Mutiny

Are you a B2B Marketer running campaigns for target accounts? Then you know the struggle: tedious and manual processes, endless delays to get things live, and sales feeling like you’re not doing enough.

That’s where Mutiny comes in. Mutiny is the fastest place to launch breakthrough campaigns for your target accounts. 

AI agents research your accounts, build personalized landing pages, and scale everything from LinkedIn ads to sales handoffs, all in one seamless workflow. No more stitching tools together. Just smarter, more impactful campaigns powered by real data. Launch in days, not weeks.

See why teams who use Mutiny generate 3X more account engagement.

Book a demo at mutinyhq.com

Guest links

LinkedIn: https://www.linkedin.com/in/kieranjflanagan/
Newsletter (The AI Marketing Generalist):https://www.kieranflanagan.io/
Podcast (Marketing Against the Grain):https://www.youtube.com/@MATGpod/videos

Host links

LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
X (Twitter): https://x.com/sophiebuona
Newsletter: https://thegtmnewsletter.substack.com/
Website: https://gtmnow.com

The GTMnow Podcast
The GTMnow 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.