The GTMnow Podcast

Okta's CRO Jon Addison joins GTMnow host Sophie to break down the full story behind Okta's remarkable revenue turnaround, the launch of Okta for AI Agents, and the go-to-market playbook that's carrying them from $3B toward a $5B ARR target.

From nearly $850M in operating losses to over $760M in operating income, Okta's transformation is one of the most significant turnaround stories in enterprise SaaS. In this episode, Jon pulls back the curtain on exactly how it happened.

In this episode:
- Why 91% of enterprises are already deploying AI agents but only 10% have a security strategy for them
- How Okta's "AI governance gap" insight became the foundation for their biggest product launch in years: Okta for AI Agents
- The GTM restructure around specialization that unlocked productivity and drove 40% higher average contract value on new product deals
- How Okta became a partner-first company: 95% of their top 100 deals in the last fiscal year were partner-led, and what operationally made that possible
- Why the first discovery call no longer exists, and how sellers need to show up differently in the AI era
- Jon's new internal sales methodology, APEX, built on Command of the Message for the AI era
- How Okta is using AI internally to transform their own go-to-market motion, from conversational intelligence to pre-sales assistants
- What the path to $5B ARR actually looks like: enterprise expansion, international growth, public sector, and the massive new TAM unlocked by non-human identity
- Jon's leadership philosophy: why human-centric selling is becoming more critical as AI takes over the repetitive work

Host: Sophie Buonassisi, SVP Marketing at GTMnow
https://www.linkedin.com/in/sophiebuonassisi

Guest: Jon Addison, CRO at Okta
https://www.linkedin.com/in/jon-addison-3399175

Timestamp:
0:00 - Cold open
1:19 - Welcome + Jon's background: from London to Silicon Valley
1:52 - How Jon got into software and identity management
4:08 - Okta for AI Agents launch announcement
5:04 - 90% of customers live with agents, only 10% confident in securing them
6:31 - What's driving the governance gap in the market
7:53 - Speed of agent innovation must be matched by security and governance
8:36 - 40% higher ACV on deals that include new products
9:43 - Why consolidation around a single identity platform is resonating
11:45 - How AI agents unlock a massive new TAM for Okta
13:05 - Okta's turnaround: from $850M operating losses to $760M operating income
13:36 - Key decision 1: GTM specialization drove productivity
15:02 - Key decision 2: becoming a partner-first company
16:14 - What cracking the partner-led model actually looks like
19:08 - How long it takes to see ROI from a partner-led pivot
20:12 - The path from $3B to $5B: enterprise, international, public sector
21:49 - Using AI internally: launching "Apex," the AI-era sales methodology
23:04 - What the Apex sales methodology entails
24:25 - Buyers now show up with strong opinions before the first call
25:44 - How discovery is changing: human-centric selling in the AI era
27:33 - Headcount and AI: what skills matter in the future
29:31 - Why relationships are Okta's core competitive advantage
30:36 - The role of experiences: F1, events, and the 7-touchpoint rule
31:47 - Broad GTM surface area: ABM, ecosys
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.

Jennifer Li, Partner at Andreessen Horowitz (a16z), breaks down why the firm allocated $1.7 billion of its latest $15 billion fund specifically toward AI infrastructure, and what she's betting on next.

Jennifer has backed ElevenLabs from Series A all the way through Series D, watching it grow to an $11 billion valuation. In this episode, she explains what she saw in voice AI before anyone else did, what makes a founder worth backing regardless of the tech, and why the next wave of AI infrastructure is being rebuilt from the ground up.

In this episode:
- Why a16z bet $1.7B on AI infrastructure (and why now)
- The shift from cloud to AI-native infrastructure: storage, compute, orchestration, memory
- How ElevenLabs crossed the uncanny valley in synthetic voice
- Voice agents as the first AI category to truly scale in the enterprise
- What "king-making" in AI go-to-market actually looks like
- The traits that made Jennifer write a check for ElevenLabs on founder conviction alone
- Open source vs. frontier models: what 2027 looks like
- Why world models and vision language models are the next unlock
- AI and human creativity: why directors and authors won't be replaced
- How a 1-2 person studio can now make a full movie

Host: Sophie Buonassisi, SVP Marketing at GTMnow
https://www.linkedin.com/in/sophiebuonassisi

Guest: Jennifer Li, General Partner at Andreessen Horowitz
https://www.linkedin.com/in/jenniferhli/
https://x.com/JenniferHli

Connect with Max: 
https://x.com/hackitmax
https://www.linkedin.com/in/maxaltschuler

Connect with Paul:
https://x.com/PaulGTM
https://www.linkedin.com/in/paulsirving

Timestamps:
0:00 - Cold open
1:06 - Max & Paul intro: are we in a bubble?
1:46 - AI vs. dot-com era: the key differences
4:55 - B2B SaaS disruption and value destruction (Thoma Bravo / Medallia)
6:39 - Intercom / Finn: crossing the chasm from legacy to AI-native
8:08 - Introducing Jennifer Lee, a16z General Partner
8:31 - Paul's key takeaway: the distribution era
9:41 - Why speed to default brand has never mattered more
11:33 - The ElevenLabs story: a16z led Series A, B, and C
12:02 - Why the seed strategy still works
13:37 - What the best founders do differently with model capabilities
15:58 - Jennifer Lee joins: why a16z raised $1.7B for infrastructure
16:22 - What existing infrastructure is being rebuilt for AI
19:19 - Specific areas a16z is focused on: models, storage, dev tools, security
20:35 - 90%+ of code now written by agents
21:52 - What Jennifer saw early in the 11 Labs / voice AI space
25:19 - Go-to-market in AI infrastructure: what's working
27:29 - Becoming the default brand: the "Kleenex effect" in AI
28:37 - What makes a founder worth backing on conviction alone
30:48 - Predictions for 2026/2027: open source catching up fast
31:39 - Most exciting new modalities: world models and vision language models
32:07 - AI and human creativity: can they coexist?
34:42 - What's blocking the creative AI future
36:05 - "The best ideas live in the graveyard"
36:57 - Closing advice: make AI tools your friends

Visit us on: https://gtmnow.com
Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow
Follow us on X (Twitter): https://x.com/GTMnow_
Follow us on
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.

Kyle Parrish joined Figma as the first-ever sales hire when the company was doing $2M in ARR and helped scale it to $950M ARR. Figma then went on to IPO (FIG).
But the path there was anything but smooth.

In this episode, Kyle breaks down what it actually took to build Figma's enterprise sales motion from scratch, including the no-discount rule that made procurement teams furious, the 40-hour interview weeks when hiring felt impossible to keep up with, and what it was like to lead a 300-person team through a failed $20B Adobe acquisition, and then have their best year immediately after.

We cover:
- Why Figma refused to discount, even when Microsoft pushed back
- How to hire the right first sales rep as a founder
- The PLG to enterprise transition most companies get wrong
- What the Adobe deal collapse actually felt like from the inside
- How Figma went from 3 products to 8 overnight and launched into an IPO
- What great sales look like in the AI era

Timestamp:
0:00 – Intro
1:02 – Guest intro: Kyle Parrish
1:35 – Joining Figma at $2M ARR in 2018
5:01 – First meeting with Dylan (Figma CEO)
6:13 – How to find your first sales hire
9:05 – Stage alignment in early hiring
11:43 – Early-stage operators need "scar tissue"
13:19 – Northstar metric at Figma
14:13 – Obsessing over customer conversations
16:44 – Building Figma's brand through community
17:31 – Scaling the "unscalable"
20:08 – In-person GTM vs. digital
22:47 – Was there a moment Figma might not make it?
24:48 – Pivoting after the Adobe deal collapsed
28:10 – Figma's no-discount rule
31:05 – Enterprise ELAs replacing discounting
34:47 – What makes a great salesperson in the AI era
36:56 – Missionaries vs. mercenaries in AI-era GTM
39:47 – Spotting the next Dropbox or Figma
43:46 – Kyle's post-Figma investing focus
45:58 – Family, travel & what's next

Guest: Kyle Parrish, former VP Sales at Figma
LinkedIn: https://www.linkedin.com/in/kparrish8/
X: https://x.com/KyleHParrish

Host: Sophie Buonassisi, SVP Marketing at GTMnow
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
X: https://x.com/sophiebuona

Visit us on: https://gtmnow.com
Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow
Follow us on X (Twitter): https://x.com/GTMnow_
Follow us on YouTube: https://www.youtube.com/@GTM_now
Follow us on TikTok: https://www.tiktok.com/@gtmnow_
Follow us on Instagram: https://www.instagram.com/gtmnow_/

Sponsors:
Nooks - the AI workspace for outbound teams: https://www.nooks.ai/gtmfund

.Tech - Domains, where the next generation of builders is planting their flag. Secure your .tech domain today from any registrar of your choice.

Transcript available under the episode here: https://gtmnow.com/tag/podcast/

Subscribe to GTMnow for the latest episodes! https://gtmnow.com
For inquiries about sponsoring the podcast, email [email protected]
GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.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.

Kyle Parrish joined Figma as the first-ever sales hire when the company was doing $2M in ARR and helped scale it to $950M ARR. Figma then went on to IPO (FIG). 
But the path there was anything but smooth.

In this episode, Kyle breaks down what it actually took to build Figma's enterprise sales motion from scratch, including the no-discount rule that made procurement teams furious, the 40-hour interview weeks when hiring felt impossible to keep up with, and what it was like to lead a 300-person team through a failed $20B Adobe acquisition, and then have their best year immediately after.

We cover:
- Why Figma refused to discount, even when Microsoft pushed back
- How to hire the right first sales rep as a founder
- The PLG to enterprise transition most companies get wrong
- What the Adobe deal collapse actually felt like from the inside
- How Figma went from 3 products to 8 overnight and launched into an IPO
- What great sales look like in the AI era

Timestamp:
0:00 – Intro 
1:02 – Guest intro: Kyle Parrish 
1:35 – Joining Figma at $2M ARR in 2018 
5:01 – First meeting with Dylan (Figma CEO) 
6:13 – How to find your first sales hire 
9:05 – Stage alignment in early hiring 
11:43 – Early-stage operators need "scar tissue" 
13:19 – Northstar metric at Figma 
14:13 – Obsessing over customer conversations 
16:44 – Building Figma's brand through community 
17:31 – Scaling the "unscalable" 
20:08 – In-person GTM vs. digital 
22:47 – Was there a moment Figma might not make it? 
24:48 – Pivoting after the Adobe deal collapsed 
28:10 – Figma's no-discount rule 
31:05 – Enterprise ELAs replacing discounting 
34:47 – What makes a great salesperson in the AI era 
36:56 – Missionaries vs. mercenaries in AI-era GTM 
39:47 – Spotting the next Dropbox or Figma 
43:46 – Kyle's post-Figma investing focus 
45:58 – Family, travel & what's next

Guest: Kyle Parrish, former VP Sales at Figma 
LinkedIn: https://www.linkedin.com/in/kparrish8/
X: https://x.com/KyleHParrish

Host: Sophie Buonassisi, SVP Marketing at GTMnow
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
X: https://x.com/sophiebuona

Visit us on: https://gtmnow.com
Follow us on LinkedIn: https://www.linkedin.com/company/gtmnow
Follow us on X (Twitter): https://x.com/GTMnow_
Follow us on YouTube: https://www.youtube.com/@GTM_now
Follow us on TikTok: https://www.tiktok.com/@gtmnow_
Follow us on Instagram: https://www.instagram.com/gtmnow_/

Sponsors: 
Nooks - the AI workspace for outbound teams: https://www.nooks.ai/gtmfund
.Tech - Domains, where the next generation of builders is planting their flag. Secure your .tech domain today from any registrar of your choice. 

Transcript available under the episode here: https://gtmnow.com/tag/podcast/

Subscribe to GTMnow for the latest episodes! https://gtmnow.com

For inquiries about sponsoring the podcast, email [email protected]

GTMnow is a media brand brought to you by VC firm, GTMfund: https://gtmfund.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 intere
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.

AI isn't just changing how we sell. It's changing how buyers make decisions before they ever talk to you.
Sam, Founder and CEO of Test Box, joins Sophie on GTMnow to break down exactly what's happening to the B2B software buying process right now, and what go-to-market leaders need to do about it immediately.
If you're a founder, CRO, or AE wondering why your pipeline feels different, this conversation will give you a clear framework for what's happening and what to do next.
What we cover:
Why 70-80% of purchase decisions are already made before the first call (and it's accelerating)
The shift from discovery calls to validation calls, and how to prepare
CEO (AI-version of SEO): how LLMs are shaping what buyers believe about your product
The "day one shortlist" shrinking from 3-4 vendors to 1-2 vendors
Agent-to-agent procurement: Sam's timeline for when AI agents fully take over buying
Why the mid-funnel is actually getting longer, not shorter
The "Fake Nothing, Prove Everything" campaign that went viral post-Series A
How Test Box runs 15 AI experiments per week across the entire company
Using Google Vertex video analysis to read prospect body language on sales calls
How to build an AI-first culture without burning out your team
Books: The 15 Commitments of Conscious Leadership, No Ego, Courageous Marketing, Good to Great

Timestamps:0:00 - Cold open
1:09 - What Test Box does
2:43 - How buying has changed
5:48 - What founders/CROs should do now
7:05 - GEO: AI version of SEO
9:02 - Why mid-funnel is expanding
21:17 - Agent-to-agent procurement
26:02 - All procurement by agents in 3-5 years
29:09 - How vendors differentiate beyond product
33:30 - The croissant campaign breakdown
45:50 - 15 AI experiments per week
47:10 - Analyzing prospects via video AI
48:29 - Building AI culture in your team
52:39 - Book recommendations

Guest: Sam Senior, Founder and CEO TestBox
Linkedin: ⁠https://www.linkedin.com/in/samuelsenior/⁠
Test Box:⁠ https://www.testbox.com⁠

Host: Sophie Buonassisi, SVP Marketing at GTMnow
LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/

Newsletter:⁠ https://thegtmnewsletter.substack.com⁠
Visit us on:⁠ https://gtmnow.com⁠
Follow us on LinkedIn: / gtmnow
Follow us on X (Twitter):⁠ https://x.com/GTMnow_⁠ 
Fo
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.