Justin sits down with Allison Skidmore, Chief Customer Officer at Optimizely, the world's first operating system for marketing teams.

Allison brings a rich perspective shaped by stints at Adobe, Stackla, Gigya, and SAP across Asia Pacific before landing in the US to lead customer success at Optimizely. This episode explores how AI is fundamentally reshaping the marketer's daily workflow, what great onboarding looks like in an AI-native world, and what the CCO role must become as organizations race to stay ahead.

Episode Notes & Key Topics

1. Allison's Career Journey

• Started in SEM at a Sydney agency later acquired by Adobe, rode the wave of digital marketing's early SaaS transition.
• Spent six years at Adobe running customer success across Asia Pacific, building offshore teams and subscription services models.
• Moved through Stackla and Gigya (acquired by SAP nine months in), then scaled the CS role across all SAP lines of business in APAC.
• Joined Optimizely two years ago after reconnecting with CEO Alex Atzberger, bringing global enterprise CS experience to a fast-growing martech platform.

2. What Stays the Same in Customer Success

• The sales-to-CS handover friction is timeless: it never goes away regardless of company size or stage.
• Digital-first customer engagement (email, offshore teams, automation) has been a constant scaling challenge for decades.
• The shift from time-and-materials professional services to subscription models remains a dominant trend.
• Tech advancements create the inflection points: AI is today's example.

3. AI and the Marketer's Day-in-the-Life

• Allison paints a vivid picture: by 10 AM, an AI-enabled marketer has completed a full week's worth of work.
• Optimizely's Opal AI product is provisioned across the entire team, enabling agent building, workflow automation, and access to tools like Claude and Gemini.
• The opportunity is not just efficiency, it's the ability to pull forward backlogged work and shrink implementation timelines (e.g., from 12 months to 3).
• The companies moving fastest are the ones blocking calendar time to train their teams on prompting and agent-building, not just giving access.

4. Reimagining Onboarding and the Customer Journey

• Allison's framework: great onboarding is the seamless alignment of three channels, human-to-human touchpoints, email marketing, and in-product experience.
• Customers now expect to self-serve answers (just like asking AI instead of calling a mechanic), human-heavy onboarding alone no longer cuts it.
• Consistency is the key: the message the customer gets in the product, in their inbox, and from their CSM should be identical, no basic repeats, no skipped steps.

5. The Evolving Role of the CCO

• The C-suite fundamentals don't change: stay curious, solve problems, skate to where the puck is going.
• Today, the puck is AI. If you can't build an agent, you can't expect your team to.
• Allison is actively realigning roles, KPIs, and commissions around AI-native execution.
• The CCO who can't leverage AI to scale themselves and reimagine their business will become extinct, just like Blockbuster.
• Lego is the positive model: reinvention again and again.

6. What's Top of Mind for 2026

• AI continues to dominate, but the customer journey evolution is a close second.
• Consumers are shifting from Google to ChatGPT and similar tools, which means brands must optimize for GEO (Generative Engine Optimization), not just SEO.
• Personalization is entering a new era: every touchpoint, not just the website.

Brent Krempges, Chief Customer Officer at Gainsight, joins the show to unpack the next evolution of Customer Success in an AI-first world.

After 12+ years at Gainsight, from implementation to global pre-sales to CCO, Brent shares how CS is shifting from seat-based software to outcome-driven operating models. We dive into AI-driven health scores, renewal agents, sentiment analysis, and the looming “retention reckoning” facing AI-native companies.

• AI will elevate — not eliminate — the importance of services.
• Floor-Deployed Engineers (FDEs) signal a return to high-touch value realization.
• Health scores are getting smarter, but “watermelon accounts” will always exist.
• Sentiment analysis from transcripts and email may replace traditional NPS.
• Many AI companies haven’t hit their renewal reality yet.
• Retention pressure is coming — especially for growth-at-all-costs AI startups.
• Before deploying agents, companies must rebuild foundational lifecycle processes.
• Think of agents as “50 interns” — would they know what to do?

In this episode of the Thread Podcast, Justin Vandehey sits down with Elizabeth Herbst-Brady, Chief Revenue Officer of Condé Nast, to explore how one of the world’s most iconic media companies is navigating transformation in the age of AI.

Elizabeth shares lessons from her career spanning media, advertising, and technology, including leadership roles at Yahoo, Snap, and Viacom, and explains why trusted brands, human creativity, and editorial authority are becoming more valuable, not less, as AI accelerates content creation.

The conversation covers how Condé Nast is using AI responsibly to enhance, not replace premium content, how revenue teams are being unified across advertising, commerce, subscriptions, and live events, and what it takes to lead teams through constant transformation with curiosity, accountability, and gratitude.

This episode is a masterclass in modern GTM leadership at the intersection of creativity, technology, and trust.

Chapters

00:00 – Welcome & Elizabeth’s Career Journey
From media and entertainment to technology and back to Condé Nast.

04:40 – Why Condé Nast, Why Now
The opportunity to lead revenue at an iconic, trust-driven brand.

07:30 – AI and the Future of Premium Content
Why AI can’t replace human creativity, taste, and editorial authority.

11:45 – Creation vs. Curation in an AI World
How Condé Nast separates content creation from AI-powered enhancement.

15:30 – Using AI to Improve Consumer Experience
Real examples from Bon Appétit and The New Yorker.

19:30 – Why LLMs Reward Credibility Over Volume
How AI changes the economics of SEO, expertise, and originality.

23:40 – Unifying Revenue Across Silos
Bringing advertising, commerce, subscriptions, and events into one revenue org.

27:50 – Leading Through Transformation
Elizabeth’s leadership framework: curiosity, accountability, and gratitude.

32:30 – What’s Next for Condé Nast & Premium Media
Why trusted brands will accelerate over the next 12–24 months.

Key Highlights & Takeaways

• AI should enhance content, not replace human voice or judgment.
• Trust, credibility, and editorial authority are premium assets in an AI era.
• LLMs reward expertise and originality, not volume or SEO tricks.
• Revenue transformation requires visibility, shared data, and cohesion across teams.
• The best leaders embrace constant change with curiosity and accountability.
• Premium media’s value proposition strengthens as information becomes noisier.

In this episode of the Thread Podcast, host Justin Vandehey sits down with Neal McCoy, VP of Customer Success and Professional Services at BigCommerce, to unpack where customer value most often breaks down after a deal is closed — and how companies can fix it.

Neal shares insights from nearly a decade building CS and PS at BigCommerce, explaining why customers don’t buy software to “solve problems,” but to make or save money. The conversation explores how unclear value realization creates friction during onboarding, why sales-to-CS handoffs fail, and how AI is reshaping customer success through better context, automation, and voice-of-the-customer insights at scale.

Key Takeaways & Highlights

• Customers buy software to make money, save money, or both — not just to solve surface-level problems
• Misalignment on value realization is the #1 reason onboarding and CS struggle post-sale
• Sales teams often assume customers understand value — they usually don’t
• The earlier value is quantified and documented in the sales cycle, the stronger the post-sale execution
• AI can eliminate manual handoff friction by summarizing calls, emails, and deal context automatically
• Traditional CS metrics like surveys and NPS are statistically weak; voice of the customer at scale is the future
• Customer success leaders must act as the primary conduit for customer insight back into product and GTM
• Personalization at scale requires cohort-based learning, not one-size-fits-all onboarding
• Fewer deals with clearer value often outperform higher-volume pipelines long term
• The best salespeople optimize for customer outcomes, not just closed deals

Chapters & Timestamps

00:00 – Welcome & Introduction
Justin introduces Neal McCoy and his background across military, fintech, digital engagement, and ecommerce.

02:00 – Neal’s Career Path & BigCommerce Journey
How Neal helped build CS and professional services as BigCommerce moved upmarket.

04:30 – Where Customer Value Breaks Down Post-Sale
Why customers trade one set of problems for another when value isn’t clearly defined.

06:45 – What CS Wishes Sales Would Hand Off (But Rarely Does)
The missing context that makes or breaks onboarding and adoption.

09:15 – AI’s Role in Fixing the Sales-to-CS Handoff
How AI can summarize deal context and remove the burden from sellers.

11:45 – Voice of the Customer vs. Traditional CS Metrics
Why surveys fail and how AI unlocks insight from unstructured customer data.

14:30 – Personalization at Scale in Ecommerce Onboarding
Using cohort-based success models across industries, regions, and merchant types.

17:15 – The Biggest Misconception Sales Leaders Have About Post-Sale
Why focusing on value may reduce conversions but increase long-term growth.

20:00 – The Future of CS, PS, and AI at BigCommerce
How AI is changing delivery models, expertise, and customer expectations.

22:30 – Closing Thoughts & What’s Next
Neal’s outlook on AI, value delivery, and helping merchants succeed long-term.

In this episode of the Thread Podcast, Justin Vandehey sits down with Jared Myatt, Senior Director of Revenue Operations at Integrate, to explore what it really takes to scale RevOps over time. Jared shares his journey from early employee to RevOps leader, reflecting on key inflection points including acquisitions, private equity ownership, and enterprise growth.

They discuss how the definition of RevOps has evolved, why data must power decision-making (not just dashboards), how culture scales through honesty and curiosity, and why alignment across GTM teams ultimately comes down to communication—not tools. This is a must-listen for anyone building RevOps in a growing SaaS organization.

Key Topics Covered

• Growing with a company from early startup to enterprise
• What RevOps actually is (and what it isn’t)
• Using data to tell real revenue stories
• Scaling culture without over-engineering it
• Career advice for aspiring RevOps leaders
• Why alignment breaks—and how to fix it
• The role of RevOps as GTM problem solvers

Suggested Chapters

00:00 – Welcome + Jared’s background
02:30 – Early ownership and pivotal moments at Integrate
04:30 – How RevOps has evolved over the years
06:00 – Using data to tell the revenue story
07:45 – Preserving culture through growth
10:45 – Career advice for moving into RevOps
13:30 – What alignment really looks like
16:45 – Integrate overview + closing

In this episode of the Thread Podcast, Justin Vandehey interviews Benjamin Roach, Director of Revenue Operations at Optio Incentives, to explore what it takes to build RevOps in the equity compensation and incentives space. Ben shares his “traditional” path from sales into RevOps, why he deliberately took a step back into a junior ops role, and how getting technical became a career unlock.

They dig into the complexities of selling and operating in equity management—where revenue can include ARR, transactional fees, and services, and where buyers span CFOs, CHROs, legal, and finance. Ben also shares his point of view on AI: where it can help participants and admins get fast answers, and why data quality and human oversight still matter. The episode closes with career advice for aspiring RevOps leaders and how to learn the craft.

Key topics covered

• Why Ben moved from sales → RevOps (and why he “took a step back” to level up)
• Equity compensation complexity: strike price, taxes, vesting, global compliance
• How Optio’s GTM motion sells “trusted partner + tech,” not just software
• Measuring growth in equity management beyond traditional ARR
• AI in equity management: where it’s useful today and where it’s risky
• Career advice: become technical, stay curious, build a broader toolbelt

Memorable moments / quotable lines

• “Stock options… were unknown to me. You get handed them and think, maybe one day I’ll make money.”
• “AI is only as good as your data models.”
• “Don’t be scared to take a step backwards.”
• “RevOps wears so many hats—you need a lot of tools on your toolbelt.”

Chapters (suggested)

00:00 – Welcome + Ben’s intro
01:00 – From sales to RevOps (and why he took a step back)
02:10 – Why the equity/incentives space pulled him in
03:30 – Aligning finance, HR, and revenue metrics
04:45 – Why revenue isn’t just ARR in equity management
05:30 – Simplifying a complex story for CFOs/CHROs/legal
06:55 – Global compliance + product readiness constraints
09:00 – AI in equity: what it can and can’t do (yet)
11:05 – Career advice for aspiring RevOps leaders
13:45 – Plug: Optio + how to connect with Ben

In this episode of the Thread Podcast, Justin talks with Tyler Will, VP of GTM Strategy & Ops at Intercom, about how modern revenue organizations are evolving in an era defined by AI, PLG-to-enterprise transitions, and go-to-market speed.

Tyler shares his journey from economic consulting and Bain, to GTM leadership at LinkedIn, to now scaling RevOps at Intercom. He breaks down the key differences between operating at a 20,000-person giant and a high-velocity SaaS company, why balancing PLG and enterprise sales motions requires intentional system and process design, and how Intercom rebuilt its routing, sales assist, and pricing guardrails to accelerate ACVs and bring clarity back to the customer journey.

The conversation digs into how AI is reshaping selling—not by replacing reps, but by giving them time back. From auto-generating QBR decks to enriching data behind the scenes, Tyler explains why AI actually makes sales more human, not less. He also shares why the next generation of RevOps talent will shift from narrow specialists to curious generalists who leverage AI, understand the full GTM workflow, and act as true co-owners of the business.

This is a high-signal episode for anyone thinking about PLG evolution, GTM design, AI-powered sales, and how RevOps must evolve to meet the moment.

Chapters

00:00 — Intro + Tyler’s Background
Justin sets up the episode; Tyler shares his path from consulting and Bain to LinkedIn to Intercom.

02:00 — Early Career Lessons: From Consulting to GTM
How economic consulting and strategy work shaped Tyler’s analytical and leadership approach.

03:30 — Operating at Scale: LinkedIn vs. Intercom
Why large enterprise GTM is committee-driven, and how smaller SaaS companies require speed, adaptability, and influence without authority.

06:00 — PLG, Sales-Led, and the Middle Ground
How Intercom balances self-serve PLG customers with enterprise sales—and why a “Sales Assist” motion has become critical.

08:30 — Redesigning Routing, Guardrails & ACV Growth
How simplifying and separating motions helped Intercom lift sales-led logos and drive higher ACVs.

10:45 — AI as an Amplifier, Not a Replacement
Why AI frees reps from low-value tasks (QBR decks, data cleanup) and makes room for more human selling.

13:20 — The Real Risk: Overvaluing Human Busywork
Why reps aren’t losing points for doing things manually—and why AI should elevate the conversation, not eliminate the human.

15:00 — The Future of RevOps Careers
Why RevOps is shifting from specialists to generalists who use AI, understand systems, and act like business owners.

18:00 — What RevOps Leaders Should Learn Next
Tyler’s advice to aspiring operators—how to become more valuable by being curious across the entire GTM ecosystem.

19:30 — Closing Thoughts + Intercom Hiring
Tyler encourages RevOps pros to embrace the field and shape the future; Justin wraps the conversation.

Episode Summary

In this episode of the Thread Podcast, host Justin Vandehey sits down with John Queally, Senior Director of Revenue Operations at Clari, to explore how RevOps is evolving in the age of AI, and what it really means to build a data-driven go-to-market organization.

John’s career spans consulting, analytics at JP Morgan, leadership roles at American Express and Qualtrics, and now Clari — one of the companies that helped define modern RevOps. He shares how his early assumption that tech companies were “amazing at data” turned out to be completely wrong, and why that realization led him to see RevOps as the spinal column and nervous system of every go-to-market organization.

Together, they dive deep into:

• How to unify fractured data systems across sales, marketing, CS, and product
• The difference between “tools” and true data architecture
• Why AI is exposing every fault line in go-to-market organizations
• The human side of RevOps: partnerships, trust, and communication
• What “world-class” looks like for RevOps in 2025 and beyond
• How to balance machine intelligence with human intuition in sales
• And how leaders can prepare for the next generation of revenue operations

Chapters

00:00 – Introduction
Justin introduces John Queally and his path from consulting and banking to RevOps leadership at Clari.

01:10 – From JP Morgan to Clari: The Data Reality Check
John shares how his early experience in finance led him to realize how disorganized data is across tech companies — and how that sparked his RevOps journey.

03:30 – Defining RevOps as the Spinal Column
Why RevOps should serve as the connective nervous system for GTM — ensuring every function operates from the same base of facts.

05:00 – What “World-Class” RevOps Looks Like Today
John explains how the definition of world-class RevOps is shifting toward data ownership, cohesive field experiences, and AI-enabled decision-making.

06:30 – AI vs. Human Intuition
The ongoing tension between automation and human instinct in sales — and why RevOps needs to serve as a checkpoint, not a replacement.

08:15 – The Future of CRM and GTM Systems
A look ahead at how the sales tech stack is evolving beyond monolithic CRMs into a connected ecosystem of specialized tools.

10:00 – Machine Learning and Predicting Customer Behavior
John shares how Clari partnered with data science firm QuadSci to achieve 94% churn prediction accuracy — and how that insight gets surfaced seamlessly to the field.

13:00 – Cross-Functional Alignment at Scale
Why true RevOps alignment comes from people, not tickets — and why John’s team embeds directly within every GTM function.

15:30 – Developing the Next Generation of RevOps Leaders
The skills operators need to thrive in this next era — including data fluency, architectural thinking, and strategic ownership.

18:00 – The AI Wake-Up Call
Why 80% of AI projects fail — and how RevOps leaders can prepare their orgs by fixing data quality and alignment first.

20:00 – Closing Thoughts
John’s reflections on RevOps as a community-driven discipline, the future of collaboration, and why every GTM leader must now own their data story.