Most European founders expanding to the US make the same hiring mistake. This episode breaks down what actually works when building a commercial team across the Atlantic.

Tired of watching US expansion burn through cash with nothing to show for it? Wondering whether to hire senior or junior first, which city to land in, or how to stop your new US team from churning out within a year?

James Isilay founded Cognism and scaled it from zero to $80M+ ARR, navigating the move from the UK to the US firsthand, including an early pivot from New York to Boston that changed the trajectory of the business. He's since advised multiple high-growth B2B software companies on strategic expansion and go-to-market.

You'll walk away with a clear framework for sequencing your US expansion: when to transplant your own people, when to start hiring locally, and the positioning work most founders skip that determines whether the whole thing sticks. This isn't theory, it's a playbook built from real decisions and real mistakes.

This one is for European and UK-based SaaS founders and GTM leaders who are planning or actively navigating US expansion. If you're deciding on your first US hire, choosing a city, or trying to figure out why your US pipeline isn't converting, this is the episode.

Key Takeaways

>> Hiring a senior US sales leader before you've built a working system on the ground is the most common and most expensive way European founders fail at US expansion.

>> Transplanting early employees from your home base creates a bridge between your existing playbooks and the new market, giving your US team access to the knowledge network that remote hires simply can't replicate.

>> Choosing a city based on where your specific industry talent lives, not prestige or personal preference, dramatically affects hiring quality, retention, and cost.

>> Founders need to find a tight ICP with high win rates in the US market before putting their foot on the pedal with sales hiring; without that foundation, you're accelerating from nothing.

Chapter Markers

00:00 - Why hiring senior in the US usually fails

02:59 - The pattern behind failed European expansions

05:17 - Starting junior vs. transplanting your own team

06:32 - How often founders need to be on the ground

07:50 - New York to Boston: why geography matters

10:01 - Choosing a city based on talent, not prestige

12:27 - The competitor that burned through a Series A in San Francisco

14:04 - Time zone overlap and the East Coast advantage

15:09 - US vs. UK sales talent: cost, churn, and calibration

17:44 - Adapting your hiring process for the US market

20:33 - Building culture across a satellite office

22:33 - Why your UK brand doesn't transfer to the US

24:44 - Reducing churn: comp, culture, and in-office presence

26:46 - Working with specialist recruiters in the US

28:55 - The one thing James would tell every founder before expanding

30:17 - Honest signals that you're ready and false ones that trick you

33:08 - Quickfire round

Useful Links & Resources

James Isilay on LinkedIn: https://www.linkedin.com/in/james-isilay/

Captivate Talent: https://www.captivatetalent.com/

Danielle Parker on LinkedIn: https://www.linkedin.com/in/daniellemessler/

Chris Gannon on LinkedIn: https://www.linkedin.com/in/gannonchristopher/

Connect With the Show

LinkedIn: https://www.linkedin.com/company/captivate-talent/

What's been your biggest surprise expanding a team into the US? Or if you're planning it right now, what's the question keeping you up at night? Drop it in the comments, we read every one and it helps shape future episodes.

If this episode gave you a clearer picture of what US expansion actually takes, subscribe and share it with a founder who's about to make the move. New episodes drop every fortnight.

Your first revenue-generating hire can unlock your Series A or quietly burn 12 months of runway. This episode breaks down how to get it right.

Hiring your first salesperson when you don't come from a sales background? You don't know what "great" looks like, sellers are experts at selling themselves, and the old playbook of poaching from a big-logo company keeps backfiring. Sound familiar?

Ben Newsome is VP of Talent and People at Cherry Ventures. He's spent his career inside the talent functions of major European VC firms, advising hundreds of early-stage B2B tech companies on their most critical GTM hires.

You'll walk away knowing exactly what behavioral traits to interview for, why the "hire from Gong" instinct usually fails at seed stage, and the concrete steps to take before you talk to a single candidate. This is a practical hiring diagnostic, not theory.

This one's for early-stage B2B founders, revenue leaders, and the VCs backing them. We cover the founding AE archetype, how to test for entrepreneurial grit in interviews, when founders hire too early, and the referencing mistakes that keep costing startups months of runway.

Key Takeaways

>> The strongest first GTM hires weight 75% toward attitude and behavior and only 25% toward experience and the interview questions you ask are the fastest way to see the difference.

>> Hiring a seasoned operator from a growth-stage company often backfires because you can hide inside a mature playbook. Early-stage demands a generalist who's already proven they can build from zero.

>> Founders should stress-test their go-to-market assumptions before opening the role, not after. The gaps you find will reshape the job description entirely.

>> Firing fast only works when you're high-conviction in your GTM strategy; if you're not, seek advice fast and audit the whole machine, not just the hire.

Chapter Markers

00:00 - The cost of getting this hire wrong

02:51 - Real examples of misfired GTM hires delaying funding rounds

04:18 - The founding AE archetype: what to actually look for

05:49 - How to interview for attitude, resilience, and entrepreneurial grit

07:57 - Why the "big logo" enterprise seller keeps failing at seed stage

10:17 - Behavioral interview questions that separate operators from talkers

13:15 - Stage specificity: identifying true early-stage operators

15:26 - How exposure and relationship-building signal a great GTM hire

17:15 - The link between first sales hire quality and Series A graduation

19:54 - How to know if a founder is actually ready for their first commercial hire

21:52 - Fire fast or coach through it? When to cut ties vs. course correct

27:40 - The founder's role: coaching, relinquishing control, and setting hires up to win

30:20 - Three things every founder should do before talking to a single candidate

32:25 - The one question Ben wishes every founder would ask him

Useful Links & Resources

• Ben Newsome on LinkedIn: https://www.linkedin.com/in/bennewsome/
• Cherry Ventures: https://www.cherry.vc/

Connect With the Show

• Captivate Talent on LinkedIn: https://www.linkedin.com/company/captivate-talent/
• Danielle Parker on LinkedIn: https://www.linkedin.com/in/daniellemessler/
• Captivate Talent website: https://www.captivatetalent.com/

What did your first GTM hire teach you, the hard way or the good way? Drop your story in the comments. If you're a founder navigating this decision right now, we'd love to hear what's tripping you up.

Visit captivatetalent.com to learn how we help B2B tech companies hire exceptional GTM talent.

Most companies say they want AI-native hires. Almost none of them can tell the real thing from a polished talking point.

You're writing "AI fluency required" into every job description, but when you sit across from a candidate, you don't actually know what good looks like. And your interview process? It's probably optimized for charisma, not competence.

Kyle Norton is CRO at Owner.com, one of the fastest-growing companies in restaurant tech B2B Tech. He leads a GTM org spanning sales, partnerships, onboarding, demand gen, rev ops, and enablement and he's built a dedicated Applied AI function inside his revenue team that most companies haven't even considered yet.

This conversation gives you a concrete framework for assessing AI fluency in interviews, a clear case for centralizing AI capability instead of spreading it thin, and a structured hiring process that replaces gut feel with repeatable data. You'll walk away knowing exactly where to invest and where to stop guessing.

Kyle breaks down the AI sophistication ladder for GTM professionals, explains why early-career hires are outperforming tenured reps at Owner.com, and makes the case for killing vibe-based interviews for good.

This one's for revenue leaders, founders, and hiring managers building teams that need to be competitive in the next two to three years.

Key Takeaways

>> Centralized AI teams produce orders-of-magnitude better output than reps tinkering side-of-desk. Kyle explains why he made Applied AI the first hire after Owner.com's Series C.

>> AI fluency matters most at senior and leverage roles like rev ops, but frontline managers and reps don't necessarily need it if the right infrastructure exists around them.

>> The fastest way to spot genuine AI fluency in an interview is to be deeply fluent yourself or have someone who is sitting in the process. Buzzwords fall apart fast under real scrutiny.

>> Structured interviews with identical questions, weighted scorecards, and separated criteria consistently outperform "vibe hiring" and they're the only way to build a data set you can actually learn from when a hire doesn't work out.

Chapter Markers

00:00 - Kyle Norton on AI fluency and hiring on vibes

01:56 - The internet comparison: why AI is already table stakes

04:48 - Where to actually learn about AI: Twitter, YouTube, and the feed algorithm

08:58 - Interviewing for AI fluency: what genuine answers look like

13:39 - Building a centralized Applied AI function inside GTM

16:45 - How the Applied AI team expanded beyond sales

19:04 - Why Owner.com shifted to early-career hiring

23:33 - Finding top talent at lesser-known companies

26:15 - The structured interview process: scorecards, mock calls, and bar raisers

32:32 - Go-to-market org structures for the next 2–3 years

36:25 - One concrete step: kill vibe hiring this week

40:09 - Danielle's closing thoughts

Useful Links & Resources

• Kyle Norton on LinkedIn: https://www.linkedin.com/in/kylecnorton/
• Owner.com: https://www.owner.com/

Connect With the Show

• Captivate Talent on LinkedIn: https://www.linkedin.com/company/captivate-talent/
• Danielle Parker on LinkedIn: https://www.linkedin.com/in/daniellemessler/
• Captivate Talent website: https://www.captivatetalent.com/

When did you last audit your interview process against real performance data? Drop your take in the comments or share the one hiring change that made the biggest difference for your team.

If this episode made you rethink how you're hiring for AI fluency or structuring your interviews, share it with a founder or revenue leader who needs to hear it. And if you're building a GTM team that needs to be competitive in the next few years, visit captivatetalent.com

Welcome to Human First.

The bar for AI fluency in go-to-market hiring has shifted dramatically and most executives haven't caught up.

You know you need to talk about AI in interviews, but you're not sure what "good" actually looks like anymore. Is using ChatGPT to brainstorm enough? Should you be building dashboards? And how do you evaluate something you're still figuring out yourself?

Andy Mowat built and scaled RevOps and demand gen at four unicorns - Box, Upwork, Culture Amp, and Carta. Now, as founder of Whispered, he's in constant conversation with senior GTM leaders about how AI is reshaping the way they hire and get hired. Few people have a broader, more grounded view of what's actually happening.

In this launch episode of Human First, Danielle Parker from Captivate Talent, and Andy get tactical about what AI fluency means right now, how it's being tested in interviews, and what you can do in the next 30 days to get across the chasm. You'll walk away with a clearer picture of what hiring managers are really asking and how to answer.

Key Takeaways

>> The AI fluency bar has moved from "curious" to "builder" in under 12 months. Using tools like Gamma or ChatGPT for slide decks is no longer enough to impress in interviews.

>> Most executives don't realize they're overselling their AI skills because the technology is moving faster than their self-assessment and many interviewers can't probe deeply enough to tell the difference.

>> The traditional take-home case study is broken and AI makes every submission look polished, so hiring managers need to rethink whether they're evaluating real thinking or just well-prompted output.

>> Hiring managers are over-indexing on "builder" without asking what's behind the question, whether it's doing more with less, flying low and high, or actually implementing AI tooling are three very different needs.

Chapter Markers

00:00 The question behind "hire a builder"

01:00 - Introduction to Andy Mowat and Whispered

01:38 - Biggest shifts in executive hiring conversations

03:33 - How AI fluency evaluation has changed

07:23 - What AI-fluent leaders actually sound like day to day

09:27 - Rev ops as the bridge role for GTM AI adoption

13:01 - How candidates oversell AI skills without realizing it

15:22 - Recognizing genuine AI passion in interviews

17:18 - Whispered's view on roles being reshaped by AI

19:23 - What rev ops looks like in two years

22:16 - The 30-day playbook to cross the AI chasm

28:30 - Is AI fluency learnable or inherent?

33:17 - Why take-home case studies are broken

38:06 - What should replace the case study

40:59 - Where go-to-market hiring is heading in 2-3 years

43:18 - One thing to do differently this week

Useful Links & Resources

• Whispered: AI platform for executive career moves
• Whispered Hiring Podcast: Andy's podcast on GTM hiring
• Claude Code by Anthropic: https://www.anthropic.com
• Lovable: No-code app building platform
• HyperBound: AI role-play platform for sales enablement

Connect With the Show

• LinkedIn: https://www.linkedin.com/company/captivate-talent/
• Website: https://www.captivatetalent.com/
• Danielle Parker on LinkedIn: https://www.linkedin.com/in/daniellemessler/

If this conversation hit home, we'd love to hear from you. What's the hardest part of evaluating AI fluency in your hiring process?

Drop a comment or send Danielle a message on LinkedIn — these are the conversations that make this show better.

Head to https://www.captivatetalent.com/ to see how Captivate Talent can help you find the right GTM leaders for what's next.