Why Your First Sales Hire Is Making or Breaking Your Series A with Ben Newsome

AI Can Rank Your Candidates, But It Shouldn't Pick Who You Hire with Cassie Chao Leemans

Most people using AI in recruiting are asking the wrong question. They want to know how much they can automate. Cassie Chao Leemans wants to know where the human has to stay in the loop, and she has built her entire workflow around that distinction. Cassie is VP of Talent at Craft Ventures, a team of one, and a recruiter with 15 years of experience scaling teams at Uber, Palantir, and Threads. Over the past year she has built her own AI-native CRM from scratch using Claude Code, with no engineering background, that automates the back-end work of recruiting while keeping every hiring decision firmly in human hands. Her take on where AI belongs in the recruiting process, and where it absolutely does not, is one of the clearest frameworks we have heard on the show. This episode is for early-stage founders thinking about their first recruiting hire, talent leaders looking to build smarter workflows without losing the human element, and anyone trying to figure out where to draw the line between AI and human judgment in hiring. Cassie covers build versus buy decisions, the danger of AI-written scorecards, why inbound has become a noise problem, and the one question every founder should ask before handing any part of their hiring process to a machine. Key Takeaways >> AI should amplify what you are already doing, not make decisions for you. The moment AI starts filtering candidates in or out without a human reviewing why, you are introducing false positives and false negatives that will cost you hires you cannot afford to lose. >> Start with your biggest pain point and automate that one thing first. You do not need to overhaul your entire workflow. Find the task you are repeating over and over and start there. >> AI-written scorecards are a red flag. If you are not the one evaluating whether a candidate collaborated well or showed initiative, you are outsourcing your own judgment to a model that was not trained on your values or your definition of great. >> The human moat in go-to-market hiring is interpersonal judgment. No AI can evaluate the nuances of how someone sells, collaborates, or shows up in a room. That assessment has to come from a human who has had the conversation. Chapter Markers (00:00) Cold open: Why humans have to stay in the loop (01:54) How Cassie built an AI-native CRM as a team of one (04:33) Build versus buy: why she stopped looking for an off-the-shelf solution (10:34) How early-stage founders should think about automating recruiting workflows (15:00) Does Cassie fear building too deep on one set of tools (22:10) Where Cassie draws the hard line between AI and human in hiring (26:45) Can you hire a great go-to-market person using AI alone (31:40) What founders get wrong about handing off recruiting (36:55) The one thing founders should and should not do with AI in recruiting (39:20) Selling versus buying market: how founders should think about talent right now (41:45) Wrap-up and where to find Cassie Useful Links & Resources Cassie Chao Leemans on LinkedIn: https://www.linkedin.com/in/cassieleemans Craft Ventures: https://www.craftventures.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/

What is a GTM Engineer? Hiring, AI and the Future of RevOps with Lauren Hughes of Justworks

Here's how to tell if you need a GTM Engineer and what to fix first. Lauren Hughes is VP of Revenue Effectiveness at JustWorks, where she rebuilt the entire function from the ground up by merging rev ops and enablement, introducing GTM engineering roles, and hiring AI enablement specialists. Roughly 75% of her team is either new or in a completely different seat than before. From this episode of Human-First, you'll walk away knowing exactly how to diagnose whether you need a GTM engineer or a Salesforce admin, how to assess builder mindset in interviews when no one has "10 years of GTM engineering experience" on their resume, and what foundation you need in place before any of it matters. This one's for founders, revenue leaders, and rev ops professionals trying to figure out what their team should actually look like right now and what it needs to become. We cover GTM hiring for technical roles, AI fluency as a hiring bar, case studies in the age of AI, and why your operating maturity determines your next hire. Key Takeaways >> If your pain is "Salesforce hygiene is bad and routing rules need fixing," you need an admin. GTM engineers are for inventing capabilities that don't exist yet, not maintaining what does. >> The strongest GTM engineer candidates deconstructed the problem from a data perspective and came with a complete system redesign, while average ones just talked about process improvements. >> Case studies are more critical than ever precisely because of AI with the real test is whether candidates can defend and explain what they built when questioned live. >> Before hiring a GTM engineer, get your data foundation right with clean infrastructure, clear ownership, and system discipline. AI and builders can't fix what's fundamentally broken underneath. Chapter Markers 00:00 - What a GTM engineer actually does 01:54 - Why JustWorks rebuilt revenue effectiveness from scratch 05:17 - How the rebuild played out: roles added, removed, and renamed 08:51 - GTM engineers vs. Salesforce admins: where the confusion comes from 14:58 - How to interview for builder mindset with no job title precedent 18:05 - Case studies in the age of AI: what's changed and what still works 21:02 - The AI fluency bar: what Lauren asks every candidate 24:08 - AI enablement roles and just-in-time personalized learning 29:52 - The flattening org: why middle management layers are thinning 33:44 - Career paths in rev ops: skills-based, not tenure-based 35:34 - What early-stage founders should do before hiring a GTM engineer 38:35 - Rev ops as the entry point for AI across the org 41:07 - Where Lauren learns: podcasts, communities, and vendor dinners 45:32 - The one thing to get right before writing a job description Useful Links & Resources * Lauren Hughes on LinkedIn: https://www.linkedin.com/in/laurenehughes10023/ [https://www.linkedin.com/in/laurenehughes10023/]  * Captivate Talent: https://www.captivatetalent.com [https://www.captivatetalent.com/] Connect With the Show * Captivate Talent on LinkedIn: https://www.linkedin.com/company/captivate-talent/ [https://www.linkedin.com/company/captivate-talent/] * Danielle Parker on LinkedIn: https://www.linkedin.com/in/daniellemessler/ [https://www.linkedin.com/in/daniellemessler/] What's your take? Is the GTM engineer title getting ahead of what most teams actually need? Drop your thoughts in the comments, or tell us what your rev ops team looks like right now. We'd love to hear how you're navigating this shift. Visit captivatetalent.com to learn how we help B2B tech companies hire exceptional GTM talent. If this episode was useful, like, subscribe, and share it with someone building out their rev ops function.

The Framework Behind a Great First GTM Hire with Rav Dhaliwal

A lot of founders get their first go-to-market hire wrong. Not because they pick the wrong resume, but because they skip the thinking that comes before the job description. You've raised the round, your investors are pushing you to scale, and you're copy-pasting job descriptions from companies ten times your size. But you don't actually know what "great" looks like for this role at your stage, and the cost of getting it wrong won't show up for 12 to 18 months. Rav Dhaliwal is a partner at Crane Venture Partners who spent the first half of his career as an operator building GTM teams at Slack, Zendesk, and Yammer. He's made every early-stage hiring mistake possible and now helps founders avoid the same traps. You'll walk away with a clear framework for deciding whether you're actually ready to hire, the math to pressure-test your plan, and a structured approach to interviewing that separates real performers from polished storytellers. This is practical, data-backed hiring advice you can use immediately. This episode is for B2B tech founders making their first (or next) GTM hire, VCs advising portfolio companies on GTM buildout, and revenue leaders navigating the shift from founder-led sales. Rav covers readiness signals, scorecard design, behavioral interviewing, and the critical transition from founder-led to founder-managed sales. Key Takeaways >> Before hiring an AE, work backward from OTE to pipeline: if you can't generate 3 - 4x qualified pipeline against their quota target, the timing isn't right, no matter what your investors say. >> The four types of salespeople willing to join before you've figured out your market are almost never the ones you want. Be aware of poor performers, lucky riders, stealth consultants, and semi-retired operators. >> A job description lists activities; a hiring scorecard defines mission, outcomes, and behavioral competencies and it's the difference between collecting useful interview data and getting sold by a good storyteller. >> Test intrinsic motivation before you test skills: why someone wants to leave, why they want to join you specifically, and whether their career goals align with what you're actually offering. Chapter Markers 00:00 - Why early-stage GTM mis-hires create management debt 02:07 - What a hiring mistake actually costs in practice 04:30 - How to know if it's the right time to hire 06:54 - The OTE-to-pipeline math every founder should run 09:32 - Pushing back when investors pressure you to scale 10:14 - Four types of salespeople who'll join too early 12:49 - Sussing out stage fit in interviews 16:04 - Behaviors vs. skills: where the conviction comes from 18:49 - Behavioral interviewing in practice with real examples 22:01 - The hiring scorecard: mission, outcomes, competencies 28:53 - Early warning signs of a GTM mis-hire 30:37 - Founder-led sales to founder-managed sales 34:38 - Why the Frankenstein job description is dangerous 36:31 - Testing intrinsic motivation in screening calls 41:18 - Key takeaways and wrap-up Useful Links & Resources * Rav Dhaliwal on LinkedIn: https://www.linkedin.com/in/ravinderdhaliwal/ [https://www.linkedin.com/in/ravinderdhaliwal/] * Who by Geoff Smart and Randy Street - the hiring framework referenced in this episode: https://whothebook.com/ [https://whothebook.com/] * Crane Venture Partners: https://crane.vc [https://crane.vc/] Connect With the Show * Captivate Talent on LinkedIn: https://www.linkedin.com/company/captivate-talent/ [https://www.linkedin.com/company/captivate-talent/] * Danielle Parker on LinkedIn: https://www.linkedin.com/in/daniellemessler/ [https://www.linkedin.com/in/daniellemessler/] * Captivate Talent website: https://www.captivatetalent.com/ [https://www.captivatetalent.com/]

How to Build a US Sales Team When You're Expanding From Europe with James Isilay

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.

Why Your First Sales Hire Is Making or Breaking Your Series A with Ben Newsome

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/ [https://www.linkedin.com/in/bennewsome/] * Cherry Ventures: https://www.cherry.vc/ [https://www.cherry.vc/] Connect With the Show * Captivate Talent on LinkedIn: https://www.linkedin.com/company/captivate-talent/ [https://www.linkedin.com/company/captivate-talent/] * Danielle Parker on LinkedIn: https://www.linkedin.com/in/daniellemessler/ [https://www.linkedin.com/in/daniellemessler/] * Captivate Talent website: https://www.captivatetalent.com/ [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 [http://captivatetalent.com] to learn how we help B2B tech companies hire exceptional GTM talent.